Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor: Structure-activity relationship of 2-arachidonoylglycerol, ether- linked analogues, and related compounds

Journal of Biological Chemistry

Volumn 274, Issue 5, 1999, Pages 2794-2801

  Sugiura, Takayuki ^a   Kodaka, Tomoko ^a   Nakane, Shinji ^a   Miyashita, Tomoyuki ^a   Kondo, Sachiko ^a   Suhara, Yoshitomo ^a   Takayama, Hiroaki ^a   Waku, Keizo ^a   Seki, Chiyo ^b   Baba, Naomichi ^b   Ishima, Yoshio ^c  

^a TEIKYO UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

^c Ishima Institute for Neurosciences   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARACHIDONOYLGLYCEROL; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ANANDAMIDE; ARACHIDONIC ACID; CALCIUM ION; CANNABINOID; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; DEXANABINOL; ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CALCIUM CELL LEVEL; CENTRAL NERVOUS SYSTEM; CHEMICAL STRUCTURE; CONFORMATION; CONTROLLED STUDY; GLIOMA CELL; MOUSE; NEUROBLASTOMA CELL; NEUROTRANSMISSION; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR BINDING;

ANIMALS; ARACHIDONIC ACIDS; CANNABINOIDS; CELL LINE; CYCLOHEXANOLS; MODELS, CHEMICAL; MORPHOLINES; NAPHTHALENES; PIPERIDINES; POLYUNSATURATED ALKAMIDES; PYRAZOLES; RATS; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROCANNABINOL;

ANIMALIA;

EID: 0033614020     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.274.5.2794     Document Type: Article

References (42)

