Structure-activity relationship of linear tetrapeptides Tic-DPhe-Arg-Trp-NH2 at the human melanocortin-4 receptor and effects on feeding behaviors in rat

Peptides

Volumn 26, Issue 10, 2005, Pages 2017-2025

  Ye, Zhixiong ^a   MacNeil, Tanya ^a   Weinberg, David H ^a   Kalyani, Rubana N ^a   Tang, Rui ^a   Strack, Alison M ^a   Murphy, Beth A ^a   Mosley, Ralph T ^a   MacIntyre, D Euan ^a   Van Der Ploeg, Lex H T ^a   Patchett, Arthur A ^a   Wyvratt, Matthew J ^a   Nargund, Ravi P ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

MSH; Agonist; Food intake; MC4R; Melanocortin; Tetrapeptide

Indexed keywords

PEPTIDE DERIVATIVE; TETRAPEPTIDE;

AMINO ACID SEQUENCE; AMINO ACID SUBSTITUTION; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BODY WEIGHT; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; FEEDING BEHAVIOR; FOOD INTAKE; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN MODIFICATION; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; APPETITE DEPRESSANTS; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; CRICETULUS; EATING; HUMANS; MALE; MODELS, MOLECULAR; OLIGOPEPTIDES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, MELANOCORTIN, TYPE 4; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 25144458392     PISSN: 01969781     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.peptides.2004.12.035     Document Type: Article

References (50)

