Novel multiple opioid ligands based on 4-aminobenzazepinone (Aba), azepinoindole (Aia) and tetrahydroisoquinoline (Tic) scaffolds

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 5, 2010, Pages 1610-1613

  Ballet, Steven ^a,b   Marczak, Ewa D ^c   Feytens, Debby ^a   Salvadori, Severo ^d   Sasaki, Yusuke ^e   Abell, Andrew D ^b   Lazarus, Lawrence H ^c   Balboni, Gianfranco ^f   Tourwé, Dirk ^a  

^a VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

^b UNIVERSITY OF ADELAIDE   (Australia)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^d UNIVERSITY OF FERRARA   (Italy)

^e TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^f UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Constrained amino acids; Designed multiple ligands; Dual opioid antagonists

Indexed keywords

4 AMINOBENZAZEPINONE; AZEPINOINDOLE; BENZAZEPINE DERIVATIVE; DELTA OPIATE RECEPTOR ANTAGONIST; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); INDOLE DERIVATIVE; MU OPIATE RECEPTOR ANTAGONIST; OPIATE; OPIATE RECEPTOR; POLYMER; SULFUR 35; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING ASSAY; DIMERIZATION; DRUG BINDING; HUMAN; HUMAN CELL; IN VITRO STUDY; MOUSE; NONHUMAN; PHARMACOPHORE; POLYMERIZATION; RECEPTOR BINDING; TRIMERIZATION;

ANIMALS; BENZAZEPINES; DIMERIZATION; DRUG DESIGN; INDOLES; LIGANDS; PROTEIN BINDING; RATS; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, MU; TETRAHYDROISOQUINOLINES;

EID: 76649141471     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.055     Document Type: Article

References (38)

