Fluorinated Beta-diketo Phosphorus Ylides Are Novel Efflux Pump Inhibitors in Bacteria

In Vivo. 2016;30(6):813-817. doi: 10.21873/invivo.10999.

Abstract

Background: One of the most important resistance mechanisms in bacteria is the increased expression of multidrug efflux pumps. To combat efflux-related resistance, the development of new efflux pump inhibitors is essential.

Materials and methods: Ten phosphorus ylides were compared based on their MDR-reverting activity in multidrug efflux pump system consisting of the subunits acridine-resistance proteins A and B (AcrA and AcrB) and the multidrug efflux pump outer membrane factor TolC (TolC) of Escherichia coli K-12 AG100 strain and its AcrAB-TolC-deleted strain. Efflux inhibition was assessed by real-time fluorimetry and the inhibition of quorum sensing (QS) was also investigated. The relative gene expression of efflux QS genes was determined by real-time reverse transcriptase quantitative polymerase chain reaction.

Results: The most potent derivative was Ph3P=C(COC2F5)CHO and its effect was more pronounced on the AcrAB-TolC-expressing E. coli strain, furthermore the most active compounds, Ph3P=C(COCF3)OMe, Ph3P=C(COC2F5)CHO and Ph3P=C(COCF3)COMe, reduced the expression of efflux pump and QS genes.

Conclusion: Phosphorus ylides might be valuable EPI compounds to reverse efflux related MDR in bacteria.

Keywords: Phosphorus ylides; bacterial AcrAB-TolC; efflux pump; multidrug resistance; quorum sensing.

MeSH terms

  • Bacterial Outer Membrane Proteins / antagonists & inhibitors
  • Bacterial Outer Membrane Proteins / genetics
  • Bacterial Outer Membrane Proteins / metabolism
  • Drug Resistance, Multiple, Bacterial / drug effects*
  • Drug Resistance, Multiple, Bacterial / genetics
  • Escherichia coli / drug effects*
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Escherichia coli Proteins / antagonists & inhibitors*
  • Escherichia coli Proteins / genetics
  • Escherichia coli Proteins / metabolism
  • Fluorometry / methods
  • Gene Deletion
  • Gene Expression Regulation, Bacterial / drug effects
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Fluorinated / pharmacology*
  • Lipoproteins / antagonists & inhibitors
  • Lipoproteins / genetics
  • Lipoproteins / metabolism
  • Membrane Transport Proteins / genetics
  • Membrane Transport Proteins / metabolism
  • Multidrug Resistance-Associated Proteins / antagonists & inhibitors*
  • Multidrug Resistance-Associated Proteins / genetics
  • Multidrug Resistance-Associated Proteins / metabolism
  • Quorum Sensing / drug effects
  • Quorum Sensing / genetics

Substances

  • AcrA protein, E coli
  • AcrB protein, E coli
  • Bacterial Outer Membrane Proteins
  • Escherichia coli Proteins
  • Hydrocarbons, Fluorinated
  • Lipoproteins
  • Membrane Transport Proteins
  • Multidrug Resistance-Associated Proteins
  • tolC protein, E coli