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1. Inorganic Sol–Gel Polymerization for Hydrogel Bioprinting

Author

Montheil, Titouan, Maumus, Marie, Valot, Laurine, Lebrun, Aureĺien, Martinez, Jean, Amblard, Muriel, Noël, Danièle, Mehdi, Ahmad, Subra, Gilles, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Cellules Souches, Plasticité Cellulaire, Médecine Régénératrice et Immunothérapies (IRMB), Centre Hospitalier Régional Universitaire [Montpellier] (CHRU Montpellier)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Montpellier (UM), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Université de Montpellier (UM)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre Hospitalier Régional Universitaire [Montpellier] (CHRU Montpellier), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
Chemistry, [CHIM.POLY]Chemical Sciences/Polymers, technology, industry, and agriculture, [CHIM.MATE]Chemical Sciences/Material chemistry, QD1-999
Abstract

International audience; An inorganic sol−gel polymerization process was used as a cross-linking reaction during three-dimensional (3D) bioprinting of cell-containing hydrogel scaffolds. Hybrid hydroxypropyl methyl cellulose (HPMC), with a controlled ratio of silylation, was prepared and isolated as a 3D-network precursor. When dissolved in a biological buffer containing human mesenchymal stem cells, it yields a bioink that can be printed during polymerization by extrusion. It is worth noting that the sol−gel process proceeded at pH 7.4 using biocompatible mode of catalysis (NaF and glycine). The printing window was determined by rheology and viscosity measurements. The physicochemical properties of hydrogels were studied. Covalent functionalization of the network can be easily performed by adding a triethoxysilyl-containing molecule; a fluorescent hybrid molecule was used as a proof of concept.

Published
2020
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2. Novel 1H-Pyrrolo[3,2-c]quinoline Based 5-HT6 Receptor Antagonists with Potential Application for the Treatment of Cognitive Disorders Associated with Alzheimer’s Disease

Author

Grychowska, Katarzyna, Satała, Grzegorz, Kos, Tomasz, Partyka, Anna, Colacino, Evelina, Chaumont-Dubel, Severine, Bantreil, Xavier, Wesołowska, Anna, Pawłowski, Maciej, Martinez, Jean, Marin, Philippe, Subra, Gilles, Bojarski, Andrzej, Lamaty, Frederic, Popik, Piotr, Zajdel, Paweł, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut de Génomique Fonctionnelle (IGF), and Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre National de la Recherche Scientifique (CNRS)

Subjects
cognition, Vogel test, Male, 0301 basic medicine, Physiology, [SDV]Life Sciences [q-bio], Phencyclidine, Pharmacology, Biochemistry, memory, Rats, Sprague-Dawley, Neuroblastoma, chemistry.chemical_compound, 0302 clinical medicine, Cyclic AMP, Sulfones, Serotonin Antagonists, Receptor, Chemistry, Quinoline, pyrrolo[3, General Medicine, Alzheimer's disease, 3. Good health, 5-HT 6 R inverse agonist, novel object recognition test, Quinolines, 5-HT6 receptor, medicine.drug, Cognitive Neuroscience, CHO Cells, 5-HT6R inverse agonist, 03 medical and health sciences, Cricetulus, Alzheimer Disease, medicine, [CHIM]Chemical Sciences, Animals, Humans, Inverse agonist, Pyrroles, Rats, Wistar, forced swim test, 2-c]quinoline, Antagonist, Cell Biology, medicine.disease, SB-742457, Rats, Disease Models, Animal, HEK293 Cells, 030104 developmental biology, Receptors, Serotonin, 5-HT6R antagonist, 5-HT 6 R antagonist, Cognition Disorders, 030217 neurology & neurosurgery
Abstract

