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

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154 results on '"Anne-marie Caminade"'

1. Specific Bifunctionalization on the Surface of Phosphorus Dendrimers Syntheses and Properties

Author: Massimo Petriccone, Régis Laurent, Cédric-Olivier Turrin, Rosa Maria Sebastián, and Anne-Marie Caminade
Subjects: dendrimer, phosphorus, bifunctionalization, polyphosphorhydrazone, properties, Organic chemistry, QD241-441
Abstract: Dendrimers are highly branched macromolecules possessing, in most cases, identical terminal functions. However, it is sometimes desirable to have two types of surface functions in order to fulfil specific properties. The stochastic functionalization is frequently used for such purposes, but the presence of an uncontrolled number of each type of terminal function, albeit acceptable for research purposes, has no practical use. Thus, it is highly desirable to find strategies suitable for the precise grafting of two different functional groups on the surface of dendrimers. The easiest way, and the most widely used, consists in using a bifunctional monomer to be grafted to all of the surface functions of the dendrimers. Two other strategies are known but are rarely used: the modification of an existing function, to generate two functions, and the sequential grafting of one function then of a second function. The three methods are illustrated in this review with polyphosphorhydrazone (PPH) dendrimers, together with their properties as catalysts, for materials, and as biological tools.
Published: 2022
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2. Straightforward synthesis of gold nanoparticles by adding water to an engineered small dendrimer

Author: Sébastien Gottis, Régis Laurent, Vincent Collière, and Anne-Marie Caminade
Subjects: colloidal suspension, complexation, dendrimer, gold nanoparticle, phosphorus, Technology, Chemical technology, TP1-1185, Science, Physics, QC1-999
Abstract: 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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3. Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

Author: Anne-Marie Caminade, Artem Zibarov, Eduardo Cueto Diaz, Aurélien Hameau, Maxime Klausen, Kathleen Moineau-Chane Ching, Jean-Pierre Majoral, Jean-Baptiste Verlhac, Olivier Mongin, and Mireille Blanchard-Desce
Subjects: bioimaging, dendrimer, fluorescence, phosphorus, two-photon absorption, Science, Organic chemistry, QD241-441
Abstract: 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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4. Amphiphilic Triazine-Phosphorus Metallodendrons Possessing Anti-Cancer Stem Cell Activity

Author: Evgeny K. Apartsin, Nadezhda Knauer, Ulf Dietrich Kahlert, and Anne-Marie Caminade
Subjects: dendrons, phosphorus, supramolecular associates, metallodrugs, copper, gold, Pharmacy and materia medica, RS1-441
Abstract: Dendritic molecules bearing metal complexes in their structure (metallodendrimers and metallodendrons) are considered prospective therapeutic entities. In particular, metallodendrons raise interest as antitumor agents for the treatment of poorly curable or drug-resistant tumors. Herein, we have synthesized amphiphilic triazine-phosphorus dendrons bearing multiple copper (II) or gold (III) complexes on the periphery and a branched hydrophobic fragment at the focal point. Due to their amphiphilic nature, metallodendrons formed single micelles (mean diameter ~9 nm) or multi-micellar aggregates (mean diameter ~60 nm) in a water solution. We have tested the antitumor activity of amphiphilic metallodendrons towards glioblastoma, a malignant brain tumor with a notoriously high level of therapy resistance, as a model disease. The metallodendrons exhibit higher cytotoxic activity towards glioblastoma stem cells (BTSC233, JHH520, NCH644, and SF188 cell lines) and U87 glioblastoma cells (IC50 was 3–6 µM for copper-containing dendron and 11–15 µM for gold-containing dendron) in comparison with temozolomide (IC50 >100 µM)—the clinical standard of care for glioblastoma. Our findings show the potential of metallodendron-based nanoformulations as antitumor entities.
Published: 2022
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5. AB5 Derivatives of Cyclotriphosphazene for the Synthesis of Dendrons and Their Applications

Author: Artem Zibarov, Abdelouahd Oukhrib, Julien Aujard Catot, Cédric-Olivier Turrin, and Anne-Marie Caminade
Subjects: cyclotriphosphazene, dendron, fluorescence, phosphorus, dendrimer, nanomaterials, Organic chemistry, QD241-441
Abstract: 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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6. Organophosphorus Chemistry for the Synthesis of Dendrimers

Author: Jean-Pierre Majoral, Régis Laurent, Maria Zablocka, and Anne-Marie Caminade
Subjects: dendrimers, phosphorus, hydrazone, phosphine, phosphonate, Organic chemistry, QD241-441
Abstract: Dendrimers are multifunctional, hyperbranched and perfectly defined macromolecules, synthesized layer after layer in an iterative manner. Besides the nature of the terminal groups responsible for most of the properties, the nature of the internal structure, and more precisely of the branching points, is also of crucial importance. For more than 15 years, we have demonstrated that the presence of phosphorus atom(s) at each branching point of the dendrimeric structure is particularly important and highly valuable for three main reasons: (i) the versatility of phosphorus chemistry that allows diversified organochemistry for the synthesis of dendrimers; (ii) the use of 31P-NMR, which is a highly valuable tool for the characterization of dendrimers; (iii) some properties (in the fields of catalysis, materials, and especially biology), that are directly connected to the nature of the internal structure and of the branching points. This review will give an overview of the methods of synthesis of phosphorus-containing dendrimers, as well on the ways to graft phosphorus derivatives as terminal groups, with emphasis on the various roles played by the chemistry of phosphorus.
Published: 2012
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7. Bifunctional Phosphorus Dendrimers and Their Properties

