Author: "Anne-marie Caminade" / Topic: 0104 chemical sciences - Searchworks@Jio Institute Digital Library Search Results

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151 results on '"Anne-marie Caminade"'

1. β-Cyclodextrin PAMAM Dendrimer: How to Overcome the Tumbling Process for Getting Fully Available Host Cavities

Author: Aurélien Hameau, Valérie Bourdon, Anne-Marie Caminade, Kathleen I. Moineau-Chane Ching, Régis Laurent, Christian Bijani, Ernesto Rivera, and Israel González-Méndez
Subjects: chemistry.chemical_classification, Cyclodextrin, 010405 organic chemistry, Dimer, Adamantane, Organic Chemistry, Trimer, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Crystallography, Monomer, chemistry, Dendrimer, Click chemistry, Physical and Theoretical Chemistry, Two-dimensional nuclear magnetic resonance spectroscopy
Abstract: The synthesis of a G0 polyamidoamide (PAMAM) dendrimer end-capped with four β-cyclodextrin (β-CD) units, named as Tetra-CD was performed by using copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). This new platform presents a considerable high water-solubility in comparison to native β-CD. Tumbling process involving half of the CD cavities in D2O was evidenced by 1H NMR spectroscopy. Interaction of adamantane with Tetra-CD has been fully investigated by 1D/2D NMR techniques and mass spectrometry besides a joint study on new β-CD monomers (named as A and B) and on a dimer (Di-CD) and a trimer (Tri-CD). The obtained results demonstrate that the tumbling effect can be shifted in the presence of an appropriate hydrophobic guest resulting in the full host-ability of the CD units in water for that guest.
Published: 2020
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2. Homogeneous catalysis with phosphorus dendrimer complexes

Author: Régis Laurent, Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), and GDR Phosphore
Subjects: Dendrimers, 010405 organic chemistry, Phosphorus, Homogeneous catalysis, 010402 general chemistry, Dendrimer effect, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Catalysis, Inorganic Chemistry, Solvent, Organometallic complexes, chemistry.chemical_compound, Monomer, chemistry, Organocatalysis, Reagent, Dendrimer, Materials Chemistry, Recycling, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Macromolecule
Abstract: International audience; Dendrimers are highly branched macromolecules, which have properties in many different fields, in particular for catalysis. This review presents an exhaustive view about complexes of phosphorus-containing dendrimers (having a phosphorus atom at each branching point), used as homogeneous catalysts in a range of reactions. First, catalysed reactions for C–C bonds formation using Pd, Rh, Ru, or Sc complexes will be displayed; then formation of C–O and C–N bonds using Cu complexes as catalysts will be shown. At the end, miscellaneous reactions catalysed without metal (organocatalysis) will be displayed. Despite their size, dendrimers are generally soluble in the reaction media, thus they afford homogeneous catalysts. However, their size is by far larger than the size of the reagents and products, thus they are generally easily separated, simply by adding a solvent in which the products are soluble, but not the dendrimers. The recovery and reuse of dendrimers (recycling) is an important advantage compared to classical monomeric catalysts, which will be emphasized in this review, together with the so-called dendrimer (or dendritic) effect, which is an enhancement of a property when the size of the dendrimer increases.
Published: 2019
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3. Design, complexing and catalytic properties of phosphorus thiazoles and benzothiazoles: a concise overview

Author: Aurélien Hameau, Xiangyang Shi, Marek Koprowski, Maria Zablocka, Serge Mignani, Anne-Marie Caminade, Jean-Pierre Majoral, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Centro de Química da Madeira, Universidade da Madeira (UMA), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Department of Bioorganic Chemistry Centre of Molecular and Macromolecular Studies Polish Academy of Sciences, Polish Academy of Sciences (PAN), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and CNRS
Subjects: chemistry.chemical_classification, Phosphorus, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, Coordination complex, chemistry.chemical_compound, chemistry, Phosphinic Acids, Materials Chemistry, Surface modification, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Heterocyclic derivatives, Phosphine
Abstract: International audience; The versatile functionalization of thiazoles and benzothiazoles at different locations in their backbone offers the possibility to design many substituted heterocyclic derivatives bearing active groups for applications in coordination chemistry, catalysis, and medicinal chemistry. The grafting of various phosphorus groups (phosphines, phosphine oxides, phosphonates, phosphinic acids, etc.) via different strategies leads to many phosphorus thiazoles and benzothiazoles acting per se as catalysts for a number of reactions for complexation with metals such as Ir, Au, Pt, Pd, and Cu, for which the catalytic properties were investigated.
Published: 2019
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4. Safe Polycationic Dendrimers as Potent Oral In Vivo Inhibitors of Mycobacterium tuberculosis : A New Therapy to Take Down Tuberculosis

Author: Andrii Karpus, Régis Laurent, Shriya Singh, Vishwa Deepak Tripathi, Jean-Pierre Majoral, Kishore K. Srivastava, Dheerj Soam, Anke Steinmetz, Ramakrishna Gandikota, Serge Mignani, Anne-Marie Caminade, Rama P. Tripathi, Swetarka Das, Arunava Dasgupta, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP), Centro de Química da Madeira, Universidade da Madeira (UMA), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CSIR-Central Drug Research Institute (CSIR-CDRI), Council of Scientific and Industrial Research [India] (CSIR), Sanofi R & D, Integrated Drug Discovery, In Vitro Biology & Pharmacology, CSIR-CDRI, FCT-Fundacao para a Ciencia e a Tecnologia (project PEst-OE/QUI/UI0674/2013, CQM, Portuguese Government funds), ARDITI (project M1420-01-0145-FEDER-000005-Centro de Quimica da Madeira-CQM+ (Madeira 14-20)), Centre National de la Recherche Scientifique (CNRS, France), Indo-French CEFIPRA (project CEFIPRA-5303-2), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Drug, Tuberculosis, Polymers and Plastics, media_common.quotation_subject, Bioengineering, 02 engineering and technology, Pharmacology, 010402 general chemistry, 01 natural sciences, Biomaterials, Mycobacterium tuberculosis, In vivo, Oral administration, Materials Chemistry, medicine, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ethambutol, media_common, Dendrons, biology, Bacteria, Chemistry, Phosphorus, 021001 nanoscience & nanotechnology, medicine.disease, biology.organism_classification, 0104 chemical sciences, 3. Good health, Streptomycin, Infectious diseases, Pharmaceuticals, 0210 nano-technology, Rifampicin, medicine.drug
Abstract: International audience; The long-term treatment of tuberculosis (TB) sometimes leads to nonadherence to treatment, resulting in multidrug-resistant (MDR) and extensively drug-resistant (XDR) tuberculosis. Inadequate bioavailability of the drug is the main factor for therapeutic failure, which leads to the development of drug-resistant cases. Therefore, there is an urgent need to design and develop novel antimycobacterial agents minimizing the period of treatment and reducing the propagation of resistance at the same time. Here, we report the development of original and noncytotoxic polycationic phosphorus dendrimers essentially of generations 0 and 1, but also of generations 2–4, with pyrrolidinium, piperidinium, and related cyclic amino groups on the surface, as new antitubercular agents active per se, meaning with intrinsic activity. The strategy is based on the phenotypic screening of a newly designed phosphorus dendrimer library (generations 0–4) against three bacterial strains: attenuated Mycobacterium tuberculosis H37Ra, virulent M. tuberculosis H37Rv, and Mangora bovis BCG. The most potent polycationic phosphorus dendrimers 1G0,HCl and 2G0,HCl are active against all three strains with minimum inhibitory concentrations (MICs) between 3.12 and 25.0 μg/mL. Both are irregularly shaped nanoparticles with highly mobile branches presenting a radius of gyration of 7 Å, a diameter of maximal 25 Å, and a solvent-accessible surface area of dominantly positive potential energy with very localized negative patches arising from the central N3P3 core, which steadily interacts with water molecules. The most interesting is 2G0,HCl, showing relevant efficacy against single-drug-resistant (SDR) M. tuberculosis H37Rv, resistant to rifampicin, isoniaid, ethambutol, or streptomycin. Importantly, 2G0,HCl displayed significant in vivo efficacy based on bacterial counts in lungs of infected Balb/C mice at a dose of 50 mg/kg oral administration once a day for 2 weeks and superior efficacy in comparison to ethambutol and rifampicin. This series of polycationic phosphorus dendrimers represents first-in-class drugs to treat TB infection, could fulfill the clinical candidate pipe of this high burden of infectious disease, and play a part in addressing the continuous demand for new drugs.
Published: 2021
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5. Hybrid phosphorus–viologen dendrimers as new soft nanoparticles: design and properties

Author: Serge Mignani, Nadia Katir, Anne-Marie Caminade, Karol Ciepluch, Dzmitry Shcharbin, Katarzyna Milowska, Maria Zablocka, Maria Bryszewska, Jean-Pierre Majoral, Abdelkrim El Kadib, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Jan Kochanowski University, Department of General Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, University of Lódź, Institute of Biophysics and Cell Engineering, NASB, Minsk, National Academy of Sciences of Belarus (NASB), Euromed Research Center, Engineering Division, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP), Centro de Química da Madeira, Universidade da Madeira (UMA), Centre National de la Recherche Scientifique (CNRS, France), COST program CA 17140, Jan Kochanowski University of Kielce, University of Lodz, Institute of Biophysics and Cell engineering, Minsk, NASB (Belarus), Euromed Research Center, Fes, (Morocco), FCT-Fundacao para a Ciencia e a Tecnologia (project PEst-OE/QUI/UI0674/2013, CQM, Portuguese Government funds), ARDITI through the project M1420-01-0145-FEDER-000005 – Centro de Quimica da Madeira – CQM+ (Madeira 14-20), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité)
Subjects: Chemistry, Phosphorus, Organic Chemistry, chemistry.chemical_element, Nanoparticle, Viologen, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Covalent bond, Dendrimer, medicine, Nanomedicine, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Hybrid material, Macromolecule, medicine.drug
Abstract: International audience; Various dendritic structures have been prepared during the last few decades and their properties have been emphasized in a number of reviews. Among these macromolecular structures, those incorporating phosphorus units – phosphorus dendrimers – or viologen linkages – viologen dendrimers – stand as the most promising in different fields spanning from chemistry, materials science to biology and nanomedicine. The association of the two complementary phosphorus and viologen structures resulted in a nascent family of structures referred to as “mixed” hybrid phosphorus–viologen dendrimers. In light of their specific properties, it is of interest to illustrate the conceptual preparation of not only a variety of sophisticated hybrid viologen–phosphorus dendrimers including classical dendrimers, but also other kinds of mixed macromolecules such as macromolecular asterisks, onion peel structures and covalent polydendrimer frameworks. Some preliminary results concerning the biological properties of these nano-objects as well as their use for the construction of organic–inorganic hybrid materials are presented.
Published: 2021
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6. Facile Synthesis of Amphiphilic Fluorescent Phosphorus Dendron-Based Micelles as Antiproliferative Agents: First Investigations

