A lysine residue of the cannabinoid receptor is critical for receptor recognition by several agonists but not WIN55212-2

Molecular Pharmacology

Volumn 49, Issue 5, 1996, Pages 891-896

  Song, Zhao Hui ^a   Bonner, Tom I ^a  

^a NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ALANINE; ANANDAMIDE; CANNABINOID DERIVATIVE; CANNABINOID RECEPTOR; CYCLIC AMP; DEXANABINOL; DRONABINOL; LYSINE; MUTANT PROTEIN; RECEPTOR PROTEIN;

AMINO ACID SUBSTITUTION; ARTICLE; CANNABIS ADDICTION; CONFORMATIONAL TRANSITION; DOSE RESPONSE; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; MOLECULAR CLONING; PRIORITY JOURNAL; PROTEIN DOMAIN; RECEPTOR AFFINITY; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

BASE SEQUENCE; CELL LINE; CYCLIC AMP; DNA PRIMERS; HUMANS; LIGANDS; LYSINE; MOLECULAR SEQUENCE DATA; MORPHOLINES; MUTAGENESIS, SITE-DIRECTED; NAPHTHALENES; RADIOLIGAND ASSAY; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029866824     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. Howlett, A. C. Cannabinoid inhibition of adenylate cyclase: biochemistry of the response in neuroblastoma cell membranes. Mol. Pharmacol. 27:429-436 (1985).
2. Devane, W. A., F A. Dysarz III, M. R. Johnson, L. S. Melvin, and A. C. Howlett. Determination and characterization of a cannabinoid receptor in the rat brain. Mol. Pharmacol. 34:605-613 (1988).
3. Matsuda, L. A., S. J. Lolait, M. J. Brownstein, A. C. Young, and T. I. Bonner. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature (Lond.) 346:561-564 (1990).
4. Gerard, C. M., C. Mollereau, G. Vassart, and M. Parmentier. Molecular cloning of a human cannabinoid receptor which is also expressed in testis. Biochem. J. 279:129-134 (1991).
5. Devane, W. A., L. Hanus, A. Breuer, R. G Pertwee, L. A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, and R. Mechoulam. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science (Washington D. C.) 238:1946-1949 (1992).
6. Munro, S., K. L. Thomas, and M. Abushaar. Molecular characterization of a peripheral receptor for cannabinoids. Nature (Lond.) 365:61-65 (1993).
7. Gaoni, Y., and R. Mechoulam. Isolation, structure and partial synthesis of an active constituent of hashish. J. Am. Chem. Soc. 86:1646-1647 (1964).
8. Razdan, R. K. Structure-activity relationships in cannabinoids. Pharmacol. Rev. 38:75-149 (1986).
9. Makriyannis, A., and R. S. Rapaka. The molecular basis of cannabinoid activity. Life Sci. 47:2173-2184 (1990).
10. Martin, B. R., D. R. Compton, B. F. Thomas, W. R. Prescott, P. J. Little, R. K. Razdan, M. R. Johnson, L. S. Melvin, R. Mechoulam, and S. J. Ward. Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacol. Biochem. Behav. 40:471-478 (1991).
11. Mechoulam, R., J. J. Feigenbaum, N. Lander, M. Segal, T. U. C. Jarb, A. J. Hiltunen, and P. Consroe. Enantiomeric cannabinoids: stereospecificity of psychotropic activity. Experientia 44:762-764 (1988).
12. Little, P. J., D. R. Compton, R. Mechoulam, and B. R. Martin. Stereochemical effects of 11-OH-delta-8-THC-dimethylheptyl. Pharmacol. Biochem. Behav. 32:661-666 (1989).
13. Johnson, M. R., and L. S. Melvin The discovery of nonclassical cannabinoid analgetics, in Cannabinoids as Therapeutic Agents (R. Mechoulam, ed.). CRC press, Boca Raton, FL, 121-145 (1986).
14. Melvin, L. S., G. M. Milne, M. R. Johnson, B. Subramaniam, G. H. Wilken, and A. C. Howlett. Structure-activity relationships for cannabinoid receptor-binding and analgesic activity: studies of bicyclic cannabinoid analogs. Mol Pharmacol. 44:1008-1015 (1993).
