Dodecyl sorbitan ethers as antimicrobials against Gram-positive bacteria

Dorine Belmessieri (1, 2, 3) , Charlotte Gozlan (1, 4) , Marie-Christine Duclos (1) , Oana Dumitrescu (2, 3) , Gérard Lina (2, 3) , Andreas Redl (4) , Nicolas Duguet (1) , Marc Lemaire (1)

1 CASYEN - Catalyse Synthèse et Environnement
2 StaPath - Pathogénie des Staphylocoques – Staphylococcal Pathogenesis
3 Centre National de Reference des Staphylocoques
4 Tereos Syral SAS

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 8μg/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=32-64μg/mL).

Mots clés: Polysorbates; Resistant bacteria; Microbial Sensitivity Tests; Acetals; Anti-Infective Agents; Antimicrobials; Drug Resistance; Bacterial; Ethers; Gram-Positive Bacteria; Sorbitan

Domaines: Chimie thérapeutique

Dorine Belmessieri, Charlotte Gozlan, Marie-Christine Duclos, Oana Dumitrescu, Gérard Lina, et al.. Dodecyl sorbitan ethers as antimicrobials against Gram-positive bacteria. Bioorganic and Medicinal Chemistry Letters, 2017, 27 (20), pp.4660-4663. ⟨10.1016/j.bmcl.2017.09.015⟩. ⟨hal-01953654⟩