3-Substituted pyrazole analogs of the cannabinoid type 1 (CB 1) receptor antagonist rimonabant: Cannabinoid agonist-like effects in mice via non-CB 1, non-CB 2 mechanism

Journal of Pharmacology and Experimental Therapeutics

Volumn 340, Issue 2, 2012, Pages 433-444

  Wiley, Jenny L ^a,b   Selley, Dana E ^b   Wang, Pinglang ^c   Kottani, Rudresha ^c   Gadthula, Srinivas ^c   Mahadeven, Anu ^c  

^a RTI INTERNATIONAL   (United States)

^b VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^c ORGANIX INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; ALKYL GROUP; BENZYL DERIVATIVE; CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR AGONIST; CANNABINOID 1 RECEPTOR ANTAGONIST; CANNABINOID 2 RECEPTOR; CANNABINOID 2 RECEPTOR AGONIST; DRONABINOL; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); O 2154; O 2155; O 4331; O 4332; O 4333; O 4334; O 4335; O 4336; O 4337; O 4339; O 4371; O 4372; O 4373; O 4423; OXAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; RADIOLIGAND; RIMONABANT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTINOCICEPTION; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FEMALE; HYPOTHERMIA; IMMOBILIZATION; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANIMALS; BINDING, COMPETITIVE; BODY TEMPERATURE; BORNANES; CELL MEMBRANE; CHO CELLS; CRICETINAE; CYCLOHEXANOLS; DRUG INVERSE AGONISM; FEMALE; FREEZING REACTION, CATALEPTIC; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; MALE; MICE; MICE, INBRED C57BL; MICE, INBRED ICR; MICE, KNOCKOUT; MOTOR ACTIVITY; PAIN THRESHOLD; PIPERIDINES; PYRAZOLES; RADIOLIGAND ASSAY; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROCANNABINOL; TRANSFECTION;

EID: 84862955862     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.111.187815     Document Type: Article

References (40)

