Inverse agonist properties of N-(piperidin-1-yl)-5-(4-chlorophenyl)-1- (2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide HCl (SR141716A) and 1-(2-chlorophenyl)-4-cyano-5-(4-methoxyphenyl)-1H-pyrazole-3-carboxylic acid phenylamide (CP-272871) for the CB1 cannabinoid receptor

Biochemical Pharmacology

Volumn 60, Issue 9, 2000, Pages 1315-1323

  Meschler, Justin P ^a   Kraichely, Dennis M ^a   Wilken, Gerald H ^a   Howlett, Allyn C ^a  

^a SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

35S GTP S binding; Adenylyl cyclase; Antagonist; Brain; Cannabinoid receptor; CP 55940; Desacetyllevonantradol; Inverse agonist; Neuroblastoma; Tonsils

Indexed keywords

1 (2 CHLOPHENYL) 4 CYANO 5 (4 METHOXYPHENYL) 1H PYRAZOLE 3 CARBOXYLIC ACID PHENYLAMIDE; 5 (4 CHLOROPHENYL) 1 (2,4 DICHLOROPHENYL) 4 METHYL N (1 PIPERIDYL) 1H PYRAZOLE 3 CARBOXAMIDE; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; CANNABINOID RECEPTOR ANTAGONIST; CARBOXYLIC ACID DERIVATIVE; CP 272871; GUANINE NUCLEOTIDE BINDING PROTEIN; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG RECEPTOR BINDING; NONHUMAN; PRIORITY JOURNAL; PROTEIN LOCALIZATION; SIGNAL TRANSDUCTION;

ANIMAL; BENZENE DERIVATIVES; CHO CELLS; CYCLIC AMP; GTP-BINDING PROTEINS; HAMSTERS; HUMAN; PIPERIDINES; PYRAZOLES; RADIOLIGAND ASSAY; RECEPTORS, DRUG; SUPPORT, U.S. GOV'T, P.H.S.; TRANSFECTION;

EID: 0034333417     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(00)00447-0     Document Type: Article

References (29)

1. Herkenham M., Lynn A.B., Little M.D., Johnson M.R., Melvin L.S., de Costa B.R., Rice K.C. Cannabinoid receptor localization in brain. Proc Natl Acad Sci USA. 87:1990;1932-1936.
2. Galiègue S., Mary S., Marchand J., Dussossoy D., Carrière D., Carayon P., Bouaboula M., Shire D., Le Fur G., Casellas P. Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem. 232:1995;54-61.
3. Howlett A.C. Pharmacology of cannabinoid receptors. Annu Rev Pharmacol Toxicol. 35:1995;607-634.
4. Pertwee R.G. Pharmacology of cannabinoid receptor ligands. Curr Med Chem. 6:1999;635-664.
5. i in the inhibition of adenylate cyclase by cannabimimetic drugs. Mol Pharmacol. 29:1986;307-313.
6. Childers S.R., Deadwyler S.A. Role of cyclic AMP in the actions of cannabinoid receptors. Biochem Pharmacol. 52:1996;819-827.
7. Rinaldi-Carmona M., Barth F., Héaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Néliat G., Caput D., Ferrara P., Soubrié P., Brelière J.C., Le Fur G. SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett. 350:1994;240-244.
8. 2 cannabinoid receptor. J Pharmacol Exp Ther. 284:1998;644-650.
9. Bouaboula M., Perrachon S., Milligan L., Canat X., Rinaldi-Carmona M., Portier M., Barth F., Calandras B., Pecceu F., Lupker J., Maffrand J.-P., Le Fur G., Casellas P. 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. 272:1997;22330-22339.
10. 1 receptor. Eur J Pharmacol. 334:1997;R1-R2.
11. Schutz W., Freissmuth M. Reverse intrinsic activity of antagonists on G protein-coupled receptors. Trends Pharmacol Sci. 13:1992;376-380.
12. Kenakin T. Pharmacological proteus? Trends Pharmacol Sci. 16:1995;256-258.
13. Milligan G., Bond R.A., Lee M. Inverse agonism Pharmacological curiosity or potential therapeutic strategy? Trends Pharmacol Sci. 16:1995;10-13.
14. Gerard C.M., Mollereau C., Vassart G., Parmentier M. Molecular cloning of a human cannabinoid receptor which is also expressed in testis. Biochem J. 279:1991;129-134.
15. Devane W.A., Dysarz F.A., Johnson M.R., Melvin L.S., Howlett A.C. Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol. 34:1988;605-613.
16. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 72:1976;248-254.
17. Kuster J.E., Stevenson J.I., Ward S.J., D'Ambra T.E., Haycock D.A. Aminoalkylindole binding in rat cerebellum Selective displacement by natural and synthetic cannabinoids . J Pharmacol Exp Ther. 264:1993;1352-1363.
18. Howlett A.C. Cannabinoid inhibition of adenylate cyclase. Biochemistry of the response in neuroblastoma cell membranes. Mol Pharmacol. 27:1985;429-436.
19. Tao Y.-P., Najafi L., Shipley S., Howlett A., Klein C. Effects of nitric oxide on adenylyl cyclase stimulation in N18TG2 neuroblastoma cells. J Pharmacol Exp Ther. 286:1998;298-304.
20. Costa T., Ogino Y., Munson P.J., Onaran H.O., Rodbard D. Drug efficacy at guanine nucleotide-binding regulatory protein-linked receptors Thermodynamic interpretation of negative antagonism and of receptor activity in the absence of ligand . Mol Pharmacol. 41:1991;549-560.
21. o-linked receptors and its allosteric regulation by monovalent cations. Life Sci. 52:1993;1899-1907.
22. Baxter G.S., Tilford N.S. Endogenous ligands and inverse agonism. Trends Pharmacol Sci. 16:1995;258-259.
23. 1 cannabinoid receptor juxtamembrane C-terminal peptide confers activation to specific G proteins in brain. Mol Pharmacol. 57:2000;162-170.
24. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 258:1992;1946-1949.
25. Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K. 2-Arachidonoylglycerol A possible endogenous cannabinoid receptor ligand in brain . Biochem Biophys Res Commun. 215:1995;89-97.
26. Di Marzo V., De Petrocellis L., Sepe N., Buono A. Biosynthesis of anandamide and related acylethanolamides in mouse J774 macrophages and N18 neuroblastoma cells. Biochem J. 316:1996;977-984.
27. Di Marzo V., De Petrocellis L., Sugiura T., Waku K. Potential biosynthetic connections between the two cannabimimetic eicosanoids, anandamide and 2-arachidonoyl-glycerol, in mouse neuroblastoma cells. Biochem Biophys Res Commun. 227:1996;281-288.
28. Deutsch D.G., Chin S.A. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol. 46:1993;791-796.
29. Maurelli S., Bisogno T., De Petrocellis L., Di Luccia A., Marino G., Di Marzo V. Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase'. FEBS Lett. 377:1995;82-86.