Conformational analysis and μ-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent

Organic and Biomolecular Chemistry

Volumn 1, Issue 17, 2003, Pages 3010-3014

  Cardillo, Giuliana ^a   Gentilucci, Luca ^a   Tolomelli, Alessandra ^a   Qasem, Ahmed R ^a   Spampinato, Santi ^a   Calienni, Maria ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; CONFORMATIONS; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL);

AFFINITIES; ENDOMORPHIN; LOW POLARITY SOLVENT; NANOMOLAR AFFINITY; OPIOID RECEPTOR AFFINITY; PEPTIDES;

NITROGEN COMPOUNDS;

CARBAMIC ACID DERIVATIVE; ENDOMORPHIN 1; LIGAND; MU OPIATE RECEPTOR; OLIGOPEPTIDE; SOLVENT;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; RAT; SYNTHESIS; TEMPERATURE;

ANIMALS; CARBAMATES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOPEPTIDES; PROTEIN CONFORMATION; RATS; RECEPTORS, OPIOID, MU; SOLVENTS; SPECTROPHOTOMETRY, INFRARED; TEMPERATURE;

EID: 0141853255     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b306161m     Document Type: Article

References (54)

1. (a) I. E. Goldberg, G. C. Rossi, S. R. Lechworth, J. P. Mathis, J. Ryan-Moro, L. Leventhal, W. Su, D. Emmel, E. A. Bolan and G. W. Pasternak, J. Pharmacol. Exp. Ther., 1998, 286, 1007-1013
2. (b) C. Harrison, S. McNulty, D. Smart, D.J. Rowbotham, D.K. Grandy, L.A. Devi and D.G. Lambert, Br. J. Pharmacol., 1999, 128, 472-478 and references therein
3. (c) K. Hosohata, T.H. Burkey, J. Alvaro-Lopez, E. Varga, V.J. Hruby, W.R. Roeske and H.I. Yamamura, Eur. J. Pharmacol., 1998, 346, 111-114
4. (d) L. J. Sim, Q. Liu, R. S. Childers and D. E. Selley, J. Neurochem., 1998, 70, 1567-1576.
5. (a) E. J. Zadina, L. Hackler, L.-J. Ge and A. J. Kastin, Nature, 1997, 386, 499-502
6. (b) E. J. Zadina, S. Martin-Schild, A. A. Gerall, A. J. Kastin, L. Hackler, L. J. Ge and X. Zhang, Ann. N. Y. Acad. Sci., 1999, 897, 136-144.
7. (a) B. N. Dhawan, F. Casselin, R. Raghubir, T. Reisine, P. B. Bradley, P. S. Portoghese and M. Hamon, Pharmacol. Rev., 1996, 48, 567-592
8. (b) G. Horvath, Pharmacol. Ther., 2000, 88, 437-463
9. (c) K. A. Carrigan, C. J. Nelson and D. T. Lysle, Psychopharmacology, 2000, 151, 299-305.
10. (a) B. T. Nall, in Mechanism of Protein Folding, ed. R. H. Pain, Oxford University Press, Oxford, 1994, p. 80
11. (b) T. Kiefhaber, R. Quaas, U. Hahn and F.X. Schmidt, Biochemistry, 1990, 29, 3053-3061
12. (c) G. Muller, M. Gurrath and K. Kessler Proteins; Struct., Funct., Genet., 1993, 15, 235-251
13. (d) T. E. Creighton, in Proteins: Structures and Molecular Properties, 2nd edn., Freeman and Company, New York, 1993, chapters 5 and 6.
14. (a) V. J. Hruby and R. S. Agnes, Biopolymers, 1999, 51, 391-410
15. (b) A. Janecka, J. Fichna, M. Mirowski and T. Janecki, Mini Rev. Med. Chem., 2002, 2, 565-572.
16. (a) B. L. Podlogar, M. G. Paterlini, D. M. Ferguson, G. C. Leo, D. A. Demeter, F. K. Brown and A. B. Reitz, FEBS Lett., 1998, 439, 13-20
17. (b) S. Fiori, C. Renner, J. Cramer, S. Pegorato and L. Moroder, J. Mol. Biol., 1999, 291, 163-175
18. (c) Y. R. Yang, T. Chiu and C.-L. Chen, Eur. J. Pharmacol., 1999, 372, 229-236
19. (d) M. G. Paterlini, F. Avitabile, B. G. Ostrowski, D. M. Ferguson and P. S. Portoghese, Biophys. J., 2000, 78, 590-599
20. (e) Y. Okada, A. Fukumizu, M. Takahashi, Y. Shimizu, Y. Tsuda, T. Yokoi, S.D. Bryant and L. H. Lazarus, Biochem. Biophys. Res. Commun., 2000, 276, 7-11
21. (f) M. Keller, C. Boissard, L. Patiny, N.N. Chung, C. Lemieux, M. Mutter and P.W. Schiller, J. Med. Chem., 2001, 44, 3896-3903