Author: Anne-Marie Caminade and Jean-Pierre Majoral
Subjects: dendrimers, dendrons, synthesis, phosphorus, fluorescence, catalysis, nanomaterials, biology, Organic chemistry, QD241-441
Abstract: Dendrimers are hyperbranched and monodisperse macromolecules, generally considered as a special class of polymers, but synthesized step-by-step. Most dendrimers have a uniform structure, with a single type of terminal function. However, it is often desirable to have at least two different functional groups. This review will discuss the case of bifunctional phosphorus-containing dendrimers, and the consequences for their properties. Besides the terminal functions, dendritic structures may have also a function at the core, or linked off-center to the core, or at the core of dendrons (dendritic wedges). Association of two dendrons having different terminal functions leads to Janus dendrimers (two faces). The internal structure can also possess functional groups on one layer, or linked to one layer, or on several layers. Finally, there are several ways to have two types of terminal functions, besides the case of Janus dendrimers: either each terminal function bears two functions sequentially, or two different functions are linked to each terminal branching point. Examples of each type of structure will be given in this review, as well as practical uses of such sophisticated structures in the fields of fluorescence, catalysis, nanomaterials and biology.
Published: 2016
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8. In Vitro Validation of the Therapeutic Potential of Dendrimer-Based Nanoformulations against Tumor Stem Cells

Author: Nadezhda Knauer, Valeria Arkhipova, Guanzhang Li, Michael Hewera, Ekaterina Pashkina, Phuong-Hien Nguyen, Maria Meschaninova, Vladimir Kozlov, Wei Zhang, Roland Croner, Anne-Marie Caminade, Jean-Pierre Majoral, Evgeny Apartsin, Ulf Kahlert, Research Institute of Fundamental and Clinical Immunology, Siberian Branch of the Russian Academy of Sciences (SB RAS), Heinrich Heine Universität Düsseldorf = Heinrich Heine University [Düsseldorf], Institute of Chemical Biology and Fundamental Medicine [Novosibirsk, Russia] (ICBFM SB RAS), Novosibirsk State University (NSU), Beijing Neurosurgical Institute [Beijing, China], University of Cologne, Capital University of Medical Sciences [Beijing] (CUMS), University Hospital Magdeburg, 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), European Union’s Horizon 2020 research and innovation programme - Marie Skłodowska-Curie grant agreement No 844217 'EUREKA', Heinrich-Heine University Düsseldorf, Germany - STIBET programme, and COST Action CA 17140 'Cancer Nanomedicine from the Bench to the Bedside' - COST (European Cooperation in Science and Technology)
Subjects: Dendrimers, Brain Neoplasms, Organic Chemistry, Phosphorus, General Medicine, Glioma, Lyn, 3D tumor models, dendrimers, phosphorus, nucleic acid therapeutics, polyelectrolyte complexes, tumor stem cells, nanomedicine, Catalysis, Computer Science Applications, Inorganic Chemistry, Polyelectrolyte complexes, Tumor stem cells, Nanomedicine, Neoplastic Stem Cells, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, RNA, Small Interfering, Glioblastoma, Molecular Biology, Spectroscopy, Nucleic acid therapeutics
Abstract: International audience; Tumor cells with stem cell properties are considered to play major roles in promoting the development and malignant behavior of aggressive cancers. Therapeutic strategies that efficiently eradicate such tumor stem cells are of highest clinical need. Herein, we performed the validation of the polycationic phosphorus dendrimer-based approach for small interfering RNAs delivery in in vitro stem-like cells as models. As a therapeutic target, we chose Lyn, a member of the Src family kinases as an example of a prominent enzyme class widely discussed as a potent anti-cancer intervention point. Our selection is guided by our discovery that Lyn mRNA expression level in glioma, a class of brain tumors, possesses significant negative clinical predictive value, promoting its potential as a therapeutic target for future molecular-targeted treatments. We then showed that anti-Lyn siRNA, delivered into Lyn-expressing glioma cell model reduces the cell viability, a fact that was not observed in a cell model that lacks Lyn-expression. Furthermore, we have found that the dendrimer itself influences various parameters of the cells such as the expression of surface markers PD-L1, TIM-3 and CD47, targets for immune recognition and other biological processes suggested to be regulating glioblastoma cell invasion. Our findings prove the potential of dendrimer-based platforms for therapeutic applications, which might help to eradicate the population of cancer cells with augmented chemotherapy resistance. Moreover, the results further promote our functional stem cell technology as suitable component in early stage drug development.
Published: 2022
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9. Curing inflammatory diseases using phosphorous dendrimers

