Novel non-β-lactam inhibitor of β-lactamase TEM-171 based on acylated phenoxyaniline

Biochimie. 2017 Jan:132:45-53. doi: 10.1016/j.biochi.2016.10.011. Epub 2016 Oct 19.

Abstract

The microbial resistance to antibiotics is a genuine global threat. Consequently, a search of new inhibitors remains of acute importance due to the increasing spread of multidrug resistance. Here we present a new type of non-β-lactam β-lactamase inhibitor PA-34 based on natural phenoxyaniline, identified using computer-assisted screening of scaffolds related to those of known low-affinity inhibitors. The compound displays reversible competitive inhibition of bacterial β-lactamase TEM-171, with a Ki of 88 μM. Using enzyme kinetics, infra-red spectroscopy, fluorescence quenching and computer docking, we propose that the inhibitor binds at the entrance to the enzyme active site. This is a novel inhibition mechanism compared to binding covalently to the catalytic serine in the active site or non-covalently to the allosteric site. The residues involved in binding the inhibitor are conserved among molecular class A β-lactamases. The identified compound and its proposed binding mode may have a potential for a regulation of the catalytic activity of a wide range of class A β-lactamases. We also hypothesise that the presented route for finding non-β-lactam compounds may be an effective and durable approach for combating bacterial antibiotic resistance.

Keywords: Antibiotic resistance; Lead discovery; Non-β-lactam inhibitor; Recombinant β-lactamase TEM.

MeSH terms

  • Acylation
  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / chemistry
  • Bacterial Proteins / metabolism
  • Binding Sites
  • Catalytic Domain
  • Computer Simulation
  • Drug Discovery / methods
  • Electrophoresis, Polyacrylamide Gel
  • Fluorescence
  • Kinetics
  • Molecular Docking Simulation
  • Molecular Structure
  • Spectroscopy, Fourier Transform Infrared / methods
  • beta-Lactamase Inhibitors / chemistry
  • beta-Lactamase Inhibitors / pharmacology*
  • beta-Lactamases / chemistry
  • beta-Lactamases / metabolism*

Substances

  • Aniline Compounds
  • Bacterial Proteins
  • beta-Lactamase Inhibitors
  • beta-Lactamases