Structure-function studies on the cyclic peptide MT-II, lactam derivative of α-melanotropin

Peptides

Volumn 20, Issue 3, 1999, Pages 401-409

  Bednarek, Maria A ^a   Silva, Maria V ^a   Arison, Byron ^a   MacNeil, Tanya ^a   Kalyani, Rubana N ^a   Huang, Ruey Ruey C ^a   Weinberg, David H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Alanine scan; Binding affinity; cAMP accumulation assay; Cyclic lactam; Enantio peptides; Melanocortin receptor; Melanocyte stimulating hormone; Retro peptides; Retro enantio peptides

Indexed keywords

CYCLIC AMP; INTERMEDIN DERIVATIVE; MELANOCORTIN RECEPTOR;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHO CELL; CONTROLLED STUDY; IN VITRO STUDY; NONHUMAN; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN STRUCTURE; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ALPHA-MSH; ANIMALS; CHO CELLS; CRICETINAE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES, CYCLIC; RECEPTORS, PITUITARY HORMONE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032852288     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0196-9781(99)00048-0     Document Type: Article

References (35)

1. Al-Obeidi F., de L Castrucci A.M., Hadley M.E., Hruby V.J. Potent and prolonged acting cyclic lactam analogues of α-melanotropin design based on molecular dynamics . J Med Chem. 32:1989;2555-2561.
2. Al-Obeidi F., Hruby V.J., Hadley M.E., Sawyer T.K., de L Castrucci A.M. Design, synthesis and biological activities of a potent and selective α-melanotropin antagonist. Int J Pept Prot Res. 35:1990;228-234.
3. Al-Obeidi F., O'Connor S.D., Job C., Hruby V.J., Pettitt B.M. NMR and quenched molecular dynamics studies of superpotent linear and cyclic α-melanotropins. J Pept Res. 51:1998;420-431.
4. Bodanszky M., Kwei J.Z. Side reactions in peptide chemistry. VII. Sequence dependence in the formation of aminosuccinyl derivatives from β-benzyl-aspartyl peptides. Int J Pept Prot Res. 12:1978;69-74.
5. Chhajlani V., Muceniece R., Wikberg J.E.S. Molecular cloning of a novel human melanocortin receptor. Biochem Biophys Res Commun. 195:1993;866-873.
6. Dorr R.T., Lines R., Levine N., Brooks C., Xiang L., Hruby V.J., Hadley M.E. Evaluation of melanotan-II, a superpotent cyclic melanotropic peptide in a pilot phase- I clinical study. Life Sci. 58:1996;1777-1784.
7. Eberle AN. The melanotropins: chemistry, physiology and mechanism of action. Karger: Basel, 1988.
8. 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 (London). 385:1997;165-168.
9. Friedinger R., Veber D. Peptides and their retro enantiomers are topologically nonidentical. J Am Chem Soc. 79:1979;6129-6130.
10. Gantz I., Shimoto Y., Konda Y., Miwa H., Dickson C.J., Yamada T. Molecular cloning, expression and characterization of a fifth melanocortin receptor. Biochem Biophys Res Commun. 200:1994;1007-1014.
11. Goodman M., Chorev M. On the concept of linear modified retro-peptide structures. Acc Chem Res. 12:1979;1-7.
12. Guichard G., Benkirane N., Zeder-Lutz G., Van Regenmortel M.H.V., Briand J.-P., Muller S. Antigenic mimicry of natural L-peptides with retro-inverso- peptidomimetics. Proc Natl Acad Sci USA. 91:1994;9765-9769.
13. Hadley M.E. The melanotropic peptides source, synthesis, chemistry, secretion and metabolism . 1989;CRC Press, Boca Raton, FL.
14. Hano K., Koida M., Kubo K., Yajima H. Evaluation of the physiological properties of D-histidyl-D- phenylalanyl-D-arginyl-D-tryptophyl-glycine in frog melanocyte. Biochem Bioph Acta. 90:1964;201-204.
15. Haskell-Luevano C., Boteju L.W., Mowa H., Dickinson C., Gantz I., Yamada T., Hadley M.E., Hruby V.J. Topographical modification of melanotropin peptide analogues with β-methyltryptophan isomers at position 9 leads to differential potencies and prolong biological activities. J Med Chem. 38:1995;4720-4729.
