Characterization of a cannabinoid CB 2 receptor-selective agonist, A-836339 [2,2,3,3-tetramethyl-cyclopropanecarboxylic acid [3-(2-methoxy-ethyl)-4,5-dimethyl-3H-thiazol-(2Z)-ylidene]- Amide], using in vitro pharmacological assays, in vivo pain models, and pharmacological magnetic resonance imaging

Journal of Pharmacology and Experimental Therapeutics

Volumn 328, Issue 1, 2009, Pages 141-151

  Yao, Betty B ^a   Hsieh, Gin ^a   Daza, Anthony V ^a   Fan, Yihong ^a   Grayson, George K ^a   Garrison, Tiffany Runyan ^a   Kouhen, Odile El ^a   Hooker, Bradley A ^a   Pai, Madhavi ^a   Wensink, Erica J ^a   Salyers, Anita K ^a   Chandran, Prasant ^a   Zhu, Chang Z ^a   Zhong, Chengmin ^a   Ryther, Keith ^a   Gallagher, Megan E ^a   Chin, Chih Liang ^a   Tovcimak, Ann E ^a   Hradil, Vincent P ^a   Fox, Gerard B ^a   Dart, Michael J ^a   Honore, Prisca ^a   Meyer, Michael D ^a   Research, Neurological Diseases ^a   more..

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2,3 DICHLOROBENZOYL) 2 METHYL 3 (2 MORPHOLINOETHYL) 5 METHOXYINDOLE; 2 METHYL 3 (1 NAPHTHOYL) 1 PROPYLINDOLE; 2,2,3,3 TETRAMETHYLCYCLOPROPANECARBOXYLIC ACID [3 (2 METHOXYETHYL) 4,5 DIMETHYL 3H THIAZOL 2 YLIDENE]AMIDE; 3 (2 IODO 5 NITROBENZOYL) 1 (1 METHYL 2 PIPERIDINYLMETHYL)INDOLE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 6 IODO 3 (4 METHOXYBENZOYL) 2 METHYL 1 (2 MORPHOLINOETHYL)INDOLE; A 796260; A 836339; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR AGONIST; CAPSAICIN; FREUND ADJUVANT; G PROTEIN COUPLED RECEPTOR; GABAPENTIN; GW 842166; ION CHANNEL; MU OPIATE RECEPTOR; RADIOLIGAND; RIMONABANT; UNCLASSIFIED DRUG; 2,2,3,3 TETRAMETHYLCYCLOPROPANE CARBOXAMIDE; 2,2,3,3-TETRAMETHYLCYCLOPROPANE CARBOXAMIDE; AMIDE; CANNABINOID 1 RECEPTOR; CYCLOPROPANE DERIVATIVE;

ALLODYNIA; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BINDING COMPETITION; CONTROLLED STUDY; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG TOLERANCE; HUMAN; HUMAN CELL; HYPERALGESIA; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; LIGAND BINDING; LOCOMOTION; MALE; MOTOR COORDINATION; NEUROPATHIC PAIN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; PAIN; POSTOPERATIVE PAIN; PRIORITY JOURNAL; RAT; RECEPTOR UPREGULATION; SKIN INCISION; SPECIES DIFFERENCE; TREATMENT DURATION; ANIMAL; CELL LINE; CHO CELL; CRICETULUS; DRUG POTENTIATION; HAMSTER; HINDLIMB; KIDNEY; METHODOLOGY; PATHOPHYSIOLOGY; PHYSIOLOGY; PRENATAL DEVELOPMENT; PSYCHOMOTOR PERFORMANCE; SKIN; SPRAGUE DAWLEY RAT;

AMIDES; ANIMALS; CELL LINE; CHO CELLS; CRICETINAE; CRICETULUS; CYCLOPROPANES; HINDLIMB; HUMANS; HYPERALGESIA; INFLAMMATION; KIDNEY; MAGNETIC RESONANCE IMAGING; MALE; PAIN; PAIN, POSTOPERATIVE; PSYCHOMOTOR PERFORMANCE; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; SKIN;

EID: 59149090322     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.108.145011     Document Type: Article

References (40)

