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Monobactames et triazoles fluorocarbonés amphiphiles : vers des systèmes catanioniques à propriétés multiples

Abstract : In the work presented in this thesis, we were interested in the conception and in the study of original catanionic systems, constituted by ionic interaction between two surfactants with opposed charges, each one bringing a specific biological property. Firstly, we synthesised different amphiphilic ionisable monobactams, with an easily flexible HLB by addition of a polyoxyethylene part. Particular physico-chemical properties of highly fluorinated surfactants led us to synthesised perfluorinated b-aminoacid, which are precursors of lactams cycles. Secondly, we studied the synthesis of different 1,2,3-triazoles, also with a perfluorinated chain, via a 1,3 dipolar cycloaddition or an intramolecular cyclisation. The physico-chemical studies of each parent surfactant, notably by the measure of the surface tension, revealed a high tensioactive power for every compound. Different catanionic systems were prepared afterwards by associating two surfactants with opposed charges, particularly a triazole and a monobactam. The measure of their tensioactive activity showed interesting synergistic effects. A preliminary study of their antibacterial properties gave promising results. Eventually, the high potential of fluorinated amphiphiles led us to the interest of other perfluorinated structures, some a-aminoacids and some imines, which could be engaged in a catanionic system study at a later date.
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Estelle Mayot. Monobactames et triazoles fluorocarbonés amphiphiles : vers des systèmes catanioniques à propriétés multiples. Autre [cond-mat.other]. Université Henri Poincaré - Nancy 1, 2007. Français. ⟨NNT : 2007NAN10136⟩. ⟨tel-01748172⟩



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