Screening for antibacterial inhibitors of the UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) using a high-throughput mass spectrometry assay

J Biomol Screen. 2010 Jan;15(1):52-61. doi: 10.1177/1087057109355319. Epub 2009 Dec 17.

Abstract

A high-throughput mass spectrometry assay to measure the catalytic activity of UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase, LpxC, is described. This reaction is essential in the biosynthesis of lipopolysaccharide (LPS) of gram-negative bacteria and is an attractive target for the development of new antibacterial agents. The assay uses the RapidFire mass spectrometry platform to measure the native LpxC substrate and the reaction product and thereby generates a ratiometric readout with minimal artifacts due to detection interference. The assay was robust in a high-throughput screen of a library of more than 700,000 compounds arrayed as orthogonal mixtures, with a median Z' factor of 0.74. Selected novel inhibitors from the screening campaign were confirmed as binding to LpxC by biophysical measurements using a thermal stability shift assay. Some inhibitors showed whole-cell antimicrobial activity against a sensitive strain of Escherichia coli with reduced LpxC activity (strain D22; minimum inhibitory concentrations ranging from 0.625-20 microg/mL). The results show that mass spectrometry-based screening is a valuable high-throughput screening tool for detecting inhibitors of enzymatic targets involving difficult to detect reactions.

MeSH terms

  • Amidohydrolases / antagonists & inhibitors*
  • Anti-Bacterial Agents / analysis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Dimethyl Sulfoxide / pharmacology
  • Enzyme Inhibitors / analysis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Enzyme Stability / drug effects
  • Escherichia coli / drug effects
  • Fluorescence
  • High-Throughput Screening Assays / methods*
  • Mass Spectrometry / methods*
  • Microbial Sensitivity Tests
  • Reproducibility of Results
  • Small Molecule Libraries / analysis
  • Small Molecule Libraries / pharmacology
  • Substrate Specificity / drug effects
  • Temperature

Substances

  • Anti-Bacterial Agents
  • Enzyme Inhibitors
  • Small Molecule Libraries
  • Amidohydrolases
  • UDP-3-O-acyl-N-acetylglucosamine deacetylase
  • Dimethyl Sulfoxide