Tricyclic pyrazoles. 4. Synthesis and biological evaluation of analogues of the robust and selective CB 2 cannabinoid ligand 1-(2′, 4′-dichlorophenyl)-6-methyl-N-piperidin-1-yl-1,4-dihydroindeno[1,2-c] pyrazole-3-carboxamide
ARTICLE;
CELL STRAIN HL 60;
DRUG RECEPTOR BINDING;
DRUG SELECTIVITY;
DRUG STRUCTURE;
DRUG SYNTHESIS;
EVALUATION;
HUMAN;
HUMAN CELL;
PROMYELOCYTIC LEUKEMIA;
PROTON NUCLEAR MAGNETIC RESONANCE;
REACTION ANALYSIS;
RECEPTOR AFFINITY;
STRUCTURE ANALYSIS;
A critical role for tyrosine residue in the cannabinoid receptors for ligand recognition
McAllister, S. D.; Tao, Q.; Barnett-Norris, J.; Buehner, K.; Hurst, D. P.; Guarnieri, F.; Reggio, P. H.; Nowell Harmon, K. W.; Cabral, G. A.; Abood, M. E. A critical role for tyrosine residue in the cannabinoid receptors for ligand recognition. Biochem. Pharmacol. 2002, 63, 2121-2136.
International Union of Pharmacology. XXVII. Classification of cannabinoid receptors
Hewlett, A. C.; Barth, F.; Bonner, T. I.; Cabral, G.; Casellas, P.; Devane, W. A.; Felder, C. C.; Herkenham, M.; Mackie, K.; Martin, B. R.; Mechoulam, R.; Pertwee, R. G. International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol. Rev. 2002, 54, 161-202.
Regulation of peripheral cannabinoid receptor CB2 phosphorylation by the inverse agonist SR 144528. Implications for receptor biological responses
Bouaboula, M.; Dussossoy, D.; Casellas, P. Regulation of peripheral cannabinoid receptor CB2 phosphorylation by the inverse agonist SR 144528. Implications for receptor biological responses. J. Biol. Chem. 1999, 274, 20397-20405.
Stimulation of peripheral cannabinoid receptor CB2 induces MCP-1 and IL-8 gene expression in human promyelocytic cell line HL60
Jbilo, O.; Derocq, J. M.; Segui, M.; Le Fur, G.; Casellas, P. Stimulation of peripheral cannabinoid receptor CB2 induces MCP-1 and IL-8 gene expression in human promyelocytic cell line HL60. FEBS Lett. 1999, 448, 273-277.
2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells
Kishimoto, S.; Kobayashi, Y.; Oka, S.; Gokoh, M.; Waku, K.; Sugiura, T. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor ligand, induces accelerated production of chemokines in HL-60 cells. J. Biochem. 2004, 135, 517-524.
New perspectives in the studies on endocannabinoid and cannabis: 2-Arachidonoylglycerol as a possible novel mediator of inflammation
Sugiura, T.; Oka, S.; Gokoh, M.; Kishimoto, S.; Waku, K. New perspectives in the studies on endocannabinoid and cannabis: 2-Arachidonoylglycerol as a possible novel mediator of inflammation. J. Pharmacol. Sci. 2004, 96, 367-375.
Cultured rat microglial cells synthesize the endocannabinoid 2-arachidonylglycerol, which increases proliferation via a CB2 receptor-dependent mechanism
Carrier, E. J.; Kearn, C. S.; Barkmeier, A. J.; Breese, N. M.; Yang, W.; Nithipatikom, K.; Pfister, S. L.; Campbell, W. B.; Hillard, C. J. Cultured rat microglial cells synthesize the endocannabinoid 2-arachidonylglycerol, which increases proliferation via a CB2 receptor-dependent mechanism. Mol. Pharmacol. 2004, 65, 999-1007.
