Dissecting the ribosomal inhibition mechanism of a new ketolide carrying an alkyl-aryl group at C-13 of its lactone ring

Int J Antimicrob Agents. 2010 Mar;35(3):235-9. doi: 10.1016/j.ijantimicag.2009.11.002. Epub 2010 Jan 4.

Abstract

Ketolides are effective not only against macrolide-sensitive bacteria but also against some macrolide-resistant strains. Here we present data regarding a new ketolide with an alkyl-aryl side chain at C-13 of its lactone ring. It behaves as a strong inhibitor of protein synthesis in a model coupled transcription/translation system, although it does not affect the accuracy of translation. In addition, detailed kinetic analysis shows that it slowly forms a very tight, slowly reversible complex with prokaryotic ribosomes, a property that could be correlated with its superior activity compared with erythromycin against Escherichia coli both in vivo and in vitro.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Escherichia coli / drug effects*
  • Humans
  • Ketolides / chemistry*
  • Ketolides / pharmacology*
  • Kinetics
  • Molecular Structure
  • Protein Biosynthesis / drug effects
  • Ribosomes / drug effects*

Substances

  • Anti-Bacterial Agents
  • Ketolides