Dodecyl sorbitan ethers as antimicrobials against Gram-positive bacteria

Bioorg Med Chem Lett. 2017 Oct 15;27(20):4660-4663. doi: 10.1016/j.bmcl.2017.09.015. Epub 2017 Sep 7.

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 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).

Keywords: Acetals; Antimicrobials; Ethers; Resistant bacteria; Sorbitan.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology*
  • Drug Resistance, Bacterial / drug effects
  • Ethers / chemistry*
  • Ethers / pharmacology*
  • Gram-Positive Bacteria / drug effects*
  • Microbial Sensitivity Tests
  • Polysorbates / chemistry

Substances

  • Anti-Infective Agents
  • Ethers
  • Polysorbates