Three-dimensional molecular models of the hMC1R melanocortin receptor: Complexes with melanotropin peptide agonists

Drug Design and Discovery

Volumn 14, Issue 3, 1996, Pages 197-211

  Haskell Luevano, Carrie ^a,b,f   Sawyer, Tomi K ^c   Trumpp Kallmeyer, Susanne ^c   Bikker, Jack A ^c   Humblet, Christine ^c   Gantz, Ira ^d   Hruby, Victor J ^a,e  

^a University of Arizona   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^c PFIZER INC   (United States)

^d UNIVERSITY OF MICHIGAN HEALTH SYSTEM   (United States)

^e UNIVERSITY OF ARIZONA   (United States)

^f OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

Author keywords

melanocyte stimulating hormone; melanotropin; MSH; GPCR model; Melanocortin; NDP MSH

Indexed keywords

ALPHA 2 ADRENERGIC RECEPTOR; ALPHA INTERMEDIN; BACTERIORHODOPSIN; INTERMEDIN; INTERMEDIN DERIVATIVE; RECEPTOR; RHODOPSIN;

AMINO ACID SEQUENCE; ARTICLE; DRUG BINDING SITE; DRUG RECEPTOR BINDING; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR MODEL;

ALPHA-MSH; AMINO ACID SEQUENCE; ANIMALS; BACTERIORHODOPSINS; CATTLE; HUMANS; MELANOCYTE-STIMULATING HORMONES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; OLIGOPEPTIDES; PEPTIDES; PROTEIN CONFORMATION; PROTEIN STRUCTURE, SECONDARY; RECEPTORS, CORTICOTROPIN; RECEPTORS, MELANOCORTIN; RHODOPSIN; SEQUENCE HOMOLOGY, AMINO ACID; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPLATES, GENETIC;

EID: 0030467905     PISSN: 10559612     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (56)

