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

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[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.
Original languageEnglish
JournalMolecular Pharmacology
Volume70
Issue number3
Pages (from-to)936-46
Number of pages10
ISSN0026-895X
DOIs
Publication statusPublished - 2006

Bibliographical note

Keywords: Amino Acid Sequence; Amino Acid Substitution; Animals; Binding Sites; COS Cells; Cells, Cultured; Cercopithecus aethiops; Epitopes; Ghrelin; Humans; Ligands; Models, Molecular; Molecular Sequence Data; Mutant Proteins; Peptide Hormones; Peptides; Protein Binding; Receptors, G-Protein-Coupled; Receptors, Ghrelin; Structure-Activity Relationship; Substance P

ID: 10150085