1. F. Al-Obeidi, A.M. de L Castrucci, M.E. Hadley, and V.J. Hruby Potent and prolonged acting cyclic lactam analogues of α-melanotropin: design based on molecular dynamics J Med Chem 32 1989 2555 2561
2. F. Al-Obeidi, M.E. Hadley, B.M. Pettitt, and V.J. Rhuby Design of a new class of superpotent cyclic α-melanotropins based on quenched dynamic simulations J Am Chem Soc 111 1989 3413 3416
3. D. Bagnol, X.Y. Lu, C.B. Kaelin, H.E. Day, M. Ollmann, and I. Gantz Anatomy of an endogenous antagonist: relationship between agouti-related protein and proopiomelanocortin in brain J Neurosci 19 1999 RC26
4. M.A. Bednarek, T. MacNeil, R.N. Kalyani, R. Tang, L.H. Van der Plaeg, and D.H. Weinberg Selective, high affinity peptide antagonists of α-melanotropin action at human melanocortin receptor 4: their synthesis and biological evaluation in vitro J Med Chem 44 2001 3665 3672
5. M.A. Bednarek, T. MacNeil, R.N. Kalyani, R. Tang, L.H. Van der Plaeg, and D.H. Weinberg 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
6. M.A. Bednarek, M.V. Silva, B. Arison, T. MacNeil, R.N. Kalyani, and R.R. Huang Structure-function studies on the cyclic peptide MT-II, lactam derivative of α-melanotropin Peptides 20 1999 401 409
7. M.A. Bednarek, T. MacNeil, R. Tang, R.N. Kalyani, L.H. Van der Plaeg, and D.H. Weinberg Potent and selective peptide agonists of alpha-melanocortin action at human melanocortin receptor 4: their synthesis and biological evaluation in vitro Biochem Biophys Res Commun 286 2001 641 645
8. S.C. Benoit, M.W. Schwartz, J.L. Lachey, M.M. Hagan, P.A. Rushing, and K.A. Blake A novel selective melanocortin-4 receptor agonist reduces food intake in rats and mice without producing aversive consequences J Neurosci 20 2000 3442 3448
9. A.M.L. Castrucci, M.E. Jadley, T.K. Sawyer, B.C. Wilkes, F. Al-Oberdi, and D.J. Staples α-Melanotropin: the minimal active sequence in the lizard skin bioassay Gen Comp Endocrinal 73 1989 157 163
10. A.S. Chen, J.M. Metzger, M.E. Trumbauer, X.M. Guan, H. Yu, and E.G. Frazier Role of the melanocortin-4 receptor in metabolic rate and food intake in mice Transgenic Res 9 2000 145 154
11. Chen L, Cheung AW, Chu X, Danho W, Swistok J, Yagaloff KA. Preparation of selective linear peptides with melanocortin-4 receptor (MC4-R) agonist activity, US Patent 6600015 (2003).
12. 2 at the human melanocortin-1 and -4 receptors: arginine substitution Bioorg Med Chem Lett 12 2002 2407 2410
13. A.W.H. Cheung, W. Danho, J. Swistok, L. Qi, G. Kurylko, and K. Rowan Structure-Activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH2 at the human melanocortin-1 and -4 receptors: histidine substitution Bioorg Med Chem Lett 13 2003 133 137
14. A.W. Cheung, W. Danho, J. Swistok, L. Qi, G. Kurylko, and K. Rowan Structure-activity relationship of cyclic peptide penta-c[Asp-His6-DPhe7-Arg8- Trp9-Lys]-NH2 at the human melanocortin-1 and -4 receptors: His6 substitution Bioorg Med Chem Lett 13 2003 1307 1311
15. D. Danho, J. Swistok, A.W.H. Cheung, G. Kurylko, L. Franco, and X.J. Chu Structure-activity relationship of linear peptide Bu-His-DPhe-Arg-Trp-Gly-NH2 at the human melanocortin-1 and -4 receptors: DPhe and Trp substitution Bioorg Med Chem Lett 13 2003 649 652
16. W. Fan, B.A. Boston, R.A. Kesterson, V.J. Hruby, and R.D. Cone Role of melanocortinergic neurons in feeding and the agouti obesity syndrome Nature 385 1997 165 168
17. W. Fan, D.M. Dinulescu, A.A. Butler, J. Zhou, D.L. Marks, and R.D. Cone The central melanocortin system can directly regulate serum insulin levels Endocrinology 141 2000 3072 3079
18. H.L. Fehm, R. Smolnik, W. Kern, G.P. McGregor, U. Bickel, and J. Born The melanocortin melanocyte-stimulating hormone/adrenocorticotropin (4-10) decreases body fat in humans J Clin Endocrinol Metab 86 2001 1144 1148
19. I. Gantz, and T.M. Fong The melanocortin system Am J Physiol Endocrinol Metab 284 2003 E468 E474
20. C. Haskell-Luevano, R.D. Cone, E.K. Monck, and Y.P. Wan 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. C. Haskell-Luevano, S. Lim, W. Yuan, R.D. Cone, and V.J. Hruby Structure activity studies of the melanocortin antagonist SHU9119 modified at the 6, 7, 8 and 9 positions Peptides 21 2002 49 57
22. C. Haskell-Luevano, T.K. Sawyer, S. Hendrata, C. North, L. Panahinia, and M. Stum Truncation studies of α-melanotropin peptides identifies tripeptide analogues exhibiting prolonged agonist bioactivity Peptides 17 1996 995 1002
23. J.R. Holder, R.M. Bauzo, Z. Xiang, and C. Haskell-Luevano Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH2 at the mouse melanocortin receptors: part 2 modifications at the Phe position J Med Chem 45 2002 3073 3081
24. J.R. Holder, R.M. Bauzo, Z. Xiang, and C. Haskell-Luevano Structure-activity relationships of the melanocortin tetrapeptide Ac-His-DPhe-Arg-Trp-NH2 at the mouse melanocortin receptors 1. modifications at the His position J Med Chem 45 2002 2801 2810
