LuxR dependent quorum sensing inhibition by N,N'-disubstituted imidazolium salts

Bioorg Med Chem. 2011 Aug 15;19(16):4868-75. doi: 10.1016/j.bmc.2011.06.075. Epub 2011 Jun 29.

Abstract

Thirty N,N'-disubstituted imidazolium salts have been synthesized and evaluated as LuxR antagonists. Substitution on one of the imidazolium nitrogen atoms includes benzhydryl, fluorenyl or cyclopentyl substituent, and alkyl chains of various lengths on the second one. Most of these compounds displayed antagonist activity, with IC(50) reaching the micromolar range for the most active ones. The disubstituted imidazolium scaffold is thus shown to be a new pertinent pharmacophore in the field of AHL dependent QS inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Drug Design
  • Humans
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Luminescent Measurements
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Targeted Therapy
  • Nitrogen / chemistry
  • Protein Binding
  • Quorum Sensing / drug effects*
  • Repressor Proteins / antagonists & inhibitors*
  • Repressor Proteins / chemical synthesis*
  • Repressor Proteins / chemistry
  • Repressor Proteins / pharmacology
  • Salts / chemistry
  • Trans-Activators / antagonists & inhibitors*
  • Trans-Activators / chemical synthesis*
  • Trans-Activators / chemistry
  • Trans-Activators / pharmacology

Substances

  • Anti-Bacterial Agents
  • Imidazoles
  • Repressor Proteins
  • Salts
  • Trans-Activators
  • LuxR autoinducer binding proteins
  • calmidazolium
  • imidazole
  • Nitrogen