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By RAFT Polymerization : Characterization and Study of Their Interaction with Proteins the Hien Ho

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By RAFT Polymerization : Characterization and Study of Their Interaction with Proteins the Hien Ho Synthesis of thermoresponsive copolymers by RAFT polymerization : characterization and study of their interaction with proteins The Hien Ho To cite this version: The Hien Ho. Synthesis of thermoresponsive copolymers by RAFT polymerization : characterization and study of their interaction with proteins. Other. Université du Maine, 2012. English. NNT : 2012LEMA1013. tel-00752921 HAL Id: tel-00752921 https://tel.archives-ouvertes.fr/tel-00752921 Submitted on 16 Nov 2012 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. IMMM-UMR CNRS n o6283 Université du Maine Equipeb Méthodologie et Synthèse des Polymères Faculté des Sciences et Techniques THESE Présentée en vue de l’obtention du grade de DOCTEUR Spécialité : Chimie et Physicochimie des polymères Par Hien The HO Synthèse de copolymères thermosensibles par polymérisation radicalaire contrôlée RAFT. Caractérisation et étude de leur interaction avec des protéines Soutenue le 19 septembre 2012, devant le jury composé de : Mme Bernadette CHARLEUX Professeur, Université Claude Bernard, Lyon1 Rapporteur Mme Sophie MONGE Maître de Conférence-HDR, Université Montpellier 2 Rapporteur M. Jean-François LUTZ Directeur de Recherche CNRS, Institut Charles Sadron Examinateur Mme Nathalie CASSE Maître de Conférence-HDR, Université du Maine Examinatrice M. Frédéric LEISING Docteur, Chercheur Associé, Société CHRYSO Examinateur M. Laurent FONTAINE Professeur, Université du Maine Directeur de thèse Mme Sagrario PASCUAL Maître de Conférence-HDR, Université du Maine Co-encadrante Mme Véronique MONTEMBAULT Maître de Conférence-HDR, Université du Maine Co-encadrante Le travail de recherche présenté dans ce mémoire a été réalisé au sein de l’Institut des Molécules et des Matériaux du Mans (IMMM, UMR CNRS 6283) de l’Université du Maine dans l’Equipe Méthodologie et Synthèse des Polymères dirigée par le Professeur Laurent FONTAINE. Je tiens tout d’abord à exprimer ma sincère gratitude au Pr. Laurent FONTAINE qui m’a accueilli dans l’équipe et m’a guidé durant toutes ces années. Je le remercie pour la confiance qu’il m’a accordée ainsi que pour les nombreuses discussions scientifiques qui m’ont permis de progresser dans ce travail. J’adresse ma profonde reconnaissance au Dr. Sagrario PASCUAL et au Dr. Véronique MONTEMBAULT pour, avant tout, leur disponibilité, mais également pour leur franchise, leur gentillesse et leurs nombreux conseils et discussions. Leurs connaissances, leur aide m’ont permis de mener à bien ce travail de recherche. Elles ont toujours été disponibles, à l’écoute de mes questions, et m’ont donné des idées pour l’avancée de mes travaux tout au long de ces trois années. Enfin, leurs nombreuses relectures et corrections de cette thèse ont été très appréciables. Pour tout cela, je les remercie vivement. Je remercie le Pr. Bernadette CHARLEUX et le Dr. Sophie MONGE pour avoir accepté de juger ce travail en tenant le rôle de rapporteurs. J’adresse également mes remerciements au Dr. Jean-François LUTZ, au Dr. Nathalie CASSE et au Dr. Frédéric LEISING pour avoir accepté de participer à ce jury. Je tiens à remercier le Dr. Jean-Claude SOUTIF pour les analyses de spectrométrie de masse MALDI-TOF, le Dr. Martin Edward LEVERE pour son aide et nos discussions scientifiques ainsi que le Dr. Nathalie CASSE et le Dr. Aurore CARUSO pour avoir guidé mes premiers pas dans l’analyse d’électrophorèse. Mes remerciements vont également à Mademoiselle Amélie DURAND pour les analyses de RMN, Madame Patricia GANGNERY pour les analyses de spectrométrie de masse, Monsieur Jean-Luc MONEGER pour la mise en route de la chromatographie d’exclusion stérique. Je voudrais associer à ces remerciements l’ensemble des personnels du Laboratoire qui m’ont aidé à progresser dans mes travaux ainsi que pour l’ambiance chaleureuse très agréable pour travailler. Je veux également remercier le Dr. Irène CAMPISTRON, Madame Anita LOISEAU et Madame Aline LAMBERT pour leur gentillesse et leur amabilité. Je remercie également tous les camarades du Laboratoire : Dao, Thuy, Marie, Flavien, Romain, Alice, Charles, Nhung, Pierre-Yves pour leurs encouragements et leur soutien et pour les agréables moments que nous avons passés ensembles. Enfin, Je voudrais également remercier le Ministère de l’Enseignement Supérieur et de la Recherche pour avoir financé ce travail de thèse. Abbreviations ACVA 4,4’-azobis(4-cyanovaleric acid) ADMP 