Chirality holds the key for potent inhibition of the botulinum neurotoxin serotype a protease

Org Lett. 2010 Feb 19;12(4):756-9. doi: 10.1021/ol902820z.

Abstract

Botulinum neurotoxin serotype A (BoNT/A) is the most toxic protein known to man and also a bioterrorism agent. As defined by our previous research targeting the etiological agent responsible for BoNT/A intoxication, a protease, we now report on the asymmetric synthesis of four new BoNT/A inhibitors; the most potent of this series is roughly 2-fold more active than the best small molecule inhibitor currently known.

Publication types

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

MeSH terms

  • Botulinum Toxins, Type A / antagonists & inhibitors*
  • Botulinum Toxins, Type A / metabolism
  • Botulinum Toxins, Type A / toxicity*
  • Catalysis
  • Clostridium / chemistry*
  • Crystallography, X-Ray
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology*
  • Molecular Structure
  • Neurotoxins / antagonists & inhibitors*
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Hydroxamic Acids
  • Neurotoxins
  • Protease Inhibitors
  • Botulinum Toxins, Type A