Synthesis and biological evaluation of the superagonist [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH

D. N. Chaturvedi, Victor J Hruby, A. M L Castrucci De, K. L. Kreutzfeld, M. E. Hadley

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The fluorescein-labeled melanotropin [N(α)-chlorotriazinylaminofluorescein-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 - 1985

Fingerprint

Melanocyte-Stimulating Hormones
Fluorescein
Bioassay
Biological Assay
Bioactivity
Peptides
Solid-Phase Synthesis Techniques
Lizards
Monophenol Monooxygenase
Melanocytes
Chymotrypsin
Anura
Melanoma
Skin
Hormones

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science

Cite this

Synthesis and biological evaluation of the superagonist [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH. / Chaturvedi, D. N.; Hruby, Victor J; Castrucci De, A. M L; Kreutzfeld, K. L.; Hadley, M. E.

In: Journal of Pharmaceutical Sciences, Vol. 74, No. 3, 1985, p. 237-240.

Research output: Contribution to journalArticle

Chaturvedi, D. N. ; Hruby, Victor J ; Castrucci De, A. M L ; Kreutzfeld, K. L. ; Hadley, M. E. / Synthesis and biological evaluation of the superagonist [N(α)-chlorotriazinylaminofluorescein-Ser1,Nle4,D-Phe7]-α-MSH. In: Journal of Pharmaceutical Sciences. 1985 ; Vol. 74, No. 3. pp. 237-240.
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AU - Hruby, Victor J

AU - Castrucci De, A. M L

AU - Kreutzfeld, K. L.

AU - Hadley, M. E.

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