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114 results on '"Cédric-Olivier Turrin"'

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

Author

Massimo Petriccone, Régis Laurent, Cédric-Olivier Turrin, Rosa Maria Sebastián, and Anne-Marie Caminade

Subjects
dendrimer, phosphorus, bifunctionalization, polyphosphorhydrazone, properties, Organic chemistry, QD241-441
Abstract

Dendrimers are highly branched macromolecules possessing, in most cases, identical terminal functions. However, it is sometimes desirable to have two types of surface functions in order to fulfil specific properties. The stochastic functionalization is frequently used for such purposes, but the presence of an uncontrolled number of each type of terminal function, albeit acceptable for research purposes, has no practical use. Thus, it is highly desirable to find strategies suitable for the precise grafting of two different functional groups on the surface of dendrimers. The easiest way, and the most widely used, consists in using a bifunctional monomer to be grafted to all of the surface functions of the dendrimers. Two other strategies are known but are rarely used: the modification of an existing function, to generate two functions, and the sequential grafting of one function then of a second function. The three methods are illustrated in this review with polyphosphorhydrazone (PPH) dendrimers, together with their properties as catalysts, for materials, and as biological tools.

Published
2022
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2. AB5 Derivatives of Cyclotriphosphazene for the Synthesis of Dendrons and Their Applications

Author

Artem Zibarov, Abdelouahd Oukhrib, Julien Aujard Catot, Cédric-Olivier Turrin, and Anne-Marie Caminade

Subjects
cyclotriphosphazene, dendron, fluorescence, phosphorus, dendrimer, nanomaterials, Organic chemistry, QD241-441
Abstract

AB5 compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction of five chlorides with one reagent, followed by the reaction of the single remaining Cl with another reagent. This particular property led to the use of such compounds as core for the synthesis of dendrons (dendritic wedges), using the five functions for growing the dendritic branches. The single function can be used for the synthesis of diverse types of dendrimers (onion peel, dumbbell-shape, Janus), for covalent or non-covalent grafting to solid surfaces, providing nanomaterials, for grafting a fluorophore, especially for studying biological mechanisms, or for self-associations to get micelles. All these properties are reviewed in this paper.

Published
2021
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3. Supramolecular and Macromolecular Matrix Nanocarriers for Drug Delivery in Inflammation-Associated Skin Diseases

Author

Ranime Jebbawi, Séverine Fruchon, Cédric-Olivier Turrin, Muriel Blanzat, and Rémy Poupot

Subjects
atopic dermatitis, dendrimer, drug delivery, nanocarrier, psoriasis, skin inflammation, Pharmacy and materia medica, RS1-441
Abstract

Skin is our biggest organ. It interfaces our body with its environment. It is an efficient barrier to control the loss of water, the regulation of temperature, and infections by skin-resident and environmental pathogens. The barrier function of the skin is played by the stratum corneum (SC). It is a lipid barrier associating corneocytes (the terminally differentiated keratinocytes) and multilamellar lipid bilayers. This intricate association constitutes a very cohesive system, fully adapted to its role. One consequence of this efficient organization is the virtual impossibility for active pharmaceutical ingredients (API) to cross the SC to reach the inner layers of the skin after topical deposition. There are several ways to help a drug to cross the SC. Physical methods and chemical enhancers of permeation are a possibility. These are invasive and irritating methods. Vectorization of the drugs through nanocarriers is another way to circumvent the SC. This mini-review focuses on supramolecular and macromolecular matrices designed and implemented for skin permeation, excluding vesicular nanocarriers. Examples highlight the entrapment of anti-inflammatory API to treat inflammatory disorders of the skin.

Published
2020
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4. An Anti-Inflammatory Poly(PhosphorHydrazone) Dendrimer Capped with AzaBisPhosphonate Groups to Treat Psoriasis

Author

Ranime Jebbawi, Abdelouahd Oukhrib, Emily Clement, Muriel Blanzat, Cédric-Olivier Turrin, Anne-Marie Caminade, Eric Lacoste, Séverine Fruchon, and Rémy Poupot

Subjects
dendrimer, drug candidate, imiquimod mouse model, inflammation, phosphonate, preclinical efficacy, Microbiology, QR1-502
Abstract

Dendrimers are nanosized, arborescent macromolecules synthesized in a stepwise fashion with attractive degrees of functionality and structure definition. This is one of the reasons why they are widely used for biomedical applications. Previously, we have shown that a poly(phosphorhydrazone) (PPH) dendrimer capped with anionic azabisphosphonate groups (so-called ABP dendrimer) has immuno-modulatory and anti-inflammatory properties towards human immune cells in vitro. Thereafter, we have shown that the ABP dendrimer has a promising therapeutic efficacy to treat models of acute and chronic inflammatory disorders in animal models. In these models, the active pharmaceutical ingredient was administered systematically (intravenous and oral administrations), but also loco-regionally in the vitreous tissue. Herein, we assessed the therapeutic efficacy of the ABP dendrimer in the preclinical mouse model of psoriasis induced by imiquimod. The ABP dendrimer was administered in phosphate-buffered saline solution via either systemic injection or topical application. We show that the topical application enabled the control of both the clinical and histopathological scores, and the control of the infiltration of macrophages in the skin of treated mice.

Published
2020
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5. Ferrocenyl Phosphorhydrazone Dendrimers Synthesis, and Electrochemical and Catalytic Properties

Author

Cédric-Olivier Turrin, Eric Manoury, and Anne-Marie Caminade

Subjects
ferrocene, dendrimer, catalysis, electrochemistry, Organic chemistry, QD241-441
Abstract

The discovery of ferrocene is often associated with the rapid growth of organometallic chemistry. Dendrimers are highly branched macromolecules that can be functionalized at will at all levels of their structure. The functionalization of dendrimers with ferrocene derivatives can be carried out easily as terminal functions on the surface, but also at the core, or at one or several layers inside the structure. This review will focus on phosphorhydrazone dendrimers functionalized with ferrocene derivatives, on the surface, at the core, at all layers or within a single layer inside the structure. The first part will describe the synthesis; the second part will concern the electrochemical properties; and the last part will give several examples concerning catalysis, with complexes of ferrocenyl phosphines used as terminal functions of dendrimers.

Published
2020
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6. Biodistribution and Biosafety of a Poly(Phosphorhydrazone) Dendrimer, an Anti-Inflammatory Drug-Candidate

Author

Séverine Fruchon, Elisabeth Bellard, Nicolas Beton, Cécile Goursat, Abdelouahd Oukhrib, Anne-Marie Caminade, Muriel Blanzat, Cédric-Olivier Turrin, Muriel Golzio, and Rémy Poupot

Subjects
azabisphosphonate, biodistribution, dendrimers, drug candidate, preclinical development, rabbit, rodents, safety, Microbiology, QR1-502
Abstract

Dendrimers are nanosized, arborescent polymers of which size and structure are perfectly controlled. This is one reason why they are widely used for biomedical purposes. Previously, we showed that a phosphorus-based dendrimer capped with anionic azabisphosphonate groups (so-called ABP dendrimer) has immuno-modulatory and anti-inflammatory properties towards human immune cells in vitro. Thereafter, we have shown that the ABP dendrimer has a promising therapeutic efficacy to treat models of chronic inflammatory disorders. On the way to clinical translation, the biodistribution and the safety of this drug-candidate has to be thoroughly assessed. In this article, we present preliminary non-clinical data regarding biodistribution, hematological safety, genotoxicity, maximal tolerated doses, and early cardiac safety of the ABP dendrimer. One of the genotoxicity assays reveals a potential mutagen effect of the item at a concentration above 200 µM, i.e., up to 100 times the active dose in vitro on human immune cells. However, as the results obtained for all the other assays show that the ABP dendrimer has promising biodistribution and safety profiles, there is no red flag raised to hamper the regulatory pre-clinical development of the ABP dendrimer.

