Structure-activity relationship and metabolic stability studies of Backbone cyclization and N-methylation of melanocortin peptides

Biopolymers - Peptide Science Section

Volumn 90, Issue 5, 2008, Pages 671-682

  Linde, Yaniv ^a   Ovadia, Oded ^b   Safrai, Eli ^a   Xiang, Zhimin ^c   Portillo, Federico P ^c   Shalev, Deborah E ^a   Haskell Luevano, Carrie ^c   Hoffman, Amnon ^b   Gilon, Chaim ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c UNIVERSITY OF FLORIDA   (United States)

Author keywords

Backbone cyclization; Fmoc chemistry; N methylation; Structure activity relationship

Indexed keywords

BACKBONE CYCLIZATION; BIOLOGICAL ACTIVITIES; BIOLOGICALLY ACTIVE PEPTIDES; CONFORMATIONAL FREEDOMS; CYCLIC PEPTIDES; DRUG LEADS; FMOC CHEMISTRY; METABOLIC STABILITIES; N-METHYLATION; ORAL ADMINISTRATIONS; STRUCTURE ACTIVITY RELATIONSHIP; WEIGHT GAINS;

ALKYLATION; AMINES; BIOACTIVITY; CONFORMATIONS; CYCLIZATION; LEAD COMPOUNDS; METABOLISM; METHYLATION; STABILITY; SYNTHESIS (CHEMICAL); SYNTHETIC APERTURES;

PEPTIDES;

CYCLOPEPTIDE; MELANOCORTIN; MELANOCORTIN RECEPTOR; PEPTIDE LIBRARY;

ANIMAL; ARTICLE; BIOSYNTHESIS; CELL LINE; CHEMISTRY; COMPARATIVE STUDY; CYCLIZATION; GENETICS; HUMAN; METABOLISM; METHYLATION; MOUSE; PROTEIN CONFORMATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; CELL LINE; CYCLIZATION; HUMANS; MELANOCORTINS; METHYLATION; MICE; PEPTIDE LIBRARY; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; RECEPTORS, MELANOCORTIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 58149194055     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21057     Document Type: Conference Paper

References (50)