International audience; Modulators of the serotonin 5-HT6 receptor (5-HT6R) offer a promising strategy for the treatment of the cognitive deficits that are associated with dementia and Alzheimer's disease. Herein, we report the design, synthesis, and characterization of a novel class of 5-HT6R antagonists that is based on the 1H-pyrrolo[3,2-c]quinoline core. The most active compounds exhibited comparable binding affinity to the reference compound, SB-742457, and markedly improved selectivity. Lead optimization led to the identification of (S)-1-[(3-chlorophenyl)sulfonyl]-4-(pyrrolidine-3-yl-amino)-1H-pyrrolo[3,2-c]quin oline (14) (Ki = 3 nM and Kb = 0.41 nM). Pharmacological characterization of the 5-HT6R's constitutive activity at Gs signaling revealed that 14 behaved as a neutral antagonist, while SB-742457 was classified as an inverse agonist. Both compounds 14 and SB-742457 reversed phencyclidine-induced memory deficits and displayed distinct procognitive properties in cognitively unimpaired animals (3 mg/kg) in NOR tasks. Compounds 14 and SB-742457 were also active in the Vogel test, yet the anxiolytic effect of 14 was 2-fold higher (MED = 3 mg/kg). Moreover, 14 produced, in a 3-fold higher dose (MED = 10 mg/kg), antidepressant-like effects that were similar to those produced by SB-742457 (MED = 3 mg/kg). Together, these data suggest that the 4-(pyrrolidine-3-yl-amino)-1H-pyrrolo[3,2-c]quinoline scaffold is an attractive molecular framework for the development of procognitive agents. The results are promising enough to warrant further detailed mechanistic studies on the therapeutic potential of 5-HT6R antagonists and inverse agonists for the treatment of cognitive decline and depression/anxiety symptoms that are comorbidities of Alzheimer's disease.

Published
2016
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3. Biomatériaux à base de collagène pour des applications en santé

Author

Echalier , Cécile, Mehdi , Ahmad, Martinez , Jean, Subra , Gilles, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier ( ICGM ICMMM ), Université Montpellier 1 ( UM1 ) -Université Montpellier 2 - Sciences et Techniques ( UM2 ) -Ecole Nationale Supérieure de Chimie de Montpellier ( ENSCM ) -Université de Montpellier ( UM ) -Centre National de la Recherche Scientifique ( CNRS ), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] ( IBMM ), Ecole Nationale Supérieure de Chimie de Montpellier ( ENSCM ) -Université de Montpellier ( UM ) -Centre National de la Recherche Scientifique ( CNRS ), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), and Mehdi, Ahmad

Subjects
[CHIM.MATE] Chemical Sciences/Material chemistry, [ CHIM.MATE ] Chemical Sciences/Material chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2018

4. The novel nonapeptide acein targets angiotensin converting enzyme in the brain and induces dopamine release

Author

Neasta, Jérémie, Valmalle, Charlène, Coyne, Anne‐Claire, Carnazzi, Eric, Subra, Gilles, Galleyrand, Jean‐Claude, Gagne, Didier, M'Kadmi, Céline, Bernad, Nicole, Bergé, Gilbert, Cantel, Sonia, Marin, Philippe, Marie, Jacky, Banères, Jean‐Louis, Kemel, Marie‐Lou, Daugé, Valérie, Puget, Karine, Martinez, Jean, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Physiopathologie des Maladies du Système Nerveux Central, Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Institut de biologie et chimie des protéines [Lyon] (IBCP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Institut de Génomique Fonctionnelle (IGF), Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre National de la Recherche Scientifique (CNRS), Centre interdisciplinaire de recherche en biologie (CIRB), Labex MemoLife, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Collège de France (CdF (institution))-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Collège de France (CdF (institution))-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Collège de France (CdF (institution))-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL), and Université Paris sciences et lettres (PSL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Male, Dopamine, striatum, [SDV]Life Sciences [q-bio], Guinea Pigs, Brain, Computational Biology, receptors, concise guide, Peptidyl-Dipeptidase A, system, Research Papers, peptide, Rats, Sprague-Dawley, rats, nucleus-accumbens, Catalytic Domain, growth-hormone, Animals, alzheimers-disease, pharmacology, Oligopeptides
Abstract