Author: Anne‐Marie Caminade, Cédric‐Olivier Turrin, Rémy Poupot, Laboratoire de chimie de coordination (LCC), 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-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), Institut Toulousain des Maladies Infectieuses et Inflammatoires (Infinity), 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), University of Toulouse, Inserm, Centre National de la Recherche Scientifique (CNRS), Gulli, Marie-Hélène, 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 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)
Subjects: Inflammation, Dendrimers, Dendrimer, Anti-Inflammatory Agents, Biomedical Engineering, Medicine (miscellaneous), Phosphorus, Bioengineering, [CHIM.COOR] Chemical Sciences/Coordination chemistry, Monocytes, Mice, Leukocytes, Mononuclear, Animals, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract: International audience; Different types of water-soluble phosphorous dendrimers have been synthesized and display many different biological properties. It has been shown in particular that phosphorous dendrimers of first generation functionalized with azabisphosphonate terminal functions are able to stimulate the human immune system ex vivo. These dendrimers are internalized by monocytes within a few seconds, and induce their anti-inflammatory activation. The presence of the dendrimers induces also the inhibition of the differentiation of monocytes into osteoclasts, the maturation of dendritic cells, and inhibits the proliferation of the proinflammatory CD4+ T lymphocytes. Finally, after 2–3 weeks of culture of peripheral blood mononuclear cells, amplifications by several tens of natural killer cells is observed. In view of all these properties, the influence of these azabisphosphonate-dendrimers has been tested in vivo with several animal models, against different chronic or acute inflammatory diseases, such as multiple sclerosis, rheumatoid arthritis, uveitis, and psoriasis, but also against myeloid leukemia, a hematological cancer. The hematological safety has been demonstrated in mice, as there is no platelet aggregation, no hemolysis, and no disturbance in the hematological formula. The safety of the azabisphosphonate-dendrimer has been assessed also with non-human primates (cynomolgus monkeys) which received repeated injections, as a de-risking pre-clinical test. Biochemical, hematological, and all immunological parameters in peripheral blood remained within a normal physiological range throughout the study, and all survived well. Other phosphorous dendrimers also display anti-inflammatory properties in vivo, in particular dendrimers functionalized with mannose derivatives, which prevent acute lung diseases when given orally (per os) to mice.
Published: 2022
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10. Engineered Stable Bioactive Per Se Amphiphilic Phosphorus Dendron Nanomicelles as a Highly Efficient Drug Delivery System To Take Down Breast Cancer In Vivo

Author: Liang Chen, Liu Cao, Mengsi Zhan, Jin Li, Dayuan Wang, Régis Laurent, Serge Mignani, Anne-Marie Caminade, Jean-Pierre Majoral, Xiangyang Shi, 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), 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 (81761148028 and 22150410324), Science and Technology Commission of Shanghai Municipality (20520710300, 21490711500, and 20DZ2254900), Shanghai Education Commission - Shanghai Leading Talents Program, 111 Project (BP0719035), NSFC-CNRS grant, FCT-Fundação para a Ciência e a Tecnologia - CQM Base Fund─UIDB/00674/2020 and Programmatic Fund─UIDP/00674/2020, and ARDITI─Agência Regional para o Desenvolvimento da Investigação Tecnologia e Inovação - project M1420-01-0145-FEDER-000005-Centro de Química da Madeira-CQM+ (Madeira 14-20 Program)
Subjects: Dendrons, Dendrimers, Drug Carriers, Polymers and Plastics, Cancer therapy, Antineoplastic Agents, Breast Neoplasms, Phosphorus, Bioengineering, Apoptosis, Peptides and proteins, Biomaterials, Drug Delivery Systems, [SDV.SP.PG]Life Sciences [q-bio]/Pharmaceutical sciences/Galenic pharmacology, Doxorubicin, Drug delivery, Materials Chemistry, Humans, Female, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Nanomicelles, Cationic phosphorus dendrons, Micelles, Cancer
Abstract: International audience; Conventional small molecular chemical drugs always have challenging limitations in cancer therapy due to their high systemic toxicity and low therapeutic efficacy. Nanotechnology has been applied in drug delivery, bringing new promising potential to realize effective cancer treatment. In this context, we develop here a new nanomicellar drug delivery platform generated by amphiphilic phosphorus dendrons (1-C17G3.HCl), which could form micelles for effective encapsulation of a hydrophobic anticancer drug doxorubicin (DOX) with a high drug loading content (42.4%) and encapsulation efficiency (96.7%). Owing to the unique dendritic rigid structure and surface hydrophilic groups, large steady void space of micelles can be created for drug encapsulation. The created DOX-loaded micelles with a mean diameter of 26.3 nm have good colloidal stability. Strikingly, we show that the drug-free micelles possess good intrinsic anticancer activity and act collectively with DOX to take down breast cancer cells in vitro and the xenografted tumor model in vivo through upregulation of Bax, PTEN, and p53 proteins for enhanced cell apoptosis. Meanwhile, the resulting 1-C17G3.HCl@DOX micelles significantly abolish the toxicity relevant to the free drug. The findings of this study demonstrate a unique nanomicelle-based drug delivery system created with the self-assembling amphiphilic phosphorus dendrons that may be adapted for chemotherapy of different cancer types.
Published: 2022
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11. 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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12. 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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13. 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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14. AB