1. Henderson, R., Baldwin, J.M., Ceska, T.A., Zemlin, F., Beckmann, E. and Downing, K.H. (1990) Model for the Structure of Bacteriorhodopsin Based on High-Resolution Electron Cryo-Microscopy. J. Mol. Biol., 213, 899-929.
2. Schertler, G.F.X., Villa, C. and Henderson, R. (1993) Projection Structure of Rhodopsin Nature, 362, 770-772.
3. Hibert, M.F., Trumpp-Kallmeyer, S., Bruinvels, A. and Hoflack, J. (1991) Three-Dimensional Models of Neurotransmitter G-Binding Protein-Coupled Receptors. Mol. Pharmacol., 40, 8-15.
4. Hutchins, C. (1994) Three-Dimensional Models of the D1 and D2 Dopamine Receptors. Endocrine Journal, 2, 7-23.
5. Trumpp-Kallmeyer, S., Hoflack, J., Bruinvels, A. and Hibert, M. (1992) Modeling of G-Protein-Coupled Receptors: Application to Dopamine, Adrenaline. Serotonin, Acetylcholine, and Mammalian Opsin Receptors. J. Med. Chem., 35, 3448-3462.
6. Teeter, M M., Froimowitz, M., Stec. B. and DuRand, C.J. (1994) Homology Modeling of the Dopamine D2 Receptor and Its Testing by Dockina of Agonists and Tricyclic Antagonists. J. Med. Chem., 37, 2874-2888.
7. Nordvall, G. and Hacksell, U. (1993) Binding-Site Modeling of the Muscarinic M1 Receptor: A Combination of Homology-Based and Indirect Approaches. J. Med. Chem., 36, 967-76.
8. Underwood, D.J., Strader, C.D., Rivero, R., Patchett, A.A., Greenlee, W. and Prendergast, K. (1994) Structural Model of Antagonist and Agonist Binding to the Angiotensin II, AT1 Subtype, G Protein Coupled Receptor. Chemistry & Biology, 1, 211-221.
9. Knapp, R.J., Malatynska, E., Collins, N., Fang, L., Wang, J.Y., Hruby, V.J., Roeske, W.R. and Yamamura, H.I. (1995) Molecular Biology and Pharmacology of Cloned Opiod Receptors. FASEB, 9, 516-525.
10. Prusis, P., Frändberg, P.-A., Muceniece, R., Kalvinsh, I. and Wikberg, J.E.S. (1995) A Three Dimensional Model for the Interaction of MSH with the Melanocortin-1 Receptor. Bwchem. Biophys. Res. Commun., 210, 205-210.
11. Mountjoy, K.G., Robbins, L.S., Mortrud, M.T. and Cone, R.D. (1992) The Cloning of a Family of Genes that Encode the Melanocortin Receptors. Science, 257, 1248-1251.
12. Chhajlani, V. and Wikberg, J.E.S (1992) Molecular Cloning and Expression of the Human Melanocyte Stimulating Hormone Receptor cDNA. FEBS Lett, 309, 417-420.
13. Chhajlani, V., Muceniece, R. and Wikberg, J.E.S. (1993) Molecular Cloning of a Novel Human Melanocortin Receptor. Biochem Biophys. Res. Commun., 195, 866-873.
14. Mountjoy, K.G. (1994) The Human Melanocyte Stinulating Hormone Receptor has Evolved to Become "Super-Sensitive" to Melanocortin Peptides. Molecular and Cellular Endocrinology, 102, R7-R11.
15. Gantz, I., Konda, Y., Tashiro, T., Shimoto, Y., Miwa, H., Munzert, G., Watson, S.J., DelValle, J. and Yamada, T. (1993) Molecular Cloning of a Novel Melanocortin Receptor. J. Biol. Chem., 268, 8246-8250.
16. Gantz, I., Miwa, H., Konda, Y., Shimoto, Y., Tashiro, T., Watson, S.J., DelValle, J. and Yamada, T. (1993) Molecular Cloning, Expression, and Gene Localization of a Fourth Melanocortin Receptor. J. Biol. Chem., 268, 15174-15179.
17. Gantz, I., Shimoto, Y., Konda, Y., Miwa, H., Dickinson. C.J. and Yamada, T. (1994) Molecular Cloning, Expression, and Characterization of a Fifth Melanocortin Receptor. Biochem. Biophvs. Res. Commun., 200, 1214-1220.
18. Roselli-Rehfuss, L., Mountjoy, K.G., Robbins, L.S., Mortrud, M.T., Low, M.J., Tatro, J.B., Entwistle, M.L., Simerly, R.B. and Cone, R.D. (1993) Identification of a Receptor for γ Melanotropin and Other Proopiomelanocortin Peptides in the Hypothalamus and Limbic System. Proc Natl Acad. Sci. USA, 90, 8856-8860.
19. De Wied, D. and Jolles, J. (1982) Neuropeptides Derived from Pro-Opiocortin: Behavioral, Physiological, and Neurochemical Effects. Physiol Rev., 62, 976-1059.
