1H-NMR studies on a potent and selective antagonist at human melanocortin receptor 4 (hMC-4R)

Biopolymers

Volumn 68, Issue 4, 2003, Pages 512-527

  Elipe, Maria Victoria Silva ^a   Mosley, Ralph T ^a   Bednarek, Maria A ^a   Arison, Byron H ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

1H NMR; Human MC 4 receptor; Molecular modeling; MTII; SHU9119

Indexed keywords

HORMONES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

RECEPTORS;

ORGANIC POLYMERS;

MELANOCORTIN 4 RECEPTOR; N ACETYL ALPHA INTERMEDIN[4-10]CYCLO[4 NORLEUCINE 5 ASPARTIC ACID 7 [3 (2 NAPHTHYL)ALANINE] 10 LYSINAMIDE]; N ACETYLNORLEUCYLCYCLO(ASPARTYLHISTIDYL DEXTRO PHENYLALANINE ARGINYLTRYPTOPHYLLYSINAMIDE); UNCLASSIFIED DRUG; CORTICOTROPIN RECEPTOR; CYCLOPEPTIDE; OLIGOPEPTIDE;

ARTICLE; BINDING KINETICS; CONFORMATIONAL TRANSITION; HORMONE RECEPTOR INTERACTION; HUMAN; MOLECULAR DYNAMICS; MOLECULAR RECOGNITION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; SYNTHESIS; THERMODYNAMICS;

HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; RECEPTOR, MELANOCORTIN, TYPE 4; RECEPTORS, CORTICOTROPIN; THERMODYNAMICS;

EID: 0038206586     PISSN: 00063525     EISSN: None     Source Type: Journal    
DOI: 10.1002/bip.10340     Document Type: Article

References (41)