Published
2019
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7. An Azabisphosphonate-Capped Poly(phosphorhydrazone) Dendrimer for the Treatment of Endotoxin-Induced Uveitis

Author

Cédric-Olivier Turrin, Jean-Marc Combette, Jean-Luc Davignon, Claire Abadie, Anne-Marie Caminade, Séverine Fruchon, and Rémy Poupot

Subjects
PPH [poly(phosphorhydrazone)] dendrimer, anti-inflammatory, uveitis, toxicity, Organic chemistry, QD241-441
Abstract

Over the last decade, different types of dendrimers have shown anti-inflammatory properties in their own right. In particular, we have shown that poly(phosphorhydrazone) (PPH) dendrimers are able to foster an efficient anti-inflammatory response in human monocytes and can resolve the main physiopathological features of chronic arthritis in mice at 1 mg/kg. Here we afford new insights into the therapeutic potential of an azabisphosphonate-capped dendrimer (dendrimer ABP). We have challenged its anti-inflammatory and immuno-modulatory properties in a robust rat model of acute uveitis induced by lipopolysaccharide (LPS). We show that dendrimer ABP at 2 µg/eye is as efficient as the “gold standard” dexamethasone at 20 µg/eye. We have demonstrated that the effect of dendrimer ABP is mediated at least through an increase of the production of the anti-inflammatory Interleukin(IL)-10 cytokine.

Published
2013
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8. Biological properties of water-soluble phosphorhydrazone dendrimers

Author

Anne-Marie Caminade, Cédric-Olivier Turrin, and Jean-Pierre Majoral

Subjects
Dendrímeros, Dendrímeros de fosforidrazona, Propriedades biológicas, Nanomedicina, Pharmacy and materia medica, RS1-441
Abstract

Dendrimers are hyperbranched and perfectly defined macromolecules, constituted of branches emanating from a central core in an iterative fashion. Phosphorhydrazone dendrimers constitute a special family of dendrimers, possessing one phosphorus atom at each branching point. The internal structure of these dendrimers is hydrophobic, but hydrophilic terminal groups can induce the solubility of the whole structure in water. Indeed, the properties of these compounds are mainly driven by the type of terminal groups their bear; this is especially true for the biological properties. For instance, positively charged terminal groups are efficient for transfection experiments, as drug carriers, as anti-prion agents, and as inhibitor of the aggregation of Alzheimer's peptides, whereas negatively charged dendrimers have anti-HIV properties and can influence the human immune system, leading to anti-inflammatory properties usable against rheumatoid arthritis. This review will give the most representative examples of the biological properties of water-soluble phosphorhydrazone dendrimers, organized depending on the type of terminal groups they bear.

Published
2013
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9. Fluorescent Groups at the Core of Phosphorus Dendrons and Their Properties

Author

Anne-Marie Caminade, Aurélien Hameau, Kathleen Moineau-Chane Ching, Cédric-Olivier Turrin, 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
Inorganic Chemistry, Dendrimers, Dendron, Organic Chemistry, Drug Discovery, [CHIM]Chemical Sciences, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, [CHIM.CATA]Chemical Sciences/Catalysis, Physical and Theoretical Chemistry, Biochemistry, Biology, Catalysis, Fluorescence
Abstract

International audience; This review presents the synthesis of dendrons (dendritic wedges) based on cyclotriphosphazene cores, in which one function is a fluorescent group, and the five remaining functions are used for growing the dendritic branches. The growing of the branches is carried out by a divergent method, using a two-step process which implies hydroxybenzaldehyde and the phosphorhydrazide H2NNMeP(S)Cl2. Four different fluorophores have been used, derived from maleimide, julolidine, pyrene, or from a near-infra-red fluorophore. Depending on the type of fluorophore and on the type of terminal functions of the dendrons, different applications have been targeted. One can cite experiments in catalysis or for the elaboration of materials, transfection experiments, the study of anti-cancer properties, and imaging in relation with the human immune system.

Published
2023
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10. Curing inflammatory diseases using phosphorous dendrimers

Author

Anne‐Marie Caminade, Cédric‐Olivier Turrin, Rémy Poupot, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Institut Toulousain des Maladies Infectieuses et Inflammatoires (Infinity), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), University of Toulouse, Inserm, Centre National de la Recherche Scientifique (CNRS), Gulli, Marie-Hélène, Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Inflammation, Dendrimers, Dendrimer, Anti-Inflammatory Agents, Biomedical Engineering, Medicine (miscellaneous), Phosphorus, Bioengineering, [CHIM.COOR] Chemical Sciences/Coordination chemistry, Monocytes, Mice, Leukocytes, Mononuclear, Animals, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract

International audience; Different types of water-soluble phosphorous dendrimers have been synthesized and display many different biological properties. It has been shown in particular that phosphorous dendrimers of first generation functionalized with azabisphosphonate terminal functions are able to stimulate the human immune system ex vivo. These dendrimers are internalized by monocytes within a few seconds, and induce their anti-inflammatory activation. The presence of the dendrimers induces also the inhibition of the differentiation of monocytes into osteoclasts, the maturation of dendritic cells, and inhibits the proliferation of the proinflammatory CD4+ T lymphocytes. Finally, after 2–3 weeks of culture of peripheral blood mononuclear cells, amplifications by several tens of natural killer cells is observed. In view of all these properties, the influence of these azabisphosphonate-dendrimers has been tested in vivo with several animal models, against different chronic or acute inflammatory diseases, such as multiple sclerosis, rheumatoid arthritis, uveitis, and psoriasis, but also against myeloid leukemia, a hematological cancer. The hematological safety has been demonstrated in mice, as there is no platelet aggregation, no hemolysis, and no disturbance in the hematological formula. The safety of the azabisphosphonate-dendrimer has been assessed also with non-human primates (cynomolgus monkeys) which received repeated injections, as a de-risking pre-clinical test. Biochemical, hematological, and all immunological parameters in peripheral blood remained within a normal physiological range throughout the study, and all survived well. Other phosphorous dendrimers also display anti-inflammatory properties in vivo, in particular dendrimers functionalized with mannose derivatives, which prevent acute lung diseases when given orally (per os) to mice.

Published
2022
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11. AB

Author

Artem, Zibarov, Abdelouahd, Oukhrib, Julien, Aujard Catot, Cédric-Olivier, Turrin, and Anne-Marie, Caminade

Subjects
catalysis, dendron, cyclotriphosphazene, Review, fluorescence, phosphorus, dendrimer, sensors, nanomedicine, nanomaterials
Abstract

AB5 compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction of five chlorides with one reagent, followed by the reaction of the single remaining Cl with another reagent. This particular property led to the use of such compounds as core for the synthesis of dendrons (dendritic wedges), using the five functions for growing the dendritic branches. The single function can be used for the synthesis of diverse types of dendrimers (onion peel, dumbbell-shape, Janus), for covalent or non-covalent grafting to solid surfaces, providing nanomaterials, for grafting a fluorophore, especially for studying biological mechanisms, or for self-associations to get micelles. All these properties are reviewed in this paper.