1. Adams IB, Compton DR, and Martin BR (1998) Assessment of anandamide interaction with the cannabinoid brain receptor: SR 141716A antagonism studies in mice and autoradiographic analysis of receptor binding in rat brain. J Pharmacol Exp Ther 284:1209-1217. (Pubitemid 28130853)
2. Bass CE, Griffin G, Grier M, Mahadevan A, Razdan RK, and Martin BR (2002) SR-141716A-induced stimulation of locomotor activity. A structure-activity relationship study. Pharmacol Biochem Behav 74:31-40.
3. Breivogel CS and Childers SR (2000) Cannabinoid agonist signal transduction in rat brain: comparison of cannabinoid agonists in receptor binding, G-protein activation, and adenylyl cyclase inhibition. J Pharmacol Exp Ther 295:328-336.
4. Cabral GA, Raborn ES, Griffin L, Dennis J, and Marciano-Cabral F (2008) CB2 receptors in the brain: role in central immune function. Br J Pharmacol 153:240-251.
5. Cheng Y and Prusoff WH (1973) Relationship between the inhibition constant (KI) and the concentration of inhibitor which causes 50 per cent inhibition (I50) on an enzymatic reaction. Biochem Pharmacol 22:3099-3108.
6. Christensen R, Kristensen PK, Bartels EM, Bliddal H, and Astrup A (2007) Efficacy and safety of the weight-loss drug rimonabant: a meta-analysis of randomised trials. Lancet 370:1706-1713. (Pubitemid 350100788)
7. Compton DR, Aceto MD, Lowe J, and Martin BR (1996) In vivo characterization of a specific cannabinoid receptor antagonist (SR141716A): inhibition of Δ9- tetrahydrocannabinol-induced responses and apparent agonist activity. J Pharmacol Exp Ther 277:586-594. (Pubitemid 27168965)
8. Compton DR, Rice KC, De Costa BR, Razdan RK, Melvin LS, Johnson MR, and Martin BR (1993) Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J Pharmacol Exp Ther 265:218-226. (Pubitemid 23320964)
9. Cooper M, Receveur JM, Bjurling E, Nørregaard PK, Nielsen PA, Sköld N, and Högberg T (2010) Exploring SAR features in diverse library of 4-cyanomethylpyrazole- 3-carboxamides suitable for further elaborations as CB1 antagonists. Bioorg Med Chem Lett 20:26-30.
10. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, and Mechoulam R (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258:1946-1949. (Pubitemid 23026736)
11. Fattore L, Cossu G, Martellotta CM, and Fratta W (2001) Intravenous self-administration of the cannabinoid CB1 receptor agonist WIN 55,212-2 in rats. Psychopharmacology (Berl) 156:410-416. (Pubitemid 32695850)
12. 1 receptor antagonist N- (piperidinyl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)- 4-methyl-1Hpyrazole- 3-carboxamide (SR141716). J Med Chem 45:2708-2719.
13. Gullapalli S, Amrutkar D, Gupta S, Kandadi MR, Kumar H, Gandhi M, Karande V, and Narayanan S (2010) Characterization of active and inactive states of CB1 receptor and the differential binding state modulation by cannabinoid agonists, antagonists and inverse agonists. Neuropharmacology 58:1215-1219.
14. Huestis MA, Gorelick DA, Heishman SJ, Preston KL, Nelson RA, Moolchan ET, and Frank RA (2001) Blockade of effects of smoked marijuana by the CB1-selective cannabinoid receptor antagonist SR141716. Arch Gen Psychiatry 58:322-328. (Pubitemid 32299527)
15. Hurst D, Umejiego U, Lynch D, Seltzman H, Hyatt S, Roche M, McAllister S, Fleischer D, Kapur A, Abood M, et al. (2006) Biarylpyrazole inverse agonists at the cannabinoid CB1 receptor: importance of the C-3 carboxamide oxygen/ lysine3.28(192) interaction. J Med Chem 49:5969-5987. (Pubitemid 44484943)
16. Institute of Laboratory Animal Resources (1996) Guide for the Care and Use of Laboratory Animals 7th ed. Institute of Laboratory Animal Resources, Commission on Life Sciences, National Research Council, Washington DC.
17. Järbe TU, Harris MY, Li C, Liu Q, and Makriyannis A (2004) Discriminative stimulus effects in rats of SR-141716 (rimonabant), a cannabinoid CB1 receptor antagonist. Psychopharmacology (Berl) 177:35-45. (Pubitemid 40109912)
18. Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, Pertwee R, and Makriyannis A (1999) Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 42:769-776. (Pubitemid 29110792)
19. Landsman RS, Burkey TH, Consroe P, Roeske WR, and Yamamura HI (1997) SR141716A is an inverse agonist at the human cannabinoid CB1 receptor. Eur J Pharmacol 334:R1-R2. (Pubitemid 27417820)
