Ghrelin receptor inverse agonists: identification of an active peptide core and its interaction epitopes on the receptor

Mol Pharmacol. 2006 Sep;70(3):936-46. doi: 10.1124/mol.106.024422. Epub 2006 Jun 23.

Abstract

[D-Arg1,D-Phe5,D-Trp7,9,Leu11]Substance P functions as a low-potency antagonist but a high-potency full inverse agonist on the ghrelin receptor. Through a systematic deletion and substitution analysis of this peptide, the C-terminal carboxyamidated pentapeptide wFwLX was identified as the core structure, which itself displayed relatively low inverse agonist potency. Mutational analysis at 17 selected positions in the main ligand-binding crevice of the ghrelin receptor demonstrated that ghrelin apparently interacts only with residues in the middle part of the pocket [i.e., between transmembrane (TM)-III, TM-VI and TM-VII]. In contrast, the inverse agonist peptides bind in a pocket that extends all the way from the extracellular end of TM-II (AspII:20) across between TM-III and TM-VI/VII to TM-V and TM-IV. The potency of the main inverse agonist could be improved up to 20-fold by a number of space-generating mutants located relatively deep in the binding pocket at key positions in TM-III, TM-IV and TM-V. It is proposed that the inverse agonists prevent the spontaneous receptor activation by inserting relatively deeply across the main ligand-binding pocket and sterically blocking the movement of TM-VI and TM-VII into their inward-bend, active conformation. The combined structure-functional analysis of both the ligand and the receptor allowed for the design of a novel, N-terminally Lys-extended analog of wFwLL, which rescued the high-potency, selective inverse agonism that was dependent upon both AspII:20 and GluIII:09. The identified pharmacophore can possibly serve as the basis for targeted discovery of also nonpeptide inverse agonists for the ghrelin receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acid Substitution
  • Animals
  • Binding Sites
  • COS Cells
  • Cells, Cultured
  • Chlorocebus aethiops
  • Epitopes / metabolism*
  • Ghrelin
  • Humans
  • Ligands
  • Models, Molecular
  • Molecular Sequence Data
  • Mutant Proteins / agonists
  • Mutant Proteins / chemistry
  • Peptide Hormones / metabolism
  • Peptides / chemistry*
  • Protein Binding
  • Receptors, G-Protein-Coupled / agonists*
  • Receptors, G-Protein-Coupled / chemistry
  • Receptors, Ghrelin
  • Structure-Activity Relationship
  • Substance P / analogs & derivatives*
  • Substance P / chemistry

Substances

  • Epitopes
  • Ghrelin
  • Ligands
  • Mutant Proteins
  • Peptide Hormones
  • Peptides
  • Receptors, G-Protein-Coupled
  • Receptors, Ghrelin
  • Substance P
  • substance P, Phe(5)-Trp(7,9)-Leu(11)-