Synthesis and evaluation of new endomorphin analogues modified at the Pro2 residue

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 15, 2009, Pages 4115-4118

  Torino, Domenica ^a   Mollica, Adriano ^b   Pinnen, Francesco ^b   Lucente, Gino ^a   Feliciani, Federica ^b   Davis, Peg ^d   Lai, Josephine ^d   Ma, Shou Wu ^d   Porreca, Frank ^d   Hruby, Victor J ^c  

^a CNR   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

^c University of Arizona   (United States)

^d UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

Author keywords

Receptors; 3,4 Didehydro (S) proline; Azetidine carboxylic acids; Didehydro alanine; Endomorphins

Indexed keywords

3,4 DEHYDROPROLINE; ALANINE DERIVATIVE; AZETIDINE 2 CARBOXYLIC ACID; AZETIDINE 3 CARBOXYLIC ACID; AZETIDINE DERIVATIVE; DEHYDROALANINE; ENDORPHIN DERIVATIVE; OPIATE RECEPTOR; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

ALANINE; ANIMALS; AZETIDINECARBOXYLIC ACID; BINDING SITES; BRAIN; CELL MEMBRANE; INHIBITORY CONCENTRATION 50; KINETICS; MODELS, CHEMICAL; OLIGOPEPTIDES; PEPTIDES; PROLINE; RATS; RECEPTORS, OPIOID, MU;

EID: 67650164757     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.06.008     Document Type: Article

References (45)

