Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH2 at the mouse melanocortin receptors Part 3: Modifications at the Arg position

Peptides

Volumn 24, Issue 1, 2003, Pages 73-82

  Holder, Jerry Ryan ^a   Xiang, Zhimin ^a   Bauzo, Rayna M ^a   Haskell Luevano, Carrie ^a  

^a UNIVERSITY OF FLORIDA   (United States)

Author keywords

MSH; G protein coupled receptors; Melanocortin; Melanotropin; MTII; POMC; SHU9119; Solid phase peptide synthesis

Indexed keywords

ACETYLHISTIDYL DEXTRO PHENYLALANYL DEXTRO ARGINYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLALANYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLARGINYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLASPARTYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLGLUTAMINYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLHOMOARGINYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLLYSYLTRYPTOPHANAMIDE; ACETYLHISTIDYL DEXTRO PHENYLALANYLPROLYLTRYPTOPHANAMIDE; MELANOCORTIN; MELANOCORTIN 1 RECEPTOR; MELANOCORTIN 3 RECEPTOR; MELANOCORTIN 4 RECEPTOR; MELANOCORTIN 5 RECEPTOR; MELANOCORTIN RECEPTOR; PEPTIDE FRAGMENT; TETRAPEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; EMBRYO; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; RECEPTOR INTRINSIC ACTIVITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ARGININE; CELL LINE; HUMANS; MICE; OLIGOPEPTIDES; RECEPTOR, MELANOCORTIN, TYPE 3; RECEPTORS, CORTICOTROPIN; RECEPTORS, MELANOCORTIN; STRUCTURE-ACTIVITY RELATIONSHIP;

AGOUTI;

EID: 0037260606     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0196-9781(02)00278-4     Document Type: Article

References (46)

