Tuning the Effects of Bacterial Membrane Permeability through Photo-Isomerization of Antimicrobial Cationic Amphiphiles

Chemistry. 2017 Sep 18;23(52):12724-12728. doi: 10.1002/chem.201703010. Epub 2017 Aug 18.

Abstract

Several important antimicrobial drugs act by permeabilizing cell membranes. In this study, we showed that the intensity of membrane permeability caused by antimicrobial cationic amphiphiles can be modified not only by their concentration but also through light-induced isomerization of their lipid segment. Two types of photo-isomerizable cationic amphiphiles were developed and the effects of photo-isomerization on bacterial growth and membrane permeability were evaluated. One photo-isomer inhibited cell growth and division, whereas the other photo-isomer led to a rapid and lethal bacterial membrane-disrupting effect. The switch from "on" to "off" can be obtained by either the cis- or trans-isomer depending on the bacterial strain and the type of cationic amphiphile. These cationic amphiphiles offer a novel tool for research and industrial applications that require light-controlled bacterial membrane permeabilization.

Keywords: antimicrobial; cationic amphiphiles; light-induced switching; membrane-permeabilizing molecules; photoisomerization.

MeSH terms

  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / metabolism
  • Anti-Infective Agents / pharmacology
  • Cations / chemistry
  • Cell Wall / drug effects
  • Cell Wall / metabolism
  • Gram-Negative Bacteria / drug effects
  • Gram-Negative Bacteria / metabolism
  • Gram-Positive Bacteria / drug effects
  • Gram-Positive Bacteria / metabolism
  • Isomerism
  • Light*
  • Microbial Sensitivity Tests
  • Microscopy, Fluorescence
  • Permeability / drug effects
  • Permeability / radiation effects

Substances

  • Anti-Infective Agents
  • Cations