The third transmembrane helix of the cannabinoid receptor plays a role in the selectivity of aminoalkylindoles for CB2, peripheral cannabinoid receptor

Journal of Pharmacology and Experimental Therapeutics

Volumn 291, Issue 2, 1999, Pages 837-844

  Chin, Chen Ni ^a,c   Murphy, James W ^a   Huffman, John W ^b   Kendall, Debra A ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b CLEMSON UNIVERSITY   (United States)

^c STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1 PENTYL 3 (1 NAPHTHOYL)INDOLE; 1 PROPYL 2 METHYL 3 (1 NAPHTHOYL)INDOLE; 2 METHYL 3 (1 NAPHTHOYL) 1 PROPYLINDOLE; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 3 (1 NAPHTHOYL) 1 PENTYLINDOLE; ALANINE; CANNABINOID RECEPTOR; CYCLIC AMP; GLYCINE; INDOLE DERIVATIVE; METHIONINE; SERINE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHO CELL; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG RESEARCH; NONHUMAN; PRIORITY JOURNAL; PROTEIN LOCALIZATION;

ANIMALS; BINDING SITES; CENTRAL NERVOUS SYSTEM; CHO CELLS; CLONING, ORGANISM; CRICETINAE; CYCLIC AMP; DNA, COMPLEMENTARY; DOSE-RESPONSE RELATIONSHIP, DRUG; FORSKOLIN; HUMANS; INDOLES; LIGANDS; MORPHOLINES; MUTAGENESIS; NAPHTHALENES; PLASMIDS; PROTEIN BINDING; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; RECOMBINANT FUSION PROTEINS; SPLEEN;