16. Haskell-Luevano C., Hendrata S., North C., Sawyer T.K., Hadley M.E., Hruby V.J., Dicknson C., Gantz I. Discovery of prototype peptidomimetic agonists at the human melanocortin receptors MC1R and MC4R. J Med Chem. 40:1997;2133-2139.
17. Haskell-Luevano C., Shenderovich M.D., Sharma S.D., Nikiforovich G., Hadley M.E., Hruby V.J. Design, synthesis and conformations of bicyclic α-melanotropin analogues. J Med Chem. 38:1995;1736-1750.
18. Haskell-Luevano C., Toth K., Boteju L.W., Job C., de L Castrucci A.M., Hadley M.E., Hruby V.J. β- Methylation of the Phe7 and Trp9 melanotropin side chain pharmacophores affects ligand-receptor interactions and prolonged biological activity. J Med Chem. 40:1997;2740-2749.
19. Haskell-Luevano C., Nikiforovich G., Sharma S.D., Yang Y.K., Dickinson C., Hruby V.J., Gantz I. Biological and conformational examination 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.
20. 2 with bulky aromatic amino acids at position 7 show high antagonist potency and selectivity at specific melanocortin receptors. J Med Chem. 38:1995;3454-3461.
21. Hruby V.J., Wilkes B.C., Hadley M.E., Al-Obeidi F., Sawyer T.K., Staples D.J., Devaux A., Dym O., Castrucci A.M., Hintz M.F., Riehm J.P., Rao K.R. α-Melanotropin the minimal active sequence in the frog skin bioassay . J Med Chem. 30:1987;2126-2130.
22. Jameson B.A., McDonnell J.M., Marini J.C., Korngold R. A rationally designed CD4 analogue inhibits experimental encephalomyelitis. Nature (London). 368:1994;744-746.
23. Kask A., Rago L., Mutulis F., Wikberg J.E.S., Schioth H.B. Selective antagonist for the melanocortin 4 receptor (HS014) increases food intake in free-feeding rats. Biochem Biophys Res Commun. 245:1998;90-93.
24. Lu D., Willard D., Patel I.R., Kadwell S., Overton L., Kost T., Lether M., Chen W., Yowchik R.P., Wilkison W.O., Cone R.D. Agouti protein is an antagonist of the melanocyte-stimulating-hormone receptor. Nature (London). 371:1994;799-802.
25. McDonnell J.M., Fushman D., Cahill S.M., Sutton B.J., Cowburn D. Solution structure of FcεRI α-chain mimetics a β-hairpin peptide and its retroenantiomer . J Am Chem Soc. 119:1997;5321-5328.
26. Momany F.A., Aubuchon J.R. Conformational energy analysis of retro-all-D-methionine enkephalin. Biopolymers. 17:1978;2609-2615.
27. Roselli-Rehfuss L., Mountjoy K.G., Robbins L.S., Mortrud M.T., Low M.J., Tatro J.B., Entwistle M.L., Simerly R.B., Cone R.D. Identification of a receptor for γ-melanotropin and other proopiomelanocortin peptides in the hypothalamus and limbic system. Proc Natl Acad Sci USA. 90:1993;8856-8860.
28. 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.
29. Sawyer T.K., Sanfilippo P.J., Hruby V.J., Engel M.H., Heward C.B., Burnett J.B., Hadley M.E. 4-Norleucine, 7-D-phenylalanine-α-melanocyte-stimulating hormone a highly potent α-melanotropin with ultraprolonged biological activity . Proc Natl Acad Sci USA. 77:1980;5754-5758.
30. Schioth H.B., Chhajlani V., Muceniece R., Klusa V., Wikberg J.E.S. Major pharmacological distinction of the ACTH receptor from other melanocortin receptors. Life Sci. 59:1996;797-801.
31. 5-10 . FEBS Lett. 19:1971;229-331.
32. Shemyakin M.M., Ovchinnikov Yu A., Ivanov V.T. Topochemical investigation on peptide systems. Angew Chem Int Ed. 8:1969;492-499.
33. Vaudry H., Eberle A.N. The melanotropic peptides. 1993;New York Academy of Science, New York.
34. Vunnam S., Juvvadi P., Rotondi K.S., Merrifield R.B. Synthesis and study of normal, enantio, retro and retroenantio isomers of cecropin A-melittin hybrids, their end group effects and selective enzyme inactivation. Int J Pept Prot Res. 51:1998;38-44.
35. Yajima H., Kiso Y. Structure-function relationships of the melanocortins. Pharmacol Ther. B1:1975;529-543.