Author: Jean-Pierre Majoral, Régis Laurent, Liang Chen, Mengsi Zhan, Anne-Marie Caminade, Jieru Qiu, Xiangyang Shi, Serge Mignani, Jérôme Bignon, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP), Centro de Química da Madeira, Universidade da Madeira (UMA), NSFC−CNRS 2019 collaboration project (21911530230, 199675), PRC program NSCF-CNRS 2019, National Key R&D Program (2017YFE0196200), Sino-French Cai Yuanpei Programme, Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité)
Subjects: Dendrimers, Aromatic compounds, Fluorophore, Biomedical Engineering, Pharmaceutical Science, Bioengineering, Protonation, Antineoplastic Agents, 02 engineering and technology, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 01 natural sciences, Micelle, Fluorescence, Hydrophobic effect, chemistry.chemical_compound, Microscopy, Electron, Transmission, Dendrimer, Cell Line, Tumor, Amphiphile, Moiety, Animals, Humans, Cells, Cultured, Micelles, Cell Proliferation, Fluorescent Dyes, Pharmacology, Dendrons, 010405 organic chemistry, Chemistry, Organic Chemistry, Phosphorus, 021001 nanoscience & nanotechnology, Combinatorial chemistry, 0104 chemical sciences, Drug Screening Assays, Antitumor, 0210 nano-technology, Hydrophobic and Hydrophilic Interactions, Biotechnology
Abstract: International audience; We designed and synthesized several families of novel amphiphilic fluorescent phosphorus dendron-based micelles showing relevant antiproliferative activities for use in the field of theranostic nanomedicine. Based on straightforward synthesis pathways, 12 amphiphilic phosphorus dendrons bearing 10 protonated cyclic amino groups (generation one), or 20 protonated amino groups (generation two), and 1 hydrophobic chain carrying 1 fluorophore moiety were created. The amphiphilic dendron micelles had the capacity to aggregate in solution using hydrophilic/hydrophobic interactions, which promoted the formation of polymeric micelles. These dendron-based micelles showed moderate to high antiproliferative activities against a panel of tumor cell lines. This paper presents for the first time the synthesis and our first investigations of new phosphorus dendron-based micelles for cancer therapy applications.
Published: 2021
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7. Revisiting Cationic Phosphorus Dendrimers as a Nonviral Vector for Optimized Gene Delivery Toward Cancer Therapy Applications

Author: Serge Mignani, Li Jin, Anne-Marie Caminade, Cao Liu, Yu Fan, Régis Laurent, Jean-Pierre Majoral, Liang Chen, Xiangyang Shi, Jieru Qiu, State Key Laboratory for Fiber & Material Modification of Donghua University, Donghua University [Shanghai], Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité), Centro de Química da Madeira, Universidade da Madeira (UMA), National Natural Science Foundation of China (21911530230, 81761148028 and 21773026), Science and Technology Commission of Shanghai Municipality (19XD1400100 and 17540712000), National Key R&D Program (2017YFE0196200), Sino-French Cai Yuanpei Programme, Collaborative NSFC−CNRS grant, FCT-Fundação para a Ciência e a Tecnologia - CQM Base Fund - UIDB/00674/2020, and Programmatic Fund - UIDP/00674/2020, ARDITI-Agência Regional para o Desenvolvimento da Investigação Tecnologia e Inovação - project M1420-01-0145-FEDER-000005 - Centro de Quımica da Madeira - CQM+ (Madeira 14-20 Program), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP)
Subjects: Dendrimers, Polymers and Plastics, Cell Survival, Genetic enhancement, Bioengineering, 02 engineering and technology, Peptides and proteins, Gene delivery, Transfection, 010402 general chemistry, 01 natural sciences, Green fluorescent protein, Flow cytometry, Biomaterials, HeLa, Neoplasms, Dendrimer, Materials Chemistry, medicine, Genetics, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Dendrons, medicine.diagnostic_test, biology, Chemistry, Gene Transfer Techniques, Cationic polymerization, Phosphorus, Genetic Therapy, 021001 nanoscience & nanotechnology, biology.organism_classification, 3. Good health, 0104 chemical sciences, Biophysics, 0210 nano-technology, HeLa Cells, Plasmids
Abstract: International audience; Gene delivery, one important cancer-therapy mode, still remains to be challenging because of the shortage of highly efficient and safe nonviral vectors. Here, we revisit the development of cationic phosphorus dendrimers by synthesizing them with different generations (G1–3) and surface ligands (1-(2-aminoethyl) pyrrolidine, 1-(3-aminopropyl) piperidine, or 1-(2-aminoethyl) piperidine) for optimized gene delivery toward cancer-gene-therapy applications. First, the synthesized dendrimer derivatives were employed to condense plasmid DNA (pDNA) encoding enhanced green fluorescent protein (EGFP) to optimize their gene-delivery efficiency by varying the dendrimer generations and surface polycationic ligands. We show that all dendrimer/pDNA polyplexes display good cytocompatibility, and the 1-(2-aminoethyl) pyrrolidine-modified protonated G1 dendrimers (1-G1) display the best gene-delivery efficiency to HeLa cells under the same conditions through flow cytometry and fluorescence microscopic imaging analyses. Hence, 1-G1 dendrimers were then used as a vector to transfect pDNA encoding both EGFP and p53 protein for cancer-gene-therapy applications. Our results reveal that under the optimized conditions, the transfection of pDNA induces the significant p53 protein expression as verified through the resulted cell cycle arrest (regulation of p21 and Cdk4/Cyclin-D1 expression) and Western blotting. The cancer-gene-therapy potential of the polyplexes was finally validated through therapy of a xenografted tumor model after intratumoral injection without systemic toxicity. The developed cationic 1-G1 dendrimers may be adopted as a powerful vector system for gene therapy of cancer, as well as for highly effective gene therapy of other diseases.
Published: 2020
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8. Potent Anticancer Efficacy of First‐In‐Class Cu II and Au III Metaled Phosphorus Dendrons with Distinct Cell Death Pathways

Author: Jérôme Bignon, Yu Fan, Jean-Pierre Majoral, Li Jin, Anne-Marie Caminade, Serge Mignani, Régis Laurent, Xiangyang Shi, Liang Chen, Jieru Qiu, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité), Centro de Química da Madeira, Universidade da Madeira (UMA), National Natural Science Foundation of China (21911530230, 21773026, and 81761148028), Sino-French Cai Yuanpei Programme, FCT - Fundacao para a Ciencia e a Tecnologia, Portuguese Government funds - CQM Strategic Project PEst-OE/ QUI/UI0674/2013, ARDITI-Agencia Regional parao Desenvolvimento da Investigacao Tecnologia - project M1420-01–0145-FEDER-000005-Centro de Quımica da Madeira-CQM+ (Madeira 14–20 Program), CNRS, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP)
Subjects: Programmed cell death, Dendrimers, Stereochemistry, Chromosomal translocation, Apoptosis, Imaging agents, Mitochondrion, 010402 general chemistry, 01 natural sciences, Catalysis, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Cytotoxicity, Alkyl, chemistry.chemical_classification, Dendrons, biology, 010405 organic chemistry, Chemistry, Cytochrome c, Organic Chemistry, General Chemistry, Antiproliferation, 3. Good health, 0104 chemical sciences, biology.protein, Fluorescent probes
Abstract: International audience; First-in-class CuII and AuIII metaled phosphorus dendrons were synthesized and showed significant antiproliferative activity against several aggressive breast cancer cell lines. The data suggest that the cytotoxicity increases with reducing length of the alkyl chains, whereas the replacement of CuII with AuIII considerably increases the antiproliferative activity of metaled phosphorus dendrons. Very interestingly, we found that the cell death pathway is related to the nature of the metal complexed by the plain dendrons. CuII metaled dendrons showed a potent caspase-independent cell death pathway, whereas AuIII metaled dendrons displayed a caspase-dependent apoptotic pathway. The complexation of plain dendrons with AuIII increased the cellular lethality versus dendrons with CuII and promoted the translocation of Bax into the mitochondria and the release of Cytochrome C (Cyto C).
Published: 2020
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9. Cyclotriphosphazene core-based dendrimers for biomedical applications: an update on recent advances

Author: Le Wang, Serge Mignani, Jean-Pierre Majoral, Yunxia Yang, Anne-Marie Caminade, Xiangyang Shi, College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Centro de Química da Madeira, Universidade da Madeira (UMA), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimer, Biomedical Engineering, General Materials Science, Nanotechnology, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 02 engineering and technology, General Chemistry, General Medicine, 010402 general chemistry, 021001 nanoscience & nanotechnology, 0210 nano-technology, 01 natural sciences, 0104 chemical sciences
Abstract: International audience; This review is focused on the recent use of cyclotriphosphazene-based dendrimers in biomedicine. Since its synthesis for the first time in 1834, cyclotriphosphazene has been an important compound of phosphorus chemistry as a scaffold, and a large number of cyclotriphosphazene derivatives have been synthesized and applied in various fields such as biology, catalysis, fluorescence, nanomaterials, etc. Today, one of the most important uses concerns its biomedical applications. In this review, the recent developments (since 2012) of cyclotriphosphazene for major pharmaceutical applications are highlighted and analyzed.
Published: 2020
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10. Redox-Switchable Transfer Hydrogenations with P -Chiral Dendritic Ferrocenyl Phosphine Complexes

Author: Anne-Marie Caminade, John Popp, Evamarie Hey-Hawkins, Institut für Anorganische Chemie, Universität Leipzig, Universität Leipzig, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), EU COST Action CM1302 Smart Inorganic Polymers (SIPs), Graduate School BuildMoNa - Universität Leipzig, Universität Leipzig [Leipzig], Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, 010405 organic chemistry, Chemistry, Phosphines, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Enantioselective synthesis, Homogeneous catalysis, [CHIM.CATA]Chemical Sciences/Catalysis, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Redox, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Dendrimer, Asymmetric catalysis, Redox-switchable catalysis, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Phosphine
Abstract: International audience; Attaining absolute control over a catalytic process and, therewith, exploiting its full potential pleases scientists in their ambitious and ongoing endeavor to perform catalysis like Nature does. In this regard, redox-switchable catalysis certainly holds great potential, constantly gaining importance in modern catalysis research. Herein, we report the application of P-stereogenic dendritic ferrocenyl phosphines in the ruthenium-catalyzed redox-switchable transfer hydrogenation of a ketone yielding an enantioenriched alcohol. By adding a chemical oxidant or reductant, the catalytic activity of the complexes was reversibly switched off and back on again over the course of the hydrogen transfer reaction. This has been rationalized mainly in terms of a distinct electronic communication between the redox-active group and the catalytic center. The highly functionalized dendritic catalysts presented here might impact the way prospective homogeneous catalysts will be designed.
Published: 2020
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11. Ferrocenyl Phosphorhydrazone Dendrimers Synthesis, and Electrochemical and Catalytic Properties

Author: Anne-Marie Caminade, Cédric-Olivier Turrin, Eric Manoury, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS (Centre National de la Recherche Scientifique), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, Metallocenes, Pharmaceutical Science, Review, 010402 general chemistry, Electrochemistry, dendrimer, 01 natural sciences, Analytical Chemistry, Catalysis, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ferrous Compounds, Physical and Theoretical Chemistry, Organometallic chemistry, catalysis, 010405 organic chemistry, Organic Chemistry, Hydrazones, ferrocene, [CHIM.CATA]Chemical Sciences/Catalysis, Combinatorial chemistry, 0104 chemical sciences, Ferrocene, chemistry, electrochemistry, Chemistry (miscellaneous), Molecular Medicine, Surface modification, Ferrocene derivatives, Oxidation-Reduction, Macromolecule
Abstract: International audience; The discovery of ferrocene is often associated with the rapid growth of organometallic chemistry. Dendrimers are highly branched macromolecules that can be functionalized at will at all levels of their structure. The functionalization of dendrimers with ferrocene derivatives can be carried out easily as terminal functions on the surface, but also at the core, or at one or several layers inside the structure. This review will focus on phosphorhydrazone dendrimers functionalized with ferrocene derivatives, on the surface, at the core, at all layers or within a single layer inside the structure. The first part will describe the synthesis; the second part will concern the electrochemical properties; and the last part will give several examples concerning catalysis, with complexes of ferrocenyl phosphines used as terminal functions of dendrimers.
Published: 2020
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12. First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC

