Structure-activity relationships of cannabinoids: A joint CoMFA and pseudoreceptor modelling study

Journal of Computer-Aided Molecular Design

Volumn 11, Issue 3, 1997, Pages 278-292

  Schmetzer, Silke ^a   Greenidge, Paulette ^b   Kovar, Karl Artur ^a   Schulze Alexandru, Meike ^a   Folkers, Gerd ^b  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b ETH ZURICH   (Switzerland)

Author keywords

CADD; Molecular modelling; Pharmacophore; YAK; 9 Tetrahydrocannabinol

Indexed keywords

ALIGNMENT; FREE ENERGY; LIGANDS; PHARMACODYNAMICS;

CADD; CANNABINOIDS; MODELLING STUDIES; MOLECULAR MODELING SOFTWARE; PHARMACOPHORES; PREDICTIVE ABILITIES; PSEUDORECEPTOR MODEL; STRUCTURE-ACTIVITY RELATIONSHIPS; YAK; Δ9-TETRAHYDROCANNABINOL;

MOLECULAR MODELING;

CANNABINOID; CANNABINOID RECEPTOR; DRUG RECEPTOR; LIGAND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFORMATION; ELECTROCHEMISTRY; PROTEIN TERTIARY STRUCTURE; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

CANNABINOIDS; COMPUTER SIMULATION; ELECTROCHEMISTRY; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN STRUCTURE, TERTIARY; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 0031138092     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1007960712989     Document Type: Article

References (40)

1. Gaoni, Y. and Mechoulam, R., J. Am. Chem. Soc., 93 (1971) 217.
2. Razdan, R.K., Pharmacol. Rev., 38 (1986) 75.
3. Kovar, K.-A., Pharm. Unserer Zeit, 3 (1981) 65.
4. Kovar, K.-A., Dtsch. Apoth. Ztg., 43 (1992) 2302.
5. Schmidbauer, W. and Scheidt, J., Handbuch der Rauschdrogen, 6th ed., Nymphenburger Verlag, München, Germany, 1981.
6. Mechoulam, R. and Lander, N., Pharm. Int., 1 (1980) 19.
7. Compton, D.R., Rice, K.C., DeCosta, B.R., Razdan, R.K., Melvin, L.S., Johnson, M.R. and Martin, B.R., J. Pharmacol. Exp. Ther., 265 (1993) 218.
8. Martin, W.J., Patrick, S.L., Coffin, P.O., Tsou, K. and Walker, J.M., Life Sci., 56 (1995) 2103.
9. Johnson, M.R., Melvin, L.S., Althuis, T.H., Bindra, J.S., Harbert, C.A., Milne, G.M. and Weissman, A., J. Clin. Pharmacol., 21 (1981) 271.
10. Johnson, M.R. and Melvin, L.S., In Mechoulam, R. (Ed.) Cannabinoids as Therapeutic Agents, CRC Press, Boca Raton, FL, U.S.A., 1986, pp. 121-146.
11. Reggio, P.H., Seltzman, H.H., Compton, D.R., Prescott, W.R., Martin, J.R. and Martin, B.R., Mol. Pharmacol., 38 (1990) 854.
12. Little, P.J., Compton, D.R., Mechoulam, R. and Martin, B.R., Biochem. Behav., 32 (1989) 661.
13. Thomas, B.F., Compton, D.R., Martin, B.R. and Semus, S.F., Mol. Pharmacol., 40 (1991) 656.
14. Howlett, A.C., Johnson, M.R., Melvin, L.S. and Milne, G.M., Mol. Pharmacol., 33 (1988) 297.
15. Reggio, P.H., Panu, A.M. and Miles, S., J. Med. Chem., 36 (1993) 1761.
16. Makriyannis, A. and Rapaka, R.S., Life Sci., 47 (1990) 2173.
17. Devan, W.A., Dysarz, F.A., Johnson, M.R., Melvin, L.S. and Howlett, A.C., Mol. Pharmacol., 34 (1988) 605.
18. Matsuda, L.A., Lolait, S.J., Brownstein, M.J., Young, A.C. and Bonner, T.J., Nature, 346 (1990) 561.
19. Sean, M., Kerrie, L.T. and Muna, A.-S., Nature, 365 (1993) 61.
20. Compton, D.R., Johnson, M.R., Melvin, L.S. and Martin, B.R., J. Pharmacol. Exp. Ther., 260 (1992) 201.
21. Cambridge Crystallographic Database, Crystallographic Data Centre, University Chemical Laboratory, Cambridge, U.K.
22. Stewart, J.J.P., MOPAC 5.0. A general molecular orbital package (QCPE 455), Frank J. Seiler Research Laboratory, Colorado Springs, CO, U.S.A.
23. Briem, H., Dissertation, Berlin, Germany, 1990.
24. Archer, R.A., Boyd, D.B., Demarco, P.V., Tyminski, L.J. and Allinger, N.L., J. Am. Chem. Soc., 92 (1970) 5200.
25. Reggio, P.H. and Mazurek, A.P., J. Mol. Struct. (THEOCHEM), 149 (1987) 331.
26. Kriwacki, R.W. and Makriyannis, A., Mol. Pharmacol., 35 (1989) 495.
27. Sufrin, J.R., Dunn, D.A. and Marshall, G.R., Mol. Pharmacol., 19 (1980) 307.
28. Marshall, G.R., Barry, C.D., Bosshard, H.E., Dammkoehler, R.A. and Dunn, D.A., Comput. Assisted Drug Design, 112 (1979) 205.
29. Marshall, G.R. and Motoc, J., In Burgen, A.S.V., Roberts, G.C.K. and Tute, M.S. (Eds.) Molecular Graphics and Drug Design, Elsevier, Amsterdam, The Netherlands, 1986, pp. 115-156.
30. Marshall, G.R. and Cramer III, R.D., Trends Pharmacol. Sci., 9 (1988) 285.
31. Hibert, M.F., Gittos, M.W., Middlemiss, D.N., Mir, A.K. and Fozard, J.R., J. Med. Chem., 31 (1988) 1087.
32. Vedani, A., Zbinden, P., Snyder, J.P. and Greenidge, P.A., J. Am. Chem. Soc., 117 (1995) 4987.
33. Still, W.C., Tempczyk, A., Hawley, R.C. and Hendrickson, T.J., J. Am. Chem. Soc., 112 (1990) 6127.
34. Thibaut, U., Folkers, G., Klebe, G., Kubinyi, H., Merz, A. and Rognan, D., In Kubinyi, H. (Ed.) 3D QSAR in Drug Design: Theory, Methods and Applications, ESCOM, Leiden, The Netherlands, 1993, pp. 711-716.
35. Rosenqvist, E. and Otterson, T., Acta Chem. Scand., B29 (1975) 379.
36. Tollenaere, J.P., Moereels, H. and Raymaekers, L.A., Atlas of the Three-dimensional Structure of Drugs, Elsevier, Amsterdam, The Netherlands, 1979, p. 232.
37. Binder, M., Edery, H. and Porath, G., In Nahas, G.G. and Paton, W.D.M. (Eds.) Marihuana Biological Effects, Analysis, Metabolism, Cellular Responses, Reproduction and Brain, Pergamon, Oxford, U.K., 1979, pp. 71-80.
38. Xie, X.-Q., Yang, D.-P., Melvin, L.S. and Makriyannis, A., J. Med. Chem., 37 (1994) 1418.
39. Thomas, B.F., Compton, D.R., Martin, B.R. and Semus, S.F., Mol. Pharmacol., 40 (1991) 656.
40. Semus, S.F., Med. Chem. Res., 1 (1992) 454.