Structure-activity studies of new melanocortin peptides containing an aromatic amino acid at the N-terminal position

Peptides. 2006 Feb;27(2):472-81. doi: 10.1016/j.peptides.2005.01.032. Epub 2005 Nov 21.

Abstract

Cyclic melanotropin peptides, designed with an aromatic amino acid substitution at the N-terminal position of the MT-II-type scaffold, were prepared by solid-phase peptide synthesis and evaluated for their ability to bind to and activate human melanocortin-1, -3, -4, and -5 receptors. The structure-activity studies of these MT-II analogues have identified a selective antagonist at the hMC4R (H-Phe-c[Asp-Pro-d-Nal(2')-Arg-Trp-Gly-Lys]-NH(2), pA(2)=8.7), a selective partial agonist at the hMC4R (H-d-Nal(2')-c[Asp-Pro-d-Phe-Arg-Trp-Gly-Lys]-NH(2), IC(50)=11nM, EC(50)=56nM), and a selective partial agonist at the hMC3R (H-d-Phe-c[Asp-Pro-d-Phe-Arg-Trp-Lys]-NH(2), IC(50)=3.7nM, EC(50)=4.9nM). Aromatic amino acid substitution at the N-terminus in conjuction with the expansion of the 23-membered cyclic lactam MT-II scaffold to a 26-membered scaffold by addition of a Gly residue in position 10 leads to melanotropin peptides with enhanced receptor selectivity.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amino Acid Sequence
  • Amino Acid Substitution
  • Cell Line
  • Cells, Cultured
  • Computer Simulation
  • Humans
  • Magnetic Resonance Spectroscopy
  • Melanocyte-Stimulating Hormones / chemical synthesis*
  • Melanocyte-Stimulating Hormones / chemistry
  • Models, Molecular
  • Molecular Sequence Data
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Protein Binding
  • Protein Conformation
  • Receptors, Melanocortin / metabolism
  • Structure-Activity Relationship

Substances

  • Peptides
  • Receptors, Melanocortin
  • Melanocyte-Stimulating Hormones