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1. Brain delivery of fibronectin through bioactive phosphorous dendrimers for Parkinson's disease treatment via cooperative modulation of microglia

Author

Waicong Dai, Mengsi Zhan, Yue Gao, Huxiao Sun, Yu Zou, Régis Laurent, Serge Mignani, Jean-Pierre Majoral, Mingwu Shen, and Xiangyang Shi

Subjects
Phosphorous dendrimers, Fibronectin, Parkinson's disease, Blood brain barrier, Combination therapy, Materials of engineering and construction. Mechanics of materials, TA401-492, Biology (General), QH301-705.5
Abstract

Effective treatment of Parkinson's disease (PD), a prevalent central neurodegenerative disorder particularly affecting the elderly population, still remains a huge challenge. We present here a novel nanomedicine formulation based on bioactive hydroxyl-terminated phosphorous dendrimers (termed as AK123) complexed with fibronectin (FN) with anti-inflammatory and antioxidative activities. The created optimized AK123/FN nanocomplexes (NCs) with a size of 223 nm display good colloidal stability in aqueous solution and can be specifically taken up by microglia through FN-mediated targeting. We show that the AK123/FN NCs are able to consume excessive reactive oxygen species, promote microglia M2 polarization and inhibit the nuclear factor-kappa B signaling pathway to downregulate inflammatory factors. With the abundant dendrimer surface hydroxyl terminal groups, the developed NCs are able to cross blood-brain barrier (BBB) to exert targeted therapy of a PD mouse model through the AK123-mediated anti-inflammation for M2 polarization of microglia and FN-mediated antioxidant and anti-inflammatory effects, thus reducing the aggregation of α-synuclein and restoring the contents of dopamine and tyrosine hydroxylase to normal levels in vivo. The developed dendrimer/FN NCs combine the advantages of BBB-crossing hydroxyl-terminated bioactive per se phosphorus dendrimers and FN, which is expected to be extended for the treatment of different neurodegenerative diseases.

Published
2024
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2. Dendritic Pyridine–Imine Copper Complexes as Metallo-Drugs

Author

Régis Laurent, Valérie Maraval, Vania Bernardes-Génisson, and Anne-Marie Caminade

Subjects
dendrimer, Schiff base, pyridine–imine, copper, metallo-drugs, cancer, Organic chemistry, QD241-441
Abstract

Since the discovery of cisplatin in the 1960s, the search for metallo-drugs that are more efficient than platinum complexes with negligible side effects has attracted much interest. Among the other metals that have been examined for potential applications as anticancer agents is copper. The interest in copper was recently boosted by the discovery of cuproptosis, a recently evidenced form of cell death mediated by copper. However, copper is also known to induce the proliferation of cancer cells. In view of these contradictory results, there is a need to find the most suitable copper chelators, among which Schiff-based derivatives offer a wide range of possibilities. Gathering several metal complexes in a single, larger entity may provide enhanced properties. Among the nanometric objects suitable for such purpose are dendrimers, precisely engineered hyperbranched macromolecules, which are outstanding candidates for improving therapy and diagnosis. In this review article, we present an overview of the use of a particular Schiff base, namely pyridine–imine, linked to the surface of dendrimers, suitable for complexing copper, and the use of such dendrimer complexes in biology, in particular against cancers.

Published
2024
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3. 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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4. 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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5. PEG-cored phosphorus dendrimers: Synthesis and functionalization

Author

Hanna Dib, Jérémy Rebière, Cyrille Rebout, Omar Alami, Saïd El Kazzouli, Nabil El Brahmi, Régis Laurent, Béatrice Delavaux-Nicot, and Anne-Marie Caminade

Subjects
Dendrimer, Polyethylene glycol (PEG), Nitrogen ligand, Phosphorhydrazone, 1,3,5-Triazine, Chemistry, QD1-999
Abstract

Dendrimers are macromolecular hyperbranched nano-structures, which properties are mainly driven by the type of their terminal functions. This paper reports the synthesis of dendritic structures built from difunctional polyethylene glycols (PEGs) used as core. Three different PEG lengths have been used: PEG300 (ca 6 CH2CH2-O units), PEG1000 (ca 22 CH2CH2-O units), and PEG2000 (ca 45 CH2CH2-O units). The first level of branching units is based on a dialdehyde of a dipiperazine triazine derivative. The second and third level of branching units are constituted of phosphorhydrazone linkages. The growing of the dendritic branches was found extremely slow with both PEG1000 and PEG2000 used as core, and was stopped early, whereas this problem was not observed with PEG300 used as core. These PEG-cored dendritic structures were finally functionalized on the surface with two types of nitrogen ligands.

Published
2022
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6. The synthesis and characterization of giant Calixarenes

Author

Vincent Guérineau, Marion Rollet, Stéphane Viel, Bénédicte Lepoittevin, Ludovic Costa, Pascale Saint-Aguet, Régis Laurent, Philippe Roger, Didier Gigmes, Cyril Martini, and Vincent Huc

Subjects
Science
Abstract

Calixarenes are cyclic oligomers obtained by condensation reactions between phenols and formaldehyde and usually include up to eight phenolic subunits. Here the authors demonstrate the synthesis of calixarenes with up to 90 phenolic subunits with up to 65% yield via a scalable process.

Published
2019
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7. Dendrimers Functionalized with Palladium Complexes of N-, N,N-, and N,N,N-Ligands

Author

Quentin Vanbellingen, Paul Servin, Anaïs Coinaud, Sonia Mallet-Ladeira, Régis Laurent, and Anne-Marie Caminade

Subjects
dendrimer, ligands, imine, palladium, complexes, phenol, Organic chemistry, QD241-441
Abstract

Pyridine, pyridine imine, and bipyridine imine ligands functionalized by a phenol have been synthesized and characterized, in many cases by X-ray diffraction. Several of these N-, N,N-, and N,N,N,-ligands have been grafted onto the surface of phosphorhydrazone dendrimers, from generation 1 to generation 3. The complexation ability of these monomers and dendrimers towards palladium(II) has been assayed. The corresponding complexes have been either isolated or prepared in situ. In both cases, the monomeric and dendritic complexes have been tested as catalysts in Heck couplings and in Sonogashira couplings. In some cases, a positive dendritic effect has been observed, that is, an increase of the catalytic efficiency proportional to the dendrimer generation.