1. Murphy, L., and Bartke, A. (eds) (1992) Marijuana/Cannabinoids: Neurobiology and Neurophysiology, CRC Press, Boca Raton, FL
2. Devane, W. A., Dysarz, F. A., III, Johnson, M. R., Melvin, L. S., and Howlett, A. C. Mol. Pharmacol. 34, 605-613
3. Matsuda, L. A., Lolait, S. J., Brownstein, M. J., Young, A. C., and Bonner, T. I. Nature 346, 561-564
4. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, Gibson, D., Mandelbaum, A., Etinger, A., and Mechoulam, R. (1992) Science, 258, 1946-1949
5. Mechoulam, R., and Fride, E. (1995) in Cannabinoid Receptors (Pertwee, R. G., ed) pp. 233-258, Academic Press, London
6. Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., and Waku, K. (1996) Biochem. Biophys. Res. Commun. 218, 113-117
7. Sugiura, T., Kondo, S., Sukagawa, A., Tonegawa, T., Nakane, S., Yamashita, A., Ishima, Y., and Waku, K. (1996) Eur. J. Biochem. 240, 53-62
8. Schmid, P. C., Krebsbach, R. J., Perry, S. R., Dettmer, T. M., Maasson, J. L., and Schmid, H. H. O. (1995) FEBS Lett. 375, 117-120; Corrigendum (1996) FEBS Lett. 385, 124-130
9. Kempe, K., Hsu, F.-F., Bohrer, A., and Turk, J. (1996) J. Biol. Chem. 271, 17287-17295
10. Felder, C. C., Nielsen, A., Briley, E. M., Palkovits, M., Priller, J., Axelrod, J., Nguyen, D. N., Richardson, J. M., Riggin, R. M., Koppel, G. A., Paul, S. M., and Becker, G. W. (1996) FEBS Lett. 393, 231-235
11. Cadas, H., di Tomaso, E., and Piomelli, D. (1997) J. Neurosci. 17, 1226-1242
12. Di Marzo, V., Fontana, A., Cadas, H., Schinelli, S., Cimino, G., Schwartz, J.-C., and Piomelli, D. (1994) Nature 372, 686-691
13. Schmid, H. H. O., Schmid, P. C., and Natarajan, V. (1996) Chem. Phys. Lipids 80, 133-142
14. Hansen, H. S., Lauritzen, L., Moesgaard, B., Strand, A. M., and Hansen, H. H. Biochem. Pharmacol. 55, 719-725
15. Deutsch, D. G., and Chin, S. A. (1993) Biochem. Pharmacol. 46, 791-796
16. Devane, W. A., and Axelrod, J. (1994) Proc. Natl. Acad. Sci. U. S. A. 91, 6698-6701
17. Kruszka, K. K., and Gross, R. W. (1994) J. Biol. Chem. 269, 14345-14348
18. Ueda, N., Kurahashi, Y., Yamamoto, S., and Tokunaga, T. (1995) J. Biol. Chem. 270, 23823-23827
19. Sugiura, T., Itoh, K., Waku, K., and Hanahan, D. J. (1994) Proc. Jpn. Conf. Biochem. Lipids 36, 71-74 (in Japanese)
20. Sugiura, T., Kondo, S., Sukagawa, A., Nakane, S., Shinoda, A., Itoh, K., Yamashita, A., and Waku, K. (1995) Biochem. Biophys. Res. Commun. 215, 89-97
21. Mechoulam, R., Ben-Shabat, S., Hanus, L., Ligumsky, M., Kaminski, N. E., Schatz, A. R., Gopher, A., Almog, S., Martin, B. R., Compton, D. R., Pertwee, Griffin, G., Bayewitch, M., Barg, J., and Vogel, Z. (1995) Biochem. Pharmacol. 50, 83-90
22. Sugiura, T., Kodaka, T., Kondo, S., Tonegawa, T., Nakane, S., Kishimoto, S., Yamashita, A., and Waku, K. (1996) Biochem. Biophys. Res. Commun. 229, 58-64
23. Sugiura, T., Kodaka, T., Kondo, S., Nakane, S., Kondo, H., Waku, K., Ishima, Watanabe, K., and Yamamoto, I. (1997) J. Biochem. 122, 890-895
24. Lee, M., Yang, K. H., and Kaminski, N. E. (1995) J. Pharmacol. Exp. Ther. 275, 529-536
25. Bisogno, T., Sepe, N., Melck, D., Maurelli, S., De Petrocellis, L., and Di Marzo, Biochem. J. 322, 671-677
26. Di Marzo, V. (1998) Biochemistry (Moscow) 63, 13-21
27. Di Marzo, V. (1998) Biochim. Biophys. Acta 1392, 153-175
28. Stella, N., Schweitzer, P., and Piomelli, D. (1997) Nature 388, 773-778
29. Sugiura, T., Kodaka, T., Kondo, S., Tonegawa, T., Nakane, S., Kishimoto, S., Yamashita, A., and Waku, K. (1997) Biochem. Biophys. Res. Commun. 233, 207-210
30. Sugiura, T., Kodaka, T., Nakane, S., Kishimoto, S., Kondo, S., and Waku, K. Biochem. Biophys. Res. Commun. 243, 838-843
31. Kondo, S., Kondo, H., Nakane, S., Kodaka, T., Tokumura, A., Waku, K., and Sugiura, T. (1998) FEBS Lett. 429, 152-156
32. Goparaju, S. K., Ueda, N., Yamaguchi, H., and Yamamoto, S. (1998) FEBS Lett., 422, 69-73
33. Di Marzo, V., Bisogno, T., Sugiura, T., Melck, D., and De Petrocellis, L. (1998) Biochem. J. 331, 15-19
34. Martin, J. B. (1953) J. Am. Chen. Soc. 75, 5482-5483
35. Herkenham, M. (1995) in Cannabinoid Receptors (Pertwee, R. G., ed) pp. 145-166, Academic Press, London
36. Gammon, C. M., Allen, A. C., and Morell, P. (1989) J. Neurochem. 53, 95-101
37. Hasegawa-Sasaki, H. (1985) Biochem. J. 232, 99-109
38. Prescott, S. M., and Majerus, P. W. (1983) J. Biol. Chem. 258, 764-769
39. Hansen, H. S., Lauritzen, L., Strand, A. M., Moesgaard, B., and Frandsen, A. Biochim. Biophys. Acta 1258, 303-308
40. Di Marzo, V., De Petrocellis, L., Sepe, N., and Buono, A. (1996) Biochem. J. 316, 977-984
41. Howlett, A. C. (1995) in Cannabinoid Receptors (Pertwee, R. G., ed) pp. 167-204, Academic Press, London
42. Deadwyler, S. A., Hampson, R. E., and Childers, S. R. (1995) in Cannabinoid Receptors (Pertwee, R. G., ed) pp. 205-231, Academic Press, London