Conopeptide-Derived κ-Opioid Agonists (Conorphins): Potent, Selective, and Metabolic Stable Dynorphin A Mimetics with Antinociceptive Properties

J Med Chem. 2016 Mar 24;59(6):2381-95. doi: 10.1021/acs.jmedchem.5b00911. Epub 2016 Feb 22.

Abstract

Opioid receptor screening of a conopeptide library led to a novel selective κ-opioid agonist peptide (conorphin T). Intensive medicinal chemistry, guided by potency, selectivity, and stability assays generated a pharmacophore model supporting rational design of highly potent and selective κ-opioid receptor (KOR) agonists (conorphins) with exceptional plasma stability. Conorphins are defined by a hydrophobic benzoprolyl moiety, a double arginine sequence, a spacer amino acid followed by a hydrophobic residue and a C-terminal vicinal disulfide moiety. The pharmacophore model was supported by computational docking studies, revealing receptor-ligand interactions similar to KOR agonist dynorphin A (1-8). A conorphin agonist inhibited colonic nociceptors in a mouse tissue model of chronic visceral hypersensitivity, suggesting the potential of KOR agonists for the treatment of chronic abdominal pain. This new conorphine KOR agonist class and pharmacophore model provide opportunities for future rational drug development and probes for exploring the role of the κ-opioid receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Abdominal Pain / drug therapy
  • Analgesics / pharmacology*
  • Animals
  • CHO Cells
  • Conus Snail / chemistry*
  • Cricetinae
  • Cricetulus
  • Cyclic AMP / biosynthesis
  • Dynorphins / pharmacology*
  • High-Throughput Screening Assays
  • Hypersensitivity / drug therapy
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Molecular Docking Simulation
  • Neurons, Afferent / drug effects
  • Peptide Library
  • Rats
  • Rats, Wistar
  • Receptors, Opioid, kappa / agonists*
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Peptide Library
  • Receptors, Opioid, kappa
  • Dynorphins
  • Cyclic AMP