Synthesis and structure-activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors

Bioorg Med Chem Lett. 2007 Dec 1;17(23):6463-6. doi: 10.1016/j.bmcl.2007.09.103. Epub 2007 Oct 9.

Abstract

Botulinum neurotoxins are the most toxic proteins currently known. Based on a recently identified potent lead structure, 2,4-dichlorocinnamic acid hydroxamate, herein we report on the structure-activity relationship of a series of hydroxamate BoNT/A inhibitors. Among them, 2-bromo-4-chlorocinnamic acid hydroxamate, 2-methyl-4-chlorocinnamic acid hydroxamate, and 2-trifluoromethyl-4-chlorocinnamic acid hydroxamate displayed comparable inhibitory activity to that of the lead structure.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Botulinum Toxins, Type A / chemical synthesis*
  • Botulinum Toxins, Type A / pharmacology*
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / pharmacology*
  • Neurotoxins / chemical synthesis
  • Neurotoxins / pharmacology
  • Peptide Hydrolases / metabolism
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / pharmacology*
  • Structure-Activity Relationship

Substances

  • Hydroxamic Acids
  • Neurotoxins
  • Protease Inhibitors
  • cinnamoylhydroxamic acid
  • Peptide Hydrolases
  • Botulinum Toxins, Type A