N-substituted aminomethanephosphonic and aminomethane-P-methylphosphinic acids as inhibitors of ureases

Amino Acids. 2012 May;42(5):1937-45. doi: 10.1007/s00726-011-0920-4. Epub 2011 May 11.

Abstract

Small unextended molecules based on the diamidophosphate structure with a covalent carbon-to-phosphorus bond to improve hydrolytic stability were developed as a novel group of inhibitors to control microbial urea decomposition. Applying a structure-based inhibitor design approach using available crystal structures of bacterial urease, N-substituted derivatives of aminomethylphosphonic and P-methyl-aminomethylphosphinic acids were designed and synthesized. In inhibition studies using urease from Bacillus pasteurii and Canavalia ensiformis, the N,N-dimethyl derivatives of both lead structures were most effective with dissociation constants in the low micromolar range (Ki=13±0.8 and 0.62±0.09 μM, respectively). Whole-cell studies on a ureolytic strain of Proteus mirabilis showed the high efficiency of N,N-dimethyl and N-methyl derivatives of aminomethane-P-methylphosphinic acids for urease inhibition in pathogenic bacteria. The high hydrolytic stability of selected inhibitors was confirmed over a period of 30 days using NMR technique.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacillus / drug effects
  • Canavalia / drug effects
  • Catalytic Domain*
  • Enzyme Inhibitors / chemical synthesis*
  • Kinetics
  • Models, Molecular
  • Phosphinic Acids / chemical synthesis*
  • Phosphinic Acids / chemistry
  • Phosphinic Acids / pharmacology
  • Phosphorus Compounds / chemistry
  • Protein Conformation
  • Proteus mirabilis / drug effects*
  • Structure-Activity Relationship
  • Urease* / antagonists & inhibitors
  • Urease* / chemistry
  • Urease* / isolation & purification

Substances

  • Enzyme Inhibitors
  • Phosphinic Acids
  • Phosphorus Compounds
  • methylphosphinic acid
  • phosphorodiamidic acid
  • Urease