Preparation of human Melanocortin-4 receptor agonist libraries: linear peptides X-Y-DPhe7-Arg8-Trp(or 2-Nal)9-Z-NH2

Bioorg Med Chem Lett. 2005 Dec 15;15(24):5504-8. doi: 10.1016/j.bmcl.2005.08.083. Epub 2005 Oct 3.

Abstract

Two libraries of hMC4R agonists, X-Y-DPhe(7)-Arg(8)-2-Nal(9)-Z-NH(2) and X-Y-DPhe(7)-Arg(8)-Trp(9)-Z-NH(2), totaling 185 peptides were prepared using Irori radiofrequency tagging technology and Argonaut Quest 210 Synthesizer, where X stands for N-caps, Y for His(6) surrogates and Z for Gly(10) surrogates. As a result of this study, His-modified pentapeptides with Trp were found to be more hMC4R potent than the corresponding 2-Nal analogs, novel N-caps and Gly surrogates were identified and 19 new peptides which are potent hMC4R agonists (EC(50) 1-15nM) and selective against hMC1R were discovered.

MeSH terms

  • Amino Acid Sequence
  • Glycine
  • Humans
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology
  • Peptide Library*
  • Receptor, Melanocortin, Type 4 / agonists*
  • Structure-Activity Relationship

Substances

  • Oligopeptides
  • Peptide Library
  • Receptor, Melanocortin, Type 4
  • Glycine