Antinociceptive pharmacology of N-(4-chlorobenzyl)-N′-(4-hydroxy-3- iodo-5-methoxybenzyl) thiourea, a high-affinity competitive antagonist of the transient receptor potential vanilloid 1 receptor

Journal of Pharmacology and Experimental Therapeutics

Volumn 321, Issue 2, 2007, Pages 791-798

  Tang, Lei ^a   Chen, Yan ^a   Chen, Zili ^a   Blumberg, Peter M ^b   Kozikowski, Alan P ^a   Wang, Zaijie Jim ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ANTINOCICEPTIVE AGENT; CAPSAICIN; CAPSAZEPINE; FORMALDEHYDE; FREUND ADJUVANT; MYELOPEROXIDASE; N (4 CHLOROBENZYL) N' (4 HYDROXY 3 IODO 5 METHOXYBENZYL)THIOUREA; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

ALLODYNIA; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFECT; DRUG EFFICACY; DRUG MECHANISM; ENZYME ACTIVITY; HYPERALGESIA; IN VIVO STUDY; MALE; MOUSE; NOCICEPTION; NONHUMAN; PAIN; PAW EDEMA; PRIORITY JOURNAL; RECEPTOR BLOCKING; TAIL FLICK TEST; WRITHING TEST;

ANALGESICS; ANIMALS; EDEMA; FREUND'S ADJUVANT; MALE; MICE; MICE, INBRED ICR; NEUTROPHIL INFILTRATION; PAIN MEASUREMENT; THIOUREA; TRPV CATION CHANNELS;

EID: 34247281575     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.106.117572     Document Type: Article

References (40)

