Calix[4]arènes fonctionnels pour ancrage sur polymère naturel et antennisation par le tripeptide RGD préparé par synthèse convergente

Abstract : The aim of this present work is dedicated to the valorization of calix[4]arene as a transition-metal complexing agent, grafted on a polymeric material, and as a drug carrier, displaying a cell recognition peptidic sequence. We describe selective monofunctionalization of a calix[4]arene, at the upper rim or at the lower rim. Nitro, amino, aldehyde and alcene functions were incorporated on the calix[4]arene lower rim, via a spacer. In the same way, an acid arm was also incorporated on the calix[4]arne upper rim. We made those monofunctionalized calix[4]arenes available into three series, depending on the number and the nature of substituent on the three residual OH groups of the calix[4]arne carried function : tetrol, trimethoxy and trisbipyridyl. The second goal is dedicated to the grafting of an amino-fonctionalized calix[4]arene, on a natural polymer, such as cellulose or dextran. We have developped a method allowing to access to a new polymeric complexing agent. We also describe the grafting-ratio, calculated by NMR, UV-Vis and titration with Cu+. The third goal is dedicated to the grafting of the cell-recognizing RGD sequence, prepared in solution by a gram-scale convergent synthesis. A RGD analogue library, functionalized by variable groups on the C- and N- terminations, were obtained with interestly yields. Those peptides were involved into a biological evaluation (cellular adhesion). Thus, cone-conformed calix[4]arene incorporating the GD or RGD peptide sequence were elaborated as preliminary models for the access to new drug-carrier molecular devices.
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Philippe Engrand. Calix[4]arènes fonctionnels pour ancrage sur polymère naturel et antennisation par le tripeptide RGD préparé par synthèse convergente. Autre. Université Henri Poincaré - Nancy 1, 2008. Français. ⟨NNT : 2008NAN10143⟩. ⟨tel-01777263⟩

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