Published
2021
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8. 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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9. Synthesis of dye/fluorescent functionalized dendrons based on cyclotriphosphazene

Author

Aurélien Hameau, Sabine Fuchs, Régis Laurent, Jean-Pierre Majoral, and Anne-Marie Caminade

Subjects
dabsyl, dansyl, dendrimer, dendron, fluorescence, Science, Organic chemistry, QD241-441
Abstract

Functionalized phenols based on tyramine were synthesized in order to be selectively grafted on to hexachlorocyclotriphosphazene, affording a variety of functionalized dendrons of type AB5. The B functions comprised fluorescent groups (dansyl) or dyes (dabsyl), whereas the A function was provided by either an aldehyde or an amine. The characterization of these dendrons is reported. An unexpected behaviour of a fluorescent and water-soluble dendron based on dansyl groups in mixtures of dioxane/water was observed.

Published
2011
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10. Novel Methinic Functionalized and Dendritic C-Scorpionates

Author

Luísa M. D. R. S. Martins, Riccardo Wanke, Telma F. S. Silva, Armando J. L. Pombeiro, Paul Servin, Régis Laurent, and Anne-Marie Caminade

Subjects
C-scorpionate, pyrazolyl, tris(pyrazolyl)methane, functionalization, coordination flexibility, dendrimer, catalyst, C-C coupling, Sonogashira, Heck, Organic chemistry, QD241-441
Abstract

The study of chelating ligands is undoubtedly one of the most significant fields of research in chemistry. The present work is directed to the synthesis of new functionalized derivatives of tripodal C-scorpionate compounds. Tris-2,2,2-(1-pyrazolyl)ethanol, HOCH2C(pz)3 (1), one of the most important derivatives of hydrotris(pyrazolyl)methane, was used as a building block for the synthesis of new functionalized C-scorpionates, aiming to expand the scope of this unexplored class of compounds. The first dendritic C-scorpionate was successfully prepared and used in the important industrial catalytic reactions, Sonogashira and Heck C-C cross-couplings.

Published
2018
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13. The Chemistry of P=N−P=X (X=S, O, NR) Linkages for the Synthesis of Dendritic Structures

Author

Valérie Maraval, Régis Laurent, Anne‐Marie Caminade, 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), and CNRS

Subjects
[CHIM.COOR]Chemical Sciences/Coordination chemistry, General Chemistry
Abstract

International audience; The Staudinger reaction between a phosphine and an azide, applied to phosphorus azides, has been used for the synthesis of a large variety of dendritic structures, incorporating P=N−P=X moieties (X = mainly S, but also O and N−R). Conjugation of the P=N bond with the P=X bond greatly stabilizes the P=N bond. Highly branched structures such as dendrons, dendrimers, Janus dendrimers, layered dendrimers, surface-block dendrimers, and diverse other dendritic structures incorporating such linkage have been elaborated. Accelerated methods of synthesis of dendrimers are also based on the Staudinger reaction. A versatile reactivity was observed exclusively on the sulfur atom of P=N−P=S linkages, such as alkylation or complexation. Alkylation on S induces a weakening of the strength of the P=S bond, which can be easily cleaved to generate phosphines able to react in Staudinger reactions inside the structure of dendrimers, thus affording highly sophisticated dendritic structures.

Published
2023
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14. Amphiphilic phosphorous dendron micelles co-deliver microRNA inhibitor and doxorubicin for augmented triple negative breast cancer therapy

Author

Liang Chen, Mengsi Zhan, Jin Li, Liu Cao, Huxiao Sun, Régis Laurent, Serge Mignani, Anne-Marie Caminade, Jean-Pierre Majoral, Xiangyang Shi, 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), Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT), National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality, Shanghai Municipal Health Commission, Collaborative NSFC-CNRS grant, FCT-Fundação para a Ciência e a Tecnologia, and ARDITI-Agência Regional para o Desenvolvimento da Investigação Tecnologia e Inovação

Subjects
[SDV.SP.PG]Life Sciences [q-bio]/Pharmaceutical sciences/Galenic pharmacology, Cancer therapy, Drug delivery, Biomedical Engineering, General Materials Science, General Chemistry, General Medicine, Gene delivery, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Cationic phosphorus dendrons, Micelles
Abstract

International audience; Combined chemo/gene therapy of cancer through different action mechanisms has been emerging to enhance the therapeutic efficacy towards cancer, and still remains a challenging task due to the lack of highly effective and biocompatible nanocarriers. In this work, we report a new nanosystem based on amphiphilic phosphorus dendron (1-C12G1) micelles to co-deliver microRNA-21 inhibitor (miR-21i) and doxorubicin (DOX) for combination therapy of triple negative breast cancer. The amphiphilic phosphorus dendron bearing a long linear alkyl chain and ten protonated pyrrolidine surface groups was prepared and was demonstrated to form micelles in water solution and have a hydrodynamic size of 103.2 nm. The micelles are shown to be stable, enable encapsulation of an anticancer drug DOX with optimal loading content (80%) and encapsulation efficiency (98%), and can compress miR-21i to form polyplexes to render it with good stability against degradation. The co-delivery system of 1-C12G1@DOX/miR-21i polyplexes has a pH-dependent DOX release profile, and can be readily phagocytosed by cancer cells to inhibit them due to the different anticancer mechanisms, which was further validated after intravenous injection to treat an orthotopic triple-negative breast tumor model in vivo. With the proven biocompatibility under the studied doses, the developed amphiphilic phosphorus dendron micelles could be developed as an effective nanomedicine formulation for synergistic cancer therapy.

Published
2023
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15. β-Cyclodextrin PAMAM Dendrimer: How to Overcome the Tumbling Process for Getting Fully Available Host Cavities

Author

Aurélien Hameau, Valérie Bourdon, Anne-Marie Caminade, Kathleen I. Moineau-Chane Ching, Régis Laurent, Christian Bijani, Ernesto Rivera, and Israel González-Méndez

Subjects
chemistry.chemical_classification, Cyclodextrin, 010405 organic chemistry, Dimer, Adamantane, Organic Chemistry, Trimer, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Crystallography, Monomer, chemistry, Dendrimer, Click chemistry, Physical and Theoretical Chemistry, Two-dimensional nuclear magnetic resonance spectroscopy
Abstract

The synthesis of a G0 polyamidoamide (PAMAM) dendrimer end-capped with four β-cyclodextrin (β-CD) units, named as Tetra-CD was performed by using copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC). This new platform presents a considerable high water-solubility in comparison to native β-CD. Tumbling process involving half of the CD cavities in D2O was evidenced by 1H NMR spectroscopy. Interaction of adamantane with Tetra-CD has been fully investigated by 1D/2D NMR techniques and mass spectrometry besides a joint study on new β-CD monomers (named as A and B) and on a dimer (Di-CD) and a trimer (Tri-CD). The obtained results demonstrate that the tumbling effect can be shifted in the presence of an appropriate hydrophobic guest resulting in the full host-ability of the CD units in water for that guest.

