2-Phenylquinoline S. aureus NorA Efflux Pump Inhibitors: Evaluation of the Importance of Methoxy Group Introduction

J Med Chem. 2018 Sep 13;61(17):7827-7848. doi: 10.1021/acs.jmedchem.8b00791. Epub 2018 Aug 17.

Abstract

Antimicrobial resistance (AMR) represents a hot topic in drug discovery. Besides the identification of new antibiotics, the use of nonantibiotic molecules to block resistance mechanisms is a powerful alternative. Bacterial efflux pumps exert an early step in AMR development by allowing bacteria to grow at subinhibitorial drug concentrations. Thus, efflux pump inhibitors (EPIs) offer a great opportunity to fight AMR. Given our experience in developing Staphylococcus aureus NorA EPIs, in this work, starting from the 2-phenylquinoline hit 1, we planned the introduction of methoxy groups on the basis of their presence in known NorA EPIs. Among the 35 different synthesized derivatives, compounds 3b and 7d exhibited the best NorA inhibition activity by restoring at very low concentrations ciprofloxacin MICs against resistant S. aureus strains. Interestingly, both compounds displayed EPI activities at nontoxic concentrations for human cells as well as highlighted promising results by preliminary pharmacokinetic studies.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors*
  • Drug Resistance, Bacterial / drug effects*
  • Hep G2 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Multidrug Resistance-Associated Proteins / antagonists & inhibitors*
  • Quinolines / chemistry
  • Quinolines / pharmacokinetics
  • Quinolines / pharmacology*
  • Staphylococcal Infections / drug therapy*
  • Staphylococcal Infections / microbiology
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship
  • Tissue Distribution

Substances

  • 2-phenylquinoline
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Multidrug Resistance-Associated Proteins
  • Quinolines
  • NorA protein, Staphylococcus