Development and in vitro characterization of a novel bifunctional μ-agonist/δ-antagonist opioid tetrapeptide

ACS Chem Biol. 2011 Dec 16;6(12):1375-81. doi: 10.1021/cb200263q. Epub 2011 Oct 11.

Abstract

The development of tolerance to and dependence on opioid analgesics greatly reduces their long-term usefulness. Previous studies have demonstrated that co-administration of a μ-opioid receptor (MOR) agonist and δ-opioid receptor (DOR) antagonist can decrease MOR agonist-induced tolerance and dependence development after chronic exposure. Clinically, a single ligand displaying multiple efficacies (e.g., MOR agonism concurrently with DOR antagonism) would be of increased value over two drugs administered simultaneously. Guided by modeling of receptor-ligand complexes we have developed a series of potent non-selective opioid tetrapeptides that have differing efficacy at MOR and DOR. In particular, our lead peptide (KSK-103) binds with equal affinity to MOR and DOR but acts as a MOR agonist with similar efficacy but greater potency than morphine and a DOR antagonist in cellular assays measuring both G protein stimulation and adenylyl cyclase inhibition.

Publication types

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

MeSH terms

  • Adenylyl Cyclase Inhibitors
  • Analgesics, Opioid / pharmacology*
  • Animals
  • CHO Cells
  • Cell Line
  • Cricetinae
  • Cross-Linking Reagents / pharmacology*
  • Drug Tolerance
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • Humans
  • Models, Molecular
  • Narcotic Antagonists / pharmacology*
  • Oligopeptides / metabolism
  • Oligopeptides / pharmacology
  • Peptides, Cyclic / metabolism
  • Peptides, Cyclic / pharmacology*
  • Rats
  • Receptors, Opioid, delta / antagonists & inhibitors*
  • Receptors, Opioid, delta / metabolism
  • Receptors, Opioid, mu / agonists*
  • Receptors, Opioid, mu / metabolism

Substances

  • Adenylyl Cyclase Inhibitors
  • Analgesics, Opioid
  • Cross-Linking Reagents
  • KSK-103
  • Narcotic Antagonists
  • Oligopeptides
  • Peptides, Cyclic
  • Receptors, Opioid, delta
  • Receptors, Opioid, mu
  • Guanosine 5'-O-(3-Thiotriphosphate)