Published
2021

12. Ferrocenyl Phosphorhydrazone Dendrimers Synthesis, and Electrochemical and Catalytic Properties

Author

Anne-Marie Caminade, Cédric-Olivier Turrin, Eric Manoury, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS (Centre National de la Recherche Scientifique), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Dendrimers, Metallocenes, Pharmaceutical Science, Review, 010402 general chemistry, Electrochemistry, dendrimer, 01 natural sciences, Analytical Chemistry, Catalysis, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ferrous Compounds, Physical and Theoretical Chemistry, Organometallic chemistry, catalysis, 010405 organic chemistry, Organic Chemistry, Hydrazones, ferrocene, [CHIM.CATA]Chemical Sciences/Catalysis, Combinatorial chemistry, 0104 chemical sciences, Ferrocene, chemistry, electrochemistry, Chemistry (miscellaneous), Molecular Medicine, Surface modification, Ferrocene derivatives, Oxidation-Reduction, Macromolecule
Abstract

International audience; The discovery of ferrocene is often associated with the rapid growth of organometallic chemistry. Dendrimers are highly branched macromolecules that can be functionalized at will at all levels of their structure. The functionalization of dendrimers with ferrocene derivatives can be carried out easily as terminal functions on the surface, but also at the core, or at one or several layers inside the structure. This review will focus on phosphorhydrazone dendrimers functionalized with ferrocene derivatives, on the surface, at the core, at all layers or within a single layer inside the structure. The first part will describe the synthesis; the second part will concern the electrochemical properties; and the last part will give several examples concerning catalysis, with complexes of ferrocenyl phosphines used as terminal functions of dendrimers.

Published
2020
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13. Three-Dimensional Directionality Is a Pivotal Structural Feature for the Bioactivity of Azabisphosphonate-Capped Poly(PhosphorHydrazone) Nanodrug Dendrimers

Author

Jean-Luc Davignon, Giovanni M. Pavan, Davide Bochicchio, Varravaddheay Ong-Meang, Matteo Garzoni, François Couderc, Myriam Hayder, Rémy Poupot, Cédric-Olivier Turrin, Anne-Marie Caminade, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Department of Innovative Technologies, University of Applied Sciences and Arts of Southern Switzerland, Scuola universitaria professionale della Svizzera italiana [Manno] (SUPSI), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Scuola universitaria professionale della Svizzera italiana = University of Applied Sciences and Arts of Southern Switzerland [Manno] (SUPSI), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), BIBAC - Chimie analytique et interactions biomolécules - matière molle biomimétique (BIBAC), and Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT)

Subjects
Male, Dendrimers, genetic structures, Polymers and Plastics, Hyperbranched polymers, Bioengineering, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Biomaterials, Mice, Molecular dynamics, Dendrimer, Materials Chemistry, Animals, Directionality, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Inbred BALB C, Inflammation, Mice, Inbred BALB C, Diphosphonates, Molecular Structure, Animal, Chemistry, Hydrazones, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Disease Models, Animal, Disease Models, Biophysics, 0210 nano-technology
Abstract

International audience; Dendrimers are nanosized, nonlinear, hyperbranched polymers whose overall 3D shape is key for their biological activity. Poly(PhosphorHydrazone) (PPH) dendrimers capped with aza-bisphosphonate (ABP) end groups are known to have anti-inflammatory properties enabling the control of inflammatory diseases in different mouse models. Here we screen the anti-inflammatory activity of a series of PPH dendrimers bearing between 2 and 16 ABP end groups in a mouse model of arthritis and confront the biological results with atomistic simulations of the dendrimers. We show that only the PPH dendrimers capped with 10 and 12 ABP end groups can control the flare of the inflammatory disease. All-atom accelerated molecular dynamics simulations show that dendrimers with a low number of ABP end groups are directional but highly flexible/dynamic and have thereby limited efficiency in establishing multivalent interactions. The largest dendrimer appears as nondirectional, having 16 ABP end groups forming patches all over the dendrimer surface. Conversely, intermediate dendrimers having 10 or 12 ABP end groups reach the best compromise between the number of surface groups and their stable directional gathering, a real maximization of multivalency.

Published
2018
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14. Biodistribution and Biosafety of a Poly(Phosphorhydrazone) Dendrimer, an Anti-Inflammatory Drug-Candidate

Author

Muriel Golzio, Elisabeth Bellard, Rémy Poupot, Abdelouahd Oukhrib, Séverine Fruchon, Cédric-Olivier Turrin, Nicolas Beton, Muriel Blanzat, Cécile Goursat, Anne-Marie Caminade, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Institut de pharmacologie et de biologie structurale (IPBS), Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), SMODD - Systèmes Moléculaires Organisés et Développement Durable (SMODD), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT), CNRS, INSERM, University of Toulouse, Toulouse-Tech-Transfer (contract I-15-1424), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Laboratoire de Biochimie [Purpan], Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut Fédératif de Biologie (IFB) - Hôpital Purpan, Hôpital Purpan [Toulouse], CHU Toulouse [Toulouse]-CHU Toulouse [Toulouse]-Hôpital Purpan [Toulouse], CHU Toulouse [Toulouse], Laboratoire de Chimie Biomoléculaires, Substances Naturelles et Réactivité, URAC16, Faculté des Sciences, Semlalia, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Centre de Physiopathologie Toulouse Purpan (ex IFR 30 et IFR 150) (CPTP), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), and FRUCHON, Séverine

Subjects
MESH: Dendrimers / adverse effects, genetic structures, [SDV]Life Sciences [q-bio], lcsh:QR1-502, Anti-Inflammatory Agents, Mutagen, 02 engineering and technology, Rabbit, Pharmacology, medicine.disease_cause, 01 natural sciences, Biochemistry, lcsh:Microbiology, MESH: Anti-Inflammatory Agents / chemistry, Mice, Biodistribution, Tissue Distribution, MESH: Animals, ComputingMilieux_MISCELLANEOUS, Chemistry, Drug candidate, Preclinical development, 021001 nanoscience & nanotechnology, MESH: Dendrimers / pharmacokinetics, 3. Good health, [SDV] Life Sciences [q-bio], MESH: Hydrazones / chemistry, Female, Safety, 0210 nano-technology, Dendrimers, MESH: Rats, medicine.drug_class, MESH: Anti-Inflammatory Agents / adverse effects, 010402 general chemistry, Rodents, Article, Anti-inflammatory, Azabisphosphonate, Immune system, MESH: Anti-Inflammatory Agents / pharmacokinetics, Dendrimer, medicine, Animals, [CHIM]Chemical Sciences, MESH: Tissue Distribution, MESH: Dendrimers / chemistry, Molecular Biology, MESH: Mice, MESH: Safety, Hydrazones, In vitro, Rats, 0104 chemical sciences, MESH: Female, Genotoxicity
Abstract

Dendrimers are nanosized, arborescent polymers of which size and structure are perfectly controlled. This is one reason why they are widely used for biomedical purposes. Previously, we showed that a phosphorus-based dendrimer capped with anionic azabisphosphonate groups (so-called ABP dendrimer) has immuno-modulatory and anti-inflammatory properties towards human immune cells in vitro. Thereafter, we have shown that the ABP dendrimer has a promising therapeutic efficacy to treat models of chronic inflammatory disorders. On the way to clinical translation, the biodistribution and the safety of this drug-candidate has to be thoroughly assessed. In this article, we present preliminary non-clinical data regarding biodistribution, hematological safety, genotoxicity, maximal tolerated doses, and early cardiac safety of the ABP dendrimer. One of the genotoxicity assays reveals a potential mutagen effect of the item at a concentration above 200 &micro, M, i.e., up to 100 times the active dose in vitro on human immune cells. However, as the results obtained for all the other assays show that the ABP dendrimer has promising biodistribution and safety profiles, there is no red flag raised to hamper the regulatory pre-clinical development of the ABP dendrimer.

