Synthesis and biological evaluation of the superagonist [Nα‐chlorotriazinylaminofluorescein‐Ser1, Nle4, D‐Phe7]‐α‐MSH

Dhirendra N. Chaturvedi, Victor J. Hruby, Ana Maria Ana, Kristie L. Kreutzfeld, Mac E. Hadley

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

The fluorescein‐labeled melanotropin [N″‐chlorotriazinyl‐aminofluorescein‐Ser1, Nle4, D‐Phe7]‐α‐MSH, was prepared by solid‐phase techniques of peptide synthesis. The biological actions of this analogue were determined in several melanocyte bioassays and were compared with the parent peptide [Nle4, D‐Phe7]‐α‐MSH and the native hormone α‐MSH. The fluorescein compound was a superpotent agonist with ∼10 times more activity than α‐MSH in both the frog and the lizard skin bioassays. Murine S91 melanoma cells assayed in vitro (tyrosinase bioassay) were as responsive to the fluorescein analogue as to α‐MSH. The analogue exhibited ultraprolonged biological activity and the biological activities were unaffected by treatment of the analogue with α‐chymotrypsin. The fluorescein‐labeled melanotropin should prove useful for melanotropin receptor characterization.

Original languageEnglish (US)
Pages (from-to)237-240
Number of pages4
JournalJournal of pharmaceutical sciences
Volume74
Issue number3
DOIs
StatePublished - Mar 1985

ASJC Scopus subject areas

  • Pharmaceutical Science

Fingerprint Dive into the research topics of 'Synthesis and biological evaluation of the superagonist [N<sup>α</sup>‐chlorotriazinylaminofluorescein‐Ser<sup>1</sup>, Nle<sup>4</sup>, D‐Phe<sup>7</sup>]‐α‐MSH'. Together they form a unique fingerprint.

  • Cite this