Design of a High-Affinity Competitive Antagonist of the Vanilloid Receptor Selective for the Calcium Entry-Linked Receptor Population

Molecular Pharmacology

Volumn 65, Issue 2, 2004, Pages 282-291

  Tóth, Attila ^a,c   Blumberg, Peter M ^a   Chen, Zili ^b   Kozikowski, Alan P ^b  

^a NATIONAL CANCER INSTITUTE   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

5 IODORESINIFERATOXIN; CALCIUM; CALCIUM ION; CALCIUM SENSING RECEPTOR; CAPSAICIN; CAPSAZEPINE; DRUG DERIVATIVE; DRUG RECEPTOR; N (4 CHLOROBENZYL) N' (4 HYDROXY 3 IODO 5 METHOXYBENZYL)THIOUREA; N-(4-CHLOROBENZYL) -N'-(4-HYDROXY-3-IODO-5-METHOXYBENZYL)THIOUREA; RECEPTOR BLOCKING AGENT; RESINIFERATOXIN; THIOUREA; UNCLASSIFIED DRUG; VANILLOID RECEPTOR; VANILLOID RECEPTOR 1; VANILLOID RECEPTOR BLOCKER; VANILLOID RECEPTOR SUBTYPE 1;

ANIMAL; ANIMAL CELL; ARTICLE; BINDING COMPETITION; CALCIUM CELL LEVEL; CALCIUM TRANSPORT; CELL MEMBRANE; CHEMISTRY; CHO CELL; COMPETITIVE INHIBITION; DOSE RESPONSE; DRUG ANALYSIS; DRUG BINDING; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; HAMSTER; HETEROLOGOUS EXPRESSION; METABOLISM; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

ANIMALS; BINDING, COMPETITIVE; CALCIUM; CAPSAICIN; CHO CELLS; CRICETINAE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; RECEPTORS, CALCIUM-SENSING; RECEPTORS, DRUG; THIOUREA; TRPV CATION CHANNELS;

EID: 1642498152     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: 10.1124/mol.65.2.282     Document Type: Article

References (46)