1. Okumu, F. W.; Pauletti, G. M.; Vander Velde, D. G.; Siahaan, T. J.; Borchardt, R. T. Pharm Res 1997, 14, 169-175.
2. Gilon, C.; Halle, D.; Chorev, M.; Selinger, Z.; Byk, G. Biopolymers 1991, 31, 745-750.
3. Biron, E.; Kessler, H. J Org Chem 2005, 70, 5183-5189.
4. Biron, E.; Chatterjee, J.; Kessler, H. J Pept Sci 2006, 12, 213-219.
5. Chatterjee, J.; Mierke, D.; Kessler, H. J Am Chem Soc 2006, 128, 15164-15172.
6. Chatterjee, J.; Ovadia, O.; Zahn, G.; Marinelli, L.; Hoffman, A.; Gilon, C.; Kessler, H. J Med Chem 2007, 50, 5878-5881.
7. Chatterjee, J.; Mierke, D. F.; Kessler, H. Chemistry 2008, 14, 1508-1517.
8. Byk, G.; Halle, D.; Zeltser, I.; Bitan, G.; Selinger, Z.; Gilon, C. J Med Chem 1996, 39, 3174-3178.
9. Friedler, A.; Zakai, N.; Karni, O.; Broder, Y. C.; Baraz, L.; Kotler, M.; Loyter, A.; Gilon, C. Biochemistry 1998, 37, 5616-5622.
10. Hess, S.; Ovadia, O.; Shalev, D. E.; Senderovich, H.; Qadri, B.; Yehezkel, T.; Salitra, Y.; Sheynis, T.; Jelinek, R.; Gilon, C.; Hoffman, A. J Med Chem 2007, 50, 6201-6211.
11. Hess, S.; Linde, Y.; Ovadia, O.; Safrai, E.; Shalev, D. E.; Swed, A.; Halbfinger, E.; Lapidot, T.; Winkler, I.; Gabinet, Y.; Faier, A.; Yarden, D.; Xiang, Z.; Portillo, F. P.; Haskell-Luevano, C.; Gilon, C.; Hoffman, A. J Med Chem 2008, 51, 1026-1034.
12. Afargan, M.; Janson, E. T.; Gelerman, G.; Rosenfeld, R.; Ziv, O.; Karpov, O.; Wolf, A.; Bracha, M.; Shohat, D.; Liapakis, G.; Gilon, C.; Hoffman, A.; Stephensky, D.; Oberg, K. Endocrinology 2001, 142, 477-486.
13. Cody, W. L.; He, J. X.; Reily, M. D.; Haleen, S. J.; Walker, D. M.; Reyner, E. L.; Stewart, B. H.; Doherty, A. M. J Med Chem 1997, 40, 2228-2240.
14. Haviv, F.; Fitzpatrick, T. D.; Swenson, R. E.; Nichols, C. J.; Mort, N. A.; Bush, E. N.; Diaz, G.; Bammert, G.; Nguyen, A.; Rhutasel, N. S. J Med Chem 1993, 36, 363-369.
15. Ali, F. E.; Bennett, D. B.; Calvo, R. R.; Elliott, J. D.; Hwang, S. M.; Ku, T. W.; Lago, M. A.; Nichols, A. J.; Romoff, T. T.; Shah, D. H. J Med Chem 1994, 37, 769-780.
16. Mazur, R. H.; James, P. A.; Tyner, D. A.; Hallinan, E. A.; Sanner, J. H.; Schulze, R. J Med Chem 1980, 23, 758-763.
17. Biron, E.; Chatterjee, J.; Ovadia, O.; Langenegger, D.; Brueggen, J.; Hoyer, D.; Schmid, H. A.; Jelinek, R.; Gilon, C.; Hoffman, A.; Kessler, H. Angew Chem Int Ed Engl 2008, 47, 2595-2599.
18. Vitoux, B.; Aubry, A.; Cung, M. T.; Boussard, G.; Marraud, M. Int J Pept Protein Res 1981, 17, 469-479.
19. Tonelli, A. Biopolymers 1976, 15, 1615-1622.
20. Manavalan, P.; Momany, F. A. Biopolymers 1980, 19, 1943-1973.
21. Ron, D.; Gilon, C.; Hanani, M.; Vromen, A.; Selinger, Z.; Chorev, M. J Med Chem 1992, 35, 2806-2811.
22. Dechantsreiter, M. A.; Planker, E.; Matha, B.; Lohof, E.; Holzemann, G.; Jonczyk, A.; Goodman, S. L.; Kessler, H. J Med Chem 1999, 42, 3033-3040.
23. Laufer, R.; Wormser, U.; Friedman, Z. Y.; Gilon, C.; Chorev, M.; Selinger, Z. Proc Natl Acad Sci USA 1985, 82, 7444-7448.
24. Laufer, R.; Gilon, C.; Chorev, M.; Selinger, Z. J Biol Chem 1986, 261, 10257-10263.
25. Rajeswaran, W. G.; Hocart, S. J.; Murphy, W. A.; Taylor, J. E.; Coy, D. H. J Med Chem 2001, 44, 1416-1421.
26. Schmidt, R.; Kalman, A.; Chung, N. N.; Lemieux, C.; Horvath, C.; Schiller, P. W. Int J Pept Protein Res 1995, 46, 47-55.
27. Cummings, D. E.; Schwartz, M. W. Nat Genet 2000, 26, 8-9.
28. Haskell-Luevano, C.; Sawyer, T. K.; Hendrata, S.; North, C.; Panahinia, L.; Stum, M.; Staples, D. J.; Castrucci, A. M.; Hadley, M. F.; Hruby, V. J. Peptides 1996, 17, 995-1002.
29. Haskell-Luevano, C.; Lim, S.; Yuan, W.; Cone, R. D.; Hruby, V. J. Peptides 2000, 21, 49-57.
30. Haskell-Luevano, C.; Holder, J. R.; Monck, E. K.; Bauzo, R. M. J Med Chem 2001, 44, 2247-2252.
31. Holder, J. R.; Haskell-Luevano, C. Ann NY Acad Sci 2003, 994, 36-48.
32. Mountjoy, K. G.; Robbins, L. S.; Mortrud, M. T.; Cone, R. D. Science 1992, 257, 1248-1251.
33. Lu, D.; Vage, D. I.; Cone, R. D. Mol Endocrinol 1998, 12, 592-604.
34. Cone, R. D.; Lu, D.; Koppula, S.; Vage, D. I.; Klungland, H.; Boston, B.; Chen, W.; Orth, D. N.; Pouton, C.; Kesterson, R. A. Recent Prog Horm Res 51: 287-317, 1996; discussion 318.
35. Fehm, H. L.; Smolnik, R.; Kern, W.; McGregor, G. P.; Bickel, U.; Born, J. J Clin Endocrinol Metab 2001, 86, 1144-1148.
36. Chen, W.; Kelly, M. A.; Opitz-Araya, X.; Thomas, R. E.; Low, M. J.; Cone, R. D. Cell 1997, 91, 789-798.
37. Gilon, C.; Hoffman, A.; Linde, Y.; Hess, S. PCT/IL 2006, 00064.
38. Pogozheva, I. D.; Chai, B. X.; Lomize, A. L.; Fong, T. M.; Weinberg, D. H.; Nargund, R. P.; Mulholland, M. W.; Gantz, I.; Mosberg, H. I. Biochemistry 2005, 44, 11329-11341.
39. Falb, E.; Yechezkel, T.; Salitra, Y.; Gilon, C. J Pept Res 1999, 53, 507-517.
40. Kessler, M.; Acuto, O.; Storelli, C.; Murer, H.; Muller, M.; Semenza, G. Biochim Biophys Acta 1978, 506, 136-154.
41. Peerce, B. E.; Fleming, R. Y.; Clarke, R. D. Biochem Biophys Res Commun 2003, 301, 8-12.
42. Peerce, B. E. Biochim Biophys Acta 1997, 1323, 45-56.
43. Chhajlani, V.; Wikberg, J. E. FEBS Lett 1992, 309, 417-420.
44. Gantz, I.; Konda, Y.; Tashiro, T.; Shimoto, Y.; Miwa, H.; Munzert, G.; Watson, S. J.; DelValle, J.; Yamada, T. J Biol Chem 1993, 268, 8246-8250.
45. Fan, W.; Boston, B. A.; Kesterson, R. A.; Hruby, V. J.; Cone, R. D. Nature 1997, 385, 165-168.
46. 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.; Camp.eld, L. A.; Burn, P.; Lee, F. Cell 1997, 88, 131-141.
47. Mergen, M.; Mergen, H.; Ozata, M.; Oner, R.; Oner, C. J Clin Endocrinol Metab 2001, 86, 3448-3451.
48. Vaisse, C.; Clement, K.; Durand, E.; Hercberg, S.; Guy-Grand, B.; Froguel, P. J Clin Invest 2000, 106, 253-262.
49. Vaisse, C.; Clement, K.; Guy-Grand, B.; Froguel, P. Nat Genet 1998, 20, 113-114.
50. Gantz, I.; Shimoto, Y.; Konda, Y.; Miwa, H.; Dickinson, C. J.; Yamada, T. Biochem Biophys Res Commun 1994, 200, 1214-1220.