Author: Ernesto Rivera, Anne-Marie Caminade, Kendra Sorroza-Martínez, Javier Illescas, Israel González-Méndez, Mireille Vonlanthen, Kathleen I. Moineau-Chane Ching, Instituto de Investigaciones en Materiales (Mexico, Mexico), Universidad Nacional Autónoma de México (UNAM), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Tecnológico Nacional de México (TecNM), Universidad Nacional Autónoma de México = National Autonomous University of Mexico (UNAM), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Quebec-Mexico Bilateral Research Program from FQRNT (Fonds québécois de la recherche sur la nature et les technologies) of Quebec, and CONACYT of Mexico (Project 279380)
Subjects: Dendrimers, Magnetic Resonance Spectroscopy, Pharmaceutical Science, chemistry.chemical_element, Phosphorus dendritic compounds, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Article, Catalysis, Analytical Chemistry, lcsh:QD241-441, lcsh:Organic chemistry, Drug Discovery, Polymer chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, CuAAC reaction, chemistry.chemical_classification, Aqueous solution, Cycloaddition Reaction, Cyclodextrin, 010405 organic chemistry, Phosphorus, beta-Cyclodextrins, Organic Chemistry, Water, hemic and immune systems, Copper, Cycloaddition, 3. Good health, 0104 chemical sciences, Solubility, chemistry, Chemistry (miscellaneous), β-cyclodextrin, Molecular Medicine, Protons, Drug carrier
Abstract: A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P3N3) core and decorated with six &beta, cyclodextrin (&beta, CD) units, named P3N3-[O-C6H4-O-(CH2)n-&beta, CD]6, where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P3N3, two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (&gt, 1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the &beta, CD units to the P3N3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the &beta, CDs cavities.
Published: 2020
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13. Straightforward synthesis of gold nanoparticles by adding water to an engineered small dendrimer

Author: Vincent Collière, Anne-Marie Caminade, Sébastien Gottis, Régis Laurent, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire réactivité et chimie des solides - UMR CNRS 7314 (LRCS), Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Picardie Jules Verne (UPJV)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS, Région Midi-Pyrénées, and GDR-CNRS 'Phosphore'
Subjects: Letter, Materials science, Gold nanoparticle, General Physics and Astronomy, Nanoreactor, lcsh:Chemical technology, 010402 general chemistry, lcsh:Technology, 01 natural sciences, Colloid, Dendrimer, Nanotechnology, lcsh:TP1-1185, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Electrical and Electronic Engineering, lcsh:Science, Spectroscopy, Colloidal suspension, lcsh:T, 010405 organic chemistry, Phosphorus, [CHIM.MATE]Chemical Sciences/Material chemistry, lcsh:QC1-999, 0104 chemical sciences, Nanoscience, Chemical engineering, Colloidal gold, Transmission electron microscopy, lcsh:Q, Complexation, lcsh:Physics
Abstract: International audience; A small water-soluble phosphorus-containing dendrimer was engineered for the complexation of gold(I) and for its reduction under mild conditions. Gold nanoparticles were obtained as colloidal suspensions simply and only when the powdered form of this dendrimer was dissolved in water, as shown by transmission electron microscopy (TEM) and energy dispersive X-ray spectroscopy (EDX) analyses. The dendrimers acted simultaneously as mild reducers and as nanoreactors, favoring the self-assembly of gold atoms and promoting the growth and stabilization of isolated gold nanoparticles. Thus, an unprecedented method for the synthesis of colloidal suspensions of water-soluble gold nanoparticles was proposed in this work.
Published: 2020
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14. π-Stacking Interactions of Graphene-Coated Cobalt Magnetic Nanoparticles with Pyrene-Tagged Dendritic Poly(Vinylidene Fluoride)

Author: Vincent Collière, Anne-Marie Caminade, Enrique Folgado, Marc Guerre, Christian Bijani, Kathleen I. Moineau-Chane Ching, Bruno Ameduri, Nidhal Mimouni, Vincent Ladmiral, Armelle Ouali, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: π-stacking, magnetic nanoparticles, Dendrimers, Materials science, Stacking, chemistry.chemical_element, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Fluorescence spectroscopy, law.invention, chemistry.chemical_compound, law, Dendrimer, Moiety, Pyrenes, Graphene, [CHIM.MATE]Chemical Sciences/Material chemistry, General Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Poly(vinylidenefluoride), [CHIM.POLY]Chemical Sciences/Polymers, chemistry, Chemical engineering, Pyrene, Magnetic nanoparticles, 0210 nano-technology, Cobalt
Abstract: International audience; This study investigates the non-covalent coating of cobalt magnetic nanoparticles (MNPs) involving a graphene surface with pyrene-tagged dendritic poly(vinylidene fluoride) (PVDF). Dendrimers bearing a pyrene moiety were selected to play the role of spacers between the graphene surface of the MNPs and the PVDF chains, the pyrene unit being expected to interact with the surface of the MNPs. The pyrene-tagged dendritic spacer 11 decorated with ten acetylenic units was prepared and fully characterized. Azido-functionalized PVDF chains were then grafted onto each branch of the dendrimer using Huisgen’s [3 + 2] cycloaddition reaction. Next, the association of the resulting pyrene-tagged dendritic PVDF 13 with commercially available Co/C MNPs by π -stacking interactions was studied by fluorescence spectroscopy. Evaluated were the stability of the π -stacking interactions when the temperature increased and the reversibility of the process when the temperature de- creased. Also, hybrid MNPs were prepared from pyrene-tagged dendrimers decorated either with acetylenic functions ( 11 ) or with PVDF branches ( 13 ), and they were characterized by transmission electron microscopy and comparative elemental analysis was carried out with naked MNPs.
Published: 2018
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15. Vibrational spectroscopic study of cationic phosphorus dendrimers with aminoethylpiperidine terminal groups

Author: Jean-Pierre Majoral, V. Tripathi, V.L. Furer, A.E. Vandyukov, Anne-Marie Caminade, Valeri I. Kovalenko, Kazan State Architect and Civil Engineering University, University of Kazan, A.E. Arbuzov Institute of Organic and Physical Chemistry (IOPC), Kazan Scientific Centre of the Russian Academy of Sciences, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Kazan National Research Technological University
Subjects: Dendrimers, Infrared spectroscopy, Protonation, 010402 general chemistry, DFT, 01 natural sciences, Analytical Chemistry, symbols.namesake, chemistry.chemical_compound, Dendrimer, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Fourier transform infrared spectroscopy, IR spectra, Instrumentation, Spectroscopy, 010405 organic chemistry, Hydrogen bond, Atomic and Molecular Physics, and Optics, 3. Good health, 0104 chemical sciences, Normal vibrations, Crystallography, chemistry, symbols, Raman spectra, Piperidine, Raman spectroscopy
Abstract: International audience; Two generations of phosphoric dendrimers with piperidine functional groups were synthesized for use in biology and medicine. Neutral samples are soluble in organic solvents but after protonation these dendrimers become water soluble and can be used for biological experiments. The FTIR and FT Raman spectra of two generations of dendrimers Gi constructed from the cyclotriphosphazene core, repeating units OC6H4CHNN(CH3)P(S)< and aminoethylpiperidine end groups NH(CH2)2C5NH11 were recorded. The study of the IR spectra shows that the NH groups form hydrogen bonds. The calculation of the molecular structure and vibrational spectra of the first generation dendrimer was performed by the method of DFT. This molecule has flat, repeating units and a plane of symmetry passing through the core. The calculation of the distribution of potential energy made it possible to classify the bands in the experimental spectra of dendrimers. Amine groups are manifested in the form of a band of NH stretching vibrations at 3389 cm−1 in the IR spectrum of G1. NH+ stretching bands located at 2646 and 2540 cm−1 in the IR spectrum of G2. The stretching vibrations of NH+ groups are noticeably shifted to low frequencies due to the formation of a hydrogen bond with the chlorine atom. The line at 1575 cm−1 in the Raman spectrum of G1 is characteristic for repeating units.
Published: 2018
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16. Three-Dimensional Directionality Is a Pivotal Structural Feature for the Bioactivity of Azabisphosphonate-Capped Poly(PhosphorHydrazone) Nanodrug Dendrimers

Author: Jean-Luc Davignon, Giovanni M. Pavan, Davide Bochicchio, Varravaddheay Ong-Meang, Matteo Garzoni, François Couderc, Myriam Hayder, Rémy Poupot, Cédric-Olivier Turrin, Anne-Marie Caminade, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Department of Innovative Technologies, University of Applied Sciences and Arts of Southern Switzerland, Scuola universitaria professionale della Svizzera italiana [Manno] (SUPSI), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Scuola universitaria professionale della Svizzera italiana = University of Applied Sciences and Arts of Southern Switzerland [Manno] (SUPSI), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), BIBAC - Chimie analytique et interactions biomolécules - matière molle biomimétique (BIBAC), and Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT)
Subjects: Male, Dendrimers, genetic structures, Polymers and Plastics, Hyperbranched polymers, Bioengineering, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Biomaterials, Mice, Molecular dynamics, Dendrimer, Materials Chemistry, Animals, Directionality, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Inbred BALB C, Inflammation, Mice, Inbred BALB C, Diphosphonates, Molecular Structure, Animal, Chemistry, Hydrazones, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Disease Models, Animal, Disease Models, Biophysics, 0210 nano-technology
Abstract: International audience; Dendrimers are nanosized, nonlinear, hyperbranched polymers whose overall 3D shape is key for their biological activity. Poly(PhosphorHydrazone) (PPH) dendrimers capped with aza-bisphosphonate (ABP) end groups are known to have anti-inflammatory properties enabling the control of inflammatory diseases in different mouse models. Here we screen the anti-inflammatory activity of a series of PPH dendrimers bearing between 2 and 16 ABP end groups in a mouse model of arthritis and confront the biological results with atomistic simulations of the dendrimers. We show that only the PPH dendrimers capped with 10 and 12 ABP end groups can control the flare of the inflammatory disease. All-atom accelerated molecular dynamics simulations show that dendrimers with a low number of ABP end groups are directional but highly flexible/dynamic and have thereby limited efficiency in establishing multivalent interactions. The largest dendrimer appears as nondirectional, having 16 ABP end groups forming patches all over the dendrimer surface. Conversely, intermediate dendrimers having 10 or 12 ABP end groups reach the best compromise between the number of surface groups and their stable directional gathering, a real maximization of multivalency.
Published: 2018
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17. Dendrimers in combination with natural products and analogues as anti-cancer agents