Author: Artem, Zibarov, Abdelouahd, Oukhrib, Julien, Aujard Catot, Cédric-Olivier, Turrin, and Anne-Marie, Caminade
Subjects: catalysis, dendron, cyclotriphosphazene, Review, fluorescence, phosphorus, dendrimer, sensors, nanomedicine, nanomaterials
Abstract: 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

15. 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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16. 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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17. 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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18. Potent Anticancer Efficacy of First-In-Class Cu

Author: Liang, Chen, Yu, Fan, Jieru, Qiu, Régis, Laurent, Jin, Li, Jérôme, Bignon, Serge, Mignani, Anne-Marie, Caminade, Xiangyang, Shi, and Jean-Pierre, Majoral
Subjects: Dendrimers, Cell Death, Molecular Structure, Metals, MCF-7 Cells, Cytochromes c, Humans, Apoptosis, Phosphorus, Mitochondria
Abstract: First-in-class Cu
Published: 2020

19. 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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20. 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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21. 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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22. 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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23. 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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24. 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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25. 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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26. 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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27. 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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28. 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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29. 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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30. 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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31. 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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32. 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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33. 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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34. 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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35. Biomaterials Made of Phosphorus Dendrimers: Toward Diagnosis Tools

Author: Béatrice Delavaux-Nicot and Anne-Marie Caminade
Subjects: chemistry, Phosphorus, Dendrimer, chemistry.chemical_element, Nanotechnology
Published: 2018
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36. EPR Characterization of Phosphorus Dendrimers as Drugs for Cancer and Neurodegenerative Diseases

Author: Barbara Klajnert-Maculewicz, Maria Francesca Ottaviani, Michela Cangiotti, Anne-Marie Caminade, and Jean-Pierre Majoral
Subjects: Chemistry, law, Dendrimer, Phosphorus, medicine, Cancer, chemistry.chemical_element, medicine.disease, Electron paramagnetic resonance, Combinatorial chemistry, law.invention
Published: 2018
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37. 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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38. Which dendrimer to attain the desired properties? Focus on phosphorhydrazone 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), 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, Phosphorhydrazone, Static Electricity, Chemical composition, Pharmaceutical Science, Nanotechnology, Review, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Polymerization, Analytical Chemistry, Polypropyleneimine, lcsh:QD241-441, Biological properties, lcsh:Organic chemistry, Biological property, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Drug Carriers, Elemental composition, Pamam dendrimers, Molecular Structure, Chemistry, Organic Chemistry, Hydrazones, Phosphorus, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Solubility, Chemistry (miscellaneous), Molecular Medicine, 0210 nano-technology
Abstract: International audience; Among the six Critical Nanoscale Design Parameters (CNDPs) proposed by Prof. Donald A. Tomalia, this review illustrates the influence of the sixth one, which concerns the elemental composition, on the properties of dendrimers. After a large introduction that summarizes different types of dendrimers that have been compared with PolyAMidoAMine (PAMAM) dendrimers, this review will focus on the properties of positively and negatively charged phosphorhydrazone (PPH) dendrimers, especially in the field of biology, compared with other types of dendrimers, in particular PAMAM dendrimers, as well as polypropyleneimine (PPI), carbosilane, and p-Lysine dendrimers.
Published: 2018
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39. Multiplexing technology for in vitro diagnosis of pathogens: the key contribution of phosphorus dendrimers

Author: Anne-Marie Caminade, Alice Senescau, Jean-Pierre Majoral, Richard Fabre, Jean Marie François, Serge Mignani, Majoral, Jean-Pierre, 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), Dendris, Laboratoire d'Ingénierie des Systèmes Biologiques et des Procédés (LISBP), Institut National de la Recherche Agronomique (INRA)-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)-Centre National de la Recherche Scientifique (CNRS), 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), National Research Agency (Agence Nationale pour la Recherche), 'BIO-TECHNOLOGIES' program [ANR 2010 BIOT 004 06], Region Midi Pyrenees [06001324, 07006292], 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 National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut National de la Recherche Agronomique (INRA), Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5), 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: DNA arrays, Materials science, [SDV.BIO]Life Sciences [q-bio]/Biotechnology, 02 engineering and technology, Computational biology, Biotechnologies, 010402 general chemistry, 01 natural sciences, Multiplexing, dendrimers, Dendrimer, amplification par pcr, General Materials Science, phosphorus, multiplexing technology, microbiologie, bactérie, Microbiology and Parasitology, nanoscience, 021001 nanoscience & nanotechnology, bacterium, Microbiologie et Parasitologie, 0104 chemical sciences, 3. Good health, phosphore, [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, 0210 nano-technology
Abstract: After the microbiology based on Pasteur's method and polymerase chain reaction (PCR), the diagnosis company named Dendris has proposed a third-generation of diagnosis enabling the search of a broad range of pathogens with strong sensitivity and specificity. This extraordinary profile was possible thanks to the use of phosphorus dendrimers for which various techniques of deposition on a given support were investigated and described and analyzed in this report.
Published: 2018
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40. Phosphorus Dendrimers as Vectors for Gene Therapy in Cancer