20. Martin BR, Compton DR, Thomas BF, Prescott WR, Little PJ, Razdan RK, Johnson MR, Melvin LS, Mechoulam R, and Ward SJ (1991) Behavioral, biochemical, and molecular modeling evaluations of cannabinoid analogs. Pharmacol Biochem Behav 40:471-478.
21. Murillo-Rodríguez E, Cabeza R, Méndez-Díaz M, Navarro L, and Prospéro-García O (2001) Anandamide-induced sleep is blocked by SR141716A, a CB1 receptor antagonist and by U73122, a phospholipase C inhibitor. Neuroreport 12:2131-2136.
22. Onaivi ES, Ishiguro H, Gong JP, Patel S, Perchuk A, Meozzi PA, Myers L, Mora Z, Tagliaferro P, Gardner E, et al. (2006) Discovery of the presence and functional expression of cannabinoid CB2 receptors in brain. Ann NY Acad Sci 1074:514-536. (Pubitemid 44532857)
23. 2+ currents by reversal of tonic CB1 cannabinoid receptor activity. Mol Pharmacol 54:1064-1072.
24. Pertwee RG, Howlett AC, Abood ME, Alexander SP, Di Marzo V, Elphick MR, Greasley PJ, Hansen HS, Kunos G, Mackie K, et al. (2010) International Union of Basic and Clinical Pharmacology. LXXIX. Cannabinoid receptors and their ligands: beyond CB1 and CB2. Pharmacol Rev 62:588-631.
25. Rinaldi-Carmona M, Barth F, Héaulme M, Alonso R, Shire D, Congy C, Soubrié P, Brelière JC, and Le Fur G (1995) Biochemical and pharmacological characterisation of SR141716A, the first potent and selective brain cannabinoid receptor antagonist. Life Sci 56:1941-1947.
26. Rinaldi-Carmona M, Barth F, Héaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J, Néliat G, and Caput D (1994) SR141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350:240-244. (Pubitemid 24268029)
27. Selley DE, Stark S, Sim LJ, and Childers SR (1996) Cannabinoid receptor stimulation of guanosine-5′-O-(3-[35S]thio)triphosphate binding in rat brain membranes. Life Sci 59:659-668.
28. 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. (Pubitemid 27166944)
29. Thomas BF, Francisco ME, Seltzman HH, Thomas JB, Fix SE, Schulz AK, Gilliam AF, Pertwee RG, and Stevenson LA (2005) Synthesis of long-chain amide analogs of the cannabinoid CB1 receptor antagonist N- (piperidinyl)-5-(4- chlorophenyl)-1- (2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3- carboxamide (SR141716) with unique binding selectivities and pharmacological activities. Bioorg Med Chem 13:5463-5474. (Pubitemid 41132623)
30. Thomas BF, Gilliam AF, Burch DF, Roche MJ, and Seltzman HH (1998) Comparative receptor binding analyses of cannabinoid agonists and antagonists. J Pharmacol Exp Ther 285:285-292. (Pubitemid 28207598)
31. Van Sickle MD, Duncan M, Kingsley PJ, Mouihate A, Urbani P, Mackie K, Stella N, Makriyannis A, Piomelli D, Davison JS, et al. (2005) Identification and functional characterization of brainstem cannabinoid CB2 receptors. Science 310:329-332. (Pubitemid 41457202)
32. Wiley JL, Barrett RL, Lowe J, Balster RL, and Martin BR (1995a) Discriminative stimulus effects of CP 55,940 and structurally dissimilar cannabinoids in rats. Neuropharmacology 34:669-676.
33. Wiley JL, Burston JJ, Leggett DC, Alekseeva OO, Razdan RK, Mahadevan A, and Martin BR (2005) CB1 cannabinoid receptor-mediated modulation of food intake in mice. Br J Pharmacol 145:293-300. (Pubitemid 40896074)
34. 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. (Pubitemid 28277896)
35. Wiley JL, Jefferson RG, Grier MC, Mahadevan A, Razdan RK, and Martin BR (2001) Novel pyrazole cannabinoids: insights into CB(1) receptor recognition and activation. J Pharmacol Exp Ther 296:1013-1022. (Pubitemid 32187377)
36. Wiley JL, Jefferson RG, Griffin G, Liddle J, Yu S, Huffman JW, and Martin BR (2002) Paradoxical pharmacological effects of deoxy-tetrahydrocannabinol analogs lacking high CB1 receptor affinity. Pharmacology 66:89-99. (Pubitemid 35007644)
37. Wiley JL, Lowe JA, Balster RL, and Martin BR (1995b) Antagonism of the discriminative stimulus effects of Δ9-tetrahydrocannabinol in rats and rhesus monkeys. J Pharmacol Exp Ther 275:1-6.
38. Wiley JL and Martin BR (2002) Cannabinoid pharmacology: implications for additional cannabinoid receptor subtypes. Chem Phys Lipids 121:57-63. (Pubitemid 36044542)
39. Wiley JL and Martin BR (2003) Cannabinoid pharmacological properties common to other centrally acting drugs. Eur J Pharmacol 471:185-193. (Pubitemid 36776413)
40. Zimmer A, Zimmer AM, Hohmann AG, Herkenham M, and Bonner TI (1999) Increased mortality, hypoactivity, and hypoalgesia in cannabinoid CB1 receptor knockout mice. Proc Natl Acad Sci U S A 96:5780-5785. (Pubitemid 29234695)