Structure-activity study of endomorphin-2 analogs with C-terminal modifications by NMR spectroscopy and molecular modeling

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 12, 2008, Pages 6415-6422

  Wang, Chang lin ^a   Yao, Jin long ^a   Yu, Ye ^a   Shao, Xuan ^a   Cui, Yun ^a   Liu, Hong mei ^a   Lai, Lu hao ^a   Wang, Rui ^a,b  

^a North West Normal University   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

C terminal modification; Conformation; Endomorphin 2; Molecular modeling; NMR spectroscopy

Indexed keywords

ENDOMORPHIN 2;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING ASSAY; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DRUG POTENCY; ESTERIFICATION; GUINEA PIG; IN VITRO STUDY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN SYNTHESIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; VAS DEFERENS;

ANIMALS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; OLIGOPEPTIDES; RADIOLIGAND ASSAY; RATS; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP;

CAVIA;

EID: 44849121073     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.05.001     Document Type: Article

References (33)

1. Zadina J.E., Hackler L., Ge L.J., and Kastin A.J. Nature 386 (1997) 499
2. Szatmári I., Biyashev D., Tömböly C., Tóth G., Mácsai M., Szabó G., Borsodi A., and Lengyel I. Biochem. Biophys. Res. Commun. 284 (2001) 771
3. Okada Y., Fujita Y., Motoyama T., Tsuda Y., Yokoi T., Li T., Sasaki Y., Ambo A., Jinsmaa Y., Bryant S.D., and Lazarus L.H. Bioorg. Med. Chem. 11 (2003) 1983
4. Yang Y.R., Chiu T.H., and Chen C.L. Eur. J. Pharmacol. 372 (1999) 229
5. Gentilucci L., and Tolomelli A. Curr. Top. Med. Chem. 4 (2004) 105
6. In Y., Minoura K., Ohishi H., Minakata H., Kamigauchi M., Sugiura M., and Ishida T. J. Pept. Res. 58 (2001) 399
7. Schwyzer R. Ann. N.Y. Acad. Sci. 297 (1977) 3
8. Yu Y., Wang C.L., Cui Y., Fan Y.Z., Liu J., Shao X., Liu H.M., and Wang R. Peptides 27 (2006) 136
9. Lengyel I., Orosz G., Biyashev D., Kocsis L., Al-Khrasani M., Rónai A., Tömböly C., Fürst Z., Tóth G., and Borsodi A. Biochem. Biophys. Res. Commun. 290 (2002) 153
10. Al-Khrasani M., Orosz G., Kocsis L., Farkas V., Magyar A., Lengyel I., Benyhe S., Borsodi A., and Rónai A.Z. Eur. J. Pharmacol. 421 (2001) 61
11. Leitgeb B. Chem. Biodivers. 4 (2007) 2703
12. Eipper B.A., and Mains R.E. Annu. Rev. Physiol. 50 (1988) 333
13. Merkler D.J. Enzyme Microb. Technol. 16 (1994) 450
14. Suwan S., Isobe M., Yamashita O., Minakata H., and Imai K. Biochem. Mol. Biol. 24 (1994) 1001
15. Imai K., Nomura T., Katsuzaki H., Komiya T., and Yamashita O. Biosci. Biotechnol. Biochem. 62 (1998) 1875
16. In Y., Minoura K., Tomoo K., Sasaki Y., Lazarus L.H., Okada Y., and Ishida T. FEBS J. 272 (2005) 5079
17. Chang K.J., Lillian A., Hazum E., Cuatrecasas P., and Chang J.K. Science 212 (1981) 75
18. Janecka A., Staniszewska R., and Fichna J. Curr. Med. Chem. 14 (2007) 201
19. Gao Y.F., Liu X., Wei J., Zhu B.B., Chen Q., and Wang R. Bioorg. Med. Chem. Lett. 15 (2005) 1847
20. Kruszynski R., Fichna J., do-Rego J.C., Janecki T., Kosson P., Pakulska W., Costentin J., and Janecka A. Bioorg. Med. Chem. 13 (2005) 6713
21. Janecka A., Kruszynski R., Fichna J., Kosson P., and Janecki T. Peptides 27 (2006) 131
22. Leitgeb B., and Tóth G. Eur. J. Med. Chem. 40 (2005) 674
23. Shao X., Gao Y.F., Zhu C.J., Liu X.H., Yao J.L., Cui Y.X., and Wang R. Bioorg. Med. Chem. 15 (2007) 3539
24. Brandl M., Weiss M.S., Jabs A., Suhnel J., and Hilgenfeld R. J. Mol. Biol. 307 (2001) 357
25. Spetea M., Otvös F., Tóth G., Nguyen T.M., Schiller P.W., Vogel Z., and Borsodi A. Peptides 19 (1998) 1091
26. Simon J., Benyhe S., Abutidze K., Borsodi A., Szücs M., Tóth G., and Wollemann M. J. Neurochem. 46 (1986) 695
27. Tömböly C., Kövér K.E., Péter A., Tourwé D., Biyashev D., Benyhe S., Borsodi A., Al-Khrasani M., Rónai A.Z., and Tóth G. J. Med. Chem. 47 (2004) 735
28. Bradford M.M. Anal. Biochem. 72 (1976) 248
29. Akiyama K., Gee K.W., Mosberg H.I., Hruby V.J., and Yamamura H.I. Proc. Natl. Acad. Sci. U.S.A. 82 (1985) 2543
30. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
31. Shook J.E., Pelton J.T., Wire W.S., Hirning L.D., Hruby V.J., and Burks T.F. J. Pharmacol. Exp. Ther. 240 (1987) 772
32. Crippen, G. M.; Havel, T. F. Distance Geometry and Molecular Conformation. Research Studies Press: Somerset, England and John Wiley: New York, 1998.
33. Nilges M., Clore G.M., and Gronenborn A.M. FEBS Lett. 239 (1988) 129