Fragment-based discovery of DNA gyrase inhibitors targeting the ATPase subunit of GyrB

Bioorg Med Chem Lett. 2016 Feb 15;26(4):1314-8. doi: 10.1016/j.bmcl.2016.01.009. Epub 2016 Jan 6.

Abstract

Inhibitors of the ATPase function of bacterial DNA gyrase, located in the GyrB subunit and its related ParE subunit in topoisomerase IV, have demonstrated antibacterial activity. In this study we describe an NMR fragment-based screening effort targeting Staphylococcus aureus GyrB that identified several attractive and novel starting points with good ligand efficiency. Fragment hits were further characterized using NMR binding studies against full-length S. aureus GyrB and Escherichia coli ParE. X-ray co-crystal structures of select fragment hits confirmed binding and suggested a path for medicinal chemistry optimization. The identification, characterization, and elaboration of one of these fragment series to a 0.265 μM inhibitor is described herein.

Keywords: DNA gyrase; Fragment-based screening; GyrB; NMR; Structure-based design.

MeSH terms

  • Adenosine Triphosphatases / metabolism
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / metabolism
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / metabolism
  • Binding Sites
  • Crystallography, X-Ray
  • DNA Gyrase / chemistry*
  • DNA Gyrase / metabolism
  • DNA Topoisomerase IV / antagonists & inhibitors
  • DNA Topoisomerase IV / metabolism
  • Drug Design
  • Escherichia coli / metabolism
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Molecular Dynamics Simulation
  • Protein Binding
  • Protein Structure, Tertiary
  • Staphylococcus aureus / enzymology
  • Topoisomerase II Inhibitors / chemistry*
  • Topoisomerase II Inhibitors / metabolism

Substances

  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Ligands
  • Topoisomerase II Inhibitors
  • Adenosine Triphosphatases
  • DNA Topoisomerase IV
  • DNA Gyrase