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.
Mots clés
Methicillin
Methyl Ethers
Listeriosis
Listeria monocytogenes
Anti-Bacterial Agents
Antimicrobial
Carbohydrate
Daptomycin
Drug Resistance
Multiple
Enterococcus faecalis
Enterococcus faecium
Ether
Glucosides
Gram-positive bacteria
Gram-Positive Bacterial Infections
Humans
Microbial Sensitivity Tests
Staphylococcal Infections
Staphylococcus aureus
Surfactant
Vancomycin
Domaines
Chimie thérapeutiqueOrigine | Fichiers produits par l'(les) auteur(s) |
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