Published
2020
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16. 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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17. 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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18. Dendrimers and hyper-branched polymers interacting with clays: fruitful associations for functional materials

Author

Mohamed Hajjaji, Béatrice Delavaux-Nicot, Régis Laurent, Anne-Marie Caminade, Abdellah Beraa, 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 physico chimie des matériaux et environnement-FSS de Marrakech (LPCME), Faculté des Sciences Semlalia [Marrakech], Université Cadi Ayyad [Marrakech] (UCA)-Université Cadi Ayyad [Marrakech] (UCA), CNRS, LIA LCMMF, 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 Faculté des Sciences Semlalia

Subjects
chemistry.chemical_classification, Materials science, Polymer science, Renewable Energy, Sustainability and the Environment, 02 engineering and technology, General Chemistry, Polymer, 021001 nanoscience & nanotechnology, Smart material, 6. Clean water, Characterization (materials science), chemistry, Dendrimer, Self-healing hydrogels, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Materials Science, 0210 nano-technology, Clay minerals
Abstract

International audience; The possibility to incorporate diverse chemical species inside clays, especially swelling clay minerals, has been known for more than two millennia, but the first examples of man-made polymers interacting with clays only date back to about 30 years ago. Dendrimers and hyper-branched polymers differ from classical polymers by their intrinsically 3-dimensional structure, and by their large number of reactive functional groups. The study of their interaction with clays/clay minerals is relatively recent. Besides the fundamental research done on these kinds of organoclays, different potential uses have already been investigated. In this review, we will present an overview of the studies dealing with the synthetic processes, and the characterization of the resulting dendrimer/hyper-branched polymer–clay mineral (nano)composites. Special attention will be focussed on the properties of these new hybrid smart materials, in different fields ranging from catalysis, trapping gases (in particular CO2 and H2), energy conversion and storage, flame retardants, and biology (biosensors, hydrogels, and drug delivery) to water treatment (wastewater and water-based drilling fluids).

Published
2019
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19. 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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20. 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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21. 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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22. In Search of a Phosphorus Dendrimer-Based Carrier of Rose Bengal: Tyramine Linker Limits Fluorescent and Phototoxic Properties of a Photosensitizer

Author

Anna Janaszewska, Monika Marcinkowska, Régis Laurent, Krzysztof Sztandera, Barbara Klajnert-Maculewicz, Michał Gorzkiewicz, Serge Mignani, Jean-Pierre Majoral, Maria Zablocka, Department of General Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, University of Lódź, 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), Department of Bioorganic Chemistry Centre of Molecular and Macromolecular Studies Polish Academy of Sciences, Polish Academy of Sciences (PAN), Centro de Química da Madeira, Universidade da Madeira (UMA), 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), Leibniz-Institut für Polymerforschung Dresden e.V. (IPF), Leibniz Association, National Science Centre, Poland (Project UMO-2017/25/B/NZ7/01304 'Phosphorus dendrimers as carriers for photosensitizers-in vivo studies', 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
0301 basic medicine, Skin Neoplasms, medicine.medical_treatment, Photodynamic therapy, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 02 engineering and technology, lcsh:Chemistry, chemistry.chemical_compound, Mice, Rose bengal, Tumor Cells, Cultured, Photosensitizer, lcsh:QH301-705.5, Spectroscopy, Drug Carriers, Photosensitizing Agents, Cell Death, Singlet Oxygen, skin cancer, Singlet oxygen, Phosphorus, General Medicine, 021001 nanoscience & nanotechnology, 3. Good health, Computer Science Applications, photodynamic therapy, rose bengal (RB), 0210 nano-technology, Dendrimers, Tyramine, Catalysis, Article, Inorganic Chemistry, 03 medical and health sciences, Dendrimer, phosphorus dendrimers, medicine, Animals, [CHIM.COOR]Chemical Sciences/Coordination chemistry, MTT assay, Physical and Theoretical Chemistry, Molecular Biology, Fluorescent Dyes, Rose Bengal, Organic Chemistry, Combinatorial chemistry, 030104 developmental biology, lcsh:Biology (General), lcsh:QD1-999, chemistry, Photochemotherapy, Carcinoma, Basal Cell, Nanocarriers, Reactive Oxygen Species, Linker
Abstract

Photodynamic therapy (PDT) is a skin cancer treatment alternative to chemotherapy and radiotherapy. This method exploits three elements: a phototoxic compound (photosensitizer), light source and oxygen. Upon irradiation by light of a specific wavelength, the photosensitizer generates reactive oxygen species triggering the cascade of reactions leading to cell death. The positive therapeutic effect of PDT may be limited due to low solubility, low tumor specificity and inefficient cellular uptake of photosensitizers. A promising approach to overcome these obstacles involves the use of nanocarrier systems. The aim of this initial study was to determine the potential of the application of phosphorus dendrimers as carriers of a photosensitizer&mdash, rose bengal (RB). The primary goal involved the synthesis and in vitro studies of covalent drug&ndash, dendrimer conjugates. Our approach allowed us to obtain RB&ndash, dendrimer conjugates with the use of tyramine as an aromatic linker between the carrier and the drug. The compounds were characterized by FT-IR, 1H NMR, 13C NMR, 31P NMR, size and zeta potential measurements and spectrofluorimetric analysis. The dialysis to check the drug release from the conjugate, flow cytometry to specify intracellular uptake, and singlet oxygen generation assay were also applied. Finally, we used MTT assay to determine the biological activity of the tested compounds. The results of our experiments indicate that the conjugation of RB to phosphorus dendrimers via the tyramine linker decreases photodynamic activity of RB.

