Alkyne-Bridged α-Conotoxin Vc1.1 Potently Reverses Mechanical Allodynia in Neuropathic Pain Models

J Med Chem. 2021 Mar 25;64(6):3222-3233. doi: 10.1021/acs.jmedchem.0c02151. Epub 2021 Mar 16.

Abstract

Several Conus-derived venom peptides are promising lead compounds for the management of neuropathic pain, with α-conotoxins being of particular interest. Modification of the interlocked disulfide framework of α-conotoxin Vc1.1 has been achieved using on-resin alkyne metathesis. Although introduction of a metabolically stable alkyne motif significantly disrupts backbone topography, the structural modification generates a potent and selective GABAB receptor agonist that inhibits Cav2.2 channels and exhibits dose-dependent reversal of mechanical allodynia in a behavioral rat model of neuropathic pain. The findings herein support the hypothesis that analgesia can be achieved via activation of GABABRs expressed in dorsal root ganglion (DRG) sensory neurons.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Alkynes / therapeutic use*
  • Analgesics / chemistry
  • Analgesics / therapeutic use*
  • Animals
  • Cells, Cultured
  • Conotoxins / chemistry
  • Conotoxins / therapeutic use*
  • Conus Snail / chemistry
  • Disease Models, Animal
  • Female
  • HEK293 Cells
  • Humans
  • Hyperalgesia / drug therapy*
  • Hyperalgesia / physiopathology
  • Male
  • Models, Molecular
  • Neuralgia / drug therapy*
  • Neuralgia / physiopathology
  • Rats
  • Rats, Sprague-Dawley
  • Xenopus

Substances

  • Alkynes
  • Analgesics
  • Conotoxins
  • alpha-conotoxin Vc1.1