α-Melanocyte stimulating hormone message and inhibitory sequences: Comparative structure-activity studies on melanocytes

Tomi K. Sawyer, Douglas J. Staples, Ana M L Castrucci, Mac E. Hadley, Fahad A. Al-Obeidi, Wayne L. Cody, Victor J Hruby

Research output: Contribution to journalArticle

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Abstract

We investigated the structure-activity relationships of α-MSH (α-melanocyte stimulating hormone) fragment derivatives of the generic formulae Ac-α-MSH(x-13)-NH2 and Ac-α-MSH(6-x)-NH2. The minimal C-terminal sequences required for melanotropic activity were 8-13 and 7-13, respectively, in the frog and lizard skin bioassays. The Arg8-Trp9 sequence appears to be a fundamental component of the minimal message sequences found to date such as α-MSH(6-9), α-MSH(8-13) and α-MSH(7-13). We discovered that Ac-α-MSH(7-10)-NH2 was a weak and selective α-MSH antagonist on the lizard skin bioassay. Analysis of α-MSH(7-10) analogues of the generic formula Ac-Xaa-Arg-Trp-Yaa-NH2 led to Ac-[D-Trp7,D-Phe10]α-MSH(7-10)-NH2, a moderately potent, specific and competitive inhibitor of α-MSH in both the frog and the lizard skin bioassays.

Original languageEnglish (US)
Pages (from-to)351-357
Number of pages7
JournalPeptides
Volume11
Issue number2
DOIs
StatePublished - 1990

Fingerprint

Melanocyte-Stimulating Hormones
Melanocytes
Lizards
Bioassay
Biological Assay
Skin
Anura
Structure-Activity Relationship

Keywords

  • Melanocytes
  • Message sequences
  • Structure-activity
  • α-Melanotropin
  • α-MSH
  • α-MSH inhibitors

ASJC Scopus subject areas

  • Biochemistry
  • Endocrinology
  • Physiology
  • Cellular and Molecular Neuroscience

Cite this

α-Melanocyte stimulating hormone message and inhibitory sequences : Comparative structure-activity studies on melanocytes. / Sawyer, Tomi K.; Staples, Douglas J.; Castrucci, Ana M L; Hadley, Mac E.; Al-Obeidi, Fahad A.; Cody, Wayne L.; Hruby, Victor J.

In: Peptides, Vol. 11, No. 2, 1990, p. 351-357.

Research output: Contribution to journalArticle

Sawyer, Tomi K. ; Staples, Douglas J. ; Castrucci, Ana M L ; Hadley, Mac E. ; Al-Obeidi, Fahad A. ; Cody, Wayne L. ; Hruby, Victor J. / α-Melanocyte stimulating hormone message and inhibitory sequences : Comparative structure-activity studies on melanocytes. In: Peptides. 1990 ; Vol. 11, No. 2. pp. 351-357.
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