Size and Substitution Effect on Antimicrobial Activity of Polythiophene Polyelectrolyte Derivatives Under Photolysis and Dark Conditions

Photochem Photobiol. 2018 Nov;94(6):1116-1123. doi: 10.1111/php.13013. Epub 2018 Oct 23.

Abstract

Cationic polythiophenes have been shown to be potent antimicrobial compounds due to their ability to absorb visible light and sensitize the production of reactive oxygen species (ROS) as well as their ability to selectively associate with and damage negatively charged cell envelopes. This study demonstrates the ability of differentially sized imidazolium- and tertiary amine-functionalized poly(3-hexylthiophene) (P3HT) to inactivate Gram-negative Escherichia coli and Gram-positive Bacillus atrophaeus under photolysis and dark conditions. Flow cytometry viability assays are used to quantify cell death. Each compound shows high levels of killing at both 1 and 10 μg mL-1 polymer concentrations for each microbial species after photoactivation as well as high levels of dark inactivation in many cases. Tertiary amine-functionalized P3HT is shown to have different killing patterns, shown by transmission electron microscopy, compared to the imidazolium-functionalized derivatives.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amines / chemistry
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Bacillus / chemistry
  • Bacillus / drug effects*
  • Bacillus / growth & development
  • Cations
  • Escherichia coli / chemistry
  • Escherichia coli / drug effects*
  • Escherichia coli / growth & development
  • Imidazoles / chemistry
  • Light
  • Microbial Sensitivity Tests
  • Microbial Viability / drug effects
  • Photolysis
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology
  • Polymerization
  • Reactive Oxygen Species / agonists
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship
  • Thiophenes / chemical synthesis
  • Thiophenes / chemistry*
  • Thiophenes / pharmacology

Substances

  • Amines
  • Anti-Bacterial Agents
  • Cations
  • Imidazoles
  • Photosensitizing Agents
  • Reactive Oxygen Species
  • Thiophenes