Published
2020
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23. Potent Anticancer Efficacy of First‐In‐Class Cu II and Au III Metaled Phosphorus Dendrons with Distinct Cell Death Pathways

Author

Jérôme Bignon, Yu Fan, Jean-Pierre Majoral, Li Jin, Anne-Marie Caminade, Serge Mignani, Régis Laurent, Xiangyang Shi, Liang Chen, Jieru Qiu, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University (CCEB), Donghua University [Shanghai], Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Cité (UPCité), Centro de Química da Madeira, Universidade da Madeira (UMA), National Natural Science Foundation of China (21911530230, 21773026, and 81761148028), Sino-French Cai Yuanpei Programme, FCT - Fundacao para a Ciencia e a Tecnologia, Portuguese Government funds - CQM Strategic Project PEst-OE/ QUI/UI0674/2013, ARDITI-Agencia Regional parao Desenvolvimento da Investigacao Tecnologia - project M1420-01–0145-FEDER-000005-Centro de Quımica da Madeira-CQM+ (Madeira 14–20 Program), CNRS, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Paris (UP)

Subjects
Programmed cell death, Dendrimers, Stereochemistry, Chromosomal translocation, Apoptosis, Imaging agents, Mitochondrion, 010402 general chemistry, 01 natural sciences, Catalysis, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Cytotoxicity, Alkyl, chemistry.chemical_classification, Dendrons, biology, 010405 organic chemistry, Chemistry, Cytochrome c, Organic Chemistry, General Chemistry, Antiproliferation, 3. Good health, 0104 chemical sciences, biology.protein, Fluorescent probes
Abstract

International audience; First-in-class CuII and AuIII metaled phosphorus dendrons were synthesized and showed significant antiproliferative activity against several aggressive breast cancer cell lines. The data suggest that the cytotoxicity increases with reducing length of the alkyl chains, whereas the replacement of CuII with AuIII considerably increases the antiproliferative activity of metaled phosphorus dendrons. Very interestingly, we found that the cell death pathway is related to the nature of the metal complexed by the plain dendrons. CuII metaled dendrons showed a potent caspase-independent cell death pathway, whereas AuIII metaled dendrons displayed a caspase-dependent apoptotic pathway. The complexation of plain dendrons with AuIII increased the cellular lethality versus dendrons with CuII and promoted the translocation of Bax into the mitochondria and the release of Cytochrome C (Cyto C).

Published
2020
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24. 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

25. 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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26. 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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27. Dendrimers-containing organoclays: Characterisation and interaction with methylene blue

Author

M. Hajjaji, Abdellah Beraa, Régis Laurent, Anne-Marie Caminade, Laboratoire de physico chimie des matériaux et environnement-FSS de Marrakech (LPCME), Faculté des Sciences Semlalia, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
Nanocomposite, Inorganic chemistry, Substituent, Geology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Montmorillonite, Adsorption, chemistry, Geochemistry and Petrology, Dendrimer, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Clay minerals, High-resolution transmission electron microscopy, Methylene blue
Abstract

International audience; The structure of organoclays composed of synthesized phosphorus-based dendrimers, which was endowed with peripheral ammonium groups, and stevensite- or montmorillonite-rich clays was examined using X-ray diffraction, high resolution transmission electron microscopy, thermal analysis and solid-state nuclear magnetic resonance. The interactions between methylene blue (MB) and the organoclays or Na+-saturated clay minerals were investigated. The results showed that both dendrimers adsorbed on Na+-saturated clay minerals by cation exchange, and that the organoclays, particularly those of the first generation dendrimers, were mainly composed of intercalated nanocomposites. As a result of the adsorption of the dendrimers, the clay hydrophilicity reduced and the dehydroxylation temperature of the clay minerals increased. Regarding the adsorption of MB on the organoclays, the results pointed out that MB mainly adsorbed as MB+ and MBH2 +, and the electronic environments of AlIV of montmorillonite and that of AlVI of stevensite were disturbed. For some organoclays, ordered structures were formed, and the Si4 + substituent (Al3 +) left the tetrahedral sheet. The thermodynamic data indicated that MB adsorbed spontaneously (− 11.3 < ∆ G° < − 0.9 kJ/mol) and the uptake of MB by montmorillonite-based organoclays was believed to occur by chemisorption. In contrast, for stevensite-based organoclays MB adsorption seemed to be accomplished by physisorption.

Published
2017
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28. The synthesis and characterization of giant Calixarenes

Author

Stéphane Viel, Ludovic Costa, Bénédicte Lepoittevin, Philippe Roger, Didier Gigmes, Cyril Martini, Vincent Guérineau, Vincent Huc, Pascale Saint-Aguet, Marion Rollet, Régis Laurent, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Radicalaire (ICR), Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie moléculaire et thioorganique (LCMT), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Le Havre Normandie (ULH), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-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), Laboratoire de chimie de coordination (LCC), 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)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), 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), 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), 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
0301 basic medicine, Science, Formaldehyde, General Physics and Astronomy, chemistry.chemical_element, 02 engineering and technology, Article, General Biochemistry, Genetics and Molecular Biology, Rubidium, 03 medical and health sciences, chemistry.chemical_compound, Calixarene, Phenol, [CHIM]Chemical Sciences, Phenols, lcsh:Science, Multidisciplinary, Condensation, General Chemistry, 021001 nanoscience & nanotechnology, Combinatorial chemistry, 3. Good health, Characterization (materials science), 030104 developmental biology, chemistry, lcsh:Q, 0210 nano-technology
Abstract

Calixarenes are cyclic oligomers obtained by condensation of suitable p-functionalised phenols with formaldehyde, usually allowing for the synthesis of the well known small calixarenes (including up to eight phenolic subunits). We report here the discovery of much larger members of this family, exhibiting sizes up to 90 phenolic subunits: the giant calixarenes. These macrocycles are obtained according to simple, easily scalable processes, in yields up to 65%. We show that the formation of these giant macrocycles is favored by an oxygen-containing-group at the para-position of the starting phenol, high concentrations of heavy alkaline bases (rubidium or cesium hydroxides) and long reaction times. A mechanism is proposed to rationalize these observations. These giant macrocycles can also be obtained in the quasi-solid state, opening interesting perspectives in the field of calixarenes chemistry. Along with their intrinsic fundamental interest, these objects are also opening interesting applicative potentialities., Calixarenes are cyclic oligomers obtained by condensation reactions between phenols and formaldehyde and usually include up to eight phenolic subunits. Here the authors demonstrate the synthesis of calixarenes with up to 90 phenolic subunits with up to 65% yield via a scalable process.