Author: João Rodrigues, Xiangyang Shi, Jean-Pierre Majoral, Serge Mignani, Maria Zablocka, Helena Tomás, Anne-Marie Caminade, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Centro de Química da Madeira, Universidade da Madeira (UMA), State Key Laboratory for Fiber & Material Modification of Donghua University, Donghua University [Shanghai], Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, Biocompatibility, Nanotechnology, 02 engineering and technology, Conjugated system, 010402 general chemistry, Endocytosis, 01 natural sciences, Faculdade de Ciências Exatas e da Engenharia, Drug Delivery Systems, Neoplasms, Dendrimer, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Cell Proliferation, Natural products, Biological Products, Drug Carriers, Chemistry, Drug carriers, General Chemistry, 021001 nanoscience & nanotechnology, Antineoplastic Agents, Phytogenic, Drug delivery systems, 0104 chemical sciences, 3. Good health, Nanomedicine, Drug delivery, Nanocarriers, 0210 nano-technology, Drug carrier
Abstract: International audience; For the first time, an overview of dendrimers in combination with natural products and analogues as anti-cancer agents is presented. This reflects the development of drug delivery systems, such as dendrimers, to tackle cancers. The most significant advantages of using dendrimers in nanomedicine are their high biocompatibility, good water solubility, and their entry - with or without encapsulated, complexed or conjugated drugs - through an endocytosis process. This strategy has accelerated over the years in order to develop nanosystems as nanocarriers, to decrease the intrinsic toxicity of anti-cancer agents, to decrease the drug side effects, to increase the efficacy of the treatment, and consequently to improve patient compliance.
Published: 2018
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18. Original Multivalent Gold(III) and Dual Gold(III)–Copper(II) Conjugated Phosphorus Dendrimers as Potent Antitumoral and Antimicrobial Agents

Author: Jean-Pierre Majoral, Régis Laurent, Sonia Ladeira, Mosto Bousmina, Eligia M. Szewczyk, Maria Bryszewska, Elzbieta Pedziwiatr-Werbicka, Anne-Marie Caminade, Serge Mignani, Thierry Cresteil, Nabil El Brahmi, Saïd El Kazzouli, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Euromed Research Center, Engineering Division, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Department of General Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, University of Lódź, Medical University of Łódź (MUL), Faculté de Pharmacie, IPSIT, Université Paris Sud, Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)
Subjects: Dendrimers, Stereochemistry, Pharmaceutical Science, chemistry.chemical_element, HL-60 Cells, 02 engineering and technology, Conjugated system, 010402 general chemistry, 01 natural sciences, Gold iii, Anti-Infective Agents, Cell Line, Tumor, Dendrimer, Drug Discovery, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Molecular Structure, Chemistry, Phosphorus, Low activity, 021001 nanoscience & nanotechnology, Antimicrobial, Combinatorial chemistry, Copper, 0104 chemical sciences, Molecular Medicine, Gold, 0210 nano-technology
Abstract: International audience; Original metallophosphorus dendrimers (generation 3, 48 terminal groups) have been prepared via the complexation of phosphorus dendrimers bearing imino-pyridino end groups with Au(III) or with both Au(III) and Cu(II). The complexation of the dendrimer with Au(III), leading to 1G3-[Au48][AuCl4]48, strongly increased the antiproliferative activities against both KB and HL-60 tumoral cell lines, showing IC50s in the low nanomolar range. It can be noticed also that this gold conjugated phosphorus dendrimer displayed low activity on the quiescent cell line EPC versus its potent antiproliferative activity against actively dividing cells. In order to evaluate the potential synergistic effect between Au(III) and Cu(II) and the influence of the number of Au(III) moieties on the surface of dendrimer against the proliferative activities, nine other original dendrimers with several surface modifications have been prepared. Whatever the number of Au(III) moieties introduced on the surface of dendrimers, all the dendrimers prepared displayed similar potency (nanomolar range) to 1G3-[Au48][AuCl4]48 against KB and HL60. In marked contrast synergistic effects on the antimicrobial activity of some of these phosphorus dendrimers are observed when both Au(III) and Cu(II) are present on the dendritic structure.
Published: 2017
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19. DFT study of IR and Raman spectra of phosphotrihydrazone dendrimer with terminal phenolic groups

Author: V.L. Furer, Anne-Marie Caminade, A.E. Vandyukov, Jean-Pierre Majoral, Valeri I. Kovalenko, Kazan State Architect and Civil Engineering University, University of Kazan, A.E. Arbuzov Institute of Organic and Physical Chemistry (IOPC), Kazan Scientific Centre of the Russian Academy of Sciences, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 010405 organic chemistry, Chemistry, Hydrogen bond, Organic Chemistry, Intermolecular force, Infrared spectroscopy, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, Inorganic Chemistry, symbols.namesake, Crystallography, Computational chemistry, Dendrimer, symbols, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Reactivity (chemistry), Density functional theory, Raman spectroscopy, Spectroscopy
Abstract: International audience; FT Raman and infrared spectra of phosphotrihydrazone (S)P[N(CH3)N=CH_C6H4_OH]3-(G0) were recorded. This compound is a zero generation phosphorus dendrimer with terminal phenolic groups. Optimal geometry and vibrational frequencies were calculated for G0 using the density functional theory (DFT). The molecule studied has C3 symmetry. In the molecule G0, each_C6H4_CH=N_N(CH3)_P arm is flat. Optimized geometric parameters correspond to experimental data. The core of the dendrimer manifests itself as a band at 647 cm−1 in the Raman spectrum of G0 related to P=S stretching. Phenolic end functions exhibit a well-defined band at 3374 cm−1 in the experimental IR spectrum of G0. The observed frequency of the OH stretching vibrations of the phenolic groups is lower than the theoretical value due to the intermolecular O_H⋯O hydrogen bond. This hydrogen bond is also responsible for the higher intensity of this band in the experimental IR spectrum compared with the theoretical value. DFT calculations suggest full assignment of normal modes. Global and local descriptors characterize the reactivity of the core and end groups.
Published: 2017
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20. Versatile Reactivity of Cyclic 1,2-Dimethylhydrazinodiphosphines

Author: Anne-Marie Caminade, Jean-Pierre Majoral, Gennady V. Oshovsky, Carine Duhayon, and M. Zablocka
Subjects: chemistry.chemical_classification, Substitution reaction, 010405 organic chemistry, Stereochemistry, Crystal structure, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Heterocyclic compound, Diphosphane, Reactivity (chemistry), Staudinger reaction, Lone pair, Cis–trans isomerism
Abstract: A versatile reactivity from the cage compound P(NMeNMe)3P is presented. The Staudinger reaction with Me3SiN3 is carried out. The crystal structure of the compound issued from the reaction on both sides (Me3SiN=P(NMeNMe)3P=NSiMe3) is reported. When the reaction occurs on only one side, the remaining free phosphorus atom is complexed with RuCl2(p-cymene). P(NMeNMe)3P reacts with PCl3, leading to the heterocyclic compound ClP(NMeNMe)2PCl. This heterocycle also displays a versatile reactivity. Substitution reaction with HNiPr2 leads to iPr2NP(NMeNMe)2PNiPr2. Very complex 1H and 13C NMR spectra suggest that the cis isomer is the largely major isomer of this compound. The cis structure is confirmed by X-ray diffraction. Besides the reaction on the P–Cl functions, the reaction on the lone pair of ClP(NMeNMe)2PCl is carried out, leading to the complex (p-cymene)Cl2RuPCl(NMeNMe)2ClPRuCl2(p-cymene). Characterization of this compound by X-ray diffraction displays a cis isomer for this compound also.
Published: 2017
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21. Dendrimers-containing organoclays: Characterisation and interaction with methylene blue

Author: M. Hajjaji, Abdellah Beraa, Régis Laurent, Anne-Marie Caminade, Laboratoire de physico chimie des matériaux et environnement-FSS de Marrakech (LPCME), Faculté des Sciences Semlalia, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées
Subjects: Nanocomposite, Inorganic chemistry, Substituent, Geology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Montmorillonite, Adsorption, chemistry, Geochemistry and Petrology, Dendrimer, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Clay minerals, High-resolution transmission electron microscopy, Methylene blue
Abstract: International audience; The structure of organoclays composed of synthesized phosphorus-based dendrimers, which was endowed with peripheral ammonium groups, and stevensite- or montmorillonite-rich clays was examined using X-ray diffraction, high resolution transmission electron microscopy, thermal analysis and solid-state nuclear magnetic resonance. The interactions between methylene blue (MB) and the organoclays or Na+-saturated clay minerals were investigated. The results showed that both dendrimers adsorbed on Na+-saturated clay minerals by cation exchange, and that the organoclays, particularly those of the first generation dendrimers, were mainly composed of intercalated nanocomposites. As a result of the adsorption of the dendrimers, the clay hydrophilicity reduced and the dehydroxylation temperature of the clay minerals increased. Regarding the adsorption of MB on the organoclays, the results pointed out that MB mainly adsorbed as MB+ and MBH2 +, and the electronic environments of AlIV of montmorillonite and that of AlVI of stevensite were disturbed. For some organoclays, ordered structures were formed, and the Si4 + substituent (Al3 +) left the tetrahedral sheet. The thermodynamic data indicated that MB adsorbed spontaneously (− 11.3 < ∆ G° < − 0.9 kJ/mol) and the uptake of MB by montmorillonite-based organoclays was believed to occur by chemisorption. In contrast, for stevensite-based organoclays MB adsorption seemed to be accomplished by physisorption.
Published: 2017
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22. Physico-chemical properties of β-diketone phosphorus-containing dendrimers

Author: Mykhailo Ianchuk, Anne-Marie Caminade, Viktoriia S. Starova, and Olga A. Zaporozhets
Subjects: 010405 organic chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Fluorescence, 0104 chemical sciences, Surface tension, Absorbance, chemistry.chemical_compound, Monomer, chemistry, Dendrimer, Acridine, Acetone, Emission spectrum
Abstract: Protolytic, absorbance and fluorescence properties of β-diketone phosphorus-containing dendrimers based on cyclotriphosphazene core were studied. Dendrimer solutions in acetone are characterized by intense absorbance band at ≈ 340 nm (ε340≈ 8.5·104L/mol·сm) and fluorescence band with maximum at 440 nm. Position of these maxima does not change in various solvents, unlike the bands of monomer β-diketone. It was found that dendrimer aggregation is accompanied by appearance of a second absorbance band ε400≈ 4.5·103L/mol·сm, by red shift of emission spectra ∆λ ≈ 10 nm and also by decrease in surface tension of acetone solution. Ability of dendrimer aggregates to solubilize organic substrates was observed with the fluorescent indicator acridine.
Published: 2017
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23. Biodistribution and Biosafety of a Poly(Phosphorhydrazone) Dendrimer, an Anti-Inflammatory Drug-Candidate