Published
2019
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15. AB5 Derivatives of Cyclotriphosphazene for the Synthesis of Dendrons and Their Applications

Author

Anne-Marie Caminade, Abdelouahd Oukhrib, Artem Zibarov, Julien Aujard Catot, Cédric-Olivier Turrin, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS, Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Fluorophore, dendron, Pharmaceutical Science, dendrimer, 010402 general chemistry, 01 natural sciences, Micelle, Catalysis, Analytical Chemistry, chemistry.chemical_compound, QD241-441, Dendrimer, Drug Discovery, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Reactivity (chemistry), phosphorus, Physical and Theoretical Chemistry, nanomaterials, DendronFluorescence, Sensors, 010405 organic chemistry, Chemistry, Organic Chemistry, cyclotriphosphazene, Grafting, Combinatorial chemistry, 0104 chemical sciences, Nanomedicine, [CHIM.POLY]Chemical Sciences/Polymers, Chemistry (miscellaneous), Covalent bond, Reagent, Molecular Medicine, fluorescence
Abstract

International audience; AB5 compounds issued from the reactivity of hexachlorocyclotriphosphazene are relatively easy to obtain using two ways: either first the reaction of one chloride with one reagent, followed by the reaction of the five remaining Cl with another reagent, or first the reaction of five chlorides with one reagent, followed by the reaction of the single remaining Cl with another reagent. This particular property led to the use of such compounds as core for the synthesis of dendrons (dendritic wedges), using the five functions for growing the dendritic branches. The single function can be used for the synthesis of diverse types of dendrimers (onion peel, dumbbell-shape, Janus), for covalent or non-covalent grafting to solid surfaces, providing nanomaterials, for grafting a fluorophore, especially for studying biological mechanisms, or for self-associations to get micelles. All these properties are reviewed in this paper.

Published
2021
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16. 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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17. 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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20. Phosphorous Dendrimers in Biology and Nanomedicine : Syntheses, Characterization, and Properties

Author

Anne-Marie Caminade, Cédric-Olivier Turrin, Jean-Pierre Majoral, Anne-Marie Caminade, Cédric-Olivier Turrin, and Jean-Pierre Majoral

Subjects
Polymers, Materials science, Biomedical engineering, Dendrimers in medicine, Dendrimers, Nanomedicine
Abstract

Dendrimers, which are hyperbranched synthetic macromolecules, have attracted researchers'increasing interest over the last three decades owing to their numerous properties, in particular, in the fields of biology and nanomedicine. This book is an up-to-date collection of the most recent achievements in the use of dendrimers in nanomedicine, exemplified by phosphorus-containing dendrimers. Starting with the synthesis and characterization of phosphorus dendrimers, the book discusses their use as biomaterials, carriers of biological entities, and anti-inflammatory drugs; in bioimaging; and against prion diseases, Alzheimer's, HIV, and cancer. It compares phosphorus dendrimers with other types of dendrimers. Supplemented with numerous references and abundant illustrations, the book opens new perspectives for the researchers working on dendrimers.

Published
2018

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

Author

Myriam Hayder, Rémy Poupot, Abdelhadi Saoudi, Anne-Marie Caminade, Roland S. Liblau, Marjorie Varilh, Cédric-Olivier Turrin, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
CD4-Positive T-Lymphocytes, Dendrimers, Encephalomyelitis, Autoimmune, Experimental, Multiple Sclerosis, genetic structures, Polymers and Plastics, Bioengineering, Pharmacology, T cell response, Biomaterials, Mice, Dendrimer, Materials Chemistry, medicine, Animals, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Cells, Cultured, Neuroinflammation, Inflammation, Chemistry, Drug candidate, Multiple sclerosis, Experimental autoimmune encephalomyelitis, Phosphorus, medicine.disease, Fingolimod, Interleukin-10, 3. Good health, Mice, Inbred C57BL, Disease Models, Animal, Interleukin 10, Immunology, medicine.drug
Abstract

International audience; Dendrimers are polyfunctional nano-objects of perfectly defined structure that can provide innovative alternatives for the treatment of chronic inflammatory diseases, including multiple sclerosis (MS). To investigate the efficiency of a recently described amino-bis(methylene phosphonate)-capped ABP dendrimer as a potential drug candidate for MS, we used the classical mouse model of MOG35–55-induced experimental autoimmune encephalomyelitis (EAE). Our study provides evidence that the ABP dendrimer prevents the development of EAE and inhibits the progression of established disease with a comparable therapeutic benefit as the approved treatment Fingolimod. We also show that the ABP dendrimer redirects the pathogenic myelin-specific CD4+ T cell response toward IL-10 production.

Published
2015
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22. Thiophosphate/Phosphonate-Containing Cross-Linked PEGs and Their Use for the Stabilization of Silver Nanoparticles

Author

Arnaud Glaria, Anne-Marie Caminade, Vincent Collière, Cédric-Olivier Turrin, and Aurélien Hameau

Subjects
chemistry.chemical_compound, Aqueous solution, chemistry, Dimethylphosphite, PEG ratio, Polymer chemistry, technology, industry, and agriculture, Silver acetate, General Chemistry, Phosphonate, Ethylene glycol, Silver nanoparticle, Thiophosphate
Abstract

A simple strategy was developed to obtain poly(ethylene glycol) (PEG)-based materials incorporating phosphonate functions and thiophosphate groups from readily accessible symmetrical PEG compounds and trifunctional thiophosphates. These materials are obtained in a two-step procedure, via the formation of THF soluble, hyperbranched PEG-based polyazomethines that are subsequently functionalized with dimethylphosphite. The resulting materials are hydrolytically degradable, and upon exposure to aqueous solutions of silver acetate they afford stable colloidal solutions of silver.

Published
2015
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23. Synthesis and characterization of bifunctional dendrimers: preliminary use for the coating of gold surfaces and the proliferation of human osteoblasts (HOB)

Author

Cédric-Olivier Turrin, Anne-Marie Caminade, Nicole Deloch, Wolfgang Knoll, Jean-Pierre Majoral, Ingo Köper, Edwin R. de Jong, 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, Max Planck Institute for Polymer Research, Max-Planck-Gesellschaft, Flinders Centre for NanoScale Science and Technology, School of Chemical and Physical Sciences, Flinders University [Adelaide, Australia], and Austrian Institute of Technology [Vienna] (AIT)

Subjects
human osteoblasts (HOB), cyclotriphosphazene, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, Grafting, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Dendrimer, Materials Chemistry, Surface modification, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Carboxylate, bifunctional water-soluble dendrimers, Surface plasmon resonance, 0210 nano-technology, Bifunctional, Cell adhesion, Macromolecule
Abstract

Open Access Article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence., Two different novel families of bifunctional water-soluble dendrimers are synthesized, using the specific functionalization of one function of the cyclotriphosphazene core. Dendrimers are grown from the 5 remaining functions, up to generation 2. Water-solubility is attained in the last step of the synthesis by grafting either ammonium terminal groups or carboxylate terminal groups, on generations 1 and 2 of these bifunctional dendrimers. 12 new compounds are synthesized and fully characterized, in particular by multi-nuclear NMR. The function linked to the core is thioctic acid, suitable for grafting onto gold, thus both types of water-soluble dendrimers can be used to coat gold surfaces. These macromolecular assemblies are characterized by surface plasmon resonance (SPR). In a preliminary attempt, the gold surfaces modified by either positively or negatively charged dendrimers are used for studying their interaction with cells. Exposed to human osteoblast cells (OBC), the influence of the surface coatings on the cell responses is investigated. Polycationic dendrimers provoke cell apoptosis, whereas negatively charged dendrimers support cell adhesion and proliferation.

