Semi-rigid tripeptide agonists of melanocortin receptors

Andrew R. Ruwe, Leonid Koikov, Zalfa Abdel-Malek, Carrie Haskell-Luevano, Marvin L. Dirain, Federico Portillo, Zhimin Xiang, Matt Wortman, James J. Knittel

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A series of 30 RCO-HfR-NH2 derivatives show preference for the mouse MC1R vs MC3-5Rs. trans-4-HOC6H4CH{double bond, long}CHCO-HfR-NH2 (13) [EC50 (nM): MC1R 83, MC3R 20500, MC4R 18130 and MC5R 935; ratio 1:246:217:11] is 11 times more potent than the lead compound LK-394 Ph(CH2)3CO-HfR-NH2 (2) and only 11 times less potent than the native tridecapeptide α-MSH at mMC1R. Differences in conformations of 2 and 13 are discussed.

Original languageEnglish (US)
Pages (from-to)5176-5181
Number of pages6
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number17
DOIs
StatePublished - Sep 1 2009

Keywords

  • Conformational analysis
  • Melanocortin agonists
  • Melanocortin receptors
  • Molecular modeling
  • N-capping
  • Peptidomimetics

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