Inhibition of jack bean urease by organobismuth compounds

Bioorg Med Chem Lett. 2006 Mar 15;16(6):1510-3. doi: 10.1016/j.bmcl.2005.12.034. Epub 2006 Jan 9.

Abstract

Inhibitory activity of organobismuth compounds, triarylbismuthanes 1 and their dihalides 2 and 3, was examined against jack bean urease. Besides triarylbismuth dichlorides 2, triarylbismuth difluorides 3 and bismuthanes 1 exhibited the activity. Of all these compounds, triphenylbismuth difluoride 3a and tris(4-fluorophenyl)bismuth dichloride 2b showed the highest activity. These results indicate that generation of the inhibitory effect is not always governed by the Lewis acidity at the bismuth center. Such a tendency of inhibition by the organobismuth compounds is in good accord with that observed in the antibacterial activity against Helicobacter pylori, suggesting that H. pylori-produced urease may be a therapeutic target by bismuth-based drugs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology
  • Bismuth / chemistry
  • Bismuth / pharmacology*
  • Fabaceae / enzymology*
  • Helicobacter Infections / drug therapy
  • Helicobacter pylori / enzymology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Saccharomyces cerevisiae / drug effects*
  • Saccharomyces cerevisiae / growth & development
  • Structure-Activity Relationship
  • Urease / antagonists & inhibitors*
  • Urease / metabolism

Substances

  • Antifungal Agents
  • Organometallic Compounds
  • Urease
  • Bismuth