Published
2019
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29. Dendrimers Functionalized with Palladium Complexes of N-, N,N-, and N,N,N-Ligands

Author

Régis Laurent, Quentin Vanbellingen, Anaïs Coinaud, Paul Servin, Anne-Marie Caminade, Sonia Mallet-Ladeira, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Technologie Servier, CNRS (Centre National de la Recherche Scientifique), GRD Phosphore, Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Imine, Pharmaceutical Science, Sonogashira coupling, chemistry.chemical_element, Ligands, 010402 general chemistry, 01 natural sciences, Article, Catalysis, Analytical Chemistry, chemistry.chemical_compound, Bipyridine, QD241-441, Complexes, Dendrimer, Drug Discovery, Pyridine, Polymer chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Phenol, 010405 organic chemistry, Chemistry, Organic Chemistry, X-ray diffraction, 0104 chemical sciences, Monomer, Chemistry (miscellaneous), Molecular Medicine, Palladium
Abstract

International audience; Pyridine, pyridine imine, and bipyridine imine ligands functionalized by a phenol have been synthesized and characterized, in many cases by X-ray diffraction. Several of these N-, N,N-, and N,N,N,-ligands have been grafted onto the surface of phosphorhydrazone dendrimers, from generation 1 to generation 3. The complexation ability of these monomers and dendrimers towards palladium(II) has been assayed. The corresponding complexes have been either isolated or prepared in situ. In both cases, the monomeric and dendritic complexes have been tested as catalysts in Heck couplings and in Sonogashira couplings. In some cases, a positive dendritic effect has been observed, that is, an increase of the catalytic efficiency proportional to the dendrimer generation.

Published
2021
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30. 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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31. Dendritic metal complexes for bioimaging. Recent advances

Author

Régis Laurent, Jean-Pierre Majoral, Aurélien Hameau, Cédric-Olivier Turrin, and Anne-Marie Caminade

Subjects
medicine.diagnostic_test, 010405 organic chemistry, Gadolinium, chemistry.chemical_element, Context (language use), 010402 general chemistry, Technetium, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Positron emission tomography, Dendrimer, Materials Chemistry, medicine, DOTA, Physical and Theoretical Chemistry, Preclinical imaging, Macromolecule
Abstract

Dendrimers are hyperbranched macromolecules, having a large number of terminal functions, easily accessible and modifiable to afford the desired properties. Metal complexes of dendrimers are frequently used as catalysts in diverse reactions, but they can be used also as innovative biological tools. This review focusses on the recent advances (last 10 years) of dendritic metal complexes used for bioimaging, essentially in vivo. Three main domains will be covered. The first one concerns luminescent complexes for optical imaging (OI). The second one is the largest one; it concerns magnetic resonance imaging (MRI) contrast agents, mostly based on gadolinium complexes. The third and last domain concerns radioactive dendrimer complexes for single photon emission computed tomography (SPECT), and also for positron emission tomography (PET). Two main radionuclides are used in this context, technetium (99mTc) and indium (111In). Two types of ligands are generally used for all these complexes in the two last domains, diethylenetriaminepentaacetic acid (DTPA), and a cyclic analogue, 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), and some of their derivatives. These complexes have been used in many cases for in vivo imaging of cancerous tumors in mice or rats.

Published
2021
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32. Du traumatisme des camps à la naissance d'une nouvelle institution : Idéologies, minoritaires et pentecôtisme tsigane en Bretagne - Tome I

Author

Régis Laurent and Régis Laurent

Abstract

Cette recherche sur le pentecôtisme tsigane se développe sur deux tomes profondément indissociables. Ce premier tome nous parle de la naissance du pentecôtisme tsigane dans le contexte traumatique de l'après-Deuxième Guerre Mondiale. Cette recherche est la première sur de cette ampleur sur le pentecôtisme tsigane. L'auteur y explique comment une minorité opprimée, pour exister, a crééé sa propre institution religieuse à partir d'un socle commun : le pentecôtisme. Cette contribution à une meilleure connaissance des'mondes tsiganes'démontre en arrière-plan l'importance des services communs comme garants de la cohésion sociale.

Published
2019

33. Les usages sociaux des pentecôtistes tsiganes : Idéologies, minoritaires et pentecôtisme tsigane en Bretagne - Tome II

Author

Régis Laurent and Régis Laurent

Abstract

Cette recherche sur le pentecôtisme tsigane se développe sur deux tomes profondément indissociables. Dans la continuité du premier, ce second tome nous parle plus longuement des forces et des idéologies dominantes qui ont intéragi avec cet avènement d'un pentecôtisme dans les mondes tsiganes et les pratiques sociales observées dans ce contexte particulier. Cette recherche est la première de cette ampleur sur le pentecôtisme tsigane. L'auteur y explique comment une minorité opprimée, pour exister, a créé sa propre institution religieuse à partir d'un socle commun : le pentecôtisme. Cette contribution à une meilleure connaissance des'mondes tsiganes'démontre en arrière-plan l'importance des services communs comme garants de la cohésion sociale.

Published
2019

34. Cyclotriphosphazene, an old compound applied to the synthesis of smart dendrimers with tailored properties

Author

Armelle Ouali, Kathleen Moineau Chane-Ching, Cyrille Rebout, Jean-Pierre Majoral, Aurélien Hameau, Anne-Marie Caminade, Cédric-Olivier Turrin, Béatrice Delavaux-Nicot, Régis Laurent, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
Dendrimers, ICPC-21, 010405 organic chemistry, Chemistry, General Chemical Engineering, Nanotechnology, General Chemistry, 010402 general chemistry, 01 natural sciences, Chemical synthesis, Phosphorus chemistry, 0104 chemical sciences, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract

The versatile reactivity of hexachlorocyclotriphosphazene (N3P3Cl6) has been developed for the synthesis of specifically engineered dendrimers. Dendrimers are hyperbranched macromolecules built by concentric layers constituted of associated monomeric units. Many of the properties of dendrimers depend on the type of their surface (terminal) functions, which are generally all identical. For some specific purposes, it is desirable to have one function that is different at the level of the core. Hexachlorocyclotriphosphazene offers the possibility to differentiate the reactivity of one (or more) Cl from the others, for producing specifically engineered dendritic tools. These specific reactions on N3P3Cl6 have produced highly dense dendrimers, Janus dendrimers (two faces), tools for functionalizing materials, with uses as catalysts, as chemical sensors, for trapping CO2, for the culture of cells, or for imaging biological events. These properties will be emphasized in this review.

