Synthesis of tritium labeled Ac-[Nle4, D-Phe7]-α-MSH4-11-NH2: A superpotent melanotropin with prolonged biological activity

Brian C. Wilkes; Victor J. Hruby; Henry I. Yamamura; Kazufumi Akiyama; Ana Marie de L. Castrucci; Mac E. Hadley; Joseph R. Andrews; Y. P. Wan

doi:10.1016/0024-3205(84)90302-3

Synthesis of tritium labeled Ac-[Nle⁴, D-Phe⁷]-α-MSH_4-11-NH₂: A superpotent melanotropin with prolonged biological activity

Brian C. Wilkes, Victor J. Hruby, Henry I. Yamamura, Kazufumi Akiyama, Ana Marie de L. Castrucci, Mac E. Hadley, Joseph R. Andrews, Y. P. Wan

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

Ac-[Nle⁴, D-Phe⁷]-α-MSH_4-11-NH₂ an octapeptide, is a melantropin analogue (Ac-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-NH₂), which is a superpotent agonist of frog and lizard skin melanocytes and mouse S 91 (Cloudman) melanoma cells. This malanotropin possesses ultraprolonged activity on melanocytes, both in vitro and in vivo, and the peptide is resistant to inactivation by serum enzymes. The tritiumlabeled congener was prepared by direct incorporation of [³H]-labeled norleucine into the peptide. The melanotropic activity of the labeled peptide is identical to the unlabeled analogue. This labeled peptide should be useful for studies on the localization and characterization of melanotropin receptors.

Original language	English (US)
Pages (from-to)	977-984
Number of pages	8
Journal	Life Sciences
Volume	34
Issue number	10
DOIs	https://doi.org/10.1016/0024-3205(84)90302-3
State	Published - Mar 5 1984

ASJC Scopus subject areas

General Biochemistry, Genetics and Molecular Biology
General Pharmacology, Toxicology and Pharmaceutics

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@article{f0af168041cb47e4951bc281e0603338,

title = "Synthesis of tritium labeled Ac-[Nle4, D-Phe7]-α-MSH4-11-NH2: A superpotent melanotropin with prolonged biological activity",

abstract = "Ac-[Nle4, D-Phe7]-α-MSH4-11-NH2 an octapeptide, is a melantropin analogue (Ac-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-NH2), which is a superpotent agonist of frog and lizard skin melanocytes and mouse S 91 (Cloudman) melanoma cells. This malanotropin possesses ultraprolonged activity on melanocytes, both in vitro and in vivo, and the peptide is resistant to inactivation by serum enzymes. The tritiumlabeled congener was prepared by direct incorporation of [3H]-labeled norleucine into the peptide. The melanotropic activity of the labeled peptide is identical to the unlabeled analogue. This labeled peptide should be useful for studies on the localization and characterization of melanotropin receptors.",

author = "Wilkes, {Brian C.} and Hruby, {Victor J.} and Yamamura, {Henry I.} and Kazufumi Akiyama and Castrucci, {Ana Marie de L.} and Hadley, {Mac E.} and Andrews, {Joseph R.} and Wan, {Y. P.}",

note = "Funding Information: Part of this work was supported by Public Health Service Grants MH-27257, MH-30626 and AM-17420 and by grant PCM-8112200, PCM-7707031 and PCM-810078 from the National Science Foundation. Dr. A. M. Castrucci is a fellow of the Conselho Nacional de Desenvolvimento Cientifico e Technologico of Brasll, Grant 600/807/82. H. F. Yamamura is a recipient of a RSDA from the National Institute of Mental Health.",

year = "1984",

month = mar,

day = "5",

doi = "10.1016/0024-3205(84)90302-3",

language = "English (US)",

volume = "34",

pages = "977--984",

journal = "Life Sciences",

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TY - JOUR

T1 - Synthesis of tritium labeled Ac-[Nle4, D-Phe7]-α-MSH4-11-NH2

T2 - A superpotent melanotropin with prolonged biological activity

AU - Wilkes, Brian C.

AU - Hruby, Victor J.

AU - Yamamura, Henry I.

AU - Akiyama, Kazufumi

AU - Castrucci, Ana Marie de L.

AU - Hadley, Mac E.

AU - Andrews, Joseph R.

AU - Wan, Y. P.

N1 - Funding Information: Part of this work was supported by Public Health Service Grants MH-27257, MH-30626 and AM-17420 and by grant PCM-8112200, PCM-7707031 and PCM-810078 from the National Science Foundation. Dr. A. M. Castrucci is a fellow of the Conselho Nacional de Desenvolvimento Cientifico e Technologico of Brasll, Grant 600/807/82. H. F. Yamamura is a recipient of a RSDA from the National Institute of Mental Health.

PY - 1984/3/5

Y1 - 1984/3/5

N2 - Ac-[Nle4, D-Phe7]-α-MSH4-11-NH2 an octapeptide, is a melantropin analogue (Ac-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-NH2), which is a superpotent agonist of frog and lizard skin melanocytes and mouse S 91 (Cloudman) melanoma cells. This malanotropin possesses ultraprolonged activity on melanocytes, both in vitro and in vivo, and the peptide is resistant to inactivation by serum enzymes. The tritiumlabeled congener was prepared by direct incorporation of [3H]-labeled norleucine into the peptide. The melanotropic activity of the labeled peptide is identical to the unlabeled analogue. This labeled peptide should be useful for studies on the localization and characterization of melanotropin receptors.

AB - Ac-[Nle4, D-Phe7]-α-MSH4-11-NH2 an octapeptide, is a melantropin analogue (Ac-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-NH2), which is a superpotent agonist of frog and lizard skin melanocytes and mouse S 91 (Cloudman) melanoma cells. This malanotropin possesses ultraprolonged activity on melanocytes, both in vitro and in vivo, and the peptide is resistant to inactivation by serum enzymes. The tritiumlabeled congener was prepared by direct incorporation of [3H]-labeled norleucine into the peptide. The melanotropic activity of the labeled peptide is identical to the unlabeled analogue. This labeled peptide should be useful for studies on the localization and characterization of melanotropin receptors.

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Synthesis of tritium labeled Ac-[Nle⁴, D-Phe⁷]-α-MSH_4-11-NH₂: A superpotent melanotropin with prolonged biological activity

Abstract

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