Published
2015
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24. Interaction studies reveal specific recognition of an anti-inflammatory polyphosphorhydrazone dendrimer by human monocytes

Author

Cédric-Olivier Turrin, Muriel Blanzat, Rémy Poupot, Giovanni M. Pavan, Anne-Marie Caminade, Matteo Garzoni, Jeremy Ledall, Séverine Fruchon, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Department of Innovative Technologies, University of Applied Sciences and Arts of Southern Switzerland, Scuola universitaria professionale della Svizzera italiana [Manno] (SUPSI), Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Scuola universitaria professionale della Svizzera italiana = University of Applied Sciences and Arts of Southern Switzerland [Manno] (SUPSI), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), and Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Dendrimers, Materials science, genetic structures, medicine.drug_class, media_common.quotation_subject, Lipid Bilayers, Cell, Anti-Inflammatory Agents, 02 engineering and technology, Molecular Dynamics Simulation, 010402 general chemistry, 01 natural sciences, Monocytes, Anti-inflammatory, Dendrimer, medicine, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Materials Science, Lipid bilayer, Internalization, Receptor, Cells, Cultured, media_common, Microscopy, Confocal, Calorimetry, Differential Scanning, Phosphorus, Biological activity, 021001 nanoscience & nanotechnology, 3. Good health, 0104 chemical sciences, medicine.anatomical_structure, Membrane, Biochemistry, Phosphatidylcholines, Biophysics, 0210 nano-technology
Abstract

International audience; Dendrimers are nano-materials with perfectly defined structure and size, and multivalency properties that confer substantial advantages for biomedical applications. Previous work has shown that phosphorus-based polyphosphorhydrazone (PPH) dendrimers capped with azabisphosphonate (ABP) end groups have immuno-modulatory and anti-inflammatory properties leading to efficient therapeutic control of inflammatory diseases in animal models. These properties are mainly prompted through activation of monocytes. Here, we disclose new insights into the molecular mechanisms underlying the anti-inflammatory activation of human monocytes by ABP-capped PPH dendrimers. Following an interdisciplinary approach, we have characterized the physicochemical and biological behavior of the lead ABP dendrimer with model and cell membranes, and compared this experimental set of data to predictive computational modelling studies. The behavior of the ABP dendrimer was compared to the one of an isosteric analog dendrimer capped with twelve azabiscarboxylate (ABC) end groups instead of twelve ABP end groups. The ABC dendrimer displayed no biological activity on human monocytes, therefore it was considered as a negative control. In detail, we show that the ABP dendrimer can bind both non-specifically and specifically to the membrane of human monocytes. The specific binding leads to the internalization of the ABP dendrimer by human monocytes. On the contrary, the ABC dendrimer only interacts non-specifically with human monocytes and is not internalized. These data indicate that the bioactive ABP dendrimer is recognized by specific receptor(s) at the surface of human monocytes.

Published
2015
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25. Dendrimers for drug delivery

Author

Anne-Marie Caminade, Cédric-Olivier Turrin, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), 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
Drug, Materials science, media_common.quotation_subject, Biomedical Engineering, RNA, Nanotechnology, General Chemistry, General Medicine, chemistry.chemical_compound, chemistry, Covalent bond, Dendrimer, Drug delivery, Biophysics, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Materials Science, Solubility, Drug metabolism, DNA, media_common
Abstract

International audience; Due to their nanometric size, dendrimers have been considered as potentially suitable as new vehicles for drug delivery since their infancy. The association of a dendrimer and a drug may occur in different ways, either through covalent or non-covalent interactions. A non-covalent interaction can be the simple encapsulation inside dendrimers that enhances the solubility of lipophilic drugs in water, or electrostatic interactions between the surface and charged drugs (or DNA, RNA, or siRNA). The covalent association may occur through stable bonds, in particular for dendrimers that are considered as active per se, or through cleavable bonds that should be cleaved only when reaching the target (often cancerous cells). In addition, the full structure of the dendrimer can be disassembled under the influence of a trigger such as pH variations. This review will present these strategies and their consequences for drug delivery.

Published
2014
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26. An Azabisphosphonate-Capped Poly(phosphorhydrazone) Dendrimer for the Treatment of Endotoxin-Induced Uveitis

Author

Jean-Marc Combette, Séverine Fruchon, Cédric-Olivier Turrin, Rémy Poupot, Claire Abadie, Anne-Marie Caminade, Jean-Luc Davignon, Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), 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
Lipopolysaccharides, genetic structures, Lipopolysaccharide, medicine.medical_treatment, Anti-Inflammatory Agents, Pharmaceutical Science, 02 engineering and technology, Pharmacology, PPH [poly(phosphorhydrazone)] dendrimer, 01 natural sciences, Dexamethasone, Monocytes, Analytical Chemistry, Mice, chemistry.chemical_compound, Drug Discovery, anti-inflammatory, Interleukin, 021001 nanoscience & nanotechnology, 3. Good health, Cytokine, Chemistry (miscellaneous), Toxicity, uveitis, Molecular Medicine, 0210 nano-technology, Uveitis, medicine.drug, Dendrimers, medicine.drug_class, Organophosphonates, 010402 general chemistry, Article, Anti-inflammatory, lcsh:QD241-441, lcsh:Organic chemistry, Dendrimer, medicine, Animals, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Organic Chemistry, Hydrazones, toxicity, medicine.disease, Rats, 0104 chemical sciences, chemistry, Immunology
Abstract

International audience; Over the last decade, different types of dendrimers have shown anti-inflammatoryproperties in their own right. In particular, we have shown that poly(phosphorhydrazone) (PPH) dendrimers are able to foster an efficient anti-inflammatory response in human monocytes and can resolve the main physiopathological features of chronic arthritis in mice at 1 mg/kg. Here we afford new insights into the therapeutic potential of an azabisphosphonate-capped dendrimer (dendrimer ABP). We have challenged its anti-inflammatory and immuno-modulatory properties in a robust rat model of acute uveitis induced by lipopolysaccharide (LPS). We show that dendrimer ABP at 2 μg/eye is as efficient as the “gold standard” dexamethasone at 20 μg/eye. We have demonstrated that the effect of dendrimer ABP is mediated at least through an increase of the production of the anti-inflammatory Interleukin(IL)-10 cytokine

Published
2013
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27. 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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28. Poly(phosphorhydrazone) dendrimers: yin and yang of monocyte activation for human NK cell amplification applied to immunotherapy against multiple myeloma

Author

Cédric-Olivier Turrin, Mary Poupot, Jean-Jacques Fournié, Rémy Poupot, Michel Attal, Anne-Marie Caminade, Séverine Fruchon, Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie de Toulouse (ICT-FR 2599), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Gulli, Marie-Hélène, Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Institut Universitaire du Cancer de Toulouse - Oncopole (IUCT Oncopole - UMR 1037), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre de Physiopathologie Toulouse Purpan (CPTP), 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), CHU Toulouse [Toulouse]-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-CHU Toulouse [Toulouse]-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre de Physiopathologie Toulouse Purpan ex IFR 30 et IFR 150 (CPTP), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)

Subjects
0301 basic medicine, [SDV.MHEP.HEM] Life Sciences [q-bio]/Human health and pathology/Hematology, Dendrimers, medicine.medical_treatment, Population, Biomedical Engineering, Pharmaceutical Science, Medicine (miscellaneous), Bioengineering, Cancer immunotherapy, NK cells, Biology, Peripheral blood mononuclear cell, Monocytes, 03 medical and health sciences, Interleukin 21, Multiple myeloma, medicine, Humans, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Cytotoxicity, education, education.field_of_study, Monocyte, [SDV.MHEP.HEM]Life Sciences [q-bio]/Human health and pathology/Hematology, Immunotherapy, [CHIM.COOR] Chemical Sciences/Coordination chemistry, 3. Good health, Killer Cells, Natural, 030104 developmental biology, medicine.anatomical_structure, Immunology, Cancer research, Leukocytes, Mononuclear, Molecular Medicine, Ex vivo
Abstract

International audience; Human natural killer (NK) cells play a key role in anti-cancer and anti-viral immunity, but their selective amplification in vitro is extremely tedious to achieve and remains one of the most challenging problems to solve for efficient NK cell-based immuno-therapeutic treatments against malignant diseases. Here we report that, when added to ex vivo culture of peripheral blood mononuclear cells from healthy volunteers or from cancer patients with multiple myeloma, poly (phosphorhydrazone) dendrimers capped with amino-bis(methylene phosphonate) end groups enable the efficient proliferation of NK cells with anti-cancer cytotoxicity in vivo. We also show that the amplification of the NK population relies on the preliminary activation of monocytes in the framework of a multistep cross-talk between monocytes and NK cells before the proliferation thereof. Thus poly(phosphorhydrazone) dendrimers represent a novel class of extremely promising drugs to develop NK-cell based anti-cancer therapies.