International audience; Background and PurposeUsing an in-house bioinformatics programme, we identified and synthesized a novel nonapeptide, H-Pro-Pro-Thr-Thr-Thr-Lys-Phe-Ala-Ala-OH. Here, we have studied its biological activity, in vitro and in vivo, and have identified its target in the brain. Experimental ApproachThe affinity of the peptide was characterized using purified whole brain and striatal membranes from guinea pigs and rats . Its effect on behaviour in rats following intra-striatal injection of the peptide was investigated. A photoaffinity UV cross-linking approach combined with subsequent affinity purification of the ligand covalently bound to its receptor allowed identification of its target. Key ResultsThe peptide bound with high affinity to a single class of binding sites, specifically localized in the striatum and substantia nigra of brains from guinea pigs and rats. When injected within the striatum of rats, the peptide stimulated in vitro and in vivo dopamine release and induced dopamine-like motor effects. We purified the target of the peptide, a similar to 151kDa protein that was identified by MS/MS as angiotensin converting enzyme (ACE I). Therefore, we decided to name the peptide acein. Conclusion and ImplicationsThe synthetic nonapeptide acein interacted with high affinity with brain membrane-bound ACE. This interaction occurs at a different site from the active site involved in the well-known peptidase activity, without modifying the peptidase activity. Acein, in vitro and in vivo, significantly increased stimulated release of dopamine from the brain. These results suggest a more important role for brain ACE than initially suspected.

Published
2016
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5. The novel nonapeptide acein targets angiotensin converting enzyme in the brain and induces dopamine release

Author

Neasta, Jérémie, Valmalle, Charlène, Coyne, Anne-Claire, Carnazzi, Eric, Subra, Gilles, Galleyrand, Jean-Claude, Gagne, Didier, M'Kadmi, Céline, Bernad, Nicole, Berge, Gilbert, Cantel, Sonia, Marin, Philippe, Marie, Jacky, Banères, Jean-Louis, Kemel, Marie-Lou, Daugé, Valérie, Puget, Karine, and Martinez, Jean

Subjects
growth-hormone, alzheimers-disease, nucleus-accumbens, concise guide, rats, striatum, system, receptors, pharmacology, peptide
Abstract

Background and PurposeUsing an in-house bioinformatics programme, we identified and synthesized a novel nonapeptide, H-Pro-Pro-Thr-Thr-Thr-Lys-Phe-Ala-Ala-OH. Here, we have studied its biological activity, in vitro and in vivo, and have identified its target in the brain. Experimental ApproachThe affinity of the peptide was characterized using purified whole brain and striatal membranes from guinea pigs and rats . Its effect on behaviour in rats following intra-striatal injection of the peptide was investigated. A photoaffinity UV cross-linking approach combined with subsequent affinity purification of the ligand covalently bound to its receptor allowed identification of its target. Key ResultsThe peptide bound with high affinity to a single class of binding sites, specifically localized in the striatum and substantia nigra of brains from guinea pigs and rats. When injected within the striatum of rats, the peptide stimulated in vitro and in vivo dopamine release and induced dopamine-like motor effects. We purified the target of the peptide, a similar to 151kDa protein that was identified by MS/MS as angiotensin converting enzyme (ACE I). Therefore, we decided to name the peptide acein. Conclusion and ImplicationsThe synthetic nonapeptide acein interacted with high affinity with brain membrane-bound ACE. This interaction occurs at a different site from the active site involved in the well-known peptidase activity, without modifying the peptidase activity. Acein, in vitro and in vivo, significantly increased stimulated release of dopamine from the brain. These results suggest a more important role for brain ACE than initially suspected.