Author: Vladimir A. Kulchitsky, Dzmitry Shcharbin, E. Pedziwiatr-Werbicka, Natallia Shcharbina, Serge Mignani, Rafael Gomez-Ramirez, M. A. Muñoz-Fernández, Jean-Pierre Majoral, J. Mata, Anne-Marie Caminade, Maria Bryszewska, Institute of Biophysics and Cell Engineering, NASB, Minsk, National Academy of Sciences of Belarus (NASB), Republican Research and Practical Center of Neurology and Neurosurgery, Department of General Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, University of Lódź, Departamento Química Orgánica y Química Inorgánica, Universidad de Alcalá, Alcalá de Henares, Universidad de Alcalá - University of Alcalá (UAH), Biomedical Research Networking Center in Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Instituto de Salud Carlos III (ISC)-ministerio de ciencia e innovacion, 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), Institute of Physiology of NASB, Laboratorio de Inmuno-Biología Molecular, Hospital General Universitario 'Gregorio Marañón'-Instituto de Investigación Sanitaria Gregorio Marañón, 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), Caminade, A.-M. and Turrin, C.-O. and Majoral, J.-P., Instituto de Salud Carlos III [Madrid] (ISC)-ministerio de ciencia e innovacion, 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: Chemistry, Genetic enhancement, Phosphorus, Cancer, chemistry.chemical_element, 02 engineering and technology, 021001 nanoscience & nanotechnology, medicine.disease, 030226 pharmacology & pharmacy, 03 medical and health sciences, 0302 clinical medicine, Dendrimer, Cancer research, medicine, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract: International audience
Published: 2018

41. Phosphorus-Based Dendrimer ABP Treats Neuroinflammation by Promoting IL-10-Producing CD4+ T Cells

Author: Myriam Hayder, Rémy Poupot, Abdelhadi Saoudi, Anne-Marie Caminade, Roland S. Liblau, Marjorie Varilh, Cédric-Olivier Turrin, 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), 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: CD4-Positive T-Lymphocytes, Dendrimers, Encephalomyelitis, Autoimmune, Experimental, Multiple Sclerosis, genetic structures, Polymers and Plastics, Bioengineering, Pharmacology, T cell response, Biomaterials, Mice, Dendrimer, Materials Chemistry, medicine, Animals, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Cells, Cultured, Neuroinflammation, Inflammation, Chemistry, Drug candidate, Multiple sclerosis, Experimental autoimmune encephalomyelitis, Phosphorus, medicine.disease, Fingolimod, Interleukin-10, 3. Good health, Mice, Inbred C57BL, Disease Models, Animal, Interleukin 10, Immunology, medicine.drug
Abstract: International audience; Dendrimers are polyfunctional nano-objects of perfectly defined structure that can provide innovative alternatives for the treatment of chronic inflammatory diseases, including multiple sclerosis (MS). To investigate the efficiency of a recently described amino-bis(methylene phosphonate)-capped ABP dendrimer as a potential drug candidate for MS, we used the classical mouse model of MOG35–55-induced experimental autoimmune encephalomyelitis (EAE). Our study provides evidence that the ABP dendrimer prevents the development of EAE and inhibits the progression of established disease with a comparable therapeutic benefit as the approved treatment Fingolimod. We also show that the ABP dendrimer redirects the pathogenic myelin-specific CD4+ T cell response toward IL-10 production.
Published: 2015
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42. Interaction studies reveal specific recognition of an anti-inflammatory polyphosphorhydrazone dendrimer by human monocytes

Author: Cédric-Olivier Turrin, Muriel Blanzat, Rémy Poupot, Giovanni M. Pavan, Anne-Marie Caminade, Matteo Garzoni, Jeremy Ledall, Séverine Fruchon, 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 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), 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), 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)-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), 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), 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)
Subjects: Dendrimers, Materials science, genetic structures, medicine.drug_class, media_common.quotation_subject, Lipid Bilayers, Cell, Anti-Inflammatory Agents, 02 engineering and technology, Molecular Dynamics Simulation, 010402 general chemistry, 01 natural sciences, Monocytes, Anti-inflammatory, Dendrimer, medicine, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Materials Science, Lipid bilayer, Internalization, Receptor, Cells, Cultured, media_common, Microscopy, Confocal, Calorimetry, Differential Scanning, Phosphorus, Biological activity, 021001 nanoscience & nanotechnology, 3. Good health, 0104 chemical sciences, medicine.anatomical_structure, Membrane, Biochemistry, Phosphatidylcholines, Biophysics, 0210 nano-technology
Abstract: International audience; Dendrimers are nano-materials with perfectly defined structure and size, and multivalency properties that confer substantial advantages for biomedical applications. Previous work has shown that phosphorus-based polyphosphorhydrazone (PPH) dendrimers capped with azabisphosphonate (ABP) end groups have immuno-modulatory and anti-inflammatory properties leading to efficient therapeutic control of inflammatory diseases in animal models. These properties are mainly prompted through activation of monocytes. Here, we disclose new insights into the molecular mechanisms underlying the anti-inflammatory activation of human monocytes by ABP-capped PPH dendrimers. Following an interdisciplinary approach, we have characterized the physicochemical and biological behavior of the lead ABP dendrimer with model and cell membranes, and compared this experimental set of data to predictive computational modelling studies. The behavior of the ABP dendrimer was compared to the one of an isosteric analog dendrimer capped with twelve azabiscarboxylate (ABC) end groups instead of twelve ABP end groups. The ABC dendrimer displayed no biological activity on human monocytes, therefore it was considered as a negative control. In detail, we show that the ABP dendrimer can bind both non-specifically and specifically to the membrane of human monocytes. The specific binding leads to the internalization of the ABP dendrimer by human monocytes. On the contrary, the ABC dendrimer only interacts non-specifically with human monocytes and is not internalized. These data indicate that the bioactive ABP dendrimer is recognized by specific receptor(s) at the surface of human monocytes.
Published: 2015
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43. Symmetrical and unsymmetrical incorporation of active biological monomers on the surface of phosphorus dendrimers