Published
2016
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29. 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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30. Solventless synthesis of Ru(0) composites stabilized with polyphosphorhydrazone (PPH) dendrons and their use in catalysis

Author

Rocío Redón, Anne-Marie Caminade, Armelle Ouali, Nidia G. García-Peña, Cédric-Olivier Turrin, Departamento de Tecnociencias,Centro de Ciencias Aplicadas y Desarrollo Tecnologico, Universidad Nacional Autonoma de Mexico, Universidad Nacional Autónoma de México (UNAM), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), 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
chemistry.chemical_classification, General Chemical Engineering, chemistry.chemical_element, Nanoparticle, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, 0104 chemical sciences, Ruthenium, Catalysis, Styrene, Sodium borohydride, chemistry.chemical_compound, chemistry, Dendrimer, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Ruthenium chloride, Alkyl
Abstract

International audience; Ruthenium nanoparticles (NPs) are prepared by milling under air ruthenium chloride (RuCl3), sodium borohydride (NaBH4) and a polyphosphorhydrazone (PPH) dendron (generation 0 to 2) having an alkyl chain at the focal point and triarylphosphines on the surface. The resulting NPs have a diameter in the 2 to 3 nm range and they are stable upon storage in solution or as powders. They can efficiently catalyze hydrogenation of styrene. The interaction between the dendrons and the NPs is studied, and the influence of the alkyl chain length and dendron generation is also discussed.

Published
2016
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31. Low generation PEGylated phosphorus-containing dendrons with phosphonate anchors

Author

Pierre Fau, Virginie Latour, Cédric-Olivier Turrin, Clément Barrière, Anne-Marie Caminade, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Dendrimer, Chemistry, Phosphorus containing, Organic Chemistry, technology, industry, and agriculture, 02 engineering and technology, Polyethylene, 010402 general chemistry, 021001 nanoscience & nanotechnology, Grafting, PEG, 01 natural sciences, Biochemistry, Phosphonate, 0104 chemical sciences, chemistry.chemical_compound, Drug Discovery, Polymer chemistry, PEG ratio, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Adhesive, 0210 nano-technology
Abstract

International audience; We present a simple strategy to obtain non-symmetrical polyethylene glycols equipped with telechelic phosphorus-containing dendrimeric moieties having adhesive phosphonate surface functions. The dendronized PEG tails were characterized by means of multi-nucleus NMR. The grafting abilities of model symmetrical PEG compounds equipped with telechelic amino-bis(methylene-dimethylphosphonates) and amino-bis(methylenephosphonic acids) were rapidly screened on plasma treated silicon wafers and activated silica.

Published
2012
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38. Fluorescent Phosphorus Dendrimers and Their Role in Supramolecular Interactions

Author

Anne-Marie Caminade, Jean-Pierre Majoral, Aurélien Hameau, Cédric-Olivier Turrin, Béatrice Delavaux-Nicot, and Mykhailo Ianchuk

Subjects
Organic Chemistry, Supramolecular chemistry, Photochemistry, Biochemistry, Fluorescence, Combinatorial chemistry, Inorganic Chemistry, Rhodamine, chemistry.chemical_compound, chemistry, Dendrimer, Phthalocyanine, Pyrene, Julolidine, Maleimide
Abstract

Several types of phosphorus-containing dendrimers bearing fluorescent derivatives in their structures are reviewed. The fluorescent groups can be used as terminal groups, or at the core, or linked to the core or to the branches of the dendritic structure. The types of fluorescent entities used are pyrene, dansyl, phthalocyanine, maleimide, julolidine, rhodamine, and fluoresceine derivatives. Some of these compounds possess interesting properties as chemical sensors, and for monitoring their penetration inside human cells.

Published
2011
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39. Phosphorus dendrimers as viewed by 31P NMR spectroscopy; synthesis and characterization

Author

Régis Laurent, Armelle Ouali, Cédric-Olivier Turrin, Anne-Marie Caminade, Béatrice Delavaux-Nicot, Cyrille Rebout, Maria Zablocka, and Jean-Pierre Majoral

Subjects
End-group, chemistry, General Chemical Engineering, Phosphorus, Dendrimer, Organic chemistry, chemistry.chemical_element, Phosphorus-31 NMR spectroscopy, General Chemistry, 31p nmr spectroscopy, Nuclear magnetic resonance spectroscopy, Combinatorial chemistry, Characterization (materials science)
Abstract

This review emphasizes the role of phosphorus for the elaboration of dendrimers and of various highly sophisticated dendritic structures, and the invaluable role played by 31P NMR for their characterization and to ascertain their purity. A few properties, highlighting the importance of phosphorus are reported at the end of this review.

Published
2010
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40. Synthesis of a Fluorescent Cationic Phosphorus Dendrimer and Preliminary Biological Studies of Its Interaction with DNA

Author

Jean-Pierre Majoral, Aleksandra Pietkiewicz, Cédric-Olivier Turrin, Anne-Marie Caminade, Barbara Nawrot, Julia Kazmierczak-Baranska, Magdalena Janicka, and Yiqian Wei

Subjects
Dendrimers, Circular dichroism, Time Factors, Fluorophore, Cell Survival, Biochemistry, Fluorescence, Cell Line, HeLa, chemistry.chemical_compound, Organophosphorus Compounds, Cations, Dendrimer, Genetics, Humans, Cytotoxicity, Dose-Response Relationship, Drug, Molecular Structure, biology, Circular Dichroism, Cationic polymerization, DNA, General Medicine, biology.organism_classification, Spectrometry, Fluorescence, Solubility, chemistry, Biophysics, Molecular Medicine, HeLa Cells, Plasmids
Abstract

The synthesis of a water-soluble phosphorus-containing dendrimer possessing a fluorophore (maleimide-type) linked to the core is described. This dendrimer is found brightly fluorescent in CH(2)Cl(2), but poorly fluorescent in water. The cytotoxicity of this compound is relatively low towards HeLa and A549 cells, and less toxic after 48 hours than after 24 hours. Association of this dendrimer with plasmid DNA (BACE-GFP) analyzed with circular dichroism (CD) indicates a possible disturbing of the helical B-type structure of DNA. The strength of this association (a "dendriplex") with BACE-GFP (also with HygEGFP) was measured by electrophoresis.

