Non-peptidic antagonists of the CGRP receptor, BIBN4096BS and MK-0974, interact with the calcitonin receptor-like receptor via methionine-42 and RAMP1 via tryptophan-74

Biochem Biophys Res Commun. 2010 Jan 1;391(1):437-42. doi: 10.1016/j.bbrc.2009.11.076. Epub 2009 Nov 13.

Abstract

The receptor for calcitonin gene-related peptide (CGRP) has been the target for the development of novel small molecule antagonists for the treatment of migraine. Two such antagonists, BIBN4096BS and MK-0974, have shown great promise in clinical trials and hence a deeper understanding of the mechanism of their interaction with the receptor is now required. The structure of the CGRP receptor is unusual since it is comprised of a hetero-oligomeric complex between the calcitonin receptor-like receptor (CRL) and an accessory protein (RAMP1). Both the CLR and RAMP1 components have extracellular domains which interact with each other and together form part of the peptide-binding site. It seems likely that the antagonist binding site will also be located on the extracellular domains and indeed Trp-74 of RAMP1 has been shown to form part of the binding site for BIBN4096BS. However, despite a chimeric study demonstrating the role of the N-terminal domain of CLR in antagonist binding, no specific residues have been identified. Here we carry out a mutagenic screen of the extreme N-terminal domain of CLR (residues 23-63) and identify a mutant, Met-42-Ala, which displays 48-fold lower affinity for BIBN4096BS and almost 900-fold lower affinity for MK-0974. In addition, we confirm that the Trp-74-Lys mutation at human RAMP1 reduces BIBN4096BS affinity by over 300-fold and show for the first time a similar effect for MK-0974 affinity. The data suggest that the non-peptide antagonists occupy a binding site close to the interface of the N-terminal domains of CLR and RAMP1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azepines / chemistry
  • Azepines / metabolism*
  • Azepines / pharmacology
  • Calcitonin Gene-Related Peptide Receptor Antagonists*
  • Calcitonin Receptor-Like Protein
  • Humans
  • Imidazoles / chemistry
  • Imidazoles / metabolism*
  • Imidazoles / pharmacology
  • Intracellular Signaling Peptides and Proteins / genetics
  • Intracellular Signaling Peptides and Proteins / metabolism*
  • Membrane Proteins / genetics
  • Membrane Proteins / metabolism*
  • Methionine / genetics
  • Methionine / metabolism
  • Piperazines / chemistry
  • Piperazines / metabolism*
  • Piperazines / pharmacology
  • Protein Structure, Tertiary
  • Quinazolines / chemistry
  • Quinazolines / metabolism*
  • Quinazolines / pharmacology
  • Receptor Activity-Modifying Protein 1
  • Receptor Activity-Modifying Proteins
  • Receptors, Calcitonin / genetics
  • Receptors, Calcitonin / metabolism*
  • Tryptophan / genetics
  • Tryptophan / metabolism

Substances

  • Azepines
  • CALCRL protein, human
  • Calcitonin Gene-Related Peptide Receptor Antagonists
  • Calcitonin Receptor-Like Protein
  • Imidazoles
  • Intracellular Signaling Peptides and Proteins
  • Membrane Proteins
  • Piperazines
  • Quinazolines
  • RAMP1 protein, human
  • Receptor Activity-Modifying Protein 1
  • Receptor Activity-Modifying Proteins
  • Receptors, Calcitonin
  • Tryptophan
  • Methionine
  • telcagepant
  • olcegepant