1. Appendino G, Munoz E, and Fiebich BL (2003) TRPV1 (vanilloid receptor, capsaicin receptor) agonists and antagonists. Expert Opin Ther Pat 13:1825-1837.
2. Bevan S, Hothi S, Hughes G, James IF, Rang HP, Shah K, Walpole CS, and Yeats JC (1992) Capsazepine: a competitive antagonist of the sensory neurone excitant capsaicin. Br J Pharmacol 107:544-552.
3. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
4. Breese NM, George AC, Pauers LE, and Stucky CL (2005) Peripheral inflammation selectively increases TRPV1 function in IB4-positive sensory neurons from adult mouse. Pain 115:37-49.
5. Caterina MJ, Leffler A, Malmberg AB, Martin WJ, Trafton J, Petersen-Zeitz KR, Koltzenburg M, Basbaum AI, and Julius D (2000) Impaired nociception and pain sensation in mice lacking the capsaicin receptor. Science (Wash DC) 288:306-313.
6. Caterina MJ, Schumacher MA, Tominaga M, Rosen TA, Levine JD, and Julius D (1997) The capsaicin receptor: a heat-activated ion channel in the pain pathway. Nature (Lond) 389:816-824.
7. Chaplan SR, Bach FW, Pogrel JW, Chung JM, and Yaksh TL (1994) Quantitative assessment of tactile allodynia in the rat paw. J Neurosci Methods 53:55-63.
8. Davis JB, Gray J, Gunthorpe MJ, Hatcher JP, Davey PT, Overend P, Harries MH, Latcham J, Clapham C, Atkinson K, et al. (2000) Vanilloid receptor-1 is essential for inflammatory thermal hyperalgesia. Nature (Lond) 405:183-187.
9. Garcia-Martinez C, Humet M, Planells-Cases R, Gomis A, Caprini M, Viana F, De La Pena E, Sanchez-Baeza F, Carbonell T, De Felipe C, et al. (2002) Attenuation of thermal nociception and hyperalgesia by VR1 blockers. Proc Natl Acad Sci USA 99:2374-2379.
10. Gavva NR, Tamir R, Qu Y, Klionsky L, Zhang TJ, Immke D, Wang J, Zhu D, Vanderah TW, Porreca F, et al. (2005) AMG 9810 [(E)-3-(4-t- butylphenyl)-N-(2,3-dihydrobenzo[b][1,4] dioxin-6-yl)acrylamide], a novel vanilloid receptor 1 (TRPV1) antagonist with antihyperalgesic properties. J Pharmacol Exp Ther 313:474-484.
11. 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.
12. Hayes P, Meadows HJ, Gunthorpe MJ, Harries MH, Duckworth DM, Cairns W, Harrison DC, Clarke CE, Ellington K, Prinjha RK, et al. (2000) Cloning and functional expression of a human orthologue of rat vanilloid receptor-1. Pain 88:205-215.
13. Honore P, Wismer CT, Mikusa J, Zhu CZ, Zhong C, Gauvin DM, Gomtsyan A, El Kouhen R, Lee CH, Marsh K, et al. (2005) A-425619 [1-isoquinolin-5-yl-3-(4- trifluoromethyl-benzyl)-urea], a novel transient receptor potential type V1 receptor antagonist, relieves pathophysiological pain associated with inflammation and tissue injury in rats. J Pharmacol Exp Ther 314:410-421.
14. Hunskaar S and Hole K (1987) The formalin test in mice: dissociation between inflammatory and non-inflammatory pain. Pain 30:103-114.
15. Iadarola MJ, Brady LS, Draisci G, and Dubner R (1988) Enhancement of dynorphin gene expression in spinal cord following experimental inflammation: stimulus specificity, behavioral parameters and opioid receptor binding. Pain 35:313-326.
16. Ikeda Y, Ueno A, Naraba H, and Oh-ishi S (2001) Involvement of vanilloid receptor VR1 and prostanoids in the acid-induced writhing responses of mice. Life Sci 69:2911-2919.
17. Kowaluk EA, Mikusa J, Wismer CT, Zhu CZ, Schweitzer E, Lynch JJ, Lee CH, Jiang M, Bhagwat SS, Gomtsyan A, et al. (2000) ABT-702 (4-amino-5-(3- bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido[2,3-d]pyrimidine), a novel orally effective adenosine kinase inhibitor with analgesic and anti-inflammatory properties. II. In vivo characterization in the rat. J Pharmacol Exp Ther 295:1165-1174.
18. Luo H, Cheng J, Han JS, and Wan Y (2004) Change of vanilloid receptor 1 expression in dorsal root ganglion and spinal dorsal horn during inflammatory nociception induced by complete Freund's adjuvant in rats. Neuroreport 15:655-658.
19. Malmberg AB, Gilbert H, McCabe RT, and Basbaum AI (2003) Powerful antinociceptive effects of the cone snail venom-derived subtype-selective NMDA receptor antagonists conantokins G and T. Pain 101:109-116.
20. Martin WJ, Loo CM, and Basbaum AI (1999) Spinal cannabinoids are anti-allodynic in rats with persistent inflammation. Pain 82:199-205.