Published
2010
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41. gem-Bisphosphonate-Ended Group Dendrimers: Design and Gadolinium Complexing Properties

Author

Jean-Pierre Majoral, Jean-Pierre Costes, Anne-Marie Caminade, Carine Duhayon, Emma Cavero, Cédric-Olivier Turrin, and Grégory Franc

Subjects
Chemistry, Gadolinium, Organic Chemistry, chemistry.chemical_element, Medicinal chemistry, Chemical synthesis, End-group, Dendrimer, Nucleophilic substitution, Michael reaction, Organic chemistry, Amine gas treating, Chelation, Physical and Theoretical Chemistry
Abstract

The synthesis of the first gem-bisphosphonate-ended group dendrimers is described using nucleophilic substitution of terminal P(S)Cl2 units of phosphorus dendrimers of generation 1 to 3 with protected aminophenols followed by deprotection of amino groups and Michael addition with vinylidene tetraisopropyl bisphosphonate. These dendrimers were found to act as chelating agents towards Gd ions.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Published
2009
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42. Dendrimers and DNA: Combinations of Two Special Topologies for Nanomaterials and Biology

Author

Jean-Pierre Majoral, Cédric-Olivier Turrin, and Anne-Marie Caminade

Subjects
Dendrimers, Genetic Vectors, Oligonucleotides, Biological Transport, Active, Nanotechnology, Biosensing Techniques, Catalysis, Nanomaterials, chemistry.chemical_compound, Dendrimer, Animals, Humans, Biochip, Oligonucleotide Array Sequence Analysis, Oligonucleotide, Organic Chemistry, Gene Transfer Techniques, DNA, General Chemistry, Combinatorial chemistry, Nanostructures, Highly sensitive, chemistry, Self-assembly, DNA microarray
Abstract

Interactions between two precisely defined three-dimensional architectures (DNA and dendrimers) are described. Highly synergetic effects occur, as illustrated in two cases: dendrimers can be used as three-dimensional linkers for oligonucleotides, affording highly sensitive microarrays (biochips), and positively charged dendrimers strongly interact with DNA, allowing penetration inside cells (genetic transfection).

Published
2008
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43. Synthesis and Properties of Dendrimers Possessing the Same Fluorophore(s) Located Either Peripherally or Off-Center

Author

Carine Duhayon, Cédric-Olivier Turrin, Serge Mazères, Grégory Franc, Jean-Pierre Majoral, Anne-Marie Caminade, and Laure Vendier

Subjects
Models, Molecular, Dendrimers, Magnetic Resonance Spectroscopy, Fluorophore, Molecular Structure, Photochemistry, Stereochemistry, Organic Chemistry, Stereoisomerism, Crystallography, X-Ray, Fluorescence, Chemical synthesis, Maleimides, End-group, chemistry.chemical_compound, Monomer, chemistry, Dendrimer, Polymer chemistry, Imide, Maleimide, Fluorescent Dyes
Abstract

Two series of phosphorus dendrimers functionalized by maleimide derivatives are synthesized, as well as three new monomeric maleimide derivatives, of which two are characterized by X-ray diffraction. The first series of phosphorus dendrimers possesses maleimide derivatives as end groups (6-48, from generation 0 to generation 3). The second series of dendrimers possesses a single copy of the same maleimide derivative linked "off-center" to a cyclotriphosphazene core, leading to dissymmetrical dendrimers; this series is synthesized from generation 0 to generation 2. The fluorescence properties of both series of dendrimers and of monomers are studied, affording new information. First, the presence of labile hydrogen extinguishes the fluorescence. Second, the grafting of the fluorophore(s) directly to the core affords highly fluorescent compounds. Finally, an original influence of the branches possessing phosphorhydrazone linkages toward the fluorescence properties is shown.

Published
2007
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44. Synthesis and Application of Phosphorus Dendrimer Immobilized Azabis(oxazolines)

Author

Florian Jaroschik, Erick Cuevas-Yañez, Anne-Marie Caminade, Jean-Pierre Majoral, Clément Padié, Cédric-Olivier Turrin, Oliver Reiser, Anja Gissibl, Markus Hager, and Ramesh Rasappan

Subjects
Ligand, Organic Chemistry, Triazole, Oxazoline, Biochemistry, Combinatorial chemistry, chemistry.chemical_compound, chemistry, Dendrimer, Click chemistry, Molecule, Organic chemistry, Polystyrene, Physical and Theoretical Chemistry, Macromolecule
Abstract

Phosphorus dendrimer immobilized azabis(oxazoline) ligands can be efficiently synthesized up to the third generation with 48 ligand molecules being attached to the periphery using click chemistry. The so-assembled macromolecules were evaluated in copper(II)-catalyzed asymmetric benzoylations, showing good yields and enantioselectivities. Moreover, the copper(II)-catalysts could be readily recovered and reused in several cycles. The globular structure of the dendritic ligands seems to prevent interference of the triazole moieties in the catalysis, contrasting MeOPEG or polystyrene bound ligands of the same type.

Published
2007
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45. Decorating step-by-step and independently the surface and the core of dendrons

Author

Inma Angurell, Jean-Pierre Majoral, Anne-Marie Caminade, Oriol Rossell, Paul Servin, Régis Laurent, Cédric-Olivier Turrin, Valérie Maraval, and Miquel Seco

Subjects
Organic Chemistry, Side reaction, chemistry.chemical_element, Alcohol, Biochemistry, Ruthenium, Rhodium, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Dendrimer, Polymer chemistry, Materials Chemistry, Organic chemistry, Phenol, Amine gas treating, Physical and Theoretical Chemistry, Phosphine
Abstract

Dendrons possessing one activated vinyl group at the core and several chlorine atoms at the end of the branches are used as starting materials to study the possibility to react independently the surface functions and the core function. In particular, the most powerful sequence of reactions for decorating them by organometallic complexes as end groups and amine or alcohol at the core has been determined. In the first step, phenol phosphines are grafted as end groups of the dendrons, and they can be used for the complexation of metals. However, these phosphines must be kept free when amines are used to react with the vinyl core in the next step. Depending on the type of phosphine end groups and on the type of function of the core (amine or alcohol), the complexation of ruthenium ([RuCl 2 ( p -cymene)] 2 ) and rhodium ([RhCl(COD)] 2 ) derivatives by the phosphine end groups can occur without side reaction at the core.

Published
2007
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46. Multiplication of Human Natural Killer Cells by Nanosized Phosphonate-Capped Dendrimers

Author

Alexandrine Maraval, Laurent Griffe, Olivier Rolland, Pascal Metivier, Jean-Pierre Majoral, Jean-Jacques Fournié, Anne-Marie Caminade, Gérard Bacquet, Mary Poupot, Rémy Poupot, Cédric-Olivier Turrin, Patrice Marchand, Poupot, Mary, Laboratoire de chimie de coordination (LCC), Institut de Chimie de Toulouse (ICT-FR 2599), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Centre de Physiopathologie de Toulouse-Purpan (INSERM U563 - CNRS UMR1037), Centre Hospitalier Universitaire de Toulouse (CHU Toulouse)-Institut Claudius Regaud-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre de lutte contre le cancer (CLCC)-Centre National de la Recherche Scientifique (CNRS), Département de Radiobiologie, Hadronthérapie et Imagerie Moléculaire (DRHIM-IPHC), Institut Pluridisciplinaire Hubert Curien (IPHC), Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de Physique Nucléaire et de Physique des Particules du CNRS (IN2P3)-Centre National de la Recherche Scientifique (CNRS), Rhodia, Centre de Recherches d'Aubervilliers (RHODIA), RHODIA, Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Centre de lutte contre le cancer (CLCC)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Hôpital Purpan [Toulouse], CHU Toulouse [Toulouse]-CHU Toulouse [Toulouse]-Institut Claudius Regaud, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-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), CHU Toulouse [Toulouse]-Institut Claudius Regaud-Hôpital Purpan [Toulouse], and CHU Toulouse [Toulouse]-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre de lutte contre le cancer (CLCC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[SDV.MHEP.HEM] Life Sciences [q-bio]/Human health and pathology/Hematology, MESH: Killer Cells, Natural, Dendrimers, Stereochemistry, Organophosphonates, 010402 general chemistry, 01 natural sciences, Catalysis, chemistry.chemical_compound, Dendrimer, Humans, ComputingMilieux_MISCELLANEOUS, MESH: Humans, MESH: Dendrimers, 010405 organic chemistry, [SDV.MHEP.HEM]Life Sciences [q-bio]/Human health and pathology/Hematology, General Chemistry, General Medicine, Phosphonate, 0104 chemical sciences, Killer Cells, Natural, chemistry, Nanoparticles, Multiplication, MESH: Organophosphonates, MESH: Nanoparticles
Abstract

International audience; no abstract

Published
2007
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47. New phosphorus dendrimers with chiral ferrocenyl phosphine-thioether ligands on the periphery for asymmetric catalysis

Author

Sandrine Vincendeau, Lucie Routaboul, Anne-Marie Caminade, Eric Manoury, Jean-Pierre Majoral, Cédric-Olivier Turrin, and Jean-Claude Daran

Subjects
Substitution reaction, Allylic rearrangement, Stereochemistry, Phosphorus, Organic Chemistry, Enantioselective synthesis, chemistry.chemical_element, Biochemistry, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Thioether, Covalent bond, Dendrimer, Polymer chemistry, Materials Chemistry, Physical and Theoretical Chemistry, Phosphine
Abstract

Chiral ferrocenyl phosphine-thioether ligands have been covalently bound on the periphery of 4 phosphorus dendrimers (generations 1–4) having a cyclotriphosphazene core and on one model compound. These new dendrimers proved to be efficient ligands for the palladium-catalyzed asymmetric allylic substitution reaction (ee up to 93%).

