Dodecyl sorbitan ethers as antimicrobials against Gram-positive bacteria

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Abstract

A range of amphiphilic sorbitan ethers has been synthesized in two steps from sorbitan following an acetalization/hydrogenolysis sequence. These sorbitan ethers and the acetal intermediates have been evaluated as antimicrobials against Gram-negative and Gram-positive bacteria. No antimicrobial activity was observed for Gram-negative bacteria. However, the compounds bearing a linear dodecyl chain exhibit antimicrobial activity (MIC as low as 8 μg/mL) against Gram-positive bacteria such as Listeria monocytogenes, Enterococcus faecalis and Staphylococcus aureus. Encouraged by these preliminary results, dodecyl sorbitan was tested against a range of resistant strains and was found to be active against vancomycin-, methicillin- and daptomycin-resistant strains (MIC = 32–64 μg/mL).

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Acknowledgments

The FINOVI foundation is acknowledged for financial support (AO9-07) to D.B. The authors also thank the company TEREOS and the Association Nationale de la Recherche et de la Technologie (ANRT) for their financial support through a CIFRE grant (2011/1660) to C.G.

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