1. Bednarek M.A., Macneil T., Kalyani R.N., Tang R., Van der Ploeg L.H., Weinberg D.H. Analogs of MTII, lactam derivatives of α-melanotropin, modified at the N-terminus, and their selectivity at human melanocortin receptors 3, 4, and 5. Biochem. Biophys. Res. Commun. 261:1999;209-213.
2. Bednarek M.A., MacNeil T., Kalyani R.N., Tang R., Van der Ploeg L.H., Weinberg D.H. Analogs of lactam derivatives of α-melanotropin with basic and acidic residues. Biochem. Biophys. Res. Commun. 272:2000;23-28.
3. Bednarek M.A., Silva M.V., Arison B., MacNeil T., Kalyani R.N., Huang R.R.et al. Structure-function studies on the cyclic peptide MT-II, lactam derivative of α-melanotropin. Peptides. 20:1999;401-409.
4. Bondebjerg J., Xiang Z., Bauzo R.M., Haskell-Luevano C., Meldal M. A solid phase approach to mouse melanocortin receptor agonists derived from a novel thioether cyclized peptidomimetic scaffold. J. Am. Chem. Soc. 124:2002;11046-11055.
5. Butler A.A., Kesterson R.A., Khong K., Cullen M.J., Pelleymounter M.A., Dekoning J.et al. A unique metabolic syndrome causes obesity in the melanocortin-3 receptor-deficient mouse. Endocrinology. 141:2000;3518-3521.
6. Carpino L.A., Han G.Y. The 9-fluorenylmethyoxycarbonsy amino-protecting group. J. Org. Chem. 37:1972;3404-3409.
7. Castrucci A.M.L., Hadley M.E., Sawyer T.K., Wilkes B.C., Al-Obeidi F., Staples D.J.et al. α-Melanotropin: the minimal active sequence in the lizard skin bioassay. Gen. Comp. Endocrinol. 73:1989;157-163.
8. Chang C., Meienhofer J. Solid-phase peptide synthesis using mild base cleavage of Nα-fluorenylmethyloxycarbonylamino acids, exemplified by a synthesis of dihydrosomatostatin. Int. J. Pept. Protein Res. 11:1978;246-249.
9. Chen A.S., Marsh D.J., Trumbauer M.E., Frazier E.G., Guan X.M., Yu H.et al. Inactivation of the mouse melanocortin-3 receptor results in increased fat mass and reduced lean body mass. Nat. Genet. 26:2000;97-102.
10. Chen W., Kelly M.A., Opitz-Araya X., Thomas R.E., Low M.J., Cone R.D. Exocrine gland dysfunction in MC5-R deficient mice: evidence for coordinated regulation of exocrine gland functions by melanocortin peptides. Cell. 91:1997;789-798.
11. Chen W., Shields T.S., Stork P.J.S., Cone R.D. A colorimetric assay for measuring activation of Gs- and Gq-coupled signaling pathways. Anal. Biochem. 226:1995;349-354.
12. Chhajlani V., Wikberg J.E.S. Molecular cloning and expression of the human melanocyte stimulating hormone receptor cDNA. FEBS Lett. 309:1992;417-420.
13. Cone R.D., Lu D., Kopula S., Vage D.I., Klungland H., Boston B.et al. The melanocortin receptors: agonists, antagonists, and the hormonal control of pigmentation. Recent Prog. Horm. Res. 51:1996;287-318.
14. Eberle, AN. The melanotropins: chemistry, physiology and mechanisms of action. Basel: Karger; 1988.
15. Fan W., Boston B.A., Kesterson R.A., Hruby V.J., Cone R.D. Role of melanocortinergic neurons in feeding and the agouti obesity syndrome. Nature. 385:1997;165-168.
16. Farooqi I.S., Yeo G.S., Keogh J.M., Aminian S., Jebb S.A., Butler G.et al. Dominant and recessive inheritance of morbid obesity associated with melanocortin 4 receptor deficiency. J. Clin. Invest. 106:2000;271-279.
17. Gantz I., Konda Y., Tashiro T., Shimoto Y., Miwa H., Munzert G.et al. Molecular cloning of a novel melanocortin receptor. J. Biol. Chem. 268:1993;8246-8250.
18. Gantz I., Shimoto Y., Konda Y., Miwa H., Dickinson C.J., Yamada T. Molecular cloning, expression, and characterization of a fifth melanocortin receptor. Biochem. Biophys. Res. Commun. 200:1994;1214-1220.
19. Haskell-Luevano, C. In vitro mutagenesis studies of melanocortin receptor coupling and ligand binding. In: Cone RD, editor. The melanocortin receptors. New Jersey: The Humana Press Inc.; 2000. p. 263-306.
20. Haskell-Luevano C., Cone R.D., Monck E.K., Wan Y.-P. Structure activity studies of the melanocortin-4 receptor by in vitro mutagenesis: identification of agouti-related protein (AGRP), melanocortin agonist and synthetic peptide antagonist interaction determinants. Biochemistry. 40:2001;6164-6179.
21. Haskell-Luevano C., Holder J.R., Monck E.K., Bauzo R.M. Characterization of melanocortin NDP-MSH agonist peptide fragments at the mouse central and peripheral melanocortin receptors. J. Med. Chem. 44:2001;2247-2252.
22. Haskell-Luevano C., Nikiforovich G.V., Sharma S.D., Yang Y.-K., Dickinson C., Hruby V.J.et al. Biological and conformational evaluation of stereochemical modifications using the template melanotropin peptide, Ac-Nle-c[Asp-His-Phe-Arg-Trp-Ala-Lys]-NH2, on human melanocortin receptors. J. Med. Chem. 40:1997;1738-1748.
23. Haskell-Luevano C., Rosenquist Å., Souers A., Kong K., Ellman J., Cone R.D. Compounds that activate the mouse melanocortin-1 receptor identified by screening a small molecule library based upon the β-turn. J. Med. Chem. 42:1999;4380-4387.