1. Zadina J.E., Hackler L., Ge L.J., and Kastin A.J. Nature 386 (1997) 499
2. Hackler L., Zadina J.E., and Ge L.J. Peptides 18 (1997) 1635
3. Horvath G. Pharmacol. Ther. 88 (2000) 437
4. Goldberg J.E., Rossi G.C., Letchworth S.R., Mathis J.P., Ryan-Moro J., Leventhal L., Su W., Emmel D., Bolan E.A., and Pasternak G.W.J. Pharmacol. Exp. Ther. 286 (1998) 1007
5. Matthes H.W., Maldonado R., Simonin F., Valverde O., Slowe S., Kitchen I., Befort K., Dierich A., LeMeur M., Dolle P., Tzavara E., Hanoune J., Roques B.P., and Kieffer B.L. Nature 383 (1996) 819
6. Tömböly Cs., Péter A., and Tóth G. Peptides 23 (2002) 1573
7. Péter A., Tóth G., Tömböly Cs., Laus G., and Tourwé D.J. Chromatographia 846 (1999) 39
8. Wilson A.M., Soignier R.D., Zadina J.E., Kastin A.J., Nores W.L., Olson R.D., and Olson G.A. Peptides 21 (2000) 1871
9. Czapla M.A., Gozal D., Alea O.A., Beckerman R.C., and Zadina J.E. Am. J. Respir. Crit. Care Med. 162 (2000) 994
10. Fichna J., Janecka A., Costentin J., and Do Rego J.-C. Pharmacol. Rev. 59 (2007) 88
11. Leitgeb B. Chem. Biodiv. 4 (2007) 2703
12. Keresztes A., Szu{combining double acute accent}cs M., Borics A., Kövér K.E., Forró E., Fülöp F., Tömböly Cs., Péter A., Páhi A., Fábián G., Murányi M., and Tóth G. J. Med. Chem. 51 (2008) 4270
13. Fichna J., Do Rego J.-C., Chung N.N., Lemieux C., Schiller P.W., Poels J., Broeck J.V., Costentin J., and Janecka A. J. Med. Chem. 50 (2007) 512
14. Cardillo G., Gentilucci L., Melchiorre P., and Spampinato S. Bioorg. Med. Chem. Lett. 10 (2000) 2755
15. Cardillo G., Gentilucci L., Qasem A.R., Sgarzi F., and Spampinato S. J. Med. Chem. 45 (2002) 2571
16. Cardillo G., Gentilucci L., Tolomelli A., Calienni M., Qasem A.R., and Spampinato S. Org. Biomol. Chem. 1 (2003) 1498
17. Doi M., Asano A., Komura E., and Ueda Y. Biochem. Biophys. Res. Commun. 297 (2002) 138
18. Yamada T., Iino M., Matsuoka N., Yanagihara R., Miyazawa T., Shirasu N., and Shimohigashi Y. Pept. Sci. 36 (1999) 441
19. Tóth G., Keresztes A., Tömböly Cs., Péter A., Fülöp F., Tourwé D., Navratilova E., Varga E., Roeske W.R., Yamamura H.I., Szu{combining double acute accent}cs M., and Borsodi A. Pure Appl. Chem. 76 (2004) 951
20. Staniszewska R., Fichna J., Gach K., Toth G., Poels J., Vanden Broeck J., and Janecka A. Chem. Biol. Drug Des. 72 (2008) 91
21. Leitgeb B., and Tóth G. Eur. J. Med. Chem. 40 (2005) 674
22. Okada Y., Fukumizu A., Takahashi M., Shimizu Y., Tsuda Y., Yokoi T., Bryant S.D., and Lazarus L.H. Biochem. Biophys. Res. Commun. 276 (2000) 7
23. Benedetti E., Di Blasio B., Pavone V., Pedone C., Felix A., and Goodman M. Biopolymers 20 (1981) 283
24. Flores-Ortega A., Casanovas J., Zanuy D., Nussinov R., and Alemán C.J. Phys. Chem. B 111 (2007) 5475
25. Moore S., Felix A.M., and Meienhofer J. J. Med. Chem. 20 (1977) 495
26. Werner S., Kasi D., and Brummond K.M. J. Comb. Chem. 9 (2007) 677
27. Szemenyei E., and Toth G.J. Labelled Compd. Radiopharm. 50 (2007) 1148
28. Toniolo C. Int. J. Pept. Protein Res. 35 (1990) 287
29. Zagari A., Némethy G., and Scheraga H.A. Biopolymers 30 (1990) 951
30. Shuman R.T., Rothenberger R.B., Campbell C.S., Smith G.F., Gifford-Moore D., Paschal J.W., and Gesellchen P.D. J. Med. Chem. 38 (1995) 4446
31. Baeza J.L., Gerona-Navarro G., Pérez de Vega M.J., García-López M.T., González-Muñiz R., and Martín-Martínez M. J. Org. Chem. 73 (2008) 1704
32. Kern D., Schutkowski M., and Drakenberg T.J. Am. Chem. Soc. 119 (1997) 8403
33. Macdonald S.J.F., Dowle M.D., Harrison L.A., Clarke G.D.E., Inglis G.G.A., Johnson M.R., Shah P., Smith R.A., Amour A., Fleetwood G., Humphreys D.C., Molloy C.R., Dixon M., Godward R.E., Wonacott A.J., Singh O.M., Hodgson S.T., and Hardy G.W. J. Med. Chem. 45 (2002) 3878
34. Fish P., Barber C.G., Brown D.G., Butt R., Collis M.J., Dickinson R.P., Henry B.T., Horne V.A., Huggins J.P., King E., O'Gara M., McCleverty D., McIntosh F., Phillips C., and Webster R. J. Med. Chem. 50 (2007) 2341
35. Klein S.I., Czekaj M., Molino B.F., and Chu V. Bioorg. Med. Chem. Lett. 7 (1997) 1773
36. Brown, W.; Dimaio, J.; Schiller, P.; Martel, R. World Patent WO 9522557, 1995, CAN, 124:30439.
37. Bodansky M. Principles of Peptide Synthesis (1984), Springer, Berlin
38. Burrage S., Raynham T., Williams G., Essex J.W., Allen C., Cardno M., Swali V., and Bradley M. Chem. Eur. J. 6 (2000) 1455
39. 7: C, 58.44; H, 5.21; N, 10.65. Found: C, 58.37; H, 5.26; N, 10.61.
40. Wang Z., Gardell L.R., Ossipov M.H., Vanderah T.W., Brennan B.B., Hochgeschwender U., Hruby V.J., Malan Jr. T.P., Lai J., and Porreca F. J. Neurosci. 21 (2001) 1779
41. Kramer T.H., Davis P., Hruby V.J., Burks T.F., and Porreca F. J. Pharmacol. Exp. Ther. 266 (1993) 577
42. Biondi B., Giannini E., Negri L., Melchiorri P., Lattanzi R., Rosso F., Ciocca L., and Rocchi R. Int. J. Pept. Res. Ther. 2 (2006) 145
43. Gentilucci L., and Tolomelli A. Curr. Top. Med. Chem. 4 (2004) 105
44. Yu Y., Shao X., Cui Y., Liu H.-M., Wang C.-L., Fan Y.-Z., Liu J., Dong S.-L., Cui Y.-X., and Wang R. Chem. Med. Chem. 2 (2007) 309
45. Podlogar B.L., Paterlini M.G., Ferguson D.M., Leo G.C., Demeter D.A., Brown F.K., and Reitz A.B. FEBS Lett. 439 (1998) 13