Potent and selective peptide agonists of α-melanocyte stimulating hormone (αMSH) action at human melanocortin receptor 5; their synthesis and biological evaluation in vitro

Chemical Biology and Drug Design

Volumn 69, Issue 5, 2007, Pages 350-355

  Bednarek, Maria A ^a   MacNeil, Tanya ^a   Tang, Rui ^a   Fong, Tung M ^a   Angeles Cabello, M ^b   Maroto, Marta ^b   Teran, Ana ^b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Medical affairs Merck sharp and Dohme ltd   (Spain)

Author keywords

Agonist; Binding affinity; cAMP accumulation assay; Melanocortin receptor 5; Melanotropins

Indexed keywords

ALPHA INTERMEDIN; AMINO ACID; HISTIDINE; MELANOCORTIN 5 RECEPTOR; N ACETYL ALPHA INTERMEDIN[4-10]CYCLO[4 NORLEUCINE 5 ASPARTIC ACID 7 [3 (2 NAPHTHYL)ALANINE] 10 LYSINAMIDE]; PEPTIDE; PIPECOLIC ACID DERIVATIVE;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING ASSAY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL;

ALPHA-MSH; ANIMALS; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; RECEPTORS, CORTICOTROPIN;

EID: 34249341749     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2007.00513.x     Document Type: Article

References (31)