20. Lerner, A.B. and McGuire, J.S. (1961) Effect of Alpha- and Beta-Melanocyte Stimulating Hormones on the Skin Colour of Man. Nature. 189, 176-179.
21. Levine, N., Sheftel, S.N., Eytan, T., Dorr, R.T., Hadley, M.E., Weinrach, J.C., Ertl, G.A., Toth, K., McGee, D.L. and Hruby, V.J. (1991) Induction of Skin Tanning by Subcutaneous Administration of a Potent Synthetic Melanotropin. J. Am Med. Assoc., 266, 2730-2736.
22. Hadley, M.E., Hruby, V.J., Levine, N., Dorr, R.T., Sharma, S.D., Sheftel, S.N., Eytan, T., Weinrach, J.C., Ertl, G.A. and Toth, K. (1992) A Melanotropic Peptide Induces Pigmentation (Tanning) of Human Skin. In Peptides 1992. Proceedings of the Twelfth American Peptide Symposium; edited by J.A. Smith and J.E. Rivier, ed., pp. 429-430. ESCOM: Leiden.
23. Sawyer, T.K., Sanfillippo, P.J., Hruby, V.J., Engel, M.H., Heward, C.B., Burnett, J.B. and Hadley, M.E. (1980) 4-Norleucine. 7-D-Phenylalanine-α-Melanocyte-Stimulating Hormone: A Highly Potent α-Melanotropin with Ultra Long Biological Activity. Proc. Natl. Acad. Sci. USA, 77, 5754-5758.
24. Al-Obeidi, F., Hadley, M.E., Pettitt, B.M. and Hruby, V.J. (1989) Design of a New Class of Superpotent Cyclic α-Melanotropins Based on Quenched Dynamic Stimulations. J. Am Chem Soc., 111, 3413-3416.
25. Al-Obeidi, F., Castrucci, A.M., Hadley, M.E. and 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.
26. Probst, W C., Snyder, L.A., Schuster, D.I., Brosius, J. and Sealfon, S.C. (1992) Sequence Alignment of the G-Protein Coupled Receptor Superfamily. DNA and Cell Biology, 11, 1-20.
27. Baldwin, J.M. (1993) The Probable Arrangement of the Helices in G Protein-Coupled Receptors. The EMBO Journal, 12, 1693-1703.
28. Weiner, P.K. and Kollmann, P.A. (1986) An All Atom Force Field for Simulations of Proteins and Nucleic Acids. J. Compta Chem., 7, 129-145.
29. Haskell-Luevano, C., Miwa, H., Dickinson, C., Hruby, V.J., Yamada, T. and Gantz, I. (1994) Binding and cAMP Studies of Melanotropin Peptides with the Cloned Human Peripheral Melanocortin Receptor, hMC1R. Biochem. Biophys. Res. Commun., 204, 1137-1142.
30. Haskell-Luevano, C., Sawyer, T.K., Hendrata, S., North, C., Panahinia, L., Stum, M., Staples, D.J., Castrucci, A.M., Hadley, M.E. and Hruby, V.J. Truncation Studies of α-Melanotropin Peptides Identifies Tripeptide Analogues Exhibiting Prolonged Agonist Bioactivity. Peptides. in press.
31. Haskell-Luevano, C., Shenderovich, M.D., Sharma, S.D., Nikiforovach, G.V., Hadley, M.E. and Hruby, V.J. (1995) Design. Synthesis. Biology and Conformations of Bicyclic α-Melanotropin Peptide Analogues. J Med. Chem., 38, 1736-1750.
32. 7] α-MSH: Discovery of a Tripeptidyl Agonist Exhibiting Sustained Bioactivity. In Ann N.Y. Acad. of Sci.: edited by V. Hubert and A.N. Eberle, ed., pp. 597-599. New York Academy of Sciences: New York.
33. Al-Obeidi, F., Hruby, V.J., Yaghoubi, N., Marwan, M.M. and Hadley, M.E. (1992) Synthesis and Biological Activities of Fatty Acid Conjugates of a Cyclic Lactam α-Melanotropin. J. Med. Chem., 35, 118-123.
34. Hruby, V.J., Wilkes, B C., Cody, W.L., Sawyer, T.K. and Hadley, M.E. (1984) Melanotropins: Structural. Conformational and Biological Considerations in the Development of Superpotent and Superprolonged Analogs. Peptide Protein Rev., 3, 1-64.
35. Sahm, U.C., Olivier, G.W J., Branch, S.K., Moss, S.H. and Pouton, C.W. (1994) Influence of a-MSH Terminal Amino Acids on Binding Affinity and Biological Activity in Melanoma Cells. Peptides, 15, 441-446.
36. Sharma, S.D., Nikiforovich, G.V., Jiang, J., Castrucci, A.M., Hadley, M.E. and Hruby, V.J. (1993) A New Class of Positively Charged Melanotropin Analogs: A New Concept in Peptide Design. In Peptides, 1992; edited by C.H. Schneider and A.N. Eberle, ed., pp. 95-96. ESCOM: Leiden.