24. Haskell-Luevano C., Sawyer T.K., Hendrata S., North C., Panahinia L., Stum M.et al. Truncation studies of α-melanotropin peptides identifies tripeptide analogues exhibiting prolonged agonist bioactivity. Peptides. 17:1996;995-1002.
25. Haskell-Luevano C., Sawyer T.K., Trumpp-Kallmeyer S., Bikker J., Humblet C., Gantz I.et al. Three-dimensional molecular models of the hMC1R melanocortin receptor: complexes with melanotropin peptide agonists. Drug Des. Discov. 14:1996;197-211.
26. Hinney A., Schmidt A., Nottebom K., Heibult O., Becker I., Ziegler A.et al. Several mutations in the melanocortin-4 receptor gene including a nonsense and a frameshift mutation associated with dominantly inherited obesity in humans. J. Clin. Endocrinol. Metab. 84:1999;1483-1486.
27. Hruby V.J., Wilkes B.C., Cody W.L., Sawyer T.K., Hadley M.E. Melanotropins: structural, conformational and biological considerations in the development of superpotent and superprolonged analogs. Pept. Protein Rev. 3:1984;1-64.
28. Hruby V.J., Wilkes B.C., Hadley M.E., Al-Obeidi F., Sawyer T.K., Staples D.J.et al. α-Melanotropin: the minimal active sequence in the frog skin bioassay. J. Med. Chem. 30:1987;2126-2130.
29. Huszar D., Lynch C.A., Fairchild-Huntress V., Dunmore J.H., Smith F.J., Kesterson R.A.et al. Targeted disruption of the melanocortin-4 receptor results in obesity in mice. Cell. 88:1997;131-141.
30. Kaiser E., Colescott R.L., Bossinger C.D., Cook P.I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34:1970;595-598.
31. Lu D., Väge D.I., Cone R.D. A ligand-mimetic model for constitutive activation of the melanocortin-1 receptor. Mol. Endocrinol. 12:1998;592-604.
32. Lu D., Willard D., Patel I.R., Kadwell S., Overton L., Kost T.et al. Agouti protein is an antagonist of the melanocyte-stimulating-hormone receptor. Nature. 371:1994;799-802.
33. Mergen M., Mergen H., Ozata M., Oner R., Oner C. Rapid communication: a novel melanocortin 4 receptor (MC4R) gene mutation associated with morbid obesity. J. Clin. Endocrinol. Metab. 86:2001;3448-3451.
34. Mountjoy K.G., Robbins L.S., Mortrud M.T., Cone R.D. The cloning of a family of genes that encode the melanocortin receptors. Science. 257:1992;1248-1251.
35. Ollmann M.M., Wilson B.D., Yang Y.-K., Kerns J.A., Chen Y., Gantz I.et al. Antagonism of central melanocortin receptors in vitro and in vivo by agouti-related protein. Science. 278:1997;135-138.
36. Pritchard L.E., Turnbull A.V., White A. Pro-opiomelanocortin processing in the hypothalamus: impact on melanocortin signalling and obesity. J. Endocrinol. 172:2002;411-421.
37. Robbins L.S., Nadeau J.H., Johnson K.R., Kelly M.A., Roselli-Rehfuss L., Baack E.et al. Pigmentation phenotypes of variant extension locus alleles result from point mutations that alter MSH receptor function. Cell. 72:1993;827-834.
38. Roselli-Rehfuss L., Mountjoy K.G., Robbins L.S., Mortrud M.T., Low M.J., Tatro J.B.et al. Identification of a receptor for γ melanotropin and other proopiomelanocortin peptides in the hypothalamus and limbic system. Proc. Natl. Acad. Sci. U.S.A. 90:1993;8856-8860.
39. Sahm U.G., Olivier G.W.J., Branch S.K., Moss S.H., Pouton C.W. Synthesis and biological evaluation of α-MSH analogs substituted with alanine. Peptides. 15:1994;1297-1302.
40. Shutter J.R., Graham M., Kinsey A.C., Scully S., Lüthy R., Stark K.L. Hypothalamic expression of ART, a novel gene related to agouti, is up-regulated in obese and diabetic mutant mice. Genes Dev. 11:1997;593-602.
41. Sina M., Hinney A., Ziegler A., Neupert T., Mayer H., Siegfried W.et al. Phenotypes in three pedigrees with autosomal dominant obesity caused by haploinsufficiency mutations in the melanocortin-4 receptor gene. Am. J. Hum. Genet. 65:1999;1501-1507.
42. Vaisse C., Clement K., Durand E., Hercberg S., Guy-Grand B., Froguel P. Melanocortin-4 receptor mutations are a frequent and heterogeneous cause of morbid obesity. J. Clin. Invest. 106:2000;253-262.
43. Vaisse C., Clement K., Guy-Grand B., Froguel P. A frameshift mutation in human MC4R is associated with a dominant form of obesity. Nat. Genet. 20:1998;113-114.
44. Yang Y., Chen M., Lai Y., Gantz I., Georgeson K.E., Harmon C.M. Molecular determinants of human melanocortin-4 receptor responsible for antagonist SHU9119 selective activity. J. Biol. Chem. 277:2002;20328-20335.
45. Yang Y., Fong T.M., Dickinson C.J., Mao C., Li J.Y., Tota M.R.et al. Molecular determinants of ligand binding to the human melanocortin-4 receptor. Biochemistry. 39:2000;14900-14911.
46. 7] melanocyte stimulating hormone with the human melanocortin-1 receptor (melanocyte α-MSH receptor). J. Biol. Chem. 272:1997;23000-23010.