1. Eberle A.N. (1998) The Melanotropins: Chemistry, Physiology and Mechanism of action. Basel : Kerger.
2. Bertagna X. (1994) Proopiomelanocortin-derived peptide. Endocrinol Metab Clin North Am 23 : 467 485.
3. Hadley M.H. editor (1998) The Melanotropic Peptides: Source, Synthesis, Chemistry, Secretion, and Metabolism. Boca Raton, Florida : CRC Press.
4. Cone R.D. (2006) Studies on the physiological functions of the melanocortin system. Endocrine Rev 27 : 736 749.
5. Starowicz K., Przewloska B. (2003) The role of melanocortins and their receptors in inflammatory processes, nerve regeneration and nociception. Life Sci 73 : 823 847.
6. Wikberg J.E.S. (2001) Melanocortin receptors: new opportunities in drug discovery. Exp Opin Ther Patents 11 : 61 76.
7. Yang Y.K., Harmon C.M. (2003) Recent developments in our understanding of melanocortin system in the regulation of food intake. Obesity Rev 4 : 239 248.
8. Bohm M., Schiller M., Stander S., Seltmann H., Li Z., Brzoska T., Metze D., Schioth H.B., Skottner A., Seiffert K., Zouboulis C.C., Luger T.A. (2002) Evidence for expression of melanocortin-1 receptor in human sebocytes in vitro and in situ. J Invest Dermatol 118 : 533 539.
9. Catania A., Gatti S., Colombo G., Lipton J.M. (2004) Targeting melanocortin receptors as a novel strategy to control inflammation. Pharmacol Rev 56 : 1 29.
10. MacNeil D.J., Howard A.D., Guan X., Fong T.M., Nargund R.P., Bednarek M.A. et al. (2002) The role of melanocortins in body weight regulation: opportunities for the treatment of obesity. Eur J Pharmacol 450 : 93 109.
11. Van der Kraan M., Adan R.A.H., Entwistle M.L., Gispen W.H., Burbach J.P.H., Tatro J.B. (1998) Expression of melanocortin-5 receptor in secretory epithelia supports a functional role in exocrine and endocrine glands. Endocrinology 139 : 2348 2355.
12. Thiboutot D., Sivarajah A., Gilliland K., Cong A., Clawson G. (2000) The melanocortin 5 receptor is expressed in human sebaceous glands in rat preputial cells. J Invest Dermatol 115 : 614 619.
13. Zhang L., Li W.H., Anthonavage M., Eisinger M. (2006) Melanocortin-5 receptor: A marker of human sebocyte differentiation. Peptides 27 : 413 420.
14. Morgan C., Cone R.D. (2006) Melanocortin-5 receptor deficiency in mice blocks a novel pathway influencing pheromone-induced aggression. Beh Gen 36 : 291 300.
15. Caldwell H.K., Lepri J.J. (2002) Disruption of the fifth melanocortin receptor alters the urinary excretion of aggression-modifying pheromones in male house mice. Chem Senses 27 : 91 94.
16. Sawyer T.K., Sanfilippo P.J., Hruby V.J., Engel M.J., Heward C.B., Burnett J.B., Hadley M.E. (1980) [Nle4,D-Phe7]-α-melanocyte-stimulating hormone: A highly potent α-melanotropin with ultralong biological activity. Proc Natl Acad Sci USA 77 : 5754 5758.
17. Al-Obeidi F., Castrucci A.M., Hadley M.E., Hruby V.J. (1989) Potent and prolonged acting cyclic lactam analogues of α-melanotropin: design based on molecular dynamics. J Med Chem 32 : 2555 2561.
18. Hruby V.J., Lu D., Sharma S.D., Castrucci A.L., Kesterson R.A., Al-Obeidi F.A., Hadley M.E., Cone R.D. (1995) Cyclic lactam alpha-melanotropin analogues of Ac-Nle4-cyclo[Asp5,D-Phe7,Lys10] alpha-melanocyte-stimulating hormone-(4-10)-NH2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors. J Med Chem 38 : 3454 3461.
19. Balse-Srinivasan P., Grieco P., Cai M., Trivedi D., Hruby V.J. (2003) Structure-activity relationships of γ-MSH analogues at the human melanocortin MC3, MC4, and MC5 receptors. Discovery of highly selective hMC3R, hMC4R, and hMC5R analogues. J Med Chem 45 : 4965 4973.
20. Balse-Srinivasan P., Grieco P., Cai M., Trivedi D., Hruby V.J. (2003) Structure-activity relationships of novel cyclic α-MSH/β-MSH hybrid analogues that lead to potent and selective ligands for the human MC3R and human MC5R. J Med Chem 46 : 3728 3733.
21. Cai M., Cai C., Mayorov A.V., Xiong C., Cabello C.M., Soloshonok V.A., Swith J.R., Trivedi D., Hruby V.J. (2004) Biological and conformational study of β-substituted prolines in MT-II template: steric effects leading to human MC5 receptor selectivity. J Pept Res 63 : 116 131.
22. Holder J.R., Marques F.F., Xiang Z., Bauzo R.M., Haskell-Luevano C. (2000) Characterization of aliphatic, cyclic, and aromatic N-terminally 'capped' His-D-Phe-Arg-Trp-NH2 tetrapeptides at the melanocortin receptors. Eur J Pharmacol 462 : 41 52.
23. Bednarek M.A., Silva M.V., Arison B., MacNeil T., Kalyani R.N., Huang R-R.C., Weinberg D.H. (1999) Structure-function studies on the cyclic peptide MT-II, lactam derivative of α-melanotropin. Peptides 20 : 401 409.
24. Bednarek M.A., MacNeil T., Kalyani R.N., Tang R., Van der Ploeg L.H.T., Weinberg D.H. (1999) 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 : 209 213.
25. Bednarek M.A., MacNeil T., Kalyani R.N., Tang R., Van der Ploeg L.H.T., Weinberg D.H. (2000) Analogs of lactam derivatives of α-melanotropin with basic and acidic residues. Biochem Biophys Res Commun 272 : 23 28.
26. Prusis P., Muceniece R., Mutule I., Mutulis F., Wikberg J.E.S. (2001) Design of new small cyclic melanocortin receptor-binding peptides using molecular modeling: role of the His residue in the melanocortin peptide core. Eur J Med Chem 36 : 137 146.
27. Haskell-Luevano C., Lim S., Yuan W., Cone R.D., Hruby V.J. (2000) Structure-activity studies of the melanocortin antagonist SHU9119 modified at the 6, 7, 8 and 9 positions. Peptides 21 : 40 57.
28. Grieco P., Balse-Srinivasan P., Han G., Weinberg D., MacNeil T., Van der Ploeg L.H.T., Hruby V.J. (2003) Extensive structure-activity studies of lactam derivatives of MT-II and SHU9119: their activity and selectivity at human melanocortin receptors 3, 4, and 5. J Pept Res 62 : 199 206.
29. Grieco P., Han G., Weinberg D., MacNeil T., Van der Ploeg L.H.T., Hruby V.J. (2002) Design and synthesis of highly potent and selective melanotropins analogues of SHU9119 modified at position 6. Biochem Biophys Res Commun 292 : 1075 1080.
30. Tan C.P., McKee K.K., Weinberg D.H., MacNeil T., Palyha O.C., Feighner D.D., Hreniuk D.L., Van der Ploeg L.H.T., MacNeil D.L., Howard A.D. (1999) Molecular analysis of a new splice variant of the human melanocortin-1 receptor. FEBS Lett 451 : 137 141.
31. Bednarek M.A., MacNeil T., Tang R., Fong T.M., Cabello M.A., Maroto M., Teran A. (2007) Potent and selective agonists of α-melanotropin (αMSH) action at human melanocortin receptor 5; linear analogs of α-melanotropin. Peptides, 28 : 1020 1028.