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Article Dans Une Revue European Journal of Medicinal Chemistry Année : 2017

Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers

Résumé

A series of amphiphilic methyl glucopyranoside ethers incorporating various alkyl chain lengths has been synthesized from commercially available methyl glucopyranosides following an acetalisation/hydrogenolysis sequence. The amphiphilic properties of ethers and acetal intermediates were evaluated. Both families exhibit excellent surfactant properties with a maximum efficiency obtained for compounds bearing a linear dodecyl chain (CMC~=~0.012~mM, γsat.~=~30~mN~m-1). Antimicrobial activity studies revealed an efficient activity (0.03~\textless~MIC~\textless~0.12~mM) against Gram-positive bacteria such as Listeria monocytogenes, Enterococcus faecalis, Enterococcus faecium and Staphylococcus aureus. More importantly, these compounds were found to be active against multi-resistant strains such as vancomycin-, methicillin- and daptomycin-resistant strains. Finally, it was found that antimicrobial activities are closely related to physicochemical properties and are also influenced by the nature of the carbohydrate moiety.
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Dates et versions

hal-01911202 , version 1 (04-06-2021)

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Dorine Belmessieri, Charlotte Gozlan, Marie-Christine Duclos, Valérie Molinier, Jean-Marie Aubry, et al.. Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers. European Journal of Medicinal Chemistry, 2017, 128, pp.98-106. ⟨10.1016/j.ejmech.2017.01.038⟩. ⟨hal-01911202⟩
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