Actions of the endocannabinoid transport inhibitor AM404 in neuropathic and inflammatory pain models

Clinical and Experimental Pharmacology and Physiology

Volumn 34, Issue 11, 2007, Pages 1186-1190

  Mitchell, Vanessa A ^b   Greenwood, Ruth ^b   Jayamanne, Angelo ^b   Vaughan, Christopher W ^a,b  

^a ROYAL NORTH SHORE HOSPITAL   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Allodynia; Endocannabinoid; Inflammation; Neuropathic; Pain

Indexed keywords

1 (2,4 DICHLOROPHENYL) 5 (4 IODOPHENYL) 4 METHYL N (1 PIPERIDYL) 1H PYRAZOLE 3 CARBOXAMIDE; ANANDAMIDE; CANNABINOID RECEPTOR AGONIST; CANNABINOID RECEPTOR ANTAGONIST; ENDOCANNABINOID TRANSPORT INHIBITOR; FREUND ADJUVANT; N (4 HYDROXYPHENYL)ARACHIDONAMIDE; UNCLASSIFIED DRUG;

ALLODYNIA; ANALGESIC ACTIVITY; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; MALE; MOTOR PERFORMANCE; NERVE LIGATION; NEUROPATHIC PAIN; NEUROPATHY; NONHUMAN; RAT; SCIATIC NERVE;

ANALGESICS; ANIMALS; ARACHIDONIC ACIDS; CARRIER PROTEINS; DISEASE MODELS, ANIMAL; ENDOCANNABINOIDS; FREUND'S ADJUVANT; INFLAMMATION; LIGATION; MALE; MOTOR ACTIVITY; PAIN; PAIN MEASUREMENT; PIPERIDINES; POLYUNSATURATED ALKAMIDES; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, CANNABINOID, CB1; SCIATIC NERVE; SCIATIC NEUROPATHY; TIME FACTORS;

EID: 34548693209     PISSN: 03051870     EISSN: 14401681     Source Type: Journal    
DOI: 10.1111/j.1440-1681.2007.04692.x     Document Type: Article

References (41)