Author: Muriel Golzio, Elisabeth Bellard, Rémy Poupot, Abdelouahd Oukhrib, Séverine Fruchon, Cédric-Olivier Turrin, Nicolas Beton, Muriel Blanzat, Cécile Goursat, Anne-Marie Caminade, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Institut de pharmacologie et de biologie structurale (IPBS), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), SMODD - Systèmes Moléculaires Organisés et Développement Durable (SMODD), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT), CNRS, INSERM, University of Toulouse, Toulouse-Tech-Transfer (contract I-15-1424), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Laboratoire de Biochimie [Purpan], Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut Fédératif de Biologie (IFB) - Hôpital Purpan, Hôpital Purpan [Toulouse], CHU Toulouse [Toulouse]-CHU Toulouse [Toulouse]-Hôpital Purpan [Toulouse], CHU Toulouse [Toulouse], Laboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences, Semlalia, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Centre de Physiopathologie Toulouse Purpan (ex IFR 30 et IFR 150) (CPTP), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), and FRUCHON, Séverine
Subjects: MESH: Dendrimers / adverse effects, genetic structures, [SDV]Life Sciences [q-bio], lcsh:QR1-502, Anti-Inflammatory Agents, Mutagen, 02 engineering and technology, Rabbit, Pharmacology, medicine.disease_cause, 01 natural sciences, Biochemistry, lcsh:Microbiology, MESH: Anti-Inflammatory Agents / chemistry, Mice, Biodistribution, Tissue Distribution, MESH: Animals, ComputingMilieux_MISCELLANEOUS, Chemistry, Drug candidate, Preclinical development, 021001 nanoscience & nanotechnology, MESH: Dendrimers / pharmacokinetics, 3. Good health, [SDV] Life Sciences [q-bio], MESH: Hydrazones / chemistry, Female, Safety, 0210 nano-technology, Dendrimers, MESH: Rats, medicine.drug_class, MESH: Anti-Inflammatory Agents / adverse effects, 010402 general chemistry, Rodents, Article, Anti-inflammatory, Azabisphosphonate, Immune system, MESH: Anti-Inflammatory Agents / pharmacokinetics, Dendrimer, medicine, Animals, [CHIM]Chemical Sciences, MESH: Tissue Distribution, MESH: Dendrimers / chemistry, Molecular Biology, MESH: Mice, MESH: Safety, Hydrazones, In vitro, Rats, 0104 chemical sciences, MESH: Female, Genotoxicity
Abstract: Dendrimers are nanosized, arborescent polymers of which size and structure are perfectly controlled. This is one reason why they are widely used for biomedical purposes. Previously, we showed that a phosphorus-based dendrimer capped with anionic azabisphosphonate groups (so-called ABP dendrimer) has immuno-modulatory and anti-inflammatory properties towards human immune cells in vitro. Thereafter, we have shown that the ABP dendrimer has a promising therapeutic efficacy to treat models of chronic inflammatory disorders. On the way to clinical translation, the biodistribution and the safety of this drug-candidate has to be thoroughly assessed. In this article, we present preliminary non-clinical data regarding biodistribution, hematological safety, genotoxicity, maximal tolerated doses, and early cardiac safety of the ABP dendrimer. One of the genotoxicity assays reveals a potential mutagen effect of the item at a concentration above 200 &micro, M, i.e., up to 100 times the active dose in vitro on human immune cells. However, as the results obtained for all the other assays show that the ABP dendrimer has promising biodistribution and safety profiles, there is no red flag raised to hamper the regulatory pre-clinical development of the ABP dendrimer.
Published: 2019
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24. Fluorescent Phosphorus Dendrimers: Towards Material and Biological Applications

Author: Anne-Marie Caminade, Jieru Qiu, Aurélien Hameau, Xiangyang Shi, Jean-Pierre Majoral, Serge Mignani, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centro de Química da Madeira, Universidade da Madeira (UMA), CRC (Chinese Research Council), PRC NSFC-CNRS 2019, ANR-17-CE09-0001,SLOW2,Ecriture en stéréo dans l'eau par un laser(2017), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, Anti-Inflammatory Agents, Biocompatible Materials, Fluorene, 010402 general chemistry, 01 natural sciences, Fluorescence, Rhodamine, chemistry.chemical_compound, Dendrimer, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Julolidine, Maleimide, Biology, Fluorescent Dyes, Diketone, Drug Carriers, 010405 organic chemistry, Phosphorus, General Chemistry, Combinatorial chemistry, 0104 chemical sciences, Nanostructures, chemistry, Nanomedicine, Synthesis design
Abstract: International audience; Fluorescent derivatives of phosphorhydrazone dendrimers are reviewed. Diverse types of fluorophores have been used, such as pyrene, naphthol, anthracene, dansyl, diketone, phthalocyanine, maleimide, julolidine, rhodamine, fluorescein, or fluorene derivatives. The fluorescent groups can be located either as terminal groups on the surface, at the core, linked to the core (off-center), or to the branches of the dendritic structure. After fundamental research on their synthesis, these compounds have been used in the fields of catalysis, nanomaterials, OLEDs, sensors and biology/nanomedicine, in particular for monitoring transfection, or for their anti-inflammatory or anti-cancer properties.
Published: 2019
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25. Metal‐based phosphorus dendrimers as novel nanotherapeutic strategies to tackle cancers: A concise overview

Author: Anne-Marie Caminade, Liang Chen, Jean-Pierre Majoral, Serge Mignani, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Zhengzhou University, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centro de Química da Madeira, Universidade da Madeira (UMA), Glycovax Pharma, FCT (Fundacão para a Ciência e a Tecnologia) - Project PEst-OE/QUI/UI0674/2013, ARDITI (Agência Regional para o Desenvolvimento da Investigação Tecnologia) - project M1420-01-0145-FEDER-000005 - Centro de Química da Madeira - CQM+ (Madeira 14-20 Program), CNRS, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, Nanomedicine for oncologic disease, Biomedical Engineering, Medicine (miscellaneous), Nanoparticle, chemistry.chemical_element, Biocompatible Materials, Bioengineering, 02 engineering and technology, Nanotechnology approaches to biology, 010402 general chemistry, 01 natural sciences, Nanoscale systems in biology, Neoplasms, Dendrimer, medicine, Animals, Humans, Moiety, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Doxorubicin, Therapeutic approaches and drug discovery, Drug discovery, Phosphorus, 021001 nanoscience & nanotechnology, Combinatorial chemistry, 0104 chemical sciences, 3. Good health, Nanomedicine, Mechanism of action, chemistry, Metals, medicine.symptom, 0210 nano-technology, medicine.drug
Abstract: International audience; Several metal-based phosphorus dendrimers were prepared. The first series developed by us was the Cu(II) series. In this series, the most potent is the third generation-Cu(II) showing original mechanism of action with activation of the pro-apoptotic Bax protein. To our knowledge, it is the first example of nanoparticles displaying Bax protein activation and then cell death through apoptosis process. Interestingly, this dendritic-Cu(II) complex showed synergistic effect with doxorubicin. Based on these interesting anti-proliferative activities, we developed Au(III)-conjugated phosphorus dendrimers. The most potent is the third generation-Au(III) dendrimer which represents also a new and promising first-in-class anti-proliferative agent against both solid and liquid tumor cell lines. Then, in order to analyze the influence of the metal moiety distribution of Cu(II) and Au(III) on the surface of dendrimers, mix Cu(II)–Au(III)-conjugated phosphorus dendrimers were also prepared and tested as anti-proliferative agents. This article is categorized under: Therapeutic Approaches and Drug Discovery > Nanomedicine for Oncologic Disease Nanotechnology Approaches to Biology > Nanoscale Systems in Biology
Published: 2019
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26. Phosphorus dendrimers functionalised with nitrogen ligands, for catalysis and biology

Author: Anne-Marie Caminade, Jean-Pierre Majoral, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and CNRS
Subjects: Dendrimers, 010405 organic chemistry, Nitrogen, Phosphorus, chemistry.chemical_element, Branching points, 010402 general chemistry, Ligands, 01 natural sciences, Combinatorial chemistry, Copper, Catalysis, 0104 chemical sciences, Inorganic Chemistry, chemistry, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Scandium, Palladium
Abstract: International audience; Phosphorus dendrimers (dendrimers having one phosphorus atom at each branching point) possess versatile properties, depending on the type of their terminal functions. This perspective article focusses on the synthesis and study of properties of phosphorus dendrimers functionalised on their surface by nitrogen ligands and their complexes. It is organized depending on the type of N-ligands (P,N ligands, N,N ligands, and N,N,N-ligands). Most properties concern catalysis, with palladium, copper, and scandium complexes. Recent advances concern anti-cancer properties, with dendrimers functionalised by copper and gold complexes of N,N-ligands.
Published: 2019
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27. Phosphorhydrazones as Useful Building Blocks for Special Architectures: Macrocycles and Dendrimers

Author: Jean-Pierre Majoral, Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), CNRS, GDR Phosphore, and ANR-17-CE09-0001,SLOW2,Ecriture en stéréo dans l'eau par un laser(2017)
Subjects: Dendrimers, Cryptands, Phosphorhydrazone, 010405 organic chemistry, Chemistry, Phosphorus, Cryptand, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 3. Good health, 0104 chemical sciences, Inorganic Chemistry, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Macrocycles
Abstract: International audience; The role of phosphorhydrazide derivatives, in particular of type RP(X)(NMeNH2)2 for the synthesis of macrocycles and of type Cl2P(X)NMeNH2 (X = O, S in both cases) for the synthesis of dendrimers, will be shown in this review. In both cases, condensation reactions with different types of aldehydes (often aromatic) afford phosphorhydrazone derivatives, which are the building blocks for these special architectures. After the synthetic aspects, selected properties related to catalysis, nanomaterials, and biology/nanomedicine will be displayed.
Published: 2019
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28. The Role of Noncovalent Interactions in the Efficiency of Dendrimers in Catalysis

Author: Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Mahmudov, K. T., Kopylovich, M. N., Guedes da Silva, M. F. C., Pombeiro, A. J. L., Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Nanoparticle, Nanotechnology, 01 natural sciences, 0104 chemical sciences, Catalysis, 010404 medicinal & biomolecular chemistry, Dendrimer, Non-covalent interactions, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Catalytic efficiency, Macromolecule
Abstract: International audience; Dendrimers are nanometric macromolecules constituted of repetitive branched units, arranged radially around a central core. They are synthesized step-by-step, generally using a divergent process from this core. Dendrimers have many properties and, among them, catalysis is a major field. Two main area are studied, on the one hand the search for a positive “dendrimer effect,” i.e. an increase in catalytic efficiency when the size of the dendrimer increases, and on the other the encapsulation of catalytically active nanoparticles inside dendrimers. In both cases, noncovalent interactions are involved. This chapter discusses the important role played by noncovalent interactions in the properties of dendrimers in catalysis. The first part concerns the dendrimer effect, then a short section considers noncovalently formed catalytic dendrimers and the final part concerns dendrimers encapsulating catalytic nanoparticles.
Published: 2019
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29. Dendrimeric Nanoparticles for Two-Photon Photodynamic Therapy and Imaging Synthesis, Photophysical Properties, Innocuousness in Daylight and Cytotoxicity under Two-Photon Irradiation in the NIR

Author: Magali Gary-Bobo, Marie Maynadier, Olivier Mongin, Mireille Blanchard-Desce, Jean-Pierre Majoral, Marcel Garcia, Anne-Marie Caminade, Aude Sourdon, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), ARED Biphobio, Région Bretagne, Centre National de la Recherche Scientifique, Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Cell Survival, medicine.medical_treatment, Nanoparticle, Breast Neoplasms, Photodynamic therapy, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Theranostic Nanomedicine, Catalysis, dendrimers, chemistry.chemical_compound, Two-photon excitation microscopy, Dendrimer, medicine, [CHIM]Chemical Sciences, Humans, Bifunctional, ComputingMilieux_MISCELLANEOUS, Fluorescent Dyes, photophysics, Photons, Photosensitizing Agents, 010405 organic chemistry, Singlet oxygen, Optical Imaging, Organic Chemistry, imaging, General Chemistry, Fluorescence, 0104 chemical sciences, Photochemotherapy, chemistry, photodynamic therapy, Covalent bond, MCF-7 Cells, Nanoparticles, Female, fluorescence, Hydrophobic and Hydrophilic Interactions
Abstract: International audience; The synthesis and the photophysical properties of a new class of fully organic monodisperse nanoparticles for combined two-photon imaging and photodynamic therapy are described. The design of such nanoparticles is based on the covalent immobilization of a dedicated quadrupolar dye that combines excellent two-photon absorbing (2PA) properties, fluorescence and singlet oxygen generation ability, in a phosphorous-based dendrimeric architecture. First, a bifunctional quadrupolar dye bearing two different grafting moieties, a phenol function and an aldehyde function, was synthesized. It was then covalently grafted through its phenol function to a phosphorus-based dendrimer scaffold of generation 1. The remaining aldehyde functions were then used to continue the dendrimer synthesis up to generation 2, introducing finally 24 water-solubilizing triethyleneglycol chains at its periphery. A dendrimer confining 12 photoactive quadrupolar units in its inner scaffold and showing water solubility was thus obtained. Interestingly, the G1 and G2 dendrimers retain some fluorescence as well as significant singlet oxygen production efficiencies while they were found to show very high 2PA cross-sections in a broad range of the NIR biological spectral window. Hydrophilic dendrimer G2 was tested in vitro on breast cancer cells, first in one- and two-photon microscopy, which allowed for visualization of their cell internalization, then in two-photon photodynamic therapy. While being nontoxic in the dark and, more importantly, under exposure to daylight, dendrimer G2 proved to be a very efficient cell-death inducer only under two-photon irradiation in the NIR.
Published: 2019
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30. Synthesis of Inorganic Dendrimers

