1,2-Benzisoselenazol-3(2H)-one Derivatives As a New Class of Bacterial Urease Inhibitors

J Med Chem. 2016 Sep 8;59(17):8125-33. doi: 10.1021/acs.jmedchem.6b00986. Epub 2016 Aug 22.

Abstract

Urease inhibitors are considered promising compounds for the treatment of ureolytic bacterial infections, particularly infections resulting from Helicobacter pylori in the gastric tract. Herein, we present the synthesis and the inhibitory activity of novel and highly effective organoselenium compounds as inhibitors of Sporosarcina pasteurii and Helicobacter pylori ureases. These studied compounds represent a class of competitive reversible urease inhibitors. The most active compound, 2-phenyl-1,2-benzisoselenazol-3(2H)-one (ebselen), displayed Ki values equal to 2.11 and 226 nM against S. pasteurii and H. pylori enzymes, respectively, indicating ebselen as one of the most potent low-molecular-weight inhibitors of bacterial ureases reported to date. Most of these molecules penetrated through the cell membrane of the Gram-negative bacteria Escherichia coli (pGEM::ureOP) in vitro. Furthermore, whole-cell studies on the H. pylori J99 reference strain confirmed the high efficiency of the examined organoselenium compounds as urease inhibitors against pathogenic bacteria.

MeSH terms

  • Azoles / chemistry*
  • Azoles / metabolism
  • Azoles / pharmacology
  • Bacterial Proteins / antagonists & inhibitors*
  • Bacterial Proteins / chemistry
  • Cell Membrane Permeability
  • Escherichia coli / drug effects
  • Escherichia coli / enzymology
  • Helicobacter pylori / drug effects
  • Helicobacter pylori / enzymology
  • Isoindoles
  • Models, Molecular
  • Organoselenium Compounds / chemistry*
  • Organoselenium Compounds / metabolism
  • Organoselenium Compounds / pharmacology
  • Recombinant Proteins / metabolism
  • Sporosarcina / enzymology
  • Urease / antagonists & inhibitors*
  • Urease / chemistry
  • Urease / metabolism

Substances

  • Azoles
  • Bacterial Proteins
  • Isoindoles
  • Organoselenium Compounds
  • Recombinant Proteins
  • ebselen
  • Urease