Published
2007
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48. Influence of Structural Parameters on the Self-Association Properties of Anti-HIV Catanionic Dendrimers

Author

Muriel Blanzat, Brigitte Tiersch, Cédric-Olivier Turrin, Anne-Marie Caminade, Alexandra Perez-Anes, Fernanda Rodrigues, Cristina Stefaniu, Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), 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)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD), Laboratoire de chimie de coordination (LCC), 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-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), Max Planck Institute of Colloids and Interfaces, Max-Planck-Gesellschaft, Institute of Chemistry, University of Potsdam, University of Potsdam, 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)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Institut für Chemie [Universität Potsdam] | Institute of Chemistry [University of Potsdam], and University of Potsdam = Universität Potsdam

Subjects
Dendrimers, Stereochemistry, Anti-HIV Agents, Galactosylceramides, HIV Envelope Protein gp120, 010402 general chemistry, 01 natural sciences, 03 medical and health sciences, Surface-Active Agents, Dynamic light scattering, Biological property, Dendrimer, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Cytotoxicity, 030304 developmental biology, 0303 health sciences, Chemistry, Anti hiv, Atomic and Molecular Physics, and Optics, Dynamic Light Scattering, 0104 chemical sciences, Biophysics, HIV-1, Institut für Chemie, Surface-active agents
Abstract

International audience; The self-association properties of anti-HIV catanionic dendrimers as multivalent galactosylceramide (GalCer)-derived inhibitors are presented. The study was designed to elucidate the origin of the relatively high cytotoxicity values of these anti-HIV catanionic dendrimers, which have previously been found to exhibit in vitro anti-HIV activity in the submicromolar range. The physicochemical properties of these catanionic dendrimers were studied to tentatively correlate the structural parameters with self-association and biological properties. We can conclude from this study that the absence of correlation between the hydrophobicity and the cytotoxicity of the catanionic systems could be explained by the partial segregation of the different partners of the catanionic entities.

Published
2015
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49. Use of a fluorescent aminodeoxylactitol to measure the stability of anti-HIV catanionic dendrimers by spectrofluorimetry

Author

Anne-Marie Caminade, Cédric-Olivier Turrin, Alexandra Perez-Anes, Muriel Blanzat, Serge Mazères, Interactions moléculaires et réactivité chimique et photochimique (IMRCP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut de Chimie de Toulouse (ICT-FR 2599), 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)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées, 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-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), Institut de pharmacologie et de biologie structurale (IPBS), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées, Institut de Chimie de Toulouse (ICT), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Institut Ecologie et Environnement (INEE), Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Fédération de Recherche Fluides, Energie, Réacteurs, Matériaux et Transferts (FERMAT), Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut National des Sciences Appliquées - Toulouse (INSA Toulouse), Institut National des Sciences Appliquées (INSA)-Université de Toulouse (UT)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), and Université de Toulouse (UT)-Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Anti hiv, Ion pairing, Organic Chemistry, Human immunodeficiency virus (HIV), Ion pairs, 010402 general chemistry, medicine.disease_cause, 01 natural sciences, Biochemistry, Fluorescence, Combinatorial chemistry, 0104 chemical sciences, Dissociation constant, chemistry, Dendrimer, Drug Discovery, medicine, Organic chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Organic acid
Abstract

International audience; The dissociation constants (KD) of anti-HIV catanionic dendrimers have been evaluated spectroscopically by means of fluorescent analogs of the aminolactitol which is involved in the stoichiometric ion pairing systems comprising PolyPhosphorHydrazone (PPH) dendrimers with various types of organic acid surface functions. This study elucidates the origin of the low therapeutic index of these anti-HIV catanionic dendrimers which were previously reported to exhibit in vitro anti-HIV activity in the sub-micromolar range.

Published
2015
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50. The key role of the scaffold on the efficiency of dendrimer nanodrugs

Author

Armelle Ouali, Alexandrine Maraval, Cédric-Olivier Turrin, Anne-Marie Caminade, Rémy Poupot, Jean-Pierre Majoral, Valeri I. Kovalenko, Marek Maly, Matteo Garzoni, Mary Poupot, Giovanni M. Pavan, Séverine Fruchon, Victor Furer, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre de Physiopathologie Toulouse Purpan (CPTP), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Centre de Recherches en Cancérologie de Toulouse (CRCT), Université Fédérale Toulouse Midi-Pyrénées, Department of Innovative Technologies, University of Applied Sciences and Arts of Southern Switzerland, Scuola universitaria professionale della Svizzera italiana [Manno] (SUPSI), 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, Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre de Physiopathologie Toulouse Purpan ex IFR 30 et IFR 150 (CPTP), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Gulli, Marie-Hélène, Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), and Scuola universitaria professionale della Svizzera italiana = University of Applied Sciences and Arts of Southern Switzerland [Manno] (SUPSI)

Subjects
Dendrimers, Scaffold, General Physics and Astronomy, Biocompatible Materials, Nanotechnology, 02 engineering and technology, Molecular Dynamics Simulation, Polypropylenes, 010402 general chemistry, 01 natural sciences, Monocytes, Article, General Biochemistry, Genetics and Molecular Biology, chemistry.chemical_compound, Molecular dynamics, Dendrimer, Humans, Polylysine, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Aza Compounds, Multidisciplinary, Bone Density Conservation Agents, Diphosphonates, Molecular Structure, General Chemistry, Silanes, [CHIM.COOR] Chemical Sciences/Coordination chemistry, Flow Cytometry, 021001 nanoscience & nanotechnology, Biocompatible material, 0104 chemical sciences, chemistry, Biophysics, Nanoparticles, 0210 nano-technology, Macromolecule
Abstract

Dendrimers are well-defined macromolecules whose highly branched structure is reminiscent of many natural structures, such as trees, dendritic cells, neurons or the networks of kidneys and lungs. Nature has privileged such branched structures for increasing the efficiency of exchanges with the external medium; thus, the whole structure is of pivotal importance for these natural networks. On the contrary, it is generally believed that the properties of dendrimers are essentially related to their terminal groups, and that the internal structure plays the minor role of an ‘innocent' scaffold. Here we show that such an assertion is misleading, using convergent information from biological data (human monocytes activation) and all-atom molecular dynamics simulations on seven families of dendrimers (13 compounds) that we have synthesized, possessing identical terminal groups, but different internal structures. This work demonstrates that the scaffold of nanodrugs strongly influences their properties, somewhat reminiscent of the backbone of proteins., The biological properties of dendrimers are thought to be largely dependent on the chemical nature of their surface. Here, the authors show that the internal scaffold of dendritic nanodrugs strongly influences their bioactivity, based on convergent information from biology and computation results.

Published
2015
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