Author: Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Hey‐Hawkins, E., and Hissler, M.
Subjects: chemistry.chemical_classification, Polymer science, 010405 organic chemistry, Chemistry, Hyperbranched polymers, Polymer, Branching points, 010402 general chemistry, Special class, 01 natural sciences, 0104 chemical sciences, Polymerization, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Quaternary carbon
Abstract: International audience; Summary Dendrimers are a special class of hyperbranched polymers, constituted of branched constitutional repeating units. Contrary to common polymers, dendrimers are not synthesized by polymerization reactions, but by the step-by-step approach around a central core unit. Most dendrimers are organic compounds with nitrogen or quaternary carbon or benzene ring as branching points, but several families of “inorganic” dendrimers have emerged, essentially based on either silicon or phosphorus as branching points. Despite the architectural similarity, organic and inorganic dendrimers differ in terms of methods of synthesis and characterization, and also by types of utilization. Inorganic dendrimers can offer completely new properties, as will be emphasized later in Chapter 10. The present chapter describes the synthesis of dendrimers comprising either silicon or phosphorus branching points with the emphasis on carbosilane and phosphorhydrazone dendrimers, both of which have obtained the largest attention of all inorganic dendrimers to date. Many other types of small dendrimers have been described in literature, but they will not be reported in this chapter, which focuses both on the above most widely used and also on the most original types of inorganic dendrimers. A few miscellaneous examples of dendrimers based on germanium, tin, or bismuth branching points will be given as well, although they are still rare among dendrimers.
Published: 2019
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31. Inorganic Dendrimers and Their Applications

Author: Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Hey‐Hawkins, E., and Hissler, M.
Subjects: chemistry.chemical_classification, Polymer science, Chemistry, Hyperbranched polymers, 02 engineering and technology, Polymer, Branching points, 010402 general chemistry, 021001 nanoscience & nanotechnology, Special class, 01 natural sciences, 0104 chemical sciences, Polymerization, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Quaternary carbon
Abstract: International audience; Summary Dendrimers are a special class of hyperbranched polymers, constituted of branched constitutional repeating units. Contrary to common polymers, dendrimers are not synthesized by polymerization reactions, but by the step-by-step approach around a central core unit. Most dendrimers are organic compounds with nitrogen or quaternary carbon or benzene ring as branching points, but several families of “inorganic” dendrimers have emerged, essentially based on either silicon or phosphorus as branching points. Despite the architectural similarity, organic and inorganic dendrimers differ in terms of methods of synthesis and characterization, and also by types of utilization. Inorganic dendrimers can offer completely new properties, as will be emphasized later in Chapter 10. The present chapter describes the synthesis of dendrimers comprising either silicon or phosphorus branching points with the emphasis on carbosilane and phosphorhydrazone dendrimers, both of which have obtained the largest attention of all inorganic dendrimers to date. Many other types of small dendrimers have been described in literature, but they will not be reported in this chapter, which focuses both on the above most widely used and also on the most original types of inorganic dendrimers. A few miscellaneous examples of dendrimers based on germanium, tin, or bismuth branching points will be given as well, although they are still rare among dendrimers.
Published: 2019
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32. Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

Author: Aurélien Hameau, Eduardo Cueto Diaz, Mireille Blanchard-Desce, Maxime Klausen, Olivier Mongin, Kathleen I. Moineau-Chane Ching, Jean-Baptiste Verlhac, Jean-Pierre Majoral, Anne-Marie Caminade, Artem Zibarov, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS, ANR-17-CE09-0001,SLOW2,Ecriture en stéréo dans l'eau par un laser(2017), European Project: 264362,EC:FP7:PEOPLE,FP7-PEOPLE-2010-ITN,TOPBIO(2010), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Centre National de la Recherche Scientifique (CNRS), Synthèse et électrosynthèse organiques (SESO), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Photon, medicine.medical_treatment, Photodynamic therapy, Review, 010402 general chemistry, 01 natural sciences, Two-photon absorption, Fluorescence, lcsh:QD241-441, lcsh:Organic chemistry, Dendrimer, medicine, lcsh:Science, ComputingMilieux_MISCELLANEOUS, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Phosphorus, Bioimaging, 0104 chemical sciences, Excited state, Biophysics, Surface modification, lcsh:Q, Macromolecule
Abstract: International audience; Different types of two-photon absorbing (TPA) fluorophores have been synthesized and specifically functionalized to be incorporated in the structure of phosphorus dendrimers (highly branched macromolecules). The TPA fluorophores were included in the periphery as terminal functions, in the core, or in the branches of the dendrimer structures, respectively. Also the functionalization in two compartments (core and surface, or branches and surface) was achieved. The consequences of the location of the fluorophores on the fluorescence and TPA properties have been studied. Several of these TPA fluorescent dendrimers have water-solubilizing functions as terminal groups, and fluorophores at the core or in the branches. They have been used as fluorescent tools in biology for different purposes, such as tracers for imaging blood vessels of living animals, for determining the phenotype of cells, for deciphering the mechanism of action of anticancer compounds, and for safer photodynamic therapy.
Published: 2019
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33. AB5 Derivatives of Cyclotriphosphazene for the Synthesis of Dendrons and Their Applications

Author: Anne-Marie Caminade, Abdelouahd Oukhrib, Artem Zibarov, Julien Aujard Catot, Cédric-Olivier Turrin, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS, Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Fluorophore, dendron, Pharmaceutical Science, dendrimer, 010402 general chemistry, 01 natural sciences, Micelle, Catalysis, Analytical Chemistry, chemistry.chemical_compound, QD241-441, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Reactivity (chemistry), phosphorus, Physical and Theoretical Chemistry, nanomaterials, DendronFluorescence, Sensors, 010405 organic chemistry, Chemistry, Organic Chemistry, cyclotriphosphazene, Grafting, Combinatorial chemistry, 0104 chemical sciences, Nanomedicine, [CHIM.POLY]Chemical Sciences/Polymers, Chemistry (miscellaneous), Covalent bond, Reagent, Molecular Medicine, fluorescence
Abstract: International audience; AB5 compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction of five chlorides with one reagent, followed by the reaction of the single remaining Cl with another reagent. This particular property led to the use of such compounds as core for the synthesis of dendrons (dendritic wedges), using the five functions for growing the dendritic branches. The single function can be used for the synthesis of diverse types of dendrimers (onion peel, dumbbell-shape, Janus), for covalent or non-covalent grafting to solid surfaces, providing nanomaterials, for grafting a fluorophore, especially for studying biological mechanisms, or for self-associations to get micelles. All these properties are reviewed in this paper.
Published: 2021
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34. Dendrimers Functionalized with Palladium Complexes of N-, N,N-, and N,N,N-Ligands

Author: Régis Laurent, Quentin Vanbellingen, Anaïs Coinaud, Paul Servin, Anne-Marie Caminade, Sonia Mallet-Ladeira, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Technologie Servier, CNRS (Centre National de la Recherche Scientifique), GRD Phosphore, Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Imine, Pharmaceutical Science, Sonogashira coupling, chemistry.chemical_element, Ligands, 010402 general chemistry, 01 natural sciences, Article, Catalysis, Analytical Chemistry, chemistry.chemical_compound, Bipyridine, QD241-441, Complexes, Dendrimer, Drug Discovery, Pyridine, Polymer chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Phenol, 010405 organic chemistry, Chemistry, Organic Chemistry, X-ray diffraction, 0104 chemical sciences, Monomer, Chemistry (miscellaneous), Molecular Medicine, Palladium
Abstract: International audience; Pyridine, pyridine imine, and bipyridine imine ligands functionalized by a phenol have been synthesized and characterized, in many cases by X-ray diffraction. Several of these N-, N,N-, and N,N,N,-ligands have been grafted onto the surface of phosphorhydrazone dendrimers, from generation 1 to generation 3. The complexation ability of these monomers and dendrimers towards palladium(II) has been assayed. The corresponding complexes have been either isolated or prepared in situ. In both cases, the monomeric and dendritic complexes have been tested as catalysts in Heck couplings and in Sonogashira couplings. In some cases, a positive dendritic effect has been observed, that is, an increase of the catalytic efficiency proportional to the dendrimer generation.
Published: 2021
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35. Copper complexes of phosphorus dendrimers and their properties

Author: Omar Alami, Saïd El Kazzouli, Anne-Marie Caminade, Régis Laurent, Nabil El Brahmi, Jean-Pierre Majoral, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université Euro Méditerranéenne de Fès (UEMF), TOUBKAL/19/88: 41405WE, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Catalysis, Inorganic Chemistry, Dendrimer, Materials Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Diketone, 010405 organic chemistry, Chemistry, organic chemicals, Phosphorus, Pyridine imine, Branching points, Grafting, Combinatorial chemistry, Copper, 0104 chemical sciences, Copper complexes, Macromolecule
Abstract: International audience; Phosphorus dendrimers are highly branched macromolecules, built with one phosphorus atom at each branching point. These dendrimers can be functionalized at will on the terminal functions. Grafting as terminal functions ligands suitable for the complexation of copper has been carried out several times, in particular with the aim of using the corresponding complexes as catalysts in a range of reactions, from O-and N-arylations and-vinylations, to the asymmetric benzoylation of linear or cyclic diols. A sequel of this work concerns the study of anticancer activity of analogous dendritic copper complexes.
Published: 2021
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36. Dendritic metal complexes for bioimaging. Recent advances

Author: Régis Laurent, Jean-Pierre Majoral, Aurélien Hameau, Cédric-Olivier Turrin, and Anne-Marie Caminade
Subjects: medicine.diagnostic_test, 010405 organic chemistry, Gadolinium, chemistry.chemical_element, Context (language use), 010402 general chemistry, Technetium, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Positron emission tomography, Dendrimer, Materials Chemistry, medicine, DOTA, Physical and Theoretical Chemistry, Preclinical imaging, Macromolecule
Abstract: Dendrimers are hyperbranched macromolecules, having a large number of terminal functions, easily accessible and modifiable to afford the desired properties. Metal complexes of dendrimers are frequently used as catalysts in diverse reactions, but they can be used also as innovative biological tools. This review focusses on the recent advances (last 10 years) of dendritic metal complexes used for bioimaging, essentially in vivo. Three main domains will be covered. The first one concerns luminescent complexes for optical imaging (OI). The second one is the largest one; it concerns magnetic resonance imaging (MRI) contrast agents, mostly based on gadolinium complexes. The third and last domain concerns radioactive dendrimer complexes for single photon emission computed tomography (SPECT), and also for positron emission tomography (PET). Two main radionuclides are used in this context, technetium (99mTc) and indium (111In). Two types of ligands are generally used for all these complexes in the two last domains, diethylenetriaminepentaacetic acid (DTPA), and a cyclic analogue, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), and some of their derivatives. These complexes have been used in many cases for in vivo imaging of cancerous tumors in mice or rats.
Published: 2021
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37. The Usefulness of Trivalent Phosphorus for the Synthesis of Dendrimers

