Antibacterial activities of fluorescent nano assembled triphenylamine phosphonium ionic liquids

Bioorg Med Chem Lett. 2016 Aug 1;26(15):3770-3. doi: 10.1016/j.bmcl.2016.05.055. Epub 2016 May 20.

Abstract

Staphylococcus aureus, a Gram positive coccal bacterium is a major cause of nosocomial infection. We report the synthesis of new triphenylamine phosphonium ionic liquids which are able to self-assemble into multiwall nanoassemblies and to reveal a strong bactericidal activity (MIC=0.5mg/L) for Gram positive bacteria (including resistant strains) comparable to that of standard antibiotics. Time kill, metabolism and fluorescence confocal microscopy studies show a quasi-instantaneously penetration of the nanoassemblies inside the bacteria resulting of a rapid blocking (30min) of their proliferation. As confirmed by rezasurin reduction monitoring, these compounds strongly affect the bacterial metabolism and a Gram positive versus Gram negative selectivity is clearly observed. These fluorescent phosphonium ionic liquid might constitute a useful tool for both translocation studies and to tackle infectious diseases related to the field of implantology.

Keywords: Antimicrobial; Fluorescent probes; Phosphonium ionic liquids; Staphylococcus aureus; Triphenylamine.

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry
  • Amines / pharmacology*
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacteria / cytology
  • Bacteria / drug effects
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • Ionic Liquids / chemical synthesis
  • Ionic Liquids / chemistry
  • Ionic Liquids / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / pharmacology*
  • Structure-Activity Relationship

Substances

  • Amines
  • Anti-Bacterial Agents
  • Fluorescent Dyes
  • Ionic Liquids
  • Organophosphorus Compounds