21. McIntyre P, McLatchie LM, Chambers A, Phillips E, Clarke M, Savidge J, Toms C, Peacock M, Shah K, Winter J, et al. (2001) Pharmacological differences between the human and rat vanilloid receptor 1 (VR1). Br J Pharmacol 132:1084-1094.
22. Nicholas RS, Winter J, Wren P, Bergmann R, and Woolf CJ (1999) Peripheral inflammation increases the capsaicin sensitivity of dorsal root ganglion neurons in a nerve growth factor-dependent manner. Neuroscience 91:1425-1433.
23. Pomonis JD, Harrison JE, Mark L, Bristol DR, Valenzano KJ, and Walker K (2003) N-(4-Tertiarybutylphenyl)-4-(3-cholorphyridin-2-yl) tetrahydropyrazine-1(2H)-carbox-amide (BCTC), a novel, orally effective vanilloid receptor 1 antagonist with analgesic properties: II. In vivo characterization in rat models of inflammatory and neuropathic pain. J Pharmacol Exp Ther 306:387-393.
24. Porreca F, Vanderah TW, Guo W, Barth M, Dodey P, Peyrou V, Luccarini JM, Junien JL, and Pruneau D (2006) Antinociceptive pharmacology of N-[[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]methyl] -2-[2-[[(4-methoxy-2,6-dimethylphenyl) sulfonyl]methylamino] ethoxy]-N-methylacetamide, fumarate (LF22-0542), a novel nonpeptidic bradykinin B1 receptor antagonist. J Pharmacol Exp Ther 318:195-205.
25. Puig S and Sorkin LS (1996) Formalin-evoked activity in identified primary afferent fibers: systemic lidocaine suppresses phase-2 activity. Pain 64:345-355.
26. Rigoni M, Trevisani M, Gazzieri D, Nadaletto R, Tognetto M, Creminon C, Davis JB, Campi B, Amadesi S, Geppetti P, et al. (2003) Neurogenic responses mediated by vanilloid receptor-1 (TRPV1) are blocked by the high affinity antagonist, iodo-resiniferatoxin. Br J Pharmacol 138:977-985.
27. Sakurada T, Katsumata K, Tan-No K, Sakurada S, and Kisara K (1992) The capsaicin test in mice for evaluating tachykinin antagonists in the spinal cord. Neuropharmacology 31:1279-1285.
28. Santos AR and Calixto JB (1997) Ruthenium red and capsazepine antinociceptive effect in formalin and capsaicin models of pain in mice. Neurosci Lett 235:73-76.
29. Siemens J, Zhou S, Piskorowski R, Nikai T, Lumpkin EA, Basbaum AI, King D, and Julius D (2006) Spider toxins activate the capsaicin receptor to produce inflammatory pain. Nature (Lond) 444:208-212.
30. Szallasi A and Appendino G (2004) Vanilloid receptor TRPV1 antagonists as the next generation of painkillers. Are we putting the cart before the horse. J Med Chem 47:2717-2723.
31. Szallasi A and Blumberg PM (1999) Vanilloid (Capsaicin) receptors and mechanisms. Pharmacol Rev 51:159-212.
32. 2+/calmodulin-dependent protein kinase II. J Pharmacol Exp Ther 317:901-909.
33. Tominaga M, Caterina MJ, Malmberg AB, Rosen TA, Gilbert H, Skinner K, Raumann BE, Basbaum AI, and Julius D (1998) The cloned capsaicin receptor integrates multiple pain-producing stimuli. Neuron 21:531-543.
34. Toth A, Blumberg PM, Chen Z, and Kozikowski AP (2004) Design of a high-affinity competitive antagonist of the vanilloid receptor selective for the calcium entry-linked receptor population. Mol Pharmacol 65:282-291.
35. Urban L and Dray A (1991) Capsazepine, a novel capsaicin antagonist, selectively antagonises the effects of capsaicin in the mouse spinal cord in vitro. Neurosci Lett 134:9-11.
36. Wahl P, Foged C, Tullin S, and Thomsen C (2001) Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Mol Pharmacol 59:9-15.
37. Walker KM, Urban L, Medhurst SJ, Patel S, Panesar M, Fox AJ, and McIntyre P (2003) The VR1 antagonist capsazepine reverses mechanical hyperalgesia in models of inflammatory and neuropathic pain. J Pharmacol Exp Ther 304:56-62.
38. Wang Y, Szabo T, Welter JD, Toth A, Tran R, Lee J, Kang SU, Suh YG, and Blumberg PM (2002) High affinity antagonists of the vanilloid receptor. Mol Pharmacol 62:947-956.
39. Wang Z, Gardell LR, Ossipov MH, Vanderah TW, Brennan MB, Hochgeschwender U, Hruby VJ, Malan TP Jr, Lai J, and Porreca F (2001) Pronociceptive actions of dynorphin maintain chronic neuropathic pain. J Neurosci 21:1779-1786.
40. Yang W, Law PY, Guo X, and Loh HH (2003) In vivo activation of a mutant mu-opioid receptor by antagonist: future direction for opiate pain treatment paradigm that lacks undesirable side effects. Proc Natl Acad Sci USA 100:2117-2121.