Three-dimensional molecular models of the hMC1R melanocortin receptor: complexes with melanotropin peptide agonists

Drug Des Discov. 1996 Dec;14(3):197-211.

Abstract

Three-dimensional molecular models of the human melanocortin receptor (hMC1R) have been developed based upon the electron cryo-microscopic structure of bacteriorhodopsin and the electron density footprint of bovine rhodopsin. alpha-Melanocyte-stimulating hormone, Ac-Ser-Tyr-Ser-Met4-Glu-His-Phe7-Arg-Trp-Gly-Lys-Pro-Val-NH2 (alpha-MSH, alpha-melanotropin), and the superpotent, prolonged acting agonists, Ac-Ser-Tyr-Ser-Nle4-Glu-His-DPhe7-Arg-Trp-Gly-Lys-Pro-Val-NH2 (NDP-MSH) and Ac-Nle4-c[Asp5-His6-DPhe7-Arg8-Trp9-Lys10]-NH2 (MTII), have been modeled into the proposed binding sites with specific ligand-receptor interactions identified. The melanotropin sidechain pharmacophores, DPhe7 and Trp9, are proposed to interact with a hydrophobic network of receptor aromatic residues in transmembrane regions 4, 5, 6, and 7. In addition, a hydrophilic network involving the ligand Arg8 and polar receptor residues located in transmembrane regions 2 and 3 were identified. Biological studies on alpha-MSH, NDP-MSH, MTII, and related peptides have been correlated with the proposed hMC1R model in terms of agonism, affinity, and prolongation. Finally, limited MC1R mutagenesis studies comparing alpha-MSH and NDP-MSH are interpreted within the context of the proposed hMC1R models.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Bacteriorhodopsins / chemistry
  • Cattle
  • Humans
  • Melanocyte-Stimulating Hormones / agonists*
  • Models, Molecular
  • Molecular Sequence Data
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Peptides / chemistry*
  • Peptides / metabolism*
  • Protein Conformation
  • Protein Structure, Secondary
  • Receptors, Corticotropin / chemistry*
  • Receptors, Corticotropin / metabolism*
  • Receptors, Melanocortin
  • Rhodopsin / chemistry
  • Sequence Homology, Amino Acid
  • Structure-Activity Relationship
  • Templates, Genetic
  • alpha-MSH / analogs & derivatives
  • alpha-MSH / chemistry
  • alpha-MSH / metabolism
  • alpha-MSH / pharmacology

Substances

  • Oligopeptides
  • Peptides
  • Receptors, Corticotropin
  • Receptors, Melanocortin
  • acetyl-norleucyl(4)-(aspartyl(5)-histidyl(6)-phenylalanyl(7)-arginyl(8)-tryptophyl(9)-lysyl(10))cyclo-alpha-MSH(4-10)amide
  • Bacteriorhodopsins
  • alpha-MSH
  • MSH, 4-Nle-7-Phe-alpha-
  • Melanocyte-Stimulating Hormones
  • Rhodopsin