Peptide deformylase inhibitors as antibacterial agents: identification of VRC3375, a proline-3-alkylsuccinyl hydroxamate derivative, by using an integrated combinatorial and medicinal chemistry approach

Antimicrob Agents Chemother. 2004 Jan;48(1):250-61. doi: 10.1128/AAC.48.1.250-261.2004.

Abstract

Peptide deformylase (PDF), a metallohydrolase essential for bacterial growth, is an attractive target for use in the discovery of novel antibiotics. Focused chelator-based chemical libraries were constructed and screened for inhibition of enzymatic activity, inhibition of Staphylococcus aureus growth, and cytotoxicity. Positive compounds were selected based on the results of all three assays. VRC3375 [N-hydroxy-3-R-butyl-3-(2-S-(tert-butoxycarbonyl)-pyrrolidin-1-ylcarbonyl)propionamide] was identified as having the most favorable properties through an integrated combinatorial and medicinal chemistry effort. This compound is a potent PDF inhibitor with a K(i) of 0.24 nM against the Escherichia coli Ni(2+) enzyme, possesses activity against gram-positive and gram-negative bacterial pathogens, and has a low cytotoxicity. Mechanistic experiments demonstrate that the compound inhibits bacterial growth through PDF inhibition. Pharmacokinetic studies of this drug in mice indicate that VRC3375 is orally bioavailable and rapidly distributed among various tissues. VRC3375 has in vivo activity against S. aureus in a murine septicemia model, with 50% effective doses of 32, 17, and 21 mg/kg of body weight after dosing by intravenous (i.v.), subcutaneous (s.c.), and oral (p.o.) administration, respectively. In murine single-dose toxicity studies, no adverse effects were observed after dosing with more than 400 mg of VRC3375 per kg by i.v., p.o., or s.c. administration. The in vivo efficacy and low toxicity of VRC3375 suggest the potential for developing this class of compounds to be used in future antibacterial drugs.

MeSH terms

  • Algorithms
  • Amidohydrolases / antagonists & inhibitors*
  • Animals
  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / pharmacokinetics
  • Anti-Infective Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Binding Sites
  • Cell Line, Tumor
  • Chelating Agents / chemistry
  • Combinatorial Chemistry Techniques
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacokinetics
  • Enzyme Inhibitors / pharmacology*
  • Escherichia coli / drug effects
  • Escherichia coli / genetics
  • Female
  • Half-Life
  • Humans
  • Hydroxamic Acids / chemical synthesis
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacokinetics
  • Hydroxamic Acids / pharmacology*
  • Lethal Dose 50
  • Mice
  • Models, Molecular
  • Peptide Library
  • Proline / analogs & derivatives
  • Proline / chemical synthesis
  • Proline / pharmacokinetics
  • Proline / pharmacology*
  • Sepsis / drug therapy
  • Sepsis / microbiology
  • Structure-Activity Relationship
  • Tissue Distribution
  • X-Ray Diffraction

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Chelating Agents
  • Enzyme Inhibitors
  • Hydroxamic Acids
  • Peptide Library
  • VRC3375
  • Proline
  • Amidohydrolases
  • peptide deformylase