1. Bennett GJ and Xie YK (1988) A peripheral mononeuropathy in rat that produces disorders of pain sensation like those seen in man. Pain 33:87-107.
2. Bingham B, Jones PG, Uveges AJ, Kotnis S, Lu P, Smith VA, Sun SC, Resnick L, Chlenov M, He Y, et al. (2007) Species-specific in vitro pharmacological effects of the cannabinoid receptor 2 (CB2) selective ligand AM1241 and its resolved enantiomers. Br J Pharmacol 151:1061-1070.
3. Brennan TJ, Vandermeulen EP, and Gebhart GF (1996) Characterization of a rat model of incisional pain. Pain 64:493-501.
4. Buntin-Mushock C, Phillip L, Moriyama K, and Palmer PP (2005) Age-dependent opioid escalation in chronic pain patients. Anesth Analg 100:1740-1745.
5. Chin CL, Tovcimak AE, Hradil VP, Seifert TR, Hollingsworth PR, Chandran P, Zhu CZ, Gauvin D, Pai M, Wetter J, et al. (2008) Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI. Br J Pharmacol 153:367-379.
6. Contet C, Filliol D, Matifas A, and Kieffer BL (2008) Morphine-induced analgesic tolerance, locomotor sensitization and physical dependence do not require modification of mu opioid receptor, cdk5 and adenylate cyclase activity. Neuropharmacology 54:475-486.
7. Dart MJ, Carroll WA, Florjancic AS, Frost JM, Gallagher ME, Kolasa T, Li T, Nelson DW, Patel MV, Peddi S, et al. (2007), inventors; Abbott Laboratories, USA, assignee. Novel iminothiazole compounds as cannabinoid receptor ligands and their preparation, pharmaceutical compositions and use in the treatment of diseases. PCT International Application World Patent WO 2007140385. 2007 Dec 6.
8. Duncan M, Kendall DA, and Ralevic V (2004) Characterization of cannabinoid modulation of sensory neurotransmission in the rat isolated mesenteric arterial bed. J Pharmacol Exp Ther 311:411-419.
9. Elmes SJ, Winyard LA, Medhurst SJ, Clayton NM, Wilson AW, Kendall DA, and Chapman V (2005) Activation of CB1 and CB2 receptors attenuates the induction and maintenance of inflammatory pain in the rat. Pain 118:327-335.
10. 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.
11. Fox A and Bevan S (2005) Therapeutic potential ofcannabinoid receptor agonists as analgesic agents. Expert Opin Investig Drugs 14:695-703.
12. Fox A, Kesingland A, Gentry C, McNair K, Patel S, Urban L, and James I (2001) The role of central and peripheral cannabinoid1 receptors in the antihyperalgesic activity of cannabinoids in a model of neuropathic pain. Pain 92:91-100.
13. Galiègue S, Mary S, Marchand J, Dussossoy D, Carrière D, Carayon P, Bouaboula M, Shire D, Le Fur G, and Casellas P (1995) Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations. Eur J Biochem 232:54-61.
14. Gallant M, Dufresne C, Gareau Y, Guay D, Leblanc Y, Prasit P, Rochette C, Sawyer N, and Slipetz DM (1996) New class of potent ligands for the human peripheral cannabinoid receptor. Bioorg Med Chem Lett 6:2263-2268.
15. Giblin GM, O'Shaughnessy CT, Naylor A, Mitchell WL, Eatherton AJ, Slingsby BP, Rawlings DA, Goldsmith P, Brown AJ, Haslam CP, et al. (2007) Discovery of 2-[(2,4-dichlorophenyl)amino]-W-[(tetrahydro-2H-pyran-4-yl)methyl]- 4-(triflu- oromethyl)-5-pyrimidinecarboxamide, a selective CB2 receptor agonist for the treatment of inflammatory pain. J Med Chem 50:2597-2600.
16. Gillen C and Maul C (2002) New pharmacological strategies for pain relief. Exp Rev Neurother 2:691-702.
17. Guindon J and Hohmann AG (2008) Cannabinoid CB2 receptors: a therapeutic target for the treatment of inflammatory and neuropathic pain. Br J Pharmacol 153:319-334.
18. Hanus L, Breuer A, Tchilibon S, Shiloah S, Goldenberg D, Horowitz M, Pertwee RG, Ross RA, Mechoulam R, and Fride E (1999) HU-308: a specific agonist for CB(2), a peripheral cannabinoid receptor. Proc Natl Acad Sci U S A 96:14228-14233.
19. Hargreaves K, Dubner R, Brown F, Flores C, and Joris J (1988) A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia. Pain 32:77-88.
20. Hohmann AG, Farthing JN, Zvonok AM, and Makriyannis A (2004) Selective activation of cannabinoid CB2 receptors suppresses hyperalgesia evoked by intradermal capsaicin. J Pharmacol Exp Ther 308:446 -453.
21. Huffman JW (1999) Cannabimimetic indoles, pyrroles and indenes. Curr Med Chem 6:705-720.
