Structure of the human κ-opioid receptor in complex with JDTic

Nature. 2012 Mar 21;485(7398):327-32. doi: 10.1038/nature10939.

Abstract

Opioid receptors mediate the actions of endogenous and exogenous opioids on many physiological processes, including the regulation of pain, respiratory drive, mood, and--in the case of κ-opioid receptor (κ-OR)--dysphoria and psychotomimesis. Here we report the crystal structure of the human κ-OR in complex with the selective antagonist JDTic, arranged in parallel dimers, at 2.9 Å resolution. The structure reveals important features of the ligand-binding pocket that contribute to the high affinity and subtype selectivity of JDTic for the human κ-OR. Modelling of other important κ-OR-selective ligands, including the morphinan-derived antagonists norbinaltorphimine and 5'-guanidinonaltrindole, and the diterpene agonist salvinorin A analogue RB-64, reveals both common and distinct features for binding these diverse chemotypes. Analysis of site-directed mutagenesis and ligand structure-activity relationships confirms the interactions observed in the crystal structure, thereby providing a molecular explanation for κ-OR subtype selectivity, and essential insights for the design of compounds with new pharmacological properties targeting the human κ-OR.

Publication types

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

MeSH terms

  • Binding Sites
  • Crystallography, X-Ray
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / metabolism
  • Diterpenes, Clerodane / pharmacology
  • Guanidines / chemistry
  • Humans
  • Models, Molecular
  • Morphinans / chemistry
  • Mutagenesis, Site-Directed
  • Naltrexone / analogs & derivatives
  • Naltrexone / chemistry
  • Naltrexone / metabolism
  • Piperidines / chemistry*
  • Piperidines / pharmacology
  • Protein Conformation
  • Receptors, Adrenergic, beta-2 / chemistry
  • Receptors, CXCR4 / chemistry
  • Receptors, CXCR4 / metabolism
  • Receptors, Opioid, kappa / antagonists & inhibitors*
  • Receptors, Opioid, kappa / chemistry*
  • Receptors, Opioid, kappa / genetics
  • Receptors, Opioid, kappa / metabolism
  • Structure-Activity Relationship
  • Tetrahydroisoquinolines / chemistry*
  • Tetrahydroisoquinolines / pharmacology

Substances

  • 17-cyclopropylmethyl-6,7-didehydro-4,5-epoxy-5'-guanidinyl-3,14-dihydroxyindolo(2',3'-6,7)morphinan
  • 22-thiocyanatosalvinorin A
  • 7-hydroxy-N-(1-((4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl)methyl)-2-methylpropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxamide
  • CXCR4 protein, human
  • Diterpenes, Clerodane
  • Guanidines
  • Morphinans
  • Piperidines
  • Receptors, Adrenergic, beta-2
  • Receptors, CXCR4
  • Receptors, Opioid, kappa
  • Tetrahydroisoquinolines
  • norbinaltorphimine
  • Naltrexone

Associated data

  • PDB/4DJH