Author: Anne-Marie Caminade, Serge Mignani, Jean-Pierre Majoral, Saïd El Kazzouli, Nabil El Brahmi, Sonia Ladeira, Régis Laurent, Mosto Bousmina, Euromed Research Center, Engineering Division, 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), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-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), 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-Institut de Chimie du CNRS (INC), 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), 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), and Université Fédérale Toulouse Midi-Pyrénées
Subjects: 010405 organic chemistry, Phosphorus, Organic Chemistry, chemistry.chemical_element, 010402 general chemistry, Grafting, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, End-group, Monomer, chemistry, Dendrimer, Drug Discovery, Nucleophilic substitution, Chlorine, Organic chemistry, Phenol, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract: International audience; Phosphorus-containing dendrimers are attractive carriers for the delivery of bioactive molecules due to their very particular architecture, globular shape and chemical and physical properties. Herein we report a simple synthetic approach of ethacrynic acid derivatives loaded-phosphorus dendrimers by symmetrical grafting of ethacrynic acid analogues by nucleophilic substitution of each chlorine of P(S)Cl2 end groups. We report also for the first time an unsymmetrical grafting of two different phenol derivatives by a selective substitution of one chlorine of P(S)Cl2 end group followed by the grafting of the second phenol.
Published: 2017
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44. Anticancer copper(II) phosphorus dendrimers are potent proapoptotic Bax activators

Author: Anne-Marie Caminade, Joël Poupon, Valérie Nicolas, Mosto Bousmina, Jean-Pierre Majoral, Serge Mignani, Thierry Cresteil, Mireille Blanchard-Desce, Nabil El Brahmi, Saïd El Kazzouli, Anke Steinmetz, Laure Eloy, 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), 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), Université Fédérale Toulouse Midi-Pyrénées, Laboratoire de Chimie Organique Hétérocyclique, Université Mohammed V de Rabat [Agdal], Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire de Toxicologie Biologique, Hôpital Lariboisière, Hôpital Lariboisière-Fernand-Widal [APHP], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP), IFR 141 - Faculté de Pharmacie - Institut Paris-Sud d'Innovation Thérapeutique (IPSIT), Université Paris Sud (Paris 11), Sanofi [Vitry-sur-Seine], SANOFI Recherche, Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Faculté de Pharmacie, IPSIT, Université Paris Sud, 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), 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 National de la Recherche Scientifique (CNRS), Hôpital Lariboisière, and 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)
Subjects: 0301 basic medicine, Programmed cell death, Dendrimers, Biological Transport, Active, Apoptosis, 010402 general chemistry, Endocytosis, 01 natural sciences, 03 medical and health sciences, Dendrimer, Cell Line, Tumor, Drug Discovery, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Mode of action, bcl-2-Associated X Protein, Pharmacology, Molecular Structure, Chemistry, Caspase 3, Organic Chemistry, Phosphorus, General Medicine, Cell cycle, 0104 chemical sciences, Cytosol, 030104 developmental biology, Biochemistry, Drug Resistance, Neoplasm, Biophysics, DNA fragmentation, Copper
Abstract: International audience; A multivalent phosphorus dendrimer 1G3 and its corresponding Cu-complex, 1G3-Cu have been recently identified as agents retaining high antiproliferative potency. This antiproliferative capacity was preserved in cell lines overexpressing the efflux pump ABC B1, whereas cross-resistance was observed in ovarian cancer cell lines resistant to cisplatin. Theoretical 3D models were constructed: the dendrimers appear as irregularly shaped disk-like nano-objects of about 22 Å thickness and 49 Å diameter, which accumulated in cells after penetration by endocytosis. To get insight in their mode of action, cell death pathways have been examined in human cancer cell lines: early apoptosis was followed by secondary necrosis after multivalent phosphorus dendrimers exposure. The multivalent plain phosphorus dendrimer 1G3 moderately activated caspase-3 activity, in contrast with the multivalent Cu-conjugated phosphorus dendrimer 1G3-Cu which strikingly reduced the caspase-3 content and activity. This decrease of caspase activity is not related to the presence of copper, since inorganic copper has no or little effect on caspase-3. Conversely the potent apoptosis activation could be related to a noticeable translocation of Bax to the mitochondria, resulting in the release of AIF into the cytosol, its translocation to the nucleus and a severe DNA fragmentation, without alteration of the cell cycle. The multivalent Cu-conjugated phosphorus dendrimer is more efficient than its non-complexed analog to activate this pathway in close relationship with the higher antiproliferative potency. Therefore, this multivalent Cu-conjugated phosphorus dendrimer 1G3-Cu can be considered as a new and promising first-in-class antiproliferative agent with a distinctive mode of action, inducing apoptosis tumor cell death through Bax activation pathway.
Published: 2017
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45. Phosphorus dendrimers for 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, chemistry.chemical_element, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Catalysis, In vivo, Neoplasms, Dendrimer, Biological property, Materials Chemistry, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Inflammation, Molecular Structure, Phosphorus, Metals and Alloys, Neurodegenerative Diseases, General Chemistry, 021001 nanoscience & nanotechnology, 3. Good health, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Nanomedicine, chemistry, Drug delivery, Ceramics and Composites, 0210 nano-technology
Abstract: International audience; From biomaterials to imaging, and from drug delivery to drugs by themselves, phosphorus-containing dendrimers offer a large palette of biological properties, depending essentially on their types of terminal functions. The most salient examples of phosphorus dendrimers used for the elaboration of bio-chips and of supports for cell cultures, for imaging biological events, and for carrying and delivering drugs or biomacromolecules are presented in this feature article. Several phosphorus dendrimers can be considered also as drugs per se (by themselves) in particular to fight against cancers, neurodegenerative diseases, and inflammation, both in vitro and in vivo. Toxicity assays are also reported.
Published: 2017
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46. Multiplurifunctionalized Phosphorus Dendrimers: Selective Functionalization of P(X)CL2 Terminal Groups