1. De Wied, D.; Jolles, J. Physiol Rev 1982, 62, 976-1059.
2. Hadley, M. E. In The Melanotropic Peptides: Source, Synthesis, Chemistry, Secretion and Metabolism. CRC Press: Boca Raton, FL, 1989.
3. Vaudry, H.; Eberle, A. N. The Melanotropic Peptides; New York Academic of Science: New York, 1993.
4. Kask, A.; Rago, L. Wikberg, J. E. S.; Schiotch, H. B. Eur J Pharmacol 1998, 360, 15-19.
5. Fan, W.; Boston, B. A.; Kesterson, R. A.; Hruby, V. J.; Cone, R. D. Nature 1997, 385, 165-168.
6. Schiotch, H. B.; Chhajlani, V.; Muceniece, R.; Klusa, V.; Wikberg, J. E. S. Life Sci 1996, 59, 797-801.
7. Gantz, I.; Shimoto, Y.; Konda, Y.; Miwa, H.; Dickson, C. J., Yamada, T. Biochem Biophys Res Commun 1994, 200, 1007-1014.
8. Wessells, H.; Fuciarelli, K.; Hansen, J.; Hadley, M. E.; Hruby, V. J.; Dorr, R.; Levine, N. J Urology 1998, 160, 389-393.
9. Wikberg, J. E. S. Eur J Pharmacology 1999, 375, 295-310.
10. Eberle, A. N. In The Melanotropins: Chemistry, Physiology and Mechanism of Action. Karger: Basel, 1988.
11. Roselli-Rehfuss, L.; Mountjoy, K. G.; Robbins, L. S.; Mortrud, M. T.; Low, M. J.; Tatro, J. B.; Entwisttle, M. L.; Simerly, R. B.; Cone, R. D. Proc Natl Acad Sci USA 1993, 90, 8856-8860.
12. Gantz, I.; Konda, Y.; Tashiro, T.; Shimoto. Y.; Miwa, H.; Munzert, G.; Warson, S. J.; Del Valle, J.; Yamada, T. J Biol Chem 1993, 268, 8246-8250.
13. Mountjoy, K. G.; Mortrud, M. T.; Low, M. J.; Simerly, R. B.; Cone, R. D. Mol Endocrinol 1994, 8, 1298-1308.
14. Fan, W.; Boston, B. A.; Kesterson, R. A.; Hruby, V. J.; Cone, R. D. Nature 1997, 385, 165-168.
15. Mountloy, K. G.; Wong, J. Mol Cell Endocrinol 1997, 128, 171-177.
16. Chen, W.; Kelly, M. A.; Opiz-Araya, X.; Thomas, R. E.; Low, M. J.; Cone, R. D. Cell 1997, 91, 789-798.
17. Al-Obedi, F.; de L. Castrucci, A. M.; Hadley, M. E.; Hruby, V. J. J Med Chem 1989, 32, 2555-2561.
18. Hruby, V. J.; Lu, D.; Sharma, S. D.; de L. Castrucci, A.; Kesterson, R. A.; Al-Obeidi, F. A.; Hadley, M. E.; Cone, R. D. J Med Chem 1995, 38, 3454-3461.
19. Kask, A.; Rago, L.; Korrovits, P.; Wikberg, J. E. S.; Schiotch, H. B. Biochem Biophys Res Commun 1998, 248, 245-249.
20. Kask, A.; Rago, L.; Mutulis, F.; Pahkla, R.; Wikberg, J. E. S.; Schiotch, H. B. Biochem Biophys Res Commun 1998, 245, 90-93.
21. Murphy, B.; Nunes, C. N.; Ronan, J. J.; Harper, C. M.; Beall, M. J.; Hanaway, M.; Fairhurst, A. M.; Van der Ploeg, L. H. T.; MacIntype, D. E.; Mellin, T. N. Neuropeptides 1998, 32, 491-497.
22. Giraudo, S. Q.; Billington, C. J.; Levine, A. S. Brain Res 1998, 809, 302-306.
23. Huszar, D.; Lynch, C. A.; Fairchild-Huntress, V.; Dunmore, J. H.; Fang, Q.; Berkemeier, L. R.; Gu, W.; Kesterson, R. A.; Boston, B. A.; Cone, R. D.; Smith, F. J.; Campfield, L. A.; Burn, P.; Lee, F. Cell 1997, 88, 131-141.
24. Bednarek, M. A.; Silva, M. V.; Arison, B.; MacNeil, T.; Kalyani, R. N.; Huang, R.-R. C.; Weinberg, D. H. Peptides 1999, 20, 401-409.
25. Bednarek, M. A.; MacNeil, T.; Kalyani, R. N.; Tang, R.; Van der Ploeg, L. H. T.; Weinberg, D. H. J Med Chem 2001, 44, 3665-3672.
26. Crippen, C. M.; Havel, T. F. Distance Geometry and Molecular Conformation; Wiley: New York, 1988.
27. Kuszewski, J.; Nilges, M.; Brunger, A. T. J Biomol NMR 1992, 2, 33-56.
28. Halgren, T. A. J Comp Chem 1999, 20, 720-729.
29. Diamond, R. Acta Crystallogr 1988, A44, 211-216.
30. Diamond, R. Protein Sci 1992, 1, 1279-1287.
31. Kearsley, S. K. Acta Crystallogr 1989, A45, 208-210.
32. Kearsley, S. K. J Comput-Aided Mol Design 1994, 8, 565-582.
33. Sugg, E. E.; Cody, W. L.; Abdel-Malek, Z.; Hadley, M. E.; Hruby, V. J. Biopolymers 1986, 25, 2029-2042.
34. Hruby, V. J.; Cody, W. L.; de Lauro Castrucci, A. M.; Hadley, M. E. Coll Czech Chem Commun 1988, 53, 2549-2573.
35. Wüthrich, K. NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
36. Prabhu, N. V.; Perkyns, J. S.; Pettitt, B. M.; Hruby, V. J. Biopolymers 1999, 50, 255-272.
37. Prabhu, N. V.; Perkyns, J. S.; Pettitt, B. M. J Peptide Res 1999, 54, 394-407.
38. Higashijima, T.; Tasumi, M.; Miyazawa, T. FEBS Lett 1975, 57, 17-178.
39. Troganis, A.; Gerothanasis, I. P.; Atahnassiou, Z.; Mavromoustakos, T.; Hawkes, G. E.; Sakarellos, C. Biopolymers 2000, 53, 72-83.
40. Haskell-Luevano, C.; Hendrata, S.; North, C.; Sawyer, T. K.; Hadley, M. E.; Hruby, V. J; Dickinson, C.; Gantz, I. J Med Chem 1997, 40, 2133-2139.
41. Shrake, A.; Rupley, J. A. J Mol Biol 1973, 79, 315-371.