15. 9-tetrahydrocannabinol. J. Pharmacol. Exp. Ther. 263:1118-1126 (1992).
16. Kuster, J. E., J. I. Stevenson, S. J. Ward, T. E. D'Ambra, and D. A. Haycock. Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids. J. Pharmacol. Exp. Ther. 264:1352-1363 (1993).
17. Mechoulam, R., S. Ben-Shabat, L. Hanus, M. Ligumsky, N. E. Kaminski, A. R. Schatz, A. Gopher, S. Almog, B. R. Martin, D. R. Compton, R. G Pertwee, G. Griffin, M. Bayewitch, J. Barg, and Z. Vogel. Identification of an endogenous 2-monoglyceride, present in canine gut, that bind to cannabinoid receptors. Biochem. Pharmacol. 50:83-90 (1995).
18. Facci, L., R. Dal Toso, S. Romanello, A. Buriani, S. D. Skaper, and A. Leon. Mast cells express a peripheral cannabinoid receptor with differential sensitivity to anandamide and palmitoylethanolamide. Proc. Natl. Acad. Sci. USA 11:3376-80 (1995).
19. Baldwin, J. M. Structure and function of receptors coupled to G proteins. Curr. Opin. Cell Biol. 6:180-190 (1994)
20. Surratt, C. K., P. S. Johnson, A. Moriwaki, B. K. Seidleck, C. J. Blaschak, J. B. Wang, and G. R. Ubl. μ Opiate receptor: charged transmembrane domain amino acids are critical for agonist recognition and intrinsic activity. J. Biol. Chem. 269:20548-20553 (1994).
21. Tomic, M., I. Sunjevaric, E. S. Savtchenko, and M. Blumenberg. A rapid and simple method for introducing specific mutations into any position of DNA leaving all other positions unaltered. Nucleic Acids Res. 18:1656 (1990).
22. Chen, C., and H. Okayama. High-efficiency transformation of mammalian cells by plasmid DNA. Mol. Cell. Biol. 7:2745-2752 (1987).
23. Felder, C. C., J. S. Veluz, H. L. Williams, E. M. Briley, and L. A. Matsuda. Cannabinoid agonists stimulate both receptor- and non-receptor-mediated signal transduction pathways in cells transfected with and expressing cannabinoid receptor clones. Mol. Pharmacol. 42:838-845 (1992).
24. Feldman, H. A. Mathematical theory of complex ligand-binding systems at equilibrium. Anal. Biochem. 48:317-338 (1972).
25. DeBlasi, A., K. O'Reilly, and H. J. Motulsky. Calculating receptor number from binding experiments using same compound as radioligand and competitor. Trends Pharmacol. Sci. 10:227-229 (1989).
26. 50) of an enzymatic reaction. Biochem. Pharmacol. 22:3099-3108 (1973).
27. 2 receptors. Mol. Pharmacol. 48:443-450 (1995).
28. Ward, W. H J., D. Timms, and A. R. Fersht. Protein engineering and the study of structure-function relationships in receptors. Trends Pharmacol. Sci. 11:280-284 (1990).
29. Lau, F. T., and A. R. Fersht. Dissection of the effector-binding site and complementation studies of Escherichia coli phosphofructokinase using site-directed mutagenesis. Biochemistry 28:6841-6847 (1989).
30. Reggio, P. H., H. H. Seltzman, D. R. Compton, W. R. Prescott, Jr., and, B. R. Martin. Investigation of the role of the phenolic hydroxyl in cannabinoid activity. Mol. Pharmacol 38:854-862 (1990).
31. Ippolito, J. A., R. S. Alexander, and D. W. Christianson. Hydrogen bond stereochemistry in protein structure and function. J. Mol. Biol. 215:457-471 (1990).
32. Pinto, J. C., F. Potie, K. C. Rice, D. Boring, M. R. Johnson, D. M. Evans, G. H. Wilken, C. H. Cantrell, and A. C. Howlett. Cannabinoid receptor binding and agonist activity of amides and esters of arachidonic acid. Mol. Pharmacol. 46:516-522 (1994).