Published
2016
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35. Novel Methinic Functionalized and Dendritic C-Scorpionates

Author

Paul Servin, Anne-Marie Caminade, Armando J. L. Pombeiro, Régis Laurent, Riccardo Wanke, Telma F. S. Silva, Luísa M. D. R. S. Martins, Centro de Química Estrutural, Faculdade de Ciências da Universidade de Lisboa, Faculdade de Ciencias da Universidade de Lisboa, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
Dendrimers, pyrazolyl, Pharmaceutical Science, Sonogashira coupling, Ligands, 010402 general chemistry, dendrimer, 01 natural sciences, Catalysis, Article, Analytical Chemistry, lcsh:QD241-441, C c coupling, lcsh:Organic chemistry, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Organic Chemicals, Physical and Theoretical Chemistry, Chelating ligands, Molecular Structure, 010405 organic chemistry, Chemistry, Organic Chemistry, Sonogashira, Combinatorial chemistry, tris(pyrazolyl)methane, 0104 chemical sciences, coordination flexibility, Chemistry (miscellaneous), Molecular Medicine, Surface modification, functionalization, C-scorpionate, Heck, C-C coupling, Methane, catalyst
Abstract

The study of chelating ligands is undoubtedly one of the most significant fields of research in chemistry. The present work is directed to the synthesis of new functionalized derivatives of tripodal C-scorpionate compounds. Tris-2,2,2-(1-pyrazolyl)ethanol, HOCH2C(pz)3 (1), one of the most important derivatives of hydrotris(pyrazolyl)methane, was used as a building block for the synthesis of new functionalized C-scorpionates, aiming to expand the scope of this unexplored class of compounds. The first dendritic C-scorpionate was successfully prepared and used in the important industrial catalytic reactions, Sonogashira and Heck C-C cross-couplings.

Published
2018
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36. Adsorption capacity of sodic- and dendrimers-modified stevensite

Author

Anne-Marie Caminade, Régis Laurent, M. Hajjaji, Abdellah Beraa, Yannick Coppel, Laboratoire de physico chimie des matériaux et environnement-FSS de Marrakech (LPCME), Faculté des Sciences Semlalia, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), 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
Chromate conversion coating, Chemistry, Diffusion, Kinetics, Inorganic chemistry, Langmuir adsorption model, Chemical modification, 020101 civil engineering, Protonation, 02 engineering and technology, Nuclear magnetic resonance spectroscopy, 021001 nanoscience & nanotechnology, 0201 civil engineering, symbols.namesake, Adsorption, Geochemistry and Petrology, symbols, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology
Abstract

The adsorption capacities of nano-sized organoclays composed of a stevensite-rich clay (R), phosphorus dendrimers (GC1 and GC2) and Na+-saturated clay were evaluated for their capacity to adsorb chromate and methylene blue (MB) in the range of 298–318 K. The adsorption kinetics and the isotherms were analysed based on kinetic equations and isotherm models and by adopting a non-linear regression procedure. In addition, the organoclays and the Na+-saturated clays were characterized principally by solid-state nuclear magnetic resonance spectroscopy. The pseudo-second-order rate equation described kinetics data well, and the adsorption rates were not limited by the intraparticle diffusion or by the liquid film diffusion. Both chemical species were adsorbed spontaneously (–31 <ΔG°T<–10 kJ/mol), but the adsorbents had a high affinity for MB species. The adsorption isotherms of chromate were fitted better by the Freundlich model, while those of MB followed the Langmuir model. Chromate adsorption took place at the edges and the free surfaces of stevensite, particularly at the protonated aluminols. MB was adsorbed as MBH2+and MB+. The MB protonation occurred at the clay surfaces, and MB+ions were located at the planar surfaces of stevensite as well as at the external surfaces of aggregates. Moreover, the tetrahedral sheet of stevensite involved in the formation of GC1-based organoclays was the subject of a partial chemical modification.

Published
2018
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39. Vibrational spectroscopic investigation of the gold complexation within the cascade structure of phosphorus-containing dendrimer

Author

Jean-Pierre Majoral, A.E. Vandyukov, Régis Laurent, Sébastien Gottis, Valeri I. Kovalenko, V.L. Furer, Anne-Marie Caminade, Kazan State Architect and Civil Engineering University, University of Kazan, A.E. Arbuzov Institute of Organic and Physical Chemistry (IOPC), Kazan Scientific Centre of the Russian Academy of Sciences, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Kazan National Research Technological University

Subjects
Chemistry, 02 engineering and technology, Interaction energy, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Quantum chemistry, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, Analytical Chemistry, Delocalized electron, Crystallography, Electron affinity, Dendrimer, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ionization energy, 0210 nano-technology, Instrumentation, HOMO/LUMO, Spectroscopy
Abstract

International audience; The interaction of the phosphoric dendrimer with gold was performed by means of vibrational spectroscopy and quantum chemistry. Stable complexes are formed with a PN−PS linkage, whereas with an isolated PS bond this does not occur. The change in geometric parameters and delocalization of electric charge under the influence of gold was discovered. The classification of bands in the experimental vibrational spectra of the dendrimer and its complex was carried out. HOMO of molecule of the dendrimer is localized on the SPNP linkage, whereas the LUMO is located on the terminal group. In the SPNP linkage there is a noticeable delocalization of the charge which leads to a change in the reactivity of this group. Interaction energy was estimated as the difference between the energies of the complex and the energies of the molecules of the dendrimer G′0 and two molecules AuCl and is equal to 25.2 eV. The ionization energy IE and electron affinity EA for AuCl are higher than for dendrimer, therefore, when the complex is formed, these quantities increases. Chemical potential and the electrophilicity index in the complex also increases.

Published
2018
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40. Recent therapeutic applications of the theranostic principle with dendrimers in oncology

Author

Xiangyang Shi, Anne-Marie Caminade, Régis Laurent, Serge Mignani, João Rodrigues, Jean-Pierre Majoral, Helena Tomás, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Université Paris Descartes - Paris 5 (UPD5), Université Sorbonne Paris Cité (USPC), Centro de Química da Madeira, Universidade da Madeira (UMA), School of Materials Science and Engineering, Northwestern Polytechnical University (NPU), School of Materials Science and Engineering, Northwestern Polytechnical University, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), State Key Laboratory for Fiber & Material Modification of Donghua University, Donghua University [Shanghai], Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Oncology, medicine.medical_specialty, Dendrimers, Materials science, Computed tomography imaging, Hyperbranched polymers, Nanoparticle, Computed tomography, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Theranostic platforms, Optical imaging, Faculdade de Ciências Exatas e da Engenharia, Magnetic resonance imaging, Gamma scintigraphy, Internal medicine, Dendrimer, medicine, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, medicine.diagnostic_test, Gamma scintigraphy imaging, 021001 nanoscience & nanotechnology, 0104 chemical sciences, 3. Good health, Microbubbles, 0210 nano-technology
Abstract

