Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers.

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 < MIC < 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. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Citation

Dorine Belmessieri, Charlotte Gozlan, Marie-Christine Duclos, Valérie Molinier, Jean-Marie Aubry, Oana Dumitrescu, Gérard Lina, Andreas Redl, Nicolas Duguet, Marc Lemaire. Synthesis, surfactant properties and antimicrobial activities of methyl glycopyranoside ethers. European journal of medicinal chemistry. 2017 Mar 10;128:98-106

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PMID: 28157594

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