Activation through cannabinoid receptors 1 and 2 on dendritic cells triggers NF-kappaB-dependent apoptosis: Novel role for endogenous and exogenous cannabinoids in immunoregulation
Do, Y.; McKallip, R. J.; Nagarkatti, M.; Nagarkatti, P. S. Activation through cannabinoid receptors 1 and 2 on dendritic cells triggers NF-kappaB-dependent apoptosis: Novel role for endogenous and exogenous cannabinoids in immunoregulation. J. Immunol. 2004, 173, 2373-2382.
Targeting CB2 cannabinoid receptors as a novel therapy to treat malignant lymphoblastic disease
McKallip, R. J.; Lombard, C.; Fisher, M.; Martin, B. R.; Ryu, S.; Grant, S.; Nagarkatti, P. S.; Nagarkatti, M. Targeting CB2 cannabinoid receptors as a novel therapy to treat malignant lymphoblastic disease. Blood 2002, 100, 627-634.
2 receptors and fatty acid amide hydrolase are selectively overexpressed in neuritic plaque-associated glia in Alzheimer disease brains
2 receptors and fatty acid amide hydrolase are selectively overexpressed in neuritic plaque-associated glia in Alzheimer disease brains. J. Neurosci. 2003, 23, 11136-11141.
Preparation and formulation of tricyclic heterocycles containing a pyrazole-3-carboxamide subunit for pharmaceutical use as cannabinoid receptor antagonists
WO 01 32,629, 2001; p 35 (Sanofi-Synthelabo, France)
Barth, F.; Millan, J.; Oustric, D.; Rinaldi, M.; Vernhet, M. Preparation and formulation of tricyclic heterocycles containing a pyrazole-3-carboxamide subunit for pharmaceutical use as cannabinoid receptor antagonists. WO 01 32,629, 2001; p 35 (Sanofi-Synthelabo, France); Chem. Abstr. 2001, 134, 340501m.
2 cannabinoid receptor by AM1241 inhibits experimental neuropathic pain: Pain inhibition by receptors not present in the CNS
2 cannabinoid receptor by AM1241 inhibits experimental neuropathic pain: pain inhibition by receptors not present in the CNS. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 10529-10533.
SR144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist
Portier, M.; Rinaldi-Carmona, M.; Pecceu, F.; Combes, T.; Poinot-Chazel, C.; Calandra, B.; Barth, F.; Le Fur, G.; Casellas, P. SR144528, an antagonist for the peripheral cannabinoid receptor that behaves as an inverse agonist. J. Pharmacol. Exp. Ther. 1999, 288, 582-589.
Genomic and functional changes induced by the activation of the peripheral cannabinoid receptor CB2 in the promyelocytic cells HL-60. Possible involvement of the CB2 receptor in cell differentiation
Derocq, J. M.; Jbilo, O.; Bouaboula, M.; Segui, M.; Clere, C.; Casellas, P. Genomic and functional changes induced by the activation of the peripheral cannabinoid receptor CB2 in the promyelocytic cells HL-60. Possible involvement of the CB2 receptor in cell differentiation. J. Biol. Chem. 2000, 275, 15621-15628.
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
Bouaboula, M.; Perrachon, S.; Milligan, L.; Canat, X.; Rinaldi-Carmona, M.; Portier, M.; Barth, F.; Calandra, 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. 1997, 272 (35), 22330-22339.
(1997)J. Biol. Chem., vol.272, Issue.35, pp. 22330-22339
CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain
Clayton, N.; Marshall, F. H.; Bountra, C.; O'Shaughnessy, C. T. CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain. Pain 2002, 96, 253-260.
A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
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. 1976, 72, 248-254.
Effect of δ-9-tetrahydrocannabinol on phosphorylated CREB in rat cerebellum: An immunohistochemical study
Casu, M. A.; Pisu, C.; Sanna, A.; Tambaro, S.; Spada, G. P.; Mongeau, R.; Pani, L. Effect of δ-9-tetrahydrocannabinol on phosphorylated CREB in rat cerebellum: an immunohistochemical study. Brain Res. 2005, 1048, 41-47.