1. Scott DA, Wright CE, Angus JA. Evidence that CB-1 and CB-2 cannabinoid receptors mediate antinociception in neuropathic pain in the rat. Pain 2004 109 : 124 31.
2. Fox A, Kesingland A, Gentry C et al. The role of central and peripheral cannabinoid (1) receptors in the antihyperalgesic activity of cannabinoids in a model of neuropathic pain. Pain 2001 92 : 91 100.
3. Bridges D, Ahmad K, Rice ASC. The synthetic cannabinoid WIN55,212-2 attenuates hyperalgesia and allodynia in a rat model of neuropathic pain. Br. J. Pharmacol. 2001 133 : 586 94.
4. Herzberg U, Eliav E, Bennett GJ, Kopin IJ. The analgesic effects of R(+)-WIN 55,212-2 mesylate, a high affinity cannabinoid agonist, in a rat model of neuropathic pain. Neurosci. Lett. 1997 221 : 157 60.
5. Clayton N, Marshall FH, Bountra C, O'Shaughnessy CT. CB1 and CB2 cannabinoid receptors are implicated in inflammatory pain. Pain 2002 96 : 253 60.
6. 9-tetrahydrocannabinol and anandamide antinociception in nonarthritic and arthritic rats. Pharmacol. Biochem. Behav. 1998 60 : 183 91.
7. Kehl LJ, Hamamoto DT, Wacnik PW et al. A cannabinoid agonist differentially attenuates deep tissue hyperalgesia in animal models of cancer and inflammatory muscle pain. Pain 2003 103 : 175 86.
8. Hanus L, Breuer A, Tchilibon S et al. HU-308: A specific agonist for CB2, a peripheral cannabinoid receptor. Proc. Natl Acad. Sci. USA 1999 96 : 14 228 33.
9. De Vry J, Denzer D, Reissmueller E et al. 3-2-Cyano-3-(trifluoromethyl) phenoxy phenyl-4,4,4-trifluoro-1-butanesulfonate (BAY 59-3074): A novel cannabinoid CB1/CB2 receptor partial agonist with antihyperalgesic and antiallodynic effects. J. Pharmacol. Exp. Ther. 2004 310 : 620 32.
10. Ibrahim MM, Deng HF, Zvonok A et al. Activation of CB2 cannabinoid receptors by AM1241 inhibits experimental neuropathic pain: Pain inhibition by receptors not present in the CNS. Proc. Natl Acad. Sci. USA 2003 100 : 10 529 33.
11. Calignano A, La Rana G, Giuffrida A, Piomelli D. Control of pain initiation by endogenous cannabinoids. Nature 1998 394 : 277 81.
12. Richardson JD, Aanonsen L, Hargreaves KM. Hypoactivity of the spinal cannabinoid system results in NMDA-dependent hyperalgesia. J. Neurosci. 1998 18 : 451 7.
13. Strangman NM, Patrick SL, Hohmann AG, Tsou K, Walker JM. Evidence for a role of endogenous cannabinoids in the modulation of acute and tonic pain sensitivity. Brain Res. 1998 813 : 323 8.
14. Beaulieu P, Bisogno T, Punwar S et al. Role of the endogenous cannabinoid system in the formalin test of persistent pain in the rat. Eur. J. Pharmacol. 2000 396 : 85 92.
15. Hillard CJ, Jarrahian A. Cellular accumulation of anandamide: Consensus and controversy. Br. J. Pharmacol. 2003 140 : 802 8.
16. Lambert DM, Fowler CJ. The endocannabinoid system: Drug targets, lead compounds, and potential therapeutic applications. J. Med. Chem. 2005 48 : 5059 87.
17. Beltramo M, Stella N, Calignano A, Lin SY, Makriyannis A, Piomelli D. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science 1997 277 : 1094 7.
18. Moore SA, Nomikos GG, Dickason-Chesterfield AK et al. Identification of a high-affinity binding site involved in the transport of endocannabinoids. Proc. Natl Acad. Sci. USA 2005 102 : 17 852 7.
19. Lopez-Rodriguez ML, Viso A, Ortega-Gutierrez S et al. Design, synthesis and biological evaluation of novel arachidonic acid derivatives as highly potent and selective endocannabinoid transporter inhibitors. J. Med. Chem. 2001 44 : 4505 8.
20. De Petrocellis L, Bisogno T, Davis JB, Pertwee RG, Di Marzo V. Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: Inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett. 2000 483 : 52 6.
21. Rodella LF, Borsani E, Rezzani R, Ricci F, Buffoli B, Bianchi R. AM404, an inhibitor of anandamide reuptake decreases Fos-immunoreactivity in the spinal cord of neuropathic rats after non-noxious stimulation. Eur. J. Pharmacol. 2005 508 : 139 46.
22. Costa B, Siniscalco D, Trovato AE et al. AM404, an inhibitor of anandamide uptake, prevents pain behaviour and modulates cytokine and apoptotic pathways in a rat model of neuropathic pain. Brit. J. Pharmacol. 2006 148 : 1022 32.
23. La Rana G, Russo R, Campolongo P et al. Modulation of neuropathic and inflammatory pain by the endocannabinoid transport inhibitor AM404 [N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide]. J. Pharmacol. Exp. Ther. 2006 317 : 1365 71.
24. Palazzo E, de Novellis V, Petrosino S et al. Neuropathic pain and the endocannabinoid system in the dorsal raphe: Pharmacological treatment and interactions with the serotonergic system. Eur. J. Neurosci. 2006 24 : 2011 20.
25. Seltzer Z, Dubner R, Shir Y. A novel behavioral model of neuropathic pain disorders produced in rats by partial sciatic nerve injury. Pain 1990 43 : 205 18.
26. Chaplan SR, Bach FW, Pogrel JW, Chung JM, Yaksh TL. Quantitative asessment of tactile allodynia in the rat paw. J. Neurosci. Methods 1994 53 : 55 63.
27. Jayamanne A, Greenwood R, Mitchell VA, Aslan S, Piomelli D, Vaughan CW. Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models. Br. J. Pharmacol. 2006 147 : 281 8.
28. Costa B, Colleoni M, Conti S et al. Repeated treatment with the synthetic cannabinoid WIN 55,212-2 reduces both hyperalgesia and production of pronociceptive mediators in a rat model of neuropathic pain. Br. J. Pharmacol. 2004 141 : 4 8.
29. Kim KJ, Yoon YW, Chung JM. Comparison of three rodent neuropathic pain models. Exp. Brain Res. 1997 113 : 200 66.
30. Holt S, Comelli F, Costa B, Fowler CJ. Inhibitors of fatty acid amide hydrolase reduce carrageenan-induced hind paw inflammation in pentobarbital-treated mice: Comparison with indomethacin and possible involvement of cannabinoid receptors. Br. J. Pharmacol. 2005 146 : 467 76.
31. Nagakura Y, Okada M, Kohara A et al. Allodynia and hyperalgesia in adjuvant-induced arthritic rats: Time course of progression and efficacy of analgesics. J. Pharmacol. Exp. Ther. 2003 306 : 490 7.
32. Zygmunt PM, Chuang HH, Movahed P, Julius D, Hogestatt ED. The anandamide transport inhibitor AM404 activates vanilloid receptors. Eur. J. Pharmacol. 2000 396 : 39 42.
33. Roberts LA, Christie MJ, Connor M. Anandamide is a partial agonist at native vanilloid receptors in acutely isolated mouse trigeminal sensory neurons. Br. J. Pharmacol. 2002 137 : 421 8.
34. Zygmunt PM, Petersson J, Andersson DA et al. Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature 1999 400 : 452 7.
35. Fegley D, Kathuria S, Mercier R et al. Anandamide transport is independent of fatty-acid amide hydrolase activity and is blocked by the hydrolysis-resistant inhibitor AM1172. Proc. Natl Acad. Sci. USA 2004 101 : 8756 61.
36. Glaser ST, Abumrad NA, Fatade F, Kaczocha M, Studholme KM, Deutsch DG. Evidence against the presence of an anandamide transporter. Proc. Natl Acad. Sci. USA 2003 100 : 4269 74.
37. Giuffrida A, de Fonseca FR, Nava F, Loubet-Lescoulie P, Piomelli D. Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404. Eur. J. Pharmacol. 2000 408 : 161 8.
38. Jarrahian A, Manna S, Edgemond WS, Campbell WB, Hillard CJ. Structure-activity relationships among N-arachidonylethanolamine (anandamide) head group analogues for the anandamide transporter. J. Neurochem. 2000 74 : 2597 606.
39. Lichtman AH, Shelton CC, Advani T, Cravatt BF. Mice lacking fatty acid amide hydrolase exhibit a cannabinoid receptor-mediated phenotypic hypoalgesia. Pain 2004 109 : 319 27.
40. Lim G, Sung B, Ji RR, Mao JR. Upregulation of spinal cannabinoid-1- receptors following nerve injury enhances the effects of WIN 55,212-2 on neuropathic pain behaviors in rats. Pain 2003 105 : 275 83.
41. Siegling A, Hofmann HA, Denzer D, Mauler F, De Vry J. Cannabinoid CB1 receptor upregulation in a rat model of chronic neuropathic pain. Eur. J. Pharmacol. 2001 415 : R5 7.