Metronidazole containing pyrazole derivatives potently inhibit tyrosyl-tRNA synthetase: design, synthesis, and biological evaluation

Chem Biol Drug Des. 2016 Oct;88(4):592-8. doi: 10.1111/cbdd.12793. Epub 2016 Jun 24.

Abstract

As an important enzyme in bacterial protein biosynthesis, tyrosyl-tRNA synthetase (TyrRS) has been an absorbing therapeutic target for exploring novel antibacterial agents. A series of metronidazole-based antibacterial agents has been synthesized and identified as TyrRS inhibitors with low cytotoxicity and significant antibacterial activity, especially against Gram-negative organisms. Of the compounds obtained, 4f is the most potent agent which inhibited the growth of Pseudomonas aeruginosa ATCC 13525 (MIC = 0.98 μg/mL) and exhibited TryRS inhibitory activity (IC50 = 0.92 μm). Docking simulation was performed to further understand its potency. Membrane-mediated apoptosis in P. aeruginosa was verified by flow cytometry.

Keywords: Pseudomonas aeruginosa; antibacterial agent; apoptosis; docking simulation; tyrosyl-tRNA synthetase.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Apoptosis / drug effects
  • Bacteria / drug effects*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Humans
  • Metronidazole / chemical synthesis
  • Metronidazole / chemistry*
  • Metronidazole / pharmacology*
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Docking Simulation
  • Pseudomonas aeruginosa / drug effects
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry*
  • Pyrazoles / pharmacology
  • Signal Transduction / drug effects
  • Tyrosine-tRNA Ligase / antagonists & inhibitors*

Substances

  • Anti-Bacterial Agents
  • Pyrazoles
  • Metronidazole
  • Tyrosine-tRNA Ligase