1. Schiller P.W. Life Sci. (2009) 10.1016/j.lfs.2009.02.025
2. Ballet S., Pietsch M., and Abell A.D. Protein Pept. Lett. 15 (2008) 668
3. Lipkowski A.W., Konecka A.M., and Sroczynska I. Peptides 3 (1982) 697
4. Lipkowski A.W., Konecka A.M., and Sadowski B. Pol. J. Pharmacol. Pharm. 34 (1982) 69
5. Costa T., Wuster M., Herz A., Shimohigashi Y., Chen H.C., and Rodbard D. Biochem. Pharmacol. 34 (1985) 25
6. Lipkowski A.W., Konecka A.M., Sroczynska I., Przewlocki R., Stala L., and Tam S.W. Life Sci. 40 (1987) 2283
7. Portoghese P.S., Lipkowski A.W., and Takemori A.E. J. Med. Chem. 30 (1987) 238
8. Gao Y.F., Zhai M.X., Liu W.-X., Liu X., Yuan Y., Qi Y.-M., and Wang R. Protein Pept. Lett. 15 (2008) 275
9. Lazarus L.H., Guglietta A., Wilson W.E., Irons B.J., and Decastiglione R. J. Biol. Chem. 264 (1989) 354
10. Portoghese P.S., Larson D.L., Yim C.B., Sayre L.M., Ronsisvalle G., Lipkowski A.W., Takemori A.E., Rice K.C., and Tam S.W. J. Med. Chem. 28 (1985) 1140
11. Takemori A.E., Yim C.B., Larson D.L., and Portoghese P.S. Eur. J. Pharmacol. 186 (1990) 285
12. Portoghese P.S., Lipkowski A.W., and Takemori A.E. Life Sci. 40 (1987) 1287
13. Portoghese P.S., Nagase H., Lipkowski A.W., Larson D.L., and Takemori A.E. J. Med. Chem. 31 (1988) 836
14. Petrov R.R., Vardanyan R.S., Lee Y.S., Ma S.W., Davis P., Begay L.J., Lai J.Y., Porreca F., and Hruby V.J. Bioorg. Med. Chem. Lett. 16 (2006) 4946
15. Lee Y.S., Petrov R., Park C.K., Ma S.W., Davis P., Lai J., Porreca F., Vardanyan R., and Hruby V.J. J. Med. Chem. 50 (2007) 5528
16. Jiang Q., Mosberg H.I., and Porreca F. Eur. J. Pharmacol. 186 (1990) 137
17. Schiller P.W., Weltrowska G., Berezowska I., Nguyen T.M.D., Wilkes B.C., Lemieux C., and Chung N.N. Biopolymers 51 (1999) 411
18. Liu Z., Zhang J., and Zhang A. Curr. Pharm. Des. 15 (2009) 682
19. Marczak E.D., Jinsmaa Y., Li T., Bryant S.D., Tsuda Y., Okada Y., and Lazarus L.H. J. Pharmacol. Exp. Ther. 323 (2007) 374
20. Weltrowska G., Lemieux C., Chung N.N., and Schiller P.W. J. Pept. Res. 63 (2004) 63
21. Ballet S., Salvadori S., Trapella C., Bryant S.D., Jinsmaa Y., Lazarus L.H., Negri L., Giannini E., Lattanzi R., Tourwé D., and Balboni G. J. Med. Chem. 49 (2006) 3990
22. Ballet S., Feytens D., De Wachter R., De Vlaeminck M., Marczak E.D., Salvadori S., de Graaf C., Rognan D., Negri L., Lattanzi R., Lazarus L.H., Tourwé D., and Balboni G. Bioorg. Med. Chem. Lett. 19 (2009) 433
23. Li T.Y., Fujita Y., Shiotani K., Miyazaki A., Tsuda Y., Ambo A., Sasaki Y., Jinsmaa Y., Marczak E.D., Bryant S.D., Salvadori S., Lazarus L.H., and Okada Y. J. Med. Chem. 48 (2005) 8035
24. Neumeyer J.L., Peng X.M., Knapp B.I., Bidlack J.M., Lazarus L.H., Salvadori S., Trapella C., and Balboni G. J. Med. Chem. 49 (2006) 5640
25. Tourwé D., Verschueren K., Frycia A., Davis P., Porreca F., Hruby V.J., Töth G., Jaspers H., Verheyden P., and Van Binst G. Biopolymers 38 (1996) 1
26. Pulka K., Feytens D., Van den Eynde I., De Wachter R., Kosson P., Misicka A., Lipkowski A., Chung N.N., Schiller P.W., and Tourwé D. Tetrahedron 63 (2007) 1459
27. Balboni G., Trapella C., Sasaki Y., Ambo A., Marczak E.D., Lazarus L.H., and Salvadori S. J. Med. Chem. 52 (2009) 5556
28. Balboni G., Fiorini S., Baldiserotto A., Trapella C., Sasaki Y., Ambo A., Marczak E.D., Lazarus L.H., and Salvadori S. J. Med. Chem. 51 (2008) 5109
29. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
30. Salvadori S., Balboni G., Guerrini R., Tomatis R., Bianchi C., Bryant S.D., Cooper P.S., and Lazarus L.H. J. Med. Chem. 40 (1997) 3100
31. Kosterlitz H.W., and Watt A.J. Br. J. Pharmacol. 33 (1968) 266
32. Salvadori S., Attila M., Balboni G., Bianchi C., Bryant S.D., Crescenzi O., Guerrini R., Picone D., Tancredi T., Temussi P.A., and Lazarus L.H. Mol. Med. 1 (1995) 678
33. Mosberg H.I., and Fowler C.B. J. Pept. Res. 60 (2002) 329
34. Portoghese P.S. J. Med. Chem. 44 (2001) 2259
35. Jinsmaa Y., Miyazaki A., Fujita Y., Li T.Y., Fujisawa Y., Shiotani K., Tsuda Y., Yokoi T., Ambo A., Sasaki Y., Bryant S.D., Lazarus L.H., and Okada Y. J. Med. Chem. 47 (2004) 2599
36. Vernall A.J., Ballet S., and Abell A.D. Tetrahedron 64 (2008) 3980
37. Minozzi, S.; Amato, L; Vecchi, S.; Davoli, M.; Kirchmayer, U.; Verster A. Cochrane Database Syst. Rev. 2006, CD001333.
38. Hall W.D., and Wodak A. Med. J. Aust. 171 (1999) 9