Author: Kathleen I. Moineau-Chane Ching, Béatrice Delavaux-Nicot, Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and CNRS
Subjects: Phosphoramidites, Dendrimers, Alkylation, Phosphines, Pharmaceutical Science, Chemistry Techniques, Synthetic, Review, 010402 general chemistry, 01 natural sciences, Analytical Chemistry, lcsh:QD241-441, Organophosphorus Compounds, Solid-phase synthesis, lcsh:Organic chemistry, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Reactivity (chemistry), Staudinger reaction, Physical and Theoretical Chemistry, Molecular Structure, 010405 organic chemistry, Oligonucleotide, Chemistry, Organic Chemistry, Phosphorus, Branching points, Combinatorial chemistry, 0104 chemical sciences, Chemistry (miscellaneous), Molecular Medicine, Macromolecule
Abstract: International audience; Dendrimers are hyperbranched macromolecules, which are synthesized step-by-step by the repetition of a series of reactions. While many different types of dendrimers are known, this review focusses on the use of trivalent phosphorus derivatives (essentially phosphines and phosphoramidites) for the synthesis of dendrimers. The first part presents dendrimers constituted of phosphines at each branching point. The other parts display the use of trivalent phosphorus derivatives during the synthesis of dendrimers. Different types of reactions have been applied to phosphines. The very first examples of phosphorus-containing dendrimers were obtained by the alkylation of phosphines. Then, several families of dendrimers were elaborated by reaction of phosphoramidites. Such a type of reaction is the base of the solid phase synthesis of oligonucleotides; it has been applied in particular for the synthesis of dendrimers constituted of oligonucleotides. Finally, the Staudinger reaction between phosphines and azides afforded different families of dendrimers, and was at the origin of accelerated methods of synthesis of dendrimers. Besides, the reactivity of the P=N-P=S linkages created by this reaction led to very original dendritic structures.
Published: 2021
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38. Cyclotriphosphazene, an old compound applied to the synthesis of smart dendrimers with tailored properties

Author: Armelle Ouali, Kathleen Moineau Chane-Ching, Cyrille Rebout, Jean-Pierre Majoral, Aurélien Hameau, Anne-Marie Caminade, Cédric-Olivier Turrin, Béatrice Delavaux-Nicot, Régis Laurent, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées
Subjects: Dendrimers, ICPC-21, 010405 organic chemistry, Chemistry, General Chemical Engineering, Nanotechnology, General Chemistry, 010402 general chemistry, 01 natural sciences, Chemical synthesis, Phosphorus chemistry, 0104 chemical sciences, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract: The versatile reactivity of hexachlorocyclotriphosphazene (N3P3Cl6) has been developed for the synthesis of specifically engineered dendrimers. Dendrimers are hyperbranched macromolecules built by concentric layers constituted of associated monomeric units. Many of the properties of dendrimers depend on the type of their surface (terminal) functions, which are generally all identical. For some specific purposes, it is desirable to have one function that is different at the level of the core. Hexachlorocyclotriphosphazene offers the possibility to differentiate the reactivity of one (or more) Cl from the others, for producing specifically engineered dendritic tools. These specific reactions on N3P3Cl6 have produced highly dense dendrimers, Janus dendrimers (two faces), tools for functionalizing materials, with uses as catalysts, as chemical sensors, for trapping CO2, for the culture of cells, or for imaging biological events. These properties will be emphasized in this review.
Published: 2016
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39. Inorganic dendrimers: recent advances for catalysis, nanomaterials, and nanomedicine

Author: Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Dendrimers, Materials science, Polymers, Hyperbranched polymers, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Catalysis, Nanomaterials, Dendrimer, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, chemistry.chemical_classification, Phosphorus, General Chemistry, Polymer, Branching points, Silanes, 021001 nanoscience & nanotechnology, Nanostructures, 0104 chemical sciences, Nanomedicine, chemistry, 0210 nano-technology
Abstract: International audience; Dendrimers are hyperbranched polymers having a perfectly defined structure because they are synthesized step-by-step in an iterative fashion, and not by polymerization reactions. Some dendrimers are considered as inorganic, as they possess inorganic atoms at each branching point. Among numerous examples, two families of inorganic dendrimers have emerged as particularly promising: silicon-containing dendrimers, particularly carbosilanes, and phosphorus-containing dendrimers, particularly phosphorhydrazones. This tutorial review will display the main properties of both families of dendrimers in the fields of catalysis, materials and biology/nanomedicine. Emphasis will be put on the most recent and promising examples.
Published: 2016
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40. Phosphorus Dendrimers as Nanotools against Cancers

Author: Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and CNRS
Subjects: Dendrimers, Phosphorhydrazone, medicine.medical_treatment, Oligonucleotides, Pharmaceutical Science, Antineoplastic Agents, Photodynamic therapy, Review, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Transfection, 010402 general chemistry, Anticancer drugs, 01 natural sciences, Analytical Chemistry, lcsh:QD241-441, lcsh:Organic chemistry, Coordination Complexes, Metal complexes, Neoplasms, Dendrimer, Drug Discovery, medicine, Animals, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, RNA, Small Interfering, Physical and Theoretical Chemistry, Photosensitizing Agents, 010405 organic chemistry, Chemistry, Organic Chemistry, Phosphorus, Genetic Therapy, Combined Modality Therapy, Small molecule, 3. Good health, 0104 chemical sciences, Nanomedicine, Photochemotherapy, Biochemistry, Chemistry (miscellaneous), Cancer cell, Molecular Medicine
Abstract: International audience; This review concerns the use of dendrimers, especially of phosphorhydrazone dendrimers, against cancers. After the introduction, the review is organized in three main topics, depending on the role played by the phosphorus dendrimers against cancers: (i) as drugs by themselves; (ii) as carriers of drugs; and (iii) as indirect inducer of cancerous cell death. In the first part, two main types of phosphorus dendrimers are considered: those functionalized on the surface by diverse organic derivatives, including known drugs, and those functionalized by diverse metal complexes. The second part will display the role of dendrimers as carriers of anticancer "drugs", which can be either small molecules or anticancer siRNAs, or the combination of both. In the third part are gathered a few examples of phosphorhydrazone dendrimers that are not cytotoxic by themselves, but which under certain circumstances induce a cytotoxic effect on cancerous cells. These examples include a positive influence on the human immune system and the combination of bioimaging with photodynamic therapy properties.
Published: 2020
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41. Novel Methinic Functionalized and Dendritic C-Scorpionates

Author: Paul Servin, Anne-Marie Caminade, Armando J. L. Pombeiro, Régis Laurent, Riccardo Wanke, Telma F. S. Silva, Luísa M. D. R. S. Martins, Centro de Química Estrutural, Faculdade de Ciências da Universidade de Lisboa, Faculdade de Ciencias da Universidade de Lisboa, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées
Subjects: Dendrimers, pyrazolyl, Pharmaceutical Science, Sonogashira coupling, Ligands, 010402 general chemistry, dendrimer, 01 natural sciences, Catalysis, Article, Analytical Chemistry, lcsh:QD241-441, C c coupling, lcsh:Organic chemistry, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Organic Chemicals, Physical and Theoretical Chemistry, Chelating ligands, Molecular Structure, 010405 organic chemistry, Chemistry, Organic Chemistry, Sonogashira, Combinatorial chemistry, tris(pyrazolyl)methane, 0104 chemical sciences, coordination flexibility, Chemistry (miscellaneous), Molecular Medicine, Surface modification, functionalization, C-scorpionate, Heck, C-C coupling, Methane, catalyst
Abstract: The study of chelating ligands is undoubtedly one of the most significant fields of research in chemistry. The present work is directed to the synthesis of new functionalized derivatives of tripodal C-scorpionate compounds. Tris-2,2,2-(1-pyrazolyl)ethanol, HOCH2C(pz)3 (1), one of the most important derivatives of hydrotris(pyrazolyl)methane, was used as a building block for the synthesis of new functionalized C-scorpionates, aiming to expand the scope of this unexplored class of compounds. The first dendritic C-scorpionate was successfully prepared and used in the important industrial catalytic reactions, Sonogashira and Heck C-C cross-couplings.
Published: 2018
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42. Doxorubicin-Conjugated PAMAM Dendrimers for pH-Responsive Drug Release and Folic Acid-Targeted Cancer Therapy

Author: Shige Wang, Xiangyang Shi, Anne-Marie Caminade, Jingyi Zhu, Yun Zheng, Jean-Pierre Majoral, Mengen Zhang, Rui Guo, Serge Mignani, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], College of Materials Science and Engineering, Donghua University, Centro de Química da Madeira, Universidade da Madeira (UMA), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Cell, Pharmaceutical Science, lcsh:RS1-441, 02 engineering and technology, Conjugated system, 010402 general chemistry, 01 natural sciences, doxorubicin, targeted cancer therapy, Article, lcsh:Pharmacy and materia medica, Dendrimer, medicine, polycyclic compounds, Doxorubicin, [CHIM.COOR]Chemical Sciences/Coordination chemistry, pH-responsive release, Tumor microenvironment, PAMAM dendrimer, Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, 3. Good health, medicine.anatomical_structure, Biochemistry, Acetylation, Cancer cell, cis-aconityl linkage, 0210 nano-technology, Conjugate, medicine.drug
Abstract: International audience; We present here the development of multifunctional doxorubicin (DOX)-conjugated poly(amidoamine) (PAMAM) dendrimers as a unique platform for pH-responsive drug release and targeted chemotherapy of cancer cells. In this work, we covalently conjugated DOX onto the periphery of partially acetylated and folic acid (FA)-modified generation 5 (G5) PAMAM dendrimers through a pH-sensitive cis-aconityl linkage to form the G5.NHAc-FA-DOX conjugates. The formed dendrimer conjugates were well characterized using different methods. We show that DOX release from the G5.NHAc-FA-DOX conjugates follows an acid-triggered manner with a higher release rate under an acidic pH condition (pH = 5 or 6, close to the acidic pH of tumor microenvironment) than under a physiological pH condition. Both in vitro cytotoxicity evaluation and cell morphological observation demonstrate that the therapeutic activity of dendrimer-DOX conjugates against cancer cells is absolutely related to the DOX drug released. More importantly, the FA conjugation onto the dendrimers allowed a specific targeting to cancer cells overexpressing FA receptors (FAR), and allowed targeted inhibition of cancer cells. The developed G5.NHAc-FA-DOX conjugates may be used as a promising nanodevice for targeted cancer chemotherapy.
Published: 2018
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43. Hydrogels of Polycationic Acetohydrazone-Modified Phosphorus Dendrimers for Biomedical Applications: Gelation Studies and Nucleic Acid Loading