Published
2016

7. Turning peptides in comb silicone polymers

Author

Jebors, Said, Pinese, Coline, Nottelet, Benjamin, Parra, Karine, Amblard, Muriel, Mehdi, Ahmad, Subra, Gilles, Martinez, Jean, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2015
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9. Switchable polymer-grafted mesoporous silica's: from polyesters to polyamides biosilica hybrid materials

Author

Jebors, S., Enjalbal, Christine, Amblard, Muriel, Subra, Gilles, Mehdi, Ahmad, Martinez, Jean, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2013
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10. From Polyesters to Polyamides Via ON Acyl Migration: An Original Multi-Transfer Reaction

Author

Tailhades, Julien, Blanquer, Sébastien, Nottelet, Benjamin, Coudane, Jean, Subra, Gilles, Verdié, Pascal, Schacht, Etienne, Martinez, Jean, Amblard, Muriel, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), and Universiteit Gent = Ghent University [Belgium] (UGENT)

Subjects
[CHIM.POLY]Chemical Sciences/Polymers, [CHIM]Chemical Sciences
Abstract

International audience; A new strategy for the synthesis of polyamides from polyesters of hydroxyl‐containing amino acids using a multi ON acyl transfer reaction was developed. This original approach allowed the synthesis of three generations of polymers from the same starting monomer. The polymerization of N‐benzyloxycarbonyl‐serine and its γ‐homologated derivative provided the Z‐protected polyesters; then the water‐soluble polycationic polyesters were obtained by removal of the Z‐protecting group; and finally the polyamides were obtained by a base‐induced multi ON acyl transfer, both in aqueous or organic medium. The key step transfer reaction was monitored by the disappearance and appearance of characteristic NMR proton signals and IR bands of polyesters and polyamides.

Published
2011
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11. On the use of Amino Acids as Starting Material for the Synthesis of Biomolecules

Author

Chevallet, Pierre, Fehrentz, Jean-Alain, Cavelier, Florine, Cristau, M., Subra, Gilles, Cantel, Sonia, Puget, K., Martinez, Jean, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

National audience

Published
2007

12. On the Use of N-Carboxyanhydrides as Interesting Starting Materials in Organic Synthesis

Author

Chevallet, Pierre, Fehrentz, Jean-Alain, Cavelier, Florine, Cristau, M., Subra, Gilles, Cantel, Sonia, Puget, K., Martinez, Jean, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2007

13. Application of time-of-flight secondary ion mass spectrometry to in situ monitoring of solid-phase peptide synthesis on the Multipin (TM) system

Author

Aubagnac, Jean-Louis, Enjalbal, Christine, Subra, Gilles, Bray, A.M., Combarieu, Robert, Martinez, Jean, Laboratoire des Amino-acides Peptides et Protéines (LAPP), Centre National de la Recherche Scientifique (CNRS)-Université Montpellier 2 - Sciences et Techniques (UM2)-Université Montpellier 1 (UM1), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Chiron Technologies, Chiron Technologies Pty Ltd, Centre de Mise en Forme des Matériaux (CEMEF), MINES ParisTech - École nationale supérieure des mines de Paris, and Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)

Subjects
time-of-flight secondary ion mass spectrometry, supported synthesis, pin, peptide, combinatorial chemistry, [SPI.MAT]Engineering Sciences [physics]/Materials
Abstract

International audience; In the rapidly growing field of combinatorial chemistry, the Multipin approach has been used for rapid and efficient multiple parallel syntheses of organic compounds. This strategy is particularly well adapted for the optimization of reaction conditions prior to chemical library syntheses, for the preparation of a wide range of compounds in relation to a lead structure or for the generation of parallel libraries involving complex multistep chemistries. In all cases, direct in situ monitoring of support-bound products would be highly valuable. In this work, time-of-flight secondary ion mass spectrometry was applied to the analysis of support-bound intermediates. The analytical method was applied to a range of crowns loaded with various dipeptides. The solid support was subjected to primary ion bombardment and characteristic ions indicative of both the peptide chain and the polymeric support were unambiguously identified. Analysis could be performed at any stage of the synthesis, and as the method is effectively non-destructive, the analyzed crowns could be further used to prepare target compounds

Published
1998
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