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Conception et synthèse bioinspirées de nucléolipides pour l'élaboration de biomatériaux

Abstract : Nucleolipids are hybrid amphiphilic low molecular weight molecules composed of two parts covalently linked: the first one being a nucleic acid, a nucleotide, a nucleoside or a nucleobase and the second a lipid. Combining the physico-chemical properties of two of the most widespread biomolecules, nucleolipids are capable of self-assemble as supramolecular structures of interest for application in the field of biomaterials. The study of the self-assembling properties of GlycoNucleoLipids, bearing a triazole moiety as a linker, demonstrated the crucial influence of the nature of the covalent linker bringing together the two parts of the nucleolipid onto the self-assembly. In this work, the synthesis of nucleolipids bearing a 1,4-diketone linker between thymidine and various lipids via the bioinspired and N-Heterocyclic Carbene organocatalyzed Stetter reaction is described. As an heteroaromatic cycle precursor, this moiety led to the formation of pyrrole skeletons via the classical Paal-Knorr reaction. The gelating properties of these original nucleolipids were evaluated and compared with the ones bearing a triazole link. Among these original synthetic nucleolipids, a lipophilic compound bearing a 1,4-diketone link exhibited the ability to form gels in oils (i.e. oleogels). A structure-properties study was realized to understand the role of each part of the molecule. This type of formulation being of particular interest for the development of lipophilic drug delivery systems, the physico-chemical properties of the oleogel were also extensively studied. The Stetter reaction exhibiting most of the « click chemistry » characteristics, eco-friendly reaction conditions were developed in aqueous media and applied to other biomolecules conjugation.
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  • HAL Id : tel-03092249, version 1

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Aladin Hamoud. Conception et synthèse bioinspirées de nucléolipides pour l'élaboration de biomatériaux. Chimie organique. Université de Bordeaux, 2018. Français. ⟨NNT : 2018BORD0250⟩. ⟨tel-03092249⟩

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