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

doi:10.1016/0196-9781(90)90092-J

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

Chemistry and Biochemistry

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

43 Scopus citations

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 language	English (US)
Pages (from-to)	351-357
Number of pages	7
Journal	Peptides
Volume	11
Issue number	2
DOIs	https://doi.org/10.1016/0196-9781(90)90092-J
State	Published - 1990

Keywords

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

ASJC Scopus subject areas

Biochemistry
Physiology
Endocrinology
Cellular and Molecular Neuroscience

Access to Document

10.1016/0196-9781(90)90092-J

Cite this

@article{72339b54bc004a8e9788a87f2d290c27,

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

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.",

keywords = "Melanocytes, Message sequences, Structure-activity, α-MSH, α-MSH inhibitors, α-Melanotropin",

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

note = "Funding Information: This work was supported by grants from the U.S. Public Health Service (AM 17420), the National Science Foundation, PCM-8412084 and DCB-8615706, and from Conselho Nacional de Desenvolvimento Cienti-rico Tecnologico 408683/88, Brazil.",

year = "1990",

doi = "10.1016/0196-9781(90)90092-J",

language = "English (US)",

volume = "11",

pages = "351--357",

journal = "Peptides",

issn = "0196-9781",

publisher = "Elsevier Inc.",

number = "2",

}

TY - JOUR

T1 - α-Melanocyte stimulating hormone message and inhibitory sequences

T2 - Comparative structure-activity studies on melanocytes

AU - Sawyer, Tomi K.

AU - Staples, Douglas J.

AU - Castrucci, Ana M.L.

AU - Hadley, Mac E.

AU - Al-Obeidi, Fahad A.

AU - Cody, Wayne L.

AU - Hruby, Victor J.

N1 - Funding Information: This work was supported by grants from the U.S. Public Health Service (AM 17420), the National Science Foundation, PCM-8412084 and DCB-8615706, and from Conselho Nacional de Desenvolvimento Cienti-rico Tecnologico 408683/88, Brazil.

PY - 1990

Y1 - 1990

N2 - 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.

AB - 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.

KW - Melanocytes

KW - Message sequences

KW - Structure-activity

KW - α-MSH

KW - α-MSH inhibitors

KW - α-Melanotropin

UR - http://www.scopus.com/inward/record.url?scp=0025210523&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0025210523&partnerID=8YFLogxK

U2 - 10.1016/0196-9781(90)90092-J

DO - 10.1016/0196-9781(90)90092-J

M3 - Article

C2 - 2162535

AN - SCOPUS:0025210523

SN - 0196-9781

VL - 11

SP - 351

EP - 357

JO - Peptides

JF - Peptides

IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this