International audience; At the intersection between treatment and diagnosis, nanoparticles technologies are strongly impacting the development of both therapeutic and diagnostic agents. Consequently, the development of novel modalities for concomitant noninvasive therapy and diagnostics known as theranostics as a single platform has gained significant interests. These multifunctional theranostic platforms include carbon-based nanomaterials (e.g., carbon nanotubes), drug conjugates, aliphatic polymers, micelles, vesicles, core-shell nanoparticles, microbubbles and dendrimers bearing different contrast agents and drugs, such as cytotoxic compounds in the oncology domain. Dendrimers emerged as a new class of highly tunable hyperbranched polymers, and have been developed as useful theranostic platforms. Magnetic resonance imaging, gamma scintigraphy, computed tomography and optical imaging are the main techniques developed with dendrimers in the theranostic domain in oncology. Different imaging agents have been used such as Gd(III), 19F, Fe2O3 (MRI), 76Br (PET), 111In, 88Y, 153Gd, 188Re, 131I (SPECT), 177Lu, gold (CT) and boronated groups, siliconnaphthalocyanines, dialkylcarbocyanines and QDs (optical imaging dyes).

Published
2018
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41. Dual properties of water-soluble Ru-PTA complexes of dendrimers: Catalysis and interaction with DNA

Author

Mar Tristany, Anne-Marie Caminade, Antonio Romerosa, Régis Laurent, Maurizio Peruzzini, Paul Servin, Federico García-Maroto, 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), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées, Area de Quimica Inorganica - Centro de Investigacion en Energia Solar (CIESOL) (CIESOL), Universidad de Almería (UAL), Istituto di Chimica dei Composti Organometallici (ICCOM), Consiglio Nazionale delle Ricerche (CNR), and Area de Bioquimica y Biologia Molecular, Universidad de Almeria

Subjects
In situ, Dendrimers, chemistry.chemical_element, Homogeneous catalysis, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, PTA phosphine, Complexes, Dendrimer, Polymer chemistry, Materials Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, 010405 organic chemistry, Chemistry, 0104 chemical sciences, Ruthenium, DNA interaction, Phenylacetylene, DNA supercoil, DNA
Abstract

International audience; Phosphorhydrazone dendrimers ended by PTA (1,3,5-triaza-7-phosphaadamantane) derivatives are used for the complexation of ruthenium. The corresponding complexes, either isolated (synthesized ex situ, i.e. preformed) or generated in situ are used as catalysts for the hydration of phenylacetylene in various conditions (ex situ or in situ, quantities, temperature, duration, co-catalyst or not, recycling). The same preformed complexes are tested for their interaction with supercoiled DNA, to afford relaxed DNA.

Published
2017
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42. 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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43. Catalysis Within Dendrimers

Author

Régis Laurent, Armelle Ouali, 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), and Poli, R.

Subjects
010405 organic chemistry, Chemistry, Asymmetric hydrogenation, Nanotechnology, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, Catalysis, Covalent bond, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Catalytic efficiency, Metal nanoparticles, ComputingMilieux_MISCELLANEOUS, Macromolecule
Abstract

Dendrimers are hyperbranched macromolecules, synthesized step by step (generation after generation) in an iterative fashion, which structure is reminiscent to that of the branches of trees. Most of their properties are due to their terminal functions, which can be easily modified at will to fulfill the desired properties. In particular, many types of catalytic entities have been used as terminal groups of dendrimers. In some cases, a dendritic effect , that is the enhancement of the catalytic properties when a catalyst is linked to a dendrimer, has been observed. It is also generally possible to recover and reuse the dendritic catalysts. The internal structure of dendrimers can also play a key-role, as it manages cavities which can accommodate the catalytic entities, and enable the substrates to interact with them. Catalytic sites included inside the structure of dendrimers are rare, excepted if they constitute the core of dendrimers (or of dendrons, which are dendritic wedges). Effect of the confinement on the catalysis outcome is generally the main aim of these works. Another type of dendritic catalytic entities taking profit of the internal structure concerns metallic nanoparticles used as core of dendrimers. In this chapter, we will gather information about catalytic entities included inside dendrimers, either covalently linked, or noncovalently entrapped, and on their syntheses. The main types of reactions studied, the role of the generation (size) of the dendrimers, their recovery and reuse, and in general the effect of the confinement inside the dendritic structures on the catalytic efficiency will be discussed.

Published
2017
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44. Poly(phosphorhydrazone) metallodendrimers. A review

Author

Anne-Marie Caminade, Régis Laurent, Armelle Ouali, 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), 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
Lanthanide, Chemistry, Nanoparticle, Nanotechnology, [CHIM.CATA]Chemical Sciences/Catalysis, Catalysis, Inorganic Chemistry, Transition metal, Dendrimer, Materials Chemistry, Surface modification, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Metal nanoparticles, ComputingMilieux_MISCELLANEOUS
Abstract

Poly(phosphorhydrazone) dendrimers constitute a versatile class of dendrimers, which can be functionalized at will at all levels of the structure (surface, core, branches) with various types of ligands (mono-, bi-, multi-dentate ligands), suitable for the complexation of different types of metals, including transition metals, lanthanides, or alkaline earths. This review is organized depending on the type of ligands. The properties of the corresponding complexes have been studied in many cases, and will be given. Most of the properties concern catalysis; a positive dendrimeric effect has been observed in many cases when the generation of the dendrimer increases. In many cases it is possible to recover the catalyst and to reuse it (up to ten times with the same efficiency). Other properties concern the field of materials, with the functionalization of the surface of electrodes, in particular with ferrocene-containing dendrimers, or the elaboration of metallic nanoparticles, and even their organization in dendritic networks. A single example of property in the field of biology is given, but it constitutes a promising result as anti-proliferative agents against cancerous cells.

Published
2014
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45. Diversified Strategies for the Synthesis of Bifunctional Dendrimeric Structures

Author

Régis Laurent, Carine Duhayon, Alexandra Chaumonnot, David Riegert, Cédric-Olivier Turrin, Sabine Fuchs, Anne-Marie Caminade, Jean-Pierre Majoral, and Anna Pla-Quintana

Subjects
Primary (chemistry), 010405 organic chemistry, Organic Chemistry, macromolecular substances, 010402 general chemistry, Grafting, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Group (periodic table), Dendrimer, Organic chemistry, 31p nmr spectroscopy, Physical and Theoretical Chemistry, Bifunctional
Abstract

The synthesis of three new families of dendrimeric compounds possessing two different types of functions is reported. These functions are triethoxysilyl group(s), potentially suitable for grafting onto materials, in particular silica, and primary amines (in their protected form), potentially suitable for trapping CO2. All these dendrimeric compounds are based on phosphorus dendrimers, and possess either one Si(OEt)3 group at the core of dendrons or of “off-centre” dendrimers, or several Si(OEt)3 groups precisely placed on half of the terminal groups. These compounds are characterized by 31P NMR spectroscopy, which affords precious information on the structure, confirmed, in one case, by the X-ray diffraction structure of a first-generation dendrimer.