37. Sharma, S.D., Nikiforovich, G.V., Jiang, J., Castrucci, A.M., Hadley, M.E. and Hruby, V.J. (1994) Cationized Melanotropin Analogues: Structure-Function Relationships. In Peptides: Chemistry and Biology; edited by R.A. Hodges and J.A. Smith, ed., pp. 398-399. ESCOM: Leiden.
38. 7]-α-MSH J of Pharmaceutical Sciences, 74, 237-240.
39. Chaturvedi, D.M., Knittel, J.J., Hruby, V.J., de L. Castrucci, A.M. and Hadley, M.E. (1984) Synthesis and Biological Actions of Highly Potent and Prolonged Acting Biotin-Labeled Melanotropins. J. Med. Chem., 27, 1406-1410.
40. Mitchell, J.B.O., Nandi, C.L., McDonald, I.K., Thornton, J.M. and Price, S.L. (1994) Amino/Aromatic Interactions in Proteins: Is the Evidence Stacked Against Hydrogen Bonding? J. Mol. Biol., 239, 315-331.
41. Levitt, M and Perutz, M. (1988) Aromatic Rings Act as Hydrogen Bond Acceptors. J. Mol. Biol., 201, 751-754.
42. Burley, S.K. and Petsko, G.A. (1986) Amino-Aromatic Interactions in Proteins. FEBS, 203, 139-143.
43. Burley, S. and Petsko, G. (1988) Weakly Polar Interactions in Proteins. Adv. Protein Chem., 39, 125-189.
44. Flocco, M. and Mowbray, S. (1994) Planar Stacting Interactions of Arginine and Aromatic Side-Charins in Proteins. J. Mol. Biol., 235, 709-717.
45. 7]-α-MSH at the Melanocortin-I Receptor. Biochem. Biophys. Res. Commun., 202, 1266-1271.
46. Zhang, D. and Weinstein, H. (1994) Polarity Conserved Positions in Transmembrane Domains of G-Protein Coupled Receptors and Bacteriorhodopsin. FEBS Letters. 337, 207-212.
47. Donnelly, D., Johnson, M.S., Blundell, T.L. and Saunders, J. (1989) An Analysis of the Periodicity of Conserved Residues in Seuerice Alignments of G-Protein Coupled Receptors. FEBS Lett., 251, 109-116.
48. Robbins, L. S., Nadeau, J.H., Johnson, K.R., Kelly, M.A., Roselli-Rehfuss, L., Baack, E., Mountjoy, K.G. and Cone, R.D. (1993) Pigmentation Phenotypes of Variant Extension Locus Alleles Result From Point Mutations That Alter MSH Receptor Function. Cell, 72, 827-834.
49. Dixon, R.A.F., Strader, C.D. and Sigal, I.S. (1988) Structure and Function of G-Protein Coupled Receptors. Annu. Rep. Med. Chem., 23, 221-233.
50. Horstman, D.A., Brandon, S., Wilson, A.L., Guyer, C.A., Cragoe, E.J. and Limbird, L.E. (1990) An Aspartate Conserved among G-Protein Receptor Confers Allosteric Regulation of α2-Adrenergic Receptors by Sodium. J. Biol. Chem., 265, 21590-21595.
51. Williams, K.A. and Deber, C-M. (1991) Proline Residues in Transmembrane Hehcies: Structural or Dynamic Role? Biochemistry, 30, 8919-8923.
52. Haskell-Luevano, C., Miwa, H., Dickinson, C., Hadley, M.E., Hruby, V.J., Yamada, T. and Gantz, I. (1996) Characterizations of the Unusual Dissociation Properties of Melanotropin Peptides From the Melanocortin Receptor, hMC1R. J. Med. Chem., 39, 432-435.
53. Bond, R.A., Leff, P., Johnson, T.D., Milano, C.A., Rockman, H.A., McMinn, T.R., Apparsundaram, S., Hyek, M.F., Kenakin, T.P., Allen, L.F. and Lefkowitz, R.J. (1995) Physiological Effects of Inverse Agonists in Transgenic Mice With Myocardial Overexpression of the β2-Adrenoceptor. Nature. 374, 272-276.
54. Schwartz, T.W., Gether, U., Schambye, H.T. and Hjorth, S.A. (1995) Molecular Mechanism of Action of Nron-peptide Ligands for Peptide Receptors. Curr. Pharm Design, 1, 325-342.
55. Haskell-Luevano, C., Boteju, L.W., Miwa, H., Dickinson, C., Gantz, I., Yamada, T., Hadley, M.E. and Hruby. V.J. (1995) Topographical Modifications of Melanotropin Peptide Analogues with β-Methyltryptophan Isomers at Position 9 Leads to Differential Potencies and Prolonged Biological Activities. J. Med. Chem., 38, 4720-4729.
56. Huang, R.-R.C , Vicario, P.P., Strader, C.D, and Fong, T.M. (1995) Identification of Residues Involved in Ligand Binding to the Neurokinin-2 Receptor. Biochemistry. 34, 10048-10055.