The conformational properties of the highly selective cannabinoid receptor ligand CP-55,940

Journal of Biological Chemistry

Volumn 271, Issue 18, 1996, Pages 10640-10647

  Xie, Xiang Qun ^a,b   Melvin, Lawrence S ^c   Makriyannis, Alexandras ^a,b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; CANNABINOID; CANNABINOID RECEPTOR;

ARTICLE; COMPUTER MODEL; DRUG CONFORMATION; DRUG SYNTHESIS; HYDROGEN BOND; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RECEPTOR BINDING;

CANNABINOIDS; CYCLOHEXANOLS; HYDROGEN BONDING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; RECEPTORS, CANNABINOID; RECEPTORS, DRUG;

EID: 15844374570     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.271.18.10640     Document Type: Article

References (35)

1. Dewey, W. L. (1986) Pharamcol. Rev. 38, 151-178
2. Mechoulam, R. (ed) (1986) Cannabincids as Therapeutics Agents, CRC Press, Inc., Boca Raton, FL
3. Howlett, A. C., Bidaut-Russell, M., Devane, W. A., Melvin, L. S., Johnson, M. R., and Herkenham, M. (1990) Trends Neurosci. 13, 420-423
4. Bouaboula, M., Rinaldi, M., Carayon, P., Carillon, C., Delpech, B., Shire, D., Le Fur, G., and Casellas, P. (1993) Eur. J. Biochem. 214, 173-180
5. Kaminski, N. E., Abood, M. E., Kessler, F. K., Martin, B. R., and Schatz, A. R. (1992) Mol. Pharmacol. 42, 736-742
6. Munro, S., Thomas, K. L., and Abu-Shaar, M. (1993) Nature 365, 61-65
7. Melvin, L. S., Johnson, M. R., Harbert, C. A., Milne, G. M., and Weissman, A. (1984) J. Med. Chem. 27, 67-71
8. Johnson, M. R., and Melvin, L. S. (1986) in Cannabinoids as Therapeutic Agents (Mechoulam, R., ed.) pp. 121-146, CRC Press, Inc., Boca Raton, FL
9. Johnson, M. R., Melvin, L. S., Althuis, T. H., Bindra, J. S., Harbert, C. A., Milne, G. M., and Weissman, A. (1981) J. Clin. Pharmacol. 21, (suppl.) 271-282
10. Howlett, A. C., Johnson, M. R., Melvin, L. S., and Milne, G. M. (1988) Mol. Pharmacol. 33, 297-302
11. Howlett, A. C., Champion, T. M., Wilken, G. H., and Mechoulam, R. (1990) Neuropharmacology 29, 161-165
12. Melvin, L. S., Milne, G. M., Johnson, M. R., Wilken, G. H., and Howlett, A. C. (1996) Mol. Neuropharmacol., in press
13. Xie, X. Q., Yang, D. P., Melvin, L. S., and Makriyannis, A. (1994) J. Med. Chem. 37, 1418-1426
14. Marion, D., and Wuthrich, K. (1983) Biochem. Biophys. Res. Comm. 113, 967-974
15. Bodenhausen, G., Kogler, H., and Ernst, R. R. (1984) J. Magn. Reson. 58, 370-388
16. Kessler, H., Oschkinat, H., and Loosli, H-R. (1987) in Methods in Stereochemical Analysis (Croasmun, W. R., and Carlson, R. M. K., eds.) Vol. 9, pp. 153-285, VCH Publishers, Inc., New York
17. Bax, A., and Subramanian, S. (1986) J. Magn. Reson. 67, 565-569
18. Diehl, F., Kellerhals, H., and Lustig, E. (1972) in NMR: Basic Principles and Progress (Diehl, P., Fluck, E., and Kosfeld, R., eds.) pp. 1-96, Springer-Verlag New York Inc., New York
19. Kriwacki, R. W., and Makriyannis, A. (1989) Mol. Pharmacol. 35, 495-503
20. Booth, H. (1969) Prog. NMR Spertrosc. 5, 149-381
21. Biosym, InsightII/DISCOVER (version 2.0.0/2.7.01 Biosym Inc., San Diego, CA
22. Rosenqvist, E., and Ottersen, T. (1975) Acta Chem. Scand. B29, 379-384
23. Hagler, A. T., Osguthorpe, D. J., Dauber-Osguthorpe, P., and Hempel, J. (1985) Science 227, 1309-1315
24. Weiner, S. J., Kollman, P. A., Case, D. A., Singh, U. C., Ghio, C., Algona, G., Profeta S., Jr., and Weiner, P. (1984) J. Am. Chem. Soc. 106, 765-784
25. Rance, M., Sorensen, O. W., Bodenhausen, G., Wagner, G., Ernst, R. R., and Wuthrich, K. (1983) Biochem. Biophys. Res. Comm. 117, 479-485
26. Fesik, S. W. (1989) in Computer-Aided Drug Design, Methods and Applications (Perun, T. J., and Propst, C. L., eds.) pp. 56-91, Marcel Dekker, Inc., New York
27. Jeffrey, G. A., and Saenger, W., eds. (1991) Hydrogen Bonding in Biological Structures, pp. 1-155, Springer-Verlag New York Inc., New York
28. Onda, M., Yamamoto, Y., Inoue, Y., and Chujo, R. (1988) Bull. Chem. Soc. Jpn. 16, 4015-4021
29. Reggio, P. H., Greer, K. V., and Cox, S. M. (1989) J. Med. Chem. 32, 1630-1635
30. Rhodes, D. G., Sarmiento, J. G., and Herbette, L. G. (1985) Mol. Pharmacol. 27, 612-623
31. Makriyannis, A. (1995) in Cannabinoid Receptors (Pertwee, R., ed) Chapter 3, pp. 87-115, Academic Press, London
32. Makriyannis, A., and Rapaka, R. S. (1990) Life Sci. 47, 2173-2184
33. Herbette, L. G. (1994) Drug Dev. Res. 33, 214-224
34. Weiner, S. J., Kollman, P. A., Nguyen, D. T., and Case, D. A. (1986) J. Comp. Chem. 7, 230-252
35. Reggio, P. H., and Mazurek, A. P. (1987) J. Mol. Struct. 149, 331-343