Published
2013
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46. 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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47. Frontispiece: Ordered Layered Dendrimers Constructed from Two Known Dendrimer Families: Inheritance and Emergence of Properties

Author

Sonia Mallet-Ladeira, Anne-Marie Caminade, Menyhárt B. Sárosi, Jean-Pierre Majoral, Béatrice Delavaux-Nicot, Alix Sournia-Saquet, Cyrille Rebout, Evamarie Hey-Hawkins, Régis Laurent, and Hanna Dib

Subjects
Piperazine, chemistry.chemical_compound, Inheritance (object-oriented programming), Chemistry, Dendrimer, Organic Chemistry, Organic chemistry, General Chemistry, Catalysis
Published
2016
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48. Coordination chemistry with phosphorus dendrimers. Applications as catalysts, for materials, and in biology

Author

Jean-Pierre Majoral, Anne-Marie Caminade, Cédric-Olivier Turrin, Régis Laurent, Armelle Ouali, 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
chemistry.chemical_classification, 010405 organic chemistry, Nanotechnology, 010402 general chemistry, Heterogeneous catalysis, 01 natural sciences, 0104 chemical sciences, Coordination complex, Catalysis, Inorganic Chemistry, chemistry, Homogeneous, Dendrimer, Materials Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Hybrid material, Metal nanoparticles, Macromolecule
Abstract

International audience; Dendrimers are hyperbranched macromolecules having a perfectly defined and multifunctionalized structure, constituted of branches emanating radially from a central core. The structure of dendrimers is particularly modular, and can incorporate in different parts coordination complexes. In this review, we will present the interplay between dendrimers and coordination chemistry in three main fields: catalysis, materials, and biology. Most of the examples will be taken from the work done with phosphorus-containing dendrimers, but the pioneering work carried out with other dendrimers will be also presented. One of the major improvements that metallodendrimers have afforded concerning catalysis is their easy recovery and reuse, bridging the gap between homogeneous and heterogeneous catalysis. Another major improvement concerns the “dendritic effect” which can afford impressive outcomes concerning the increase of yield and of enantioselectivity, together with a decrease of the leaching of metals, and consequently of waste. Dendrimers can be used also for the synthesis and stabilization of metallic nanoparticles, for the modification of metallic surfaces at the nanometric scale, and for the synthesis of mesoscopically ordered hybrid materials. Finally metallodendrimers have high potency against cancerous cell lines, and they appear to operate via a different mechanism of action compared with native metallodrugs, opening new avenues for the search of improved anti-cancer agents.

Published
2016
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49. Ordered layered dendrimers constructed from two known dendrimer families: Inheritance and emergence of properties

Author

Jean-Pierre Majoral, Cyrille Rebout, Régis Laurent, Hanna Dib, Sonia Mallet-Ladeira, Menyhárt B. Sárosi, Alix Sournia-Saquet, Béatrice Delavaux-Nicot, Evamarie Hey-Hawkins, 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), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées, Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC), Institut für Anorganische Chemie, Universität Leipzig, and Universität Leipzig [Leipzig]

Subjects
010405 organic chemistry, Chemistry, Dendrimer, Organic Chemistry, Organic chemistry, Thermal stability, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences
Abstract

International audience; A new concept is presented, namely the synthesis of dendrimers intrinsically composed in alternation of building blocks pertaining to two known families of dendrimers: phosphorhydrazone dendrimers and triazine–piperazine dendrimers. These mixed dendrimers with layered controlled architecture inherit their easy 31P NMR characterization and their thermal stability from the phosphorhydrazone family, and their decreased solubility from the triazine–piperazine family. However, they have also their own and original characteristics. Both parent families are white powders, whereas the mixed dendrimers are yellow, orange, or red powders, depending on the generation. DFT calculations were carried out on model dendrons to understand these special color features. Remarkably, these dendrimers incorporating redox-active organic entities allow for the first time the monitoring of the growth of an organic dendrimer by electrochemistry while highlighting an even–odd generation behavior.

Published
2016
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50. Removal of chromate from aqueous solutions by dendrimers-clay nanocomposites

Author

Abdellah Beraa, Anne-Marie Caminade, Mohamed Hajjaji, Régis Laurent, Béatrice Delavaux-Nicot, Laboratoire de physico chimie des matériaux et environnement-FSS de Marrakech (LPCME), Faculté des Sciences Semlalia, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées

Subjects
Nanocomposite, Materials science, Aqueous solution, Chromate conversion coating, Inorganic chemistry, Cationic polymerization, 020101 civil engineering, Ocean Engineering, 02 engineering and technology, 021001 nanoscience & nanotechnology, Pollution, 0201 civil engineering, chemistry.chemical_compound, Montmorillonite, Adsorption, chemistry, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Thermal analysis, Water Science and Technology
Abstract

International audience; Nanocomposites of phosphorus-based dendrimers and montmorillonite were prepared and examined using X-ray diffraction, thermal analysis, solid-state nuclear magnetic resonance, and high-resolution transmission electron microscope. The adsorption of chromate by the nanocomposites and the basic clay was studied in the temperature range 298-318 K. For the latter purpose, the kinetics was followed and adsorption isotherms were plotted. The results showed that intercalated nanocomposites (GC1-AT) were formed with the first generation of cationic dendrimers. The use of the second generation of cationic dendrimers resulted in the formation of a mixture of exfoliated and intercalated nanocomposites (GC2-AT). For both dendrimers, adsorption was by cation exchange. The kinetics of the adsorption of chromate on both nanocomposites and Na-saturated montmorillonite (Na-AT) followed the pseudo-second-order equation and the rate constants varied in 0.08-0.19 g/mmol s-1. The rate-limiting steps were discussed on the basis of the results of the external mass transfer and the internal diffusion models. The experimental isotherms fitted will the model of Temkin, and chromate adsorption was an endothermic process and occurred spontaneously (-13

Published
2016
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