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), 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, Stereochemistry, Phosphorus, Organic Chemistry, chemistry.chemical_element, Branching points, 010402 general chemistry, 01 natural sciences, Biochemistry, 0104 chemical sciences, Inorganic Chemistry, Terminal (electronics), chemistry, Dendrimer, Surface modification, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Reactivity (chemistry), Macromolecule
Abstract: International audience; AbstractDendrimers are hyperbranched macromolecules constituted of repetitive branched units. They are synthesized step-by-step, a method which ensures a perfectly defined structure. This mini-review reports examples of rare ?multiplurifunctionalized? dendrimers that have several types of functional groups precisely located on each terminal branching point. They are obtained thanks to the specificity of the reactivity of each Cl of P(X)Cl2 (X = generally S, but also O) terminal groups on the surface of poly(phosphorhydrazone) dendrimers.
Published: 2014
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47. Original Multivalent Copper(II)-Conjugated Phosphorus Dendrimers and Corresponding Mononuclear Copper(II) Complexes with Antitumoral Activities

Author: Nabil El Brahmi, Geneviève Aubert, Anne-Marie Caminade, Mosto Bousmina, El Mokhtar Essassi, Régis Laurent, Saïd El Kazzouli, Serge Mignani, Jean-Pierre Majoral, Thierry Cresteil, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-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: Dendrimers, Carps, Stereochemistry, Pharmaceutical Science, chemistry.chemical_element, Antineoplastic Agents, Biocompatible Materials, HL-60 Cells, 02 engineering and technology, Conjugated system, 010402 general chemistry, 01 natural sciences, Cell Line, Metal, Inhibitory Concentration 50, chemistry.chemical_compound, Cell Line, Tumor, Dendrimer, Drug Discovery, Pyridine, Animals, Humans, Molecule, Methylene, Cytotoxicity, Cell Proliferation, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Phosphorus, 021001 nanoscience & nanotechnology, Copper, 3. Good health, 0104 chemical sciences, Nanomedicine, Models, Chemical, chemistry, Drug Design, visual_art, visual_art.visual_art_medium, Molecular Medicine, 0210 nano-technology
Abstract: International audience; Novel multivalent copper(II)-conjugated phosphorus dendrimers and their corresponding mononuclear copper(II) complexes were synthesized, characterized, and screened for antiproliferative activity against human cancer cell lines. Selected copper ligands were grafted on the surface of phosphorus dendrimers of generation G(n) (n = 1 to 3): N-(pyridin-2-ylmethylene)ethanamine for dendrimers 1G(n), N-(di(pyridin-2-yl)methylene)ethanamine for dendrimers 2G(n), and 2-(2-methylenehydrazinyl)pyridine for dendrimers 3G(n). The results indicated that the most potent derivatives are 1G(n) and 1G(n)-Cu versus 2G(n), 2G(n)-Cu, and 3G(n), 3G(n)-Cu. A direct relationship between the growth inhibitory effect and the number of terminal moieties or the amount of copper complexed to the dendrimer was observed in copper-complexed 1 series and noncomplexed 1 series. These data clearly suggested that cytotoxicity increased with the number of terminal moieties available and was boosted by the presence of complexed Cu atoms. Importantly, no cytotoxic effect was observed with CuCl2 at the same concentrations. Finally, 1G3 and 1G3-Cu have been selected for antiproliferative studies against a panel of tumor cell lines: 1G3 and 1G3-Cu demonstrated potent antiproliferative activities with IC50 values ranging 0.3-1.6 μM. Interestingly, the complexation of the terminal ligands of 1G3 dendrimers by copper(II) metal strongly increased the IC50 values in noncancer cells lines referred to as "safety" cell lines.
Published: 2013
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48. Effect of viologen–phosphorus dendrimers on acetylcholinesterase and butyrylcholinesterase activities

