Peptide deformylase inhibitors as potent antimycobacterial agents

Antimicrob Agents Chemother. 2006 Nov;50(11):3665-73. doi: 10.1128/AAC.00555-06. Epub 2006 Sep 11.

Abstract

Peptide deformylase (PDF) catalyzes the hydrolytic removal of the N-terminal formyl group from nascent proteins. This is an essential step in bacterial protein synthesis, making PDF an attractive target for antibacterial drug development. Essentiality of the def gene, encoding PDF from Mycobacterium tuberculosis, was demonstrated through genetic knockout experiments with Mycobacterium bovis BCG. PDF from M. tuberculosis strain H37Rv was cloned, expressed, and purified as an N-terminal histidine-tagged recombinant protein in Escherichia coli. A novel class of PDF inhibitors (PDF-I), the N-alkyl urea hydroxamic acids, were synthesized and evaluated for their activities against the M. tuberculosis PDF enzyme as well as their antimycobacterial effects. Several compounds from the new class had 50% inhibitory concentration (IC50) values of <100 nM. Some of the PDF-I displayed antibacterial activity against M. tuberculosis, including MDR strains with MIC90 values of <1 microM. Pharmacokinetic studies of potential leads showed that the compounds were orally bioavailable. Spontaneous resistance towards these inhibitors arose at a frequency of < or =5 x 10(-7) in M. bovis BCG. DNA sequence analysis of several spontaneous PDF-I-resistant mutants revealed that half of the mutants had acquired point mutations in their formyl methyltransferase gene (fmt), which formylated Met-tRNA. The results from this study validate M. tuberculosis PDF as a drug target and suggest that this class of compounds have the potential to be developed as novel antimycobacterial agents.

MeSH terms

  • Administration, Oral
  • Amidohydrolases / antagonists & inhibitors*
  • Animals
  • Anti-Bacterial Agents* / pharmacokinetics
  • Blotting, Southern
  • Buffers
  • Culture Media
  • DNA Mutational Analysis
  • DNA, Bacterial / genetics
  • Databases, Genetic
  • Drug Resistance, Bacterial
  • Escherichia coli / drug effects
  • Escherichia coli / genetics
  • Female
  • Injections, Intravenous
  • Mice
  • Microbial Sensitivity Tests
  • Mycobacterium / drug effects*
  • Mycobacterium / genetics
  • Mycobacterium bovis / drug effects
  • Mycobacterium bovis / genetics
  • Mycobacterium tuberculosis / drug effects
  • Mycobacterium tuberculosis / genetics
  • Plasmids / genetics
  • Protease Inhibitors / pharmacokinetics
  • Protease Inhibitors / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Buffers
  • Culture Media
  • DNA, Bacterial
  • Protease Inhibitors
  • Amidohydrolases
  • peptide deformylase