3-Arylpropionylhydroxamic acid derivatives as Helicobacter pylori urease inhibitors: Synthesis, molecular docking and biological evaluation

Bioorg Med Chem. 2016 Oct 1;24(19):4519-4527. doi: 10.1016/j.bmc.2016.07.052. Epub 2016 Jul 25.

Abstract

Helicobacter pylori urease is involved in several physiologic responses such as stomach and duodenal ulcers, adenocarcinomas and stomach lymphomas. Thus, inhibition of urease is taken for a good chance to treat H. pylori-caused infections, we have therefore focused our efforts on seeking novel urease inhibitors. Here, a series of arylpropionylhydroxamic acids were synthesized and evaluated for urease inhibition. Out of these compounds, 3-(2-benzyloxy-5-chlorophenyl)-3-hydroxypropionylhydroxamic acid (d24) was the most active inhibitor with IC50 of 0.15±0.05μM, showing a mixed inhibition with both competitive and uncompetitive aspects. Non-linear fitting of kinetic data gives kinetics parameters of 0.13 and 0.12μg·mL(-1) for Ki and Ki', respectively. The plasma protein binding assays suggested that d24 exhibited moderate binding to human and rabbit plasma proteins.

Keywords: 3-Arylpropionylhydroxamic acid; H. pylori urease inhibitor; Kinetics study; Non-linear fitting; Plasma protein binding.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology*
  • Blood Proteins / metabolism
  • Helicobacter Infections / drug therapy
  • Helicobacter Infections / microbiology
  • Helicobacter pylori / drug effects*
  • Helicobacter pylori / enzymology*
  • Humans
  • Hydroxamic Acids / chemistry*
  • Hydroxamic Acids / metabolism
  • Hydroxamic Acids / pharmacology*
  • Kinetics
  • Molecular Docking Simulation
  • Rabbits
  • Structure-Activity Relationship
  • Urease / antagonists & inhibitors*
  • Urease / metabolism

Substances

  • Anti-Bacterial Agents
  • Blood Proteins
  • Hydroxamic Acids
  • Urease