Author: Alya G. Venyaminova, Audrey Malrin-Fournol, Elena I. Ryabchikova, Anne-Marie Caminade, Alina E Grigoryeva, Evgeny K. Apartsin, Jean-Pierre Majoral, Serge Mignani, Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of the Russian Academy of Sciences (SB RAS), IMT École nationale supérieure des Mines d'Albi-Carmaux (IMT Mines Albi), Institut Mines-Télécom [Paris] (IMT), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centro de Química da Madeira, Universidade da Madeira (UMA), Université Sorbonne Paris Cité (USPC), University of Madeira [Funchal], Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Pharmaceutical Science, chemistry.chemical_element, Girard reagents, lcsh:RS1-441, 02 engineering and technology, Polyethylene glycol, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, macromolecular substances, 010402 general chemistry, 01 natural sciences, complex mixtures, Article, lcsh:Pharmacy and materia medica, chemistry.chemical_compound, Dendrimer, phosphorus dendrimers, hydrogels, oligonucleotides, Phosphorus, technology, industry, and agriculture, 021001 nanoscience & nanotechnology, 0104 chemical sciences, [SDV.SP.PG]Life Sciences [q-bio]/Pharmaceutical sciences/Galenic pharmacology, chemistry, Chemical engineering, Reagent, Self-healing hydrogels, Nucleic acid, Surface modification, functionalization, Pyridinium, 0210 nano-technology
Abstract: In this work, we report the assemblage of hydrogels from phosphorus dendrimers in the presence of biocompatible additives and the study of their interactions with nucleic acids. As precursors for hydrogels, phosphorus dendrimers of generations 1&ndash, 3 based on the cyclotriphosphazene core and bearing ammonium or pyridinium acetohydrazones (Girard reagents) on the periphery have been synthesized. The gelation was done by the incubation of dendrimer solutions in water or phosphate-buffered saline in the presence of biocompatible additives (glucose, glycine or polyethylene glycol) to form physical gels. Physical properties of gels have been shown to depend on the gelation conditions. Transmission electron microscopy revealed structural units and well-developed network structures of the hydrogels. The hydrogels were shown to bind nucleic acids efficiently. In summary, hydrogels of phosphorus dendrimers represent a useful tool for biomedical applications.
Published: 2018
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44. Fluorescent (Phosphorus) Dendrimers and Their Use in Biology

Author: Anne-Marie Caminade and Aurelien Hameau
Subjects: chemistry, Dendrimer, Phosphorus, chemistry.chemical_element, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 0210 nano-technology, 01 natural sciences, Fluorescence, Combinatorial chemistry, 0104 chemical sciences
Published: 2018
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45. Methods for Characterizing (Phosphorus) Dendrimers

Author: Anne-Marie Caminade and Régis Laurent
Subjects: chemistry, 010405 organic chemistry, Phosphorus, Dendrimer, Inorganic chemistry, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences
Published: 2018
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46. Enhanced Delivery of Therapeutic siRNA into Glioblastoma Cells Using Dendrimer-Entrapped Gold Nanoparticles Conjugated with β-Cyclodextrin

Author: Jieru Qiu, Xiangyang Shi, Lingdan Kong, Xueyan Cao, Jean-Pierre Majoral, Aijun Li, Anne-Marie Caminade, Serge Mignani, Lu Wang, Ping Wei, Shanghai Tenth People's Hospital, Tongji University, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centro de Química da Madeira, Universidade da Madeira (UMA), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Small interfering RNA, General Chemical Engineering, 02 engineering and technology, 010402 general chemistry, PAMAM dendrimers, 01 natural sciences, Article, lcsh:Chemistry, chemistry.chemical_compound, gene silencing, Western blot, Dendrimer, medicine, Gene silencing, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Viability assay, ComputingMilieux_MISCELLANEOUS, medicine.diagnostic_test, Chemistry, β-CD, Transfection, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Vascular endothelial growth factor, lcsh:QD1-999, Colloidal gold, gold nanoparticles, siRNA, Biophysics, 0210 nano-technology
Abstract: International audience; We describe a safe and highly effective non-viral vector system based on β-cyclodextrin (β-CD)-modified dendrimer-entrapped gold nanoparticles (Au DENPs) for improved delivery small interfering RNA (siRNA) to glioblastoma cells. In our approach, we utilized amine-terminated generation 5 poly(amidoamine) dendrimers partially grafted with β-CD as a nanoreactor to entrap Au NPs. The acquired β-CD-modified Au DENPs (Au DENPs-β-CD) were complexed with two different types of therapeutic siRNA (B-cell lymphoma/leukemia-2 (Bcl-2) siRNA and vascular endothelial growth factor (VEGF) siRNA). The siRNA compression ability of the Au DENPs-β-CD was evaluated by various methods. The cytocompatibility of the vector/siRNA polyplexes was assessed by viability assay of cells. The siRNA transfection capability of the formed Au DENPs-β-CD vector was evaluated by flow cytometric assay of the cellular uptake of the polyplexes and Western blot assays of the Bcl-2 and VEGF protein expression. Our data reveals that the formed Au DENPs-β-CD carrier enables efficiently delivery of siRNA to glioma cells, has good cytocompatibility once complexed with the siRNA, and enables enhanced gene silencing to inhibit the expression of Bcl-2 and VEGF proteins. The developed Au DENPs-β-CD vector may be used for efficient siRNA delivery to different biosystems for therapeutic purposes.
Published: 2018
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47. Vibrational spectroscopic investigation of the gold complexation within the cascade structure of phosphorus-containing dendrimer

Author: Jean-Pierre Majoral, A.E. Vandyukov, Régis Laurent, Sébastien Gottis, Valeri I. Kovalenko, V.L. Furer, Anne-Marie Caminade, Kazan State Architect and Civil Engineering University, University of Kazan, A.E. Arbuzov Institute of Organic and Physical Chemistry (IOPC), Kazan Scientific Centre of the Russian Academy of Sciences, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Kazan National Research Technological University
Subjects: Chemistry, 02 engineering and technology, Interaction energy, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Quantum chemistry, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, Analytical Chemistry, Delocalized electron, Crystallography, Electron affinity, Dendrimer, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ionization energy, 0210 nano-technology, Instrumentation, HOMO/LUMO, Spectroscopy
Abstract: International audience; The interaction of the phosphoric dendrimer with gold was performed by means of vibrational spectroscopy and quantum chemistry. Stable complexes are formed with a PN−PS linkage, whereas with an isolated PS bond this does not occur. The change in geometric parameters and delocalization of electric charge under the influence of gold was discovered. The classification of bands in the experimental vibrational spectra of the dendrimer and its complex was carried out. HOMO of molecule of the dendrimer is localized on the SPNP linkage, whereas the LUMO is located on the terminal group. In the SPNP linkage there is a noticeable delocalization of the charge which leads to a change in the reactivity of this group. Interaction energy was estimated as the difference between the energies of the complex and the energies of the molecules of the dendrimer G′0 and two molecules AuCl and is equal to 25.2 eV. The ionization energy IE and electron affinity EA for AuCl are higher than for dendrimer, therefore, when the complex is formed, these quantities increases. Chemical potential and the electrophilicity index in the complex also increases.
Published: 2018
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48. Synthesis of dissymmetric phosphorus dendrimers using an unusual protecting group

Author: Evgeny K. Apartsin, Jean-Pierre Majoral, Anne-Marie Caminade, Serge Mignani, Alya G. Venyaminova, Institute of Chemical Biology and Fundamental Medicine [Novosibirsk, Russia] (ICBFM SB RAS), Siberian Branch of the Russian Academy of Sciences (SB RAS), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Phosphorus, chemistry.chemical_element, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, Monomer, chemistry, Dendrimer, Polymer chemistry, Materials Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Protecting group
Abstract: International audience; The presence of an azido group directly linked to phosphorus functionalized monomeric species allows the synthesis of neutral or polycationic original phosphorus dendrimers of reduced symmetry bearing branches of different generations on the core.
Published: 2018
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49. Recent therapeutic applications of the theranostic principle with dendrimers in oncology

Author: Xiangyang Shi, Anne-Marie Caminade, Régis Laurent, Serge Mignani, João Rodrigues, Jean-Pierre Majoral, Helena Tomás, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Centro de Química da Madeira, Universidade da Madeira (UMA), School of Materials Science and Engineering, Northwestern Polytechnical University (NPU), School of Materials Science and Engineering, Northwestern Polytechnical University, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), State Key Laboratory for Fiber & Material Modification of Donghua University, Donghua University [Shanghai], Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Oncology, medicine.medical_specialty, Dendrimers, Materials science, Computed tomography imaging, Hyperbranched polymers, Nanoparticle, Computed tomography, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Theranostic platforms, Optical imaging, Faculdade de Ciências Exatas e da Engenharia, Magnetic resonance imaging, Gamma scintigraphy, Internal medicine, Dendrimer, medicine, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, medicine.diagnostic_test, Gamma scintigraphy imaging, 021001 nanoscience & nanotechnology, 0104 chemical sciences, 3. Good health, Microbubbles, 0210 nano-technology
Abstract: International audience; At the intersection between treatment and diagnosis, nanoparticles technologies are strongly impacting the development of both therapeutic and diagnostic agents. Consequently, the development of novel modalities for concomitant noninvasive therapy and diagnostics known as theranostics as a single platform has gained significant interests. These multifunctional theranostic platforms include carbon-based nanomaterials (e.g., carbon nanotubes), drug conjugates, aliphatic polymers, micelles, vesicles, core-shell nanoparticles, microbubbles and dendrimers bearing different contrast agents and drugs, such as cytotoxic compounds in the oncology domain. Dendrimers emerged as a new class of highly tunable hyperbranched polymers, and have been developed as useful theranostic platforms. Magnetic resonance imaging, gamma scintigraphy, computed tomography and optical imaging are the main techniques developed with dendrimers in the theranostic domain in oncology. Different imaging agents have been used such as Gd(III), 19F, Fe2O3 (MRI), 76Br (PET), 111In, 88Y, 153Gd, 188Re, 131I (SPECT), 177Lu, gold (CT) and boronated groups, siliconnaphthalocyanines, dialkylcarbocyanines and QDs (optical imaging dyes).
Published: 2018
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50. Synthesis and study of the vibrational spectra of a first generation phosphorus-containing dendrimer with pyridyl functional groups

Author: Valeri I. Kovalenko, Anne-Marie Caminade, V. Tripathi, Jean-Pierre Majoral, V.L. Furer, A.E. Vandyukov, Kazan State Architect and Civil Engineering University, University of Kazan, A.E. Arbuzov Institute of Organic and Physical Chemistry (IOPC), Kazan Scientific Centre of the Russian Academy of Sciences, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Kazan National Research Technological University
Subjects: Steric effects, 010405 organic chemistry, Hydrogen bond, Organic Chemistry, Infrared spectroscopy, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Analytical Chemistry, Inorganic Chemistry, NMR spectra database, Crystallography, chemistry.chemical_compound, chemistry, Dendrimer, Amide, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, HOMO/LUMO, Spectroscopy
Abstract: A new phosphorus-containing dendrimer of the first-generation with potential pharmacological activity was synthesized and studied by spectral methods. The FTIR, FT Raman, 1 H and 31 P NMR spectra of the first generation dendrimer G 1 with a cyclotriphosphazene core, six branches O C 6 H 4 CH N N(CH 3 ) P(S) O C 6 H 4 (CH 2 ) 2 NH CO C 5 NH 4 were recorded. Amide groups of the dendrimer participate in the formation of an intermolecular hydrogen bond. Structure, geometric parameters, the frequency and intensity of the bands in the vibrational spectra were calculated using DFT with PBE functional and TZ2P basis set. Spectral characteristics, charge distribution and reactivity of the core, repeating units and terminal groups of the dendrimer were determined. The first-generation dendrimer molecule has the shape of a concave lens with a slightly non-planar cyclotriphosphazene core and flat repeating units. Repeating units are arranged symmetrically on three on each side of the core, there are no steric hindrances in it and the end groups are able to enter into subsequent reactions and dendrimer has a sufficiently large cavity for accommodating guest molecules. The HOMO covers the repeating units with a noticeable conjugation and the LUMO belongs to the terminal groups.
Published: 2018
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