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.
Univ Lyon, Université Claude Bernard Lyon1, CNRS, INSA-Lyon, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, (ICBMS), UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), 43 Boulevard du 11 novembre 1918, F-69622 Villeurbanne Cedex, France; Univ Lyon, Université Claude Bernard Lyon 1, Ecole Normale Supérieure de Lyon, CNRS, UMR5308, International Center for Infectiology Research (CIRI), Inserm U1111, 7 rue Guillaume Paradin, F-69008 Lyon, France; Centre National de Référence des Staphylocoques, 59 Boulevard Louis Pinel, F-69677 Bron Cedex, France.
Dorine
D
Belmessieri
Univ Lyon, Université Claude Bernard Lyon1, CNRS, INSA-Lyon, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, (ICBMS), UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), 43 Boulevard du 11 novembre 1918, F-69622 Villeurbanne Cedex, France; Tereos Syral SAS, Z.I et Portuaire, B.P.32, 67390 Marckolsheim, France.
Charlotte
C
Gozlan
Univ Lyon, Université Claude Bernard Lyon1, CNRS, INSA-Lyon, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, (ICBMS), UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), 43 Boulevard du 11 novembre 1918, F-69622 Villeurbanne Cedex, France.
Marie-Christine
MC
Duclos
Univ. Lille, CNRS, ENSCL, UMR 8181, UCCS - Unité de Catalyse et Chimie du Solide, F-59000 Lille, Cité Scientifique, France.
Valérie
V
Molinier
Univ. Lille, CNRS, ENSCL, UMR 8181, UCCS - Unité de Catalyse et Chimie du Solide, F-59000 Lille, Cité Scientifique, France.
Jean-Marie
JM
Aubry
Univ Lyon, Université Claude Bernard Lyon 1, Ecole Normale Supérieure de Lyon, CNRS, UMR5308, International Center for Infectiology Research (CIRI), Inserm U1111, 7 rue Guillaume Paradin, F-69008 Lyon, France; Centre National de Référence des Staphylocoques, 59 Boulevard Louis Pinel, F-69677 Bron Cedex, France.
Oana
O
Dumitrescu
Univ Lyon, Université Claude Bernard Lyon 1, Ecole Normale Supérieure de Lyon, CNRS, UMR5308, International Center for Infectiology Research (CIRI), Inserm U1111, 7 rue Guillaume Paradin, F-69008 Lyon, France; Centre National de Référence des Staphylocoques, 59 Boulevard Louis Pinel, F-69677 Bron Cedex, France.
Gérard
G
Lina
Tereos Syral SAS, Z.I et Portuaire, B.P.32, 67390 Marckolsheim, France.
Andreas
A
Redl
Univ Lyon, Université Claude Bernard Lyon1, CNRS, INSA-Lyon, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, (ICBMS), UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), 43 Boulevard du 11 novembre 1918, F-69622 Villeurbanne Cedex, France. Electronic address: nicolas.duguet@univ-lyon1.fr.
Nicolas
N
Duguet
Univ Lyon, Université Claude Bernard Lyon1, CNRS, INSA-Lyon, CPE-Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, (ICBMS), UMR 5246, Equipe CAtalyse, SYnthèse et ENvironnement (CASYEN), 43 Boulevard du 11 novembre 1918, F-69622 Villeurbanne Cedex, France. Electronic address: marc.lemaire.chimie@univ-lyon1.fr.
Marc
M
Lemaire
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology*; D017576:Daptomycin / Q000494:pharmacology; D018432:Drug Resistance, Multiple / Q000187:drug effects; D013293:Enterococcus faecalis / Q000187:drug effects* / Q000254:growth & development; D016984:Enterococcus faecium / Q000187:drug effects* / Q000254:growth & development; D005960:Glucosides / Q000737:chemistry*; D016908:Gram-Positive Bacterial Infections / Q000188:drug therapy / Q000382:microbiology; D006801:Humans; D008089:Listeria monocytogenes / Q000187:drug effects* / Q000254:growth & development; D008088:Listeriosis / Q000188:drug therapy / Q000382:microbiology; D008712:Methicillin / Q000494:pharmacology; D008738:Methyl Ethers / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D013203:Staphylococcal Infections / Q000188:drug therapy / Q000382:microbiology; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000254:growth & development; D014640:Vancomycin / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D005960:Glucosides; D008738:Methyl Ethers; D014640:Vancomycin; D017576:Daptomycin; D008712:Methicillin
Antimicrobial; Carbohydrate; Ether; Gram-positive bacteria; Surfactant