Structure-guided design and development of novel benzimidazole class of compounds targeting DNA gyraseB enzyme of Staphylococcus aureus

Bioorg Med Chem. 2014 Nov 1;22(21):5970-87. doi: 10.1016/j.bmc.2014.09.008. Epub 2014 Sep 16.

Abstract

The gyraseB subunit of Staphylococcus aureus DNA gyrase is a well-established and validated target though less explored for the development of novel antimicrobial agents. Starting from the available structural information in PDB (3TTZ), we identified a novel series of benzimidazole used as inhibitors of DNA gyraseB with low micromolar inhibitory activity by employing structure-based drug design strategy. Subsequently, this chemical class of DNA gyrase inhibitors was extensively investigated biologically through in vitro assays, biofilm inhibition assays, cytotoxicity, and in vivo studies. The binding affinity of the most potent inhibitor 10 was further ascertained biophysically through differential scanning fluorimetry. Further, the most potent analogues did not show any signs of cardiotoxicity in Zebra fish ether-a-go-go-related gene (zERG), a major breakthrough among the previously reported cardiotoxic gyraseB inhibitors.

Keywords: Antibacterial activity; Biofilm; Cytotoxicity; DNA gyraseB; hERG inhibition.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Anti-Bacterial Agents / therapeutic use
  • Benzimidazoles / chemistry*
  • Benzimidazoles / pharmacology
  • Benzimidazoles / therapeutic use
  • DNA Gyrase / chemistry
  • DNA Gyrase / metabolism*
  • Female
  • HEK293 Cells
  • Humans
  • Mice
  • Models, Molecular
  • Staphylococcal Infections / drug therapy*
  • Staphylococcal Infections / microbiology
  • Staphylococcus aureus / chemistry
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / enzymology*
  • Topoisomerase II Inhibitors / chemistry*
  • Topoisomerase II Inhibitors / pharmacology
  • Topoisomerase II Inhibitors / therapeutic use
  • Zebrafish

Substances

  • Anti-Bacterial Agents
  • Benzimidazoles
  • Topoisomerase II Inhibitors
  • benzimidazole
  • DNA Gyrase