22. Ibrahim MM, Porreca F, Lai J, Albrecht PJ, Rice FL, Khodorova A, Davar G, Makriyannis A, Vanderah TW, Mata HP, et al. (2005) CB2 cannabinoid receptor activation produces antinociception by stimulating peripheral release of endogenous opioids. Proc Natl Acad Sci U S A 102:3093-3098.
23. Ibrahim MM, Rude ML, Stagg NJ, Mata HP, Lai J, Vanderah TW, Porreca F, Buckley NE, Makriyannis A, and Malan TP Jr (2006) CB cannabinoid receptor mediation of antinociception. Pain 122:36 -42.
24. Joshi SK, Hernandez G, Mikusa JP, Zhu CZ, Zhong C, Salyers A, Wismer CT, Chandran P, Decker MW, and Honore P (2006) Comparison of antinociceptive actions of standard analgesics in attenuating capsaicin and nerve-injury-induced mechanical hypersensitivity. Neuroscience 143:587-596.
25. Malan TP Jr, Ibrahim MM, Deng H, Liu Q, Mata HP, Vanderah T, Porreca F, and Makriyannis A (2001) CB2 cannabinoid receptor-mediated peripheral antinociception. Pain 93:239 -245.
26. Markman JD and Philip A (2007) Interventional approaches to pain management. Anesthesiol Clin 25:883-898, viii.
27. 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 346:561-564.
28. McGaraughty S, Chu KL, Dart MJ, Yao BB and Meyer MD (2008) A CB2 receptor agonist, A-836339, modulates WDR neuronal activity in neuropathic rats: contributions of spinal and peripheral CB2 receptors. Neuroscience, doi:10.1016/j.neuroscienc.2008.11.015.
29. Monory K, Tzavara ET, Lexime J, Ledent C, Parmentier M, Borsodi A, and Hanoune J (2002) Novel, not adenylyl cyclase-coupled cannabinoid binding site in cerebellum of mice. Biochem Biophys Res Commun 292:231-235.
30. Munro S, Thomas KL, and Abu-Shaar M (1993) Molecular characterization of a peripheral receptor for cannabinoids. Nature 365:61-65.
31. Ohta H, Ishizaka T, Tatsuzuki M, Yoshinaga M, Iida I, Yamaguchi T, Tomishima Y, Futaki N, Toda Y, and Saito S (2008) Imine derivatives as new potent and selective CB2 cannabinoid receptor agonists with an analgesic action. Bioorg Med Chem 16:1111-1124.
32. Russo EB, Guy GW, and Robson PJ (2007) Cannabis, pain, and sleep: lessons from therapeutic clinical trials of Sativex, a cannabis-based medicine. Chem Biodivers 4:1729-1743.
33. Shire D, Calandra B, Rinaldi-Carmona M, Oustric D, Pessegue B, Bonnin-Cabanne O, Le Fur G, Caput D, and Ferrara P (1996) Molecular cloning, expression and function of the murine CB2 peripheral cannabinoid receptor. Biochim Biophys Acta 1307:132-136.
34. 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.
35. Valenzano KJ, Tafesse L, Lee G, Harrison JE, Boulet JM, Gottshall SL, Mark L, Pearson MS, Miller W, Shan S, et al. (2005) Pharmacological and pharmacokinetic characterization of the cannabinoid receptor 2 agonist, GW405833, utilizing rodent models of acute and chronic pain, anxiety, ataxia and catalepsy. Neuropharmacology 48:658-672.
36. Whiteside GT, Gottshall SL, Boulet JM, Chaffer SM, Harrison JE, Pearson MS, Turchin PI, Mark L, Garrison AE, and Valenzano KJ (2005) A role for cannabinoid receptors, but not endogenous opioids, in the antinociceptive activity of the CB2-selective agonist, GW405833. Eur J Pharmacol 528:65-72.
37. Yamamoto W, Mikami T, and Iwamura H (2008) Involvement ofcentral cannabinoid CB2 receptor in reducing mechanical allodynia in a mouse model of neuropathic pain. Eur J Pharmacol 583:56 -61.
38. Yao BB, Hsieh GC, Frost JM, Fan Y, Garrison TR, Daza AV, Grayson GK, Zhu CZ, Pai M, Chandran P, et al. (2008) In vitro and in vivo characterization ofA-796260: a selective cannabinoid CB2 receptor agonist exhibiting analgesic activity in rodent pain models. Br J Pharmacol 153:390 -401.
39. Yao BB, Mukherjee S, Fan Y, Garrison TR, Daza AV, Grayson GK, Hooker BA, Dart MJ, Sullivan JP, and Meyer MD (2006) In vitro pharmacological characterization of AM1241: a protean agonist at the cannabinoid CB2 receptor? Br J Pharmacol 149:145-154.
40. Zhang J, Hoffert C, Vu HK, Groblewski T, Ahmad S, and O'Donnell D (2003) Induction of CBCB2 receptor expression in the rat spinal cord of neuropathic but not inflammatory chronic pain models. Eur J Neurosci 17:2750-2754.