25. J.R. Holder, and C. Haskell-Luevano Melanocortin ligands: 30 years of structure-activity relationship (SAR) studies Med Res Rev 24 2004 325 356
26. J.R. Holder, Z. Xiang, R.M. Bauzo, and C. Haskell-Luevano 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 24 2003 73 82
27. 2 at the mouse melanocortin receptors 4. Modifications at the Trp position J Med Chem 45 2002 5736 5744
28. 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
29. V.J. Hruby, B.C. Wilkes, M.E. Hadley, F. Al-Obeidi, T.K. Sawyer, and D.J. Staples α-Melanotropin: the minimal active sequence in the frog skin bioassay J Med Chem 30 1987 2126 2130
30. L. Illum Nasal drug delivery: new developments and strategies Drug Discov Today 7 2002 1184 1189
31. A. Kask, F. Mutulis, R. Muceniece, R. Pahkla, I. Mutule, and J.E. Wikberg Discovery of a novel superpotent and selective melanocortin-4 receptor antagonist (HS024): evaluation in vitro and in vivo Endocrinology 139 1998 5006 5014
32. A. Kask, L. Rago, P. Korrovits, J.E. Wikberg, and H.B. Schioth Evidence that orexigenic effects of melanocortin 4 receptor antagonist HS014 are mediated by neuropeptide Y Biochem Biophys Res Commun 248 1998 245 249
33. M.D. Miller, R.P. Sheridan, and S.K. Kearsley SQ - a program for rapidly producing pharmacophorically relevant molecular superpositions J Med Chem 42 1999 1505 1514
34. K.G. Mountjoy, M.T. Mortrud, M.J. Low, R.B. Simerly, and R.D. Cone Localization of the melanocortin-4 receptor (MC4-R) in neuroendocrine and autonomic control circuits in the brain Mol Endocrinol 8 1994 1298 1308
35. B. Murphy, C.N. Nunes, J. Ronan, M. Hanaway, A.M. Fairhurst, and T.N. Mellin Centrally administered MTII affects feeding, drinking, temperature, and activity in the Sprague-Dawley rat J Appl Physiol 89 2000 273 282
36. B. Murphy, C.N. Nunes, J.J. Ronan, C.M. Harper, M.J. Beall, and M. Hanaway Melanocortin mediated inhibition of feeding behavior in rats Neuropeptides (Edinburgh) 32 1998 491 497
37. S. Obici, Z. Feng, J. Tan, L. Liu, G. Karkanias, and L. Rossetti Central melanocortin receptors regulate insulin action J Clin Invest 108 2001 1079 1085
38. Tetrapeptide 1, His-DPhe-Arg-Trp-NH2 has been reported at the human melanocortin-4 receptor previously (Ref 44, Ki = 416 nM and EC50 = 8.7 nM). The smaller EC50 value than Ki value is possibly due to the use of a transient expression system for determination of EC50 since activation properties are dependent on expression level per cell.
39. C.B. Saper, T. Chou, and J. Elmquist The need to feed: homeostatic and hedonic control of eating Neuron 36 2002 199 211
40. T.K. Sawyer, P. Sanfilippo, V.J. Hruby, M.H. Engel, C.B. Heward, and J.B. Burnett 4-Norleucine 7-d-phenylalanine-α-melanocyte-stimulating hormone: a highly potent α-melanotropin with ultralong biological activity Proc Natl Acad Sci USA 77 1980 5754 5758
41. I.K. Sebhat, W.J. Martin, Z. Ye, K. Barakat, R.T. Mosley, and D.B.R. Johnston Design and pharmacology of N-[(3R)-1,2,3,4-tetrahydroisoquinolinium-3- yl carbonyl]-(1R)-1-(4-chlorobenzyl)-2-[4-cyclohexyl-4-(1H-1,2,4-triazol-1- ylmeth yl)piperidin-1-yl]-2-oxoethylamine (1), a potent, selective melanocortin subtype-4 receptor (MC4R) agonist J Med Chem 45 2002 4589
42. I. Sebhat, Z. Ye, M. Bednarek, D. Weinberg, R. Nargund, and T.M. Fong Melanocortin-4 receptor agonists and antagonists: chemistry and potential therapeutic utilities Ann Rep Med Chem 38 2003 31 40
43. G.V. Skuladottir, L. Jonsson, J.O. Skarphedinsson, F. Mutulis, R. Muceniece, and A. Raine Long term orexigenic effect of a novel melanocortin-4 receptor selective antagonist Br J Pharmacol 126 1999 27 34
44. C.P. Tan, K.K. McKee, D.H. Weinberg, T. MacNeil, O.C. Palyha, and S.D. Feighner Molecular analysis of a new splice variant of the human melanocortin-1 receptor FEBS Lett 451 1999 137 141
45. J. Voisey, L. Carroll, and A. van Daal Melanocortins and their receptors and antagonists Curr Drug Targ 4 2003 586 597
46. D.L. Williams, J.M. Kaplan, and H.J. Grill The role of the dorsal vagal complex and the vagus nerve in feeding effects of melanocortin-3/4 receptor stimulation Endocrinology 141 2000 1332 1337
47. Y. Yang, T.M. Fong, C.J. Dickinson, C. Mao, J.Y. Li, and M.R. Tota Molecular determinants of ligand binding to the human melanocortin-4 receptor Biochemistry 39 2000 14900 14911
48. Y.K. Yang, and C.M. Harmon Recent developments in our understanding of melanocortin system in the regulation of food intake Obes Rev 4 2003 239 248
49. Ye Z, et al. Unpublished results.
50. I.A. Zimanyi, and M.A. Pelleymounter The role of melanocortin peptides and receptors in regulation of energy balance Curr Pharm Des 9 2003 627 641