Botulinum neurotoxin A protease: discovery of natural product exosite inhibitors

J Am Chem Soc. 2010 Mar 10;132(9):2868-9. doi: 10.1021/ja910761y.

Abstract

A new mechanistic class of BoNT/A zinc metalloprotease inhibitors, from Echinacea, exemplified by the natural product d-chicoric acid (I1) is disclosed. A detailed evaluation of chicoric acid's mechanism of inhibition reveals that the inhibitor binds to an exosite, displays noncompetitive partial inhibition, and is synergistic with a competitive active site inhibitor when used in combination. Other components found in Echinacea, I3 and I4, were also inhibitors of the protease.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Biological Factors / chemical synthesis
  • Biological Factors / chemistry
  • Biological Factors / pharmacology*
  • Botulinum Toxins, Type A / antagonists & inhibitors*
  • Botulinum Toxins, Type A / metabolism
  • Caffeic Acids / chemical synthesis
  • Caffeic Acids / chemistry
  • Caffeic Acids / pharmacology
  • Chlorogenic Acid / chemical synthesis
  • Chlorogenic Acid / chemistry
  • Chlorogenic Acid / pharmacology
  • Clostridium botulinum / enzymology*
  • Hydroxamic Acids / chemical synthesis
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology
  • Molecular Conformation
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Phenols / pharmacology
  • Protease Inhibitors / chemical synthesis
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Succinates / chemical synthesis
  • Succinates / chemistry
  • Succinates / pharmacology

Substances

  • Biological Factors
  • Caffeic Acids
  • Hydroxamic Acids
  • Phenols
  • Protease Inhibitors
  • Succinates
  • Chlorogenic Acid
  • Botulinum Toxins, Type A
  • chicoric acid
  • caftaric acid