2-(dodecylthiocarbonothioylthio)-2-methylpropionic acid-3-azido-1- propanol ester ADVN 2,2’-azobis(2,4-dimethylvaleronitrile) AIBN 2,2’-azobisisobutyronitrile AMA allyl methacrylate AN acrylonitrile AOI 2-(acryloyloxy)ethylisocyanate ATR attenuated total reflection ATRP atom transfer radical polymerization n-BA n-butyl acrylate t-BA tert -butyl acrylate t-BDB tert -butyl dithiobenzoate n-BMA n-butyl methacrylate t-BMA tert -butyl methacrylate BPO dibenzoyl peroxide bpy 2,2’-bipyridine BSA bovin serum albumin BSPA 3-(benzylsulfanylthiocarbonylsulfanyl)propionic acid BuAc butyl acetate CCMA cyclic carbonate methacrylate CDB cumyl dithiobenzoate CMP 2-(1-carboxy-1-methylethylsulfanylthiocarbonylsulfanyl)-2- methylpropionic acid CPAD 4-(4-cyanopentanoic acid) dithiobenzoate CPC 1-cyanoethyl 2-pyrrolidone-1-carbodithioate CPDA cumyl phenyldithioacetate CPDB 2-cyanoprop-2-yl dithiobenzoate CPDN 2-cyanoprop-2-yl-1-dithionaphthalate CPFDB 2-cyanoprop-2-yl-4-fluoro dithiobenzoate CRP controlled radical polymerization CTA chain transfer agent DCM dichloromethane DCTB trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile DEAM N,N -diethyl acrylamide DEAEMA 2-(diethylamino)ethyl methacrylate DEGMEMA diethylene glycol methyl ether methacrylate DEPMA diethoxypropyl methacrylate DIPEA diisopropylethylamine DLS dynamic light scattering DMA N,N -dimethyl acrylamide DMAc N,N -dimethyl acetamide DMAEMA 2-(dimethylamino)ethyl methacrylate DMF N,N -dimethylformamide DMP 2-dodecylsulfanylthiocarbonylsulfanyl-2-methylpropionic acid DMPP dimethylphenyl phosphine DMSO dimethylsulfoxide dNbpy 4,4’-bis(5-nonyl)-2,2’-bipyridine DP n number-average polymerization degree DTT dithiothreitol EA ethyl acrylate EAc ethyl acetate EBB ethyl-2-bromobutyrate EBiB ethyl 2-bromoisobutyrate EDC 1-ethyl-3-(3-dimethylamino)-propyl) carbodiimine 2-EHA 2-ethylhexyl acrylate EMA ethyl methacrylate EPDTB 1-(ethoxy carbonyl) prop-1-yl dithiobenzoate ES epoxystyrene FPLC cation-exchange fast protein liquid chromatography FT-IR Fourier transform infra-red GA glycidyl acrylate GMA glycidyl methacrylate HEA 2-hydroxyethyl acrylate HEMA 2-hydroxyethyl methacrylate HIPE high internal phase emulsion HMA hostasol methacrylate HMTETA 1,1,4,7,10,10-hexamethyltriethylenetetramine HPLC high performance liquid chromatography HPMA N -(2-hydroxypropyl) methacrylamide HRMS high resolution mass spectrometry H-TETA (1,1,4,7,10,10-hexakis) hexyl-1,4,7,10-tetraazadecane I isoprene IBA isobornyl acrylate ICEMA isocyanatoethyl methacrylate IFN interferon-2 a IPDI 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate IPDM 2-isopropenyl-4,4-dimethylazlactone LA lauryl acrylate LCST lower critical solution temperature LMA lauryl methacrylate MA methyl acrylate macroCTA macromolecular chain transfer agent MAh maleic anhydride MALDI-TOF matrix-assisted laser desorption and ionization time of flight MAMA-SG1 N-(2-methylpropyl)- N-(1-diethylphosphono-2,2-dimethylpropyl)- O-(2- carboxylprop-2-yl)hydroxylamine MBTTCP methyl-2-( n-butyltrithiocarbonyl) propanoate MCPDB S-methoxycarbonylphenylmethyl dithiobenzoate MEK methylethyl ketone MEO 2MA 2-(2-methoxyethoxy)ethyl methacrylate Me 6TREN tris[2-(dimethylamino)ethyl] amine MIP molecular imprinted polymers MMA methyl methacrylate Mn number-average molecular weight 1 Mn,NMR number-average molecular weight determined by H NMR spectroscopy Mn,SEC number-average molecular weight determined by SEC Mn,th theoretical number-average molecular weight MPC 2-methacryloyloxyethylphosphorylcholine Mw weight-average molecular weight MWNT multi-walled carbon nanotube NAM N-acryloylmorpholine NAS N-acryloyloxysuccinimide NHS N-hydroxysuccinimidyl NHSVB N-oxysuccinimidyl-4-vinylbenzoate NIPAM N-isopropyl acrylamide NMAS N-methacryloyloxysuccinimide NMP nitroxide-mediated polymerization NMR nuclear magnetic resonance NRC nitroxide radical coupling NVP N-vinylpyrrolidone OEGMA oligo(ethylene glycol)methyl ether acrylate ODN oligonucleotide PABTC 2-( n-butyltrithiocarbonylthio)propionic acid P( n-BA) poly( n-butyl acrylate) P( t-BA) poly( tert -butyl acrylate) P( n-BMA) poly( n-butyl methacrylate) P( t-BMA) poly( tert -butyl methacrylate) PBS phosphate buffered saline PCCMA poly(cyclic carbonate methacrylate) PCEMA 2-(phenoxycarbonyloxy)ethyl methacrylate PDEGMEMA poly(diethylene glycol monomethyl ether methacrylate) PDEPMA poly(diethoxypropyl methacrylate) PDI polydispersity index PDMA poly( N,N -dimethyl acrylamide) PDMAEMA poly((2-dimethylamino)ethyl methacrylate) PDMDETA N,N’,N’,N’’,N’’ -pentamethyldiethylenetriamine PEA poly(ethyl acrylate) PEBr 1-phenylethyl bromide PEG poly(ethylene glycol) PEGA poly(ethylene glycol) monomethyl ether acrylate
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