22. (g) Y. Okada, Y. Fujita, T. Motoyama, Y. Tsuda, T. Yokoi, T. Li, Y. Sasaki, A. Ambo, Y. Jinsmaa, S. D. Bryant and L. H. Lazarus, Bioorg. Med. Chem., 2003, 11, 1983-1994.
23. (a) G. Cardillo, L. Gentilucci, A. R. Qasem, F. Sgarzi and S. Spampinato, J. Med. Chem., 2002, 45, 2571-2578
24. (b) G. Cardillo, L. Gentilucci, P. Melchiorre and S. Spampinato, Bioorg. Med. Chem. Lett., 2000, 10, 2755-2758
25. (c) G. Cardillo, L. Gentilucci, A. Tolomelli, M. Calienni, A. R. Qasem and S. Spampinato, Org. Biomol. Chem., 2003, 1, 1498-1502
26. (d) M. Royo, F. Sgarzi, J. Ferrara-Sinfreu, F. Alberico, L. Gentilucci and G. Cardillo, J. Pept. Sci., 2002, 8 (suppl.), 180.
27. (a) J. L. Fauchère, Methods Princip. Med. Chem., 1996, 4, 355-373
28. (b) M. A. Morelli Castiglione, F. Bisaccia, S. Spisani, M. De Biasi, S. Traniello and A. M. Tamburro, J. Pept. Res., 1997, 49, 492-499
29. (c) D. Picone, A. D'Ursi, A. Motta, T. Tancredi and P. A. Temussi, Eur. J. Biochem., 1990, 192, 433-439
30. (a) M. Kaway and G. S. Fasman, J. Am. Chem. Soc., 1978, 100, 3630-3632
31. (b) M. Crisma, G. D. Fasman, H. Balaram and P. Balaram, Int. J. Pept. Protein Res., 1984, 23, 411-419
32. (c) M. Sugawara, K. Tonan and S.-i. Ikawa, Spectrochim. Acta, Part A, 2001, 57 1305-1316
33. (d) B. Ishimoto, K. Tonan and S. Ikawa, Spectrochim. Acta, Part A, 2000, 56, 201-209
34. (e) Y. Jin, K. Tonan and S. Ikawa, Spectrochim. Acta. Part A, 2002, 58, 2795-2802
35. M. Eguchi, R. Y. W. Shen, J. P. Shea, M. S. Lee and M. Kahn, J. Med. Chem., 2002, 45, 1395-1398 and references cited therein.
36. P. W. Schiller, in Opioids I, A. Hertz, Ed., Springer-Verlag: Berlin, 1993, 681-710.
37. D. Seebach, P. E. Ciceri, M. Overhand, B. Juan and D. Rigo, Helv. Chim. Acta, 1996, 79, 2043-2065.
38. G. Boussard and M. Marraud, J. Am. Chem. Soc., 1985, 107, 1825-1828.
39. (a) G. M. Bonora, C. Mapelli, C. Toniolo, R. R. Wilkening and E. S. Stevens, Int. J. Biol. Macromol., 1984, 6, 179-188
40. (b) R. R. Gardner, G. P. Liang and S. H. Gellman, J. Am. Chem. Soc., 1995, 1173, 3280-3281
41. (c) A. M. Tamburro, V. Guantieri and A. Scatturin, Int. J. Biol. Macromol., 1984, 6, 241-248
42. (d) S. H. Gellman, G. P. Dado, G.-B. Liang and B. R. Adams, J. Am. Chem. Soc., 1991, 113, 1164-1173
43. (e) J. T. Blank, D. J. Guerin and S. J. Miller, Org. Lett., 2000, 1, 1247-1249
44. (f) E. S. Stevens, N. Sugawara, G. M. Bonora and C. Toniolo, J. Am. Chem. Soc., 1980, 102, 7048-7050.
45. (a) M. Macdonald and J. Aube, Curr. Org. Chem., 2001, 5, 417-438.
46. (b) C. Park and K. Burgess, J. Comb. Chem., 2001, 3, 257-266.
47. G. B. Liang, C. J. Rito and S. H. Gellman, J. Am. Chem. Soc., 1992, 114, 4440-4442.
48. R. K. Konat, D. F. Mierke, H. Kessler, B. Kutscher, M. Bernd and R. Voegeli, Helv. Chim. Acta, 1993, 76, 1649-1666.
49. L. Belvisi, C. Gennari, A. Mielgo, D. Potenza and C. Scolastico, Eur. J. Org. Chem., 1999, 589-400.
50. Y. V. Venkatachalapathi, B. V. Venkataram Prasad and P. Balaram, Biochemistry, 1982, 21, 5502-5509.
51. 2.6 ppb is the normally accepted upper limit for a hydrogen-bonded NH in chloroform: I.G. Jones, W. Jones and M. North, J. Org. Chem., 1998, 63, 1505-1513.
52. Y. N. Belokon, V. I. Tarorov, V. I. Maleev, T. F. Savel'eva and M.G. Ryzhov, Tetrahedron: Asymmetry, 1998, 9, 4249-4252.
53. HYPERCHEM 5.1 Release Pro for Windows Molecular Modeling System (Hypercube Inc., Copyright © 1999)
54. -1 protein; incubation buffer: 50 mM TRIS.0.1% BSA pH 7.4 at 4°C.