Author: Anne-Marie Caminade, Nadia Katir, Karol Ciepluch, Barbara Klajnert, Abdelkrim El Kadib, Monika Weber, Maria Bryszewska, Jean-Pierre Majoral, Łódź University of Technology, 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 Institute for Nanomaterials and Nanotechnology - INANOTECH (MOROCCO)
Subjects: Dendrimers, Static Electricity, 02 engineering and technology, Biochemistry, Fluorescence, Viologens, Viologen-phosphorus dendrimers, 03 medical and health sciences, chemistry.chemical_compound, Structural Biology, Dendrimer, Humans, Enzyme activity, Molecular Biology, Acetylcholinesterase (AChE), Butyrylcholinesterase, 030304 developmental biology, Cholinesterase, chemistry.chemical_classification, Butyrylcholinesterase (BChE), 0303 health sciences, biology, Circular Dichroism, Erythrocyte Membrane, Neurodegenerative diseases, Active site, Phosphorus, General Medicine, 021001 nanoscience & nanotechnology, Acetylcholinesterase, Enzyme assay, 3. Good health, Amino acid, Enzyme, chemistry, biology.protein, 0210 nano-technology
Abstract: 0141-8130; The inhibition of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) is the first step in checking whether new compounds can be considered as drugs for treating neurodegenerative diseases. The effect of viologen-phosphorus dendrimers on AChE and BChE activities was studied. The results show that the effects on the cholinesterase activities depend on dendrimer type and size. Viologen dendrimers can interact with the enzymes in two ways: they can bind either to a peripheral site of the enzyme or to amino acids located near the active site, inhibiting catalysis by both cholinesterases. All tested non-toxic viologen-phosphorus dendrimers inhibited the activities of both cholinesterases, showing their potential as new drugs for treating neurodegenerative diseases.
Published: 2013
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49. Synthesis and characterization of dendritic structures incorporating phosphorus, sulfur, and silicon

Author: Anne-Marie Caminade, Aurélien Hameau, Clément Padié, Jean-Pierre Majoral, Carine Duhayon, 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: chemistry.chemical_classification, Trimethylsilyl, Silicon, 010405 organic chemistry, Phosphorus, Organic Chemistry, chemistry.chemical_element, Alkyne, 010402 general chemistry, 01 natural sciences, Biochemistry, Sulfur, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Group (periodic table), Dendrimer, Polymer chemistry, Organic chemistry, Phenol, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract: Two new families of small phosphorus-containing dendrons, having as core either a phenol protected by a t-butyldimethylsilyl group or a terminal alkyne protected by a trimethylsilyl group have been synthesized. Both families comprise P, S, and Si (and other elements) in their structure. The structure of one of the smallest dendron, having a P(S)Cl2 terminal group, has been determined by X-ray crystallography, showing an almost planar arrangement of a large part of the structure. The P(S)Cl2 terminal group is particularly suitable for further functionalization, as illustrated by the grafting of amines, aldehydes, and dansyl derivatives. These functions were grafted thanks to the reactivity of amines and phenols in basic conditions, demonstrating the compatibility of these reactions with the presence of the protecting groups. Deprotection attempts proved to be difficult, in particular for the purification of the deprotected products. All compounds have been characterized at least by 1H, 13C, and 31P NMR.
Published: 2016
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50. Phosphorus-containing dendrimers against α-synuclein fibril formation

Author: Katarzyna Milowska, Maria Bryszewska, Jean-Pierre Majoral, Anne-Marie Caminade, and Teresa Gabryelak
Subjects: Alpha-synuclein, Dendrimers, Circular dichroism, Stereochemistry, Biocompatible Materials, Phosphorus, macromolecular substances, General Medicine, Biochemistry, Fluorescence, Protein Structure, Secondary, Fluorescence spectroscopy, Phosphates, chemistry.chemical_compound, chemistry, Structural Biology, Dendrimer, alpha-Synuclein, Humans, Thioflavin, Protein Multimerization, Tyrosine, Spectroscopy, Molecular Biology
Abstract: The aim of this work was to study the effect of phosphorus-containing dendrimers (generations G3 and G4) on the fibrillation of α-synuclein (ASN). The inhibition of fibril formation (filamentous and aggregates) is a potential therapeutic strategy for neurodegenerative disorders such as Parkinson's and other motor disorder neurodegenerative diseases. The interaction between phosphorus-containing dendrimers and ASN was studied by fluorescence spectroscopy. The decrease in the fluorescence intensity of intrisinic tyrosine was the most marked change in the fluorescence intensity observed upon addition of dendrimers. Furthermore, the effect of dendrimers on ASN fibril formation was studied using circular dichroism (CD) spectroscopy and CD studies were complemented by fluorescence assays using the dye thioflavin T (ThT). The results showed that phosphorus-containing dendrimers G3 and G4 inhibited fibril formation, when they were used in the ASN/dendrimer ratios 1:0.1 and 1:0.5. However, the higher concentrations of dendrimers did not show this effect.
Published: 2012
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