Discovery and refinement of a new structural class of potent peptide deformylase inhibitors

J Med Chem. 2007 Jan 11;50(1):10-20. doi: 10.1021/jm060910c.

Abstract

New classes of antibiotics are urgently needed to counter increasing levels of pathogen resistance. Peptide deformylase (PDF) was originally selected as a specific bacterial target, but a human homologue, the inhibition of which causes cell death, was recently discovered. We developed a dual-screening strategy for selecting highly effective compounds with low inhibition effect against human PDF. We selected a new scaffold in vitro that discriminated between human and bacterial PDFs. Analyses of structure-activity relationships identified potent antibiotics such as 2-(5-bromo-1H-indol-3-yl)-N-hydroxyacetamide (6b) with the same mode of action in vivo as previously identified PDF inhibitors but without the apoptotic effects of these inhibitors in human cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Amidohydrolases / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Apoptosis / drug effects
  • Bacillus subtilis / drug effects
  • Escherichia coli / drug effects
  • Escherichia coli / enzymology
  • Geobacillus stearothermophilus / enzymology
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Indoles / pharmacology
  • KB Cells
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Structure-Activity Relationship

Substances

  • 2-(5-bromo-1H-indol-3-yl)-N-hydroxyacetamide
  • Anti-Bacterial Agents
  • Hydroxamic Acids
  • Indoles
  • Amidohydrolases
  • peptide deformylase