EID: 0032741185     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Abadji V, Lin S, Taha G, Griffin G, Stevenson LA, Pertwee RG and Makriyannis A (1994) (R)-Methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability. J Med Chem 37:1889-1893.
2. 8. J Neurochem 72:2032-2038.
3. Abood ME, Tao Q, McAllister SD and Hurst DP (1998) A critical role for a tyrosine residue in the cannabinoid receptors for recognition of several compounds excluding the indoles. 1998 Symposium on the Cannabinoids International Cannabinoid Research Society, Burlington, VT.
4. 9-Tetrahydrocannabinol antagonizes the peripheral cannabinoid receptor-mediated inhibition of adenylyl cyclase. J Biol Chem 271:9902-9905.
5. Bell MR, D'Ambra TE, Kumar V, Eissenstat MA, Herrmann JL Jr, Wtzel JR, Rosi D, Philion RE, Daum SJ, Hlasta DJ, Kullnig RK, Ackerman JH, Haubrich DR, Luttinger DA, Baizman ER, Miller MS and Ward SJ (1991) Antinociceptive (aminoalkyl)indoles. J Med Chem 34:1099-1110.
6. Bouaboula M, Perrachon S, Milligan L, Canat X, Rinaldi-Carmona M, Portier M, Barth F, Calandra B, Pecceu F, Lupker J, Maffrand JP, Le Fur G and Casellas, P (1997) A selective inverse agonist for central cannabinoid receptor inhibits mitogen-activated protein kinase activation stimulated by insulin or insulin-like growth factor 1: Evidence for a new model of receptor/ligand interactions. J Biol Chem 272:22330-22339.
7. 50) of an enzyme reaction. Biochem Pharmacol 22:2099-3108.
8. Chin CN, Lucas-Lenard JM, Abadji V and Kendall DA (1998) Ligand binding and modulation of cyclic AMP levels depend on the chemical nature of residue 192 of the human cannabinoid receptor 1. J Neurochem 70:366-373.
9. Felder CC, Joyce KE, Briley EM, Mansouri J, Mackie K, Blond O, Lai Y, Ma AL and Mitchell RL (1995) Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors. Mol Pharmacol 48:443-450.
10. Gallant M (1996) New class of potent ligands for the human peripheral cannabinoid receptor. Biol Med Chem Lett 6:2263-2268.
11. Gareau Y, Dufresne C, Gallant M, Rochette C, Sawyer N, Slipetz DM, Tremblay N, Weech PK, Metters KM and Labelle M (1996) Structure activity relationships of tetrahydrocannabinol analogues on human cannabinoid receptors. Biol Med Chem Lett 6:189-194.
12. Gerard CM, Mollereau C, Vassart G and Parmentier M (1991) Molecular cloning of a human cannabinoid receptor which is also expressed in testis. Biochem J 279: 129-134.
13. i in the inhibition of adenylate cyclase by cannabimimetic drugs. Mol Pharmacol 29:307-313.
14. Huffman JW, Dai D, Martin BR and Compton DR (1994) Design, synthesis and pharmacology of cannabimimetic indoles. Biol Med Chem Lett 4:563-566.
15. Huffman JW, Yu S, Showalter V, Abood ME, Bramblett RD and Reggio PH (1996) Synthesis and pharmacology of a very potent cannabinoid lacking a phenolic hydroxyl with high affinity for the CB2 receptor. J Med Chem 89:3875-3877.
16. Khanolkar AD, Abadji V, Lin S, Hill WA, Taha G, Abouzid K, Meng Z, Fan P and Makriyannis A (1996) Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem 39:4515-4519.
17. Kumar V, Alexander MD, Bell MR, Eissenstat MA, Casiano FM, Chippari SM, Haycock DA, Luttinger DA, Kuster JE, Miller MS, Stevenson JI and Ward SJ (1995) Morpholinoalkylindenes as antinociceptive agents: Novel cannabinoid receptor agonists. Bioorg Med Chem Lett 5:381-386.
18. Lu D, Khanolkar A, Meng Z, Fan P, Reggio PH and Makriyannis A (1997) CB1/CB2 selective cannabinoids by conformational constraint of the side chain. 1997 Symposium on the Cannabinoids, International Cannabinoid Research Society. Burlington, VT.
19. Mackie K and Hille B (1992) Cannabinoids inhibit N-type calcium channels in neuroblastoma-glioma cells. Proc Natl Acad Sci USA 89:3825-3829.
20. Mackie K, Lai Y, Westenbroek R and Mitchell R (1995) Cannabinoids activate an inwardly rectifying potassium conductance and inhibit Q-type calcium currents in AtT20 cells transfected with rat brain cannabinoid receptor. J Neurosci 15:6552-6561.
21. Matsuda LA, Lolait SJ, Brownstein MJ, Young AC and Bonner TI (1990) Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature (Lond) 346:561-564.
22. Munro S, Thomas KL and Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature (Lond) 365:61-65.
23. Reggio PH, Basu-Dutt S, Barnett-Norris J, Castro MT, Hurst DP, Seltzman HH, Roche MJ, Gilliam AF, Thomas BF, Stevenson LA, Pertwee RG and Abood ME (1998) The bioactive conformation of aminoalkylindoles at the cannabinoid CB1and CB2 receptors: Insights gained from (E)- and (Z)-naphthyliden indenes. J Med Chem 41:5177-5187.
24. Rinaldi-Carmona M, Barth F, Heaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J and Neliat G (1994) SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350:240-244.
25. Rinaldi-Carmona M, Barth F, Millan J, Derocq JM, Casellas P, Congy C, Oustric D, Sarran M, Bouaboula M, Calandra B, Portie RM, Shire D, Breliere JC and Le Fur G (1998) SR 144528, the first potent and selective antagonist of the CB2 cannabinoid receptor. J Pharmacol Exp Ther 284:644-650.
26. Shire D, Calandra B, Delpech M, Dumont X, Kaghad M, Le Fur G, Caput D and Ferrara P (1996) Structure features of the central cannabinoid CB1 receptor involved in the binding of the specific CB1 antagonist SR141716A. J Biol Chem 271:6941-6946.
27. Showalter VM, Compton DR, Martin BR and Abood ME (1996) Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): Identification of cannabinoid receptor subtype selective ligands. J Pharmacol Exp Ther 278:989-999.
28. Slipetz DM, O'Neill GP, Favreau L, Dufresne C, Gallant M, Gareau Y, Guay D, Labelle M and Metters KM (1995) Activation of the human peripheral cannabinoid receptor results in inhibition of adenylyl cyclase. Mol Pharmacol 48:352-361.
29. Song ZH and Bonner TI (1996) A lysine residue of the cannabinoid receptor is critical to receptor recognition by several agonists but not WIN 55,212-2. Mol Pharmacol 49:891-896.
30. Song ZH and Reggio PH (1998) The difference between the CB1 and CB2 cannabinoid receptors at position 5.46 is crucial for the selectivity of WIN 55,212-2 for CB2.1998 Symposium on the Cannabinoids. International Cannabinoid Research Society, Burlington, VT.
31. Wiley JL, Compton DR, Dai D, Lainton JA, Phillips M, Huffman JW and Martin BR (1998) Structure-activity relationships of indole- and pyrrole-derived cannabinoids. J Pharmacol Exp Ther 285:995-1004