1. 45Ca uptake and for high affinity binding in cultured rat dorsal root ganglion neurons and dorsal root ganglion membranes. Brain Res Mol Brain Res 35:173-182.
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. Bhave G, Zhu W, Wang H, Brasier DJ, Oxford GS, and Gereau RW IV (2002) cAMP-dependent protein kinase regulates desensitization of the capsaicin receptor (VR1) by direct phosphorylation. Neuron 35:721-731.
4. Caterina MJ and Julius D (2001) The vanilloid receptor: a molecular gateway to the pain pathway. Annu Rev Neurosci 24:487-517.
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. 2-mediated inhibition. Nature (Lond) 411:957-962.
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. 2+ stores in the dorsal root ganglion cells of adult rats. Biochem Biophys Res Commun 285:1114-1120.
10. 3 purinoceptor and IB4 binding sites. J Neurosci 11:946-958.
11. Hwang SW, Cho H, Kwak J, Lee SY, Kang CJ, Jung J, Cho S, Min KH, Sur YG, Kim D, et al. (2000) Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances. Proc Natl Acad Sci USA 97:6155-6160.
12. Jahnel R, Dreger M, Gillen C, Bender O, Kurreck J, and Hucho F (2001) Biochemical characterization of the vanilloid receptor 1 expressed in a dorsal root ganglia derived cell line. Eur J Biochem 268:5489-5496.
13. Jordt SE, Tominaga M, and Julius D (2000) Acid potentiation of the capsaicin receptor determined by a key extracellular site. Proc Natl Acad Sci USA 97:8134-8139.
14. Jordt SE and Julius D (2002) Molecular basis for species-specific sensitivity to "hot" chili peppers. Cell 108:421-430.
15. Jung J, Hwang SW, Kwak J, Lee SY, Kang CJ, Kim WB, Kim D, and Oh U (1999) Capsaicin binds to the intracellular domain of the capsaicin-activated ion channel. J Neurosci 19:529-538.
16. Kedei N, Szabo T, Lile JD, Treanor JJ, Olah Z, Iadarola MJ, and Blumberg PM (2001) Analysis of the quaternary structure of vanilloid receptor 1. J Biol Chem 276:28613-28619.
17. Kress M and Zeilhofer HU (1999) Capsaicin, protons and heat: new excitement about nociceptors. Trends Pharmacol Sci 20:112-118.
18. Lee J, Lee J, Szabo T, Gonzalez AF, Welter JD, and Blumberg PM (2001) N-(3-Acyloxy-2-benzylpropyl)-N′-dihydroxytetrahydrobenzazepine and tetrahydroisoquinoline thiourea analogues as vanilloid receptor ligands. Bioorg Med Chem 9:1713-1720.
19. 2+ by vanilloid receptor 1 in rat dorsal root ganglion neurons. J Biol Chem 278:5462-5472.
20. Marshall IC, Owen DE, Cripps TV, Davis JB, McNulty S, and Smart D (2003) Activation of vanilloid receptor 1 by resiniferatoxin mobilizes calcium from inositol 1, 4, 5-trisphosphate-sensitive stores. Br J Pharmacol 138:172-176.
21. Numazaki M, Tominaga T, Toyooka H, and Tominaga M (2002) Direct phosphorylation of capsaicin receptor VR1 by protein kinase Cε and identification of two target serine residues. J Biol Chem 277:13375-13378.
22. Olah Z, Karai L, and Iadarola MJ (2001a) Anandamide activates vanilloid receptor 1 (VR1) at acidic pH in dorsal root ganglia neurons and cells ectopically expressing VR1. J Biol Chem 276:31163-31170.
23. Olah Z, Karai L, and Iadarola MJ (2002) Protein kinase Ca is required for vanilloid receptor 1 activation. Evidence for multiple signaling pathways. J Biol Chem 277:35752-35769.
24. Olah Z, Szabo T, Karai L, Hough C, Fields RD, Caudle RM, Blumberg PM, and Iadarola MJ (2001b) Ligand induced dynamic membrane changes and cell deletion conferred by vanilloid receptor 1. J Biol Chem 276:11021-11030.
25. Park HG, Park MK, Choi JY, Choi SH, Lee J, Park BS, Kim MG, Suh YG, Cho H, Oh U, et al. (2003) Synthesis of N,N′,N″-trisubstituted thiourea derivatives and their antagonist effect on the vanilloid receptor. Bioorg Med Chem Lett 13:601-604.
26. Pomonis JD, Harrison JE, Mark L, Bristol DR, Valenzano KJ and Walker K (2003) BCTC (N-(4-t-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropryazine-1(2H) -carbox-amide), 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.
27. Premkumar LS and Ahern GP (2000) Induction of vanilloid receptor channel activity by protein kinase C. Nature (Lond) 408:985-990.
28. 2 binding site as a determinant of capsaicin receptor sensitivity. Science (Wash DC) 300:1284-1288.
29. Robbins W (2000) Clinical applications of capsaicinoids. Clin J Pain 16:S86-S89.
30. Szallasi A and Blumberg PM (1989) Resiniferatoxin, a phorbol-related diterpene, acts as an ultrapotent analog of capsaicin, the irritant constituent in red pepper. Neuroscience 30:515-520.
31. Szallasi A and Blumberg PM (1999) Vanilloid (Capsaicin) receptors and mechanisms. Pharmacol Rev 51:159-212.
32. Szallasi A, Blumberg PM, Annicelli LL, Krause JE, and Cortright DN (1999) The cloned rat vanilloid receptor VR1 mediates both R-type binding and C-type calcium response in dorsal root ganglion neurons. Mol Pharmacol 56:581-587.
33. Turner H, Fleig A, Stokes A, Kinet JP, and Penner R (2003) Discrimination of intracellular calcium store subcompartments using TRPV1 (transient receptor potential channel, vanilloid subfamily member 1) release channel activity. Biochem J 371:341-350.
34. Valenzano KJ, Grant ER, Wu G, Hachicha M, Schmid L, Tafesse L, Sun Q, Rotshteyn Y, Francis J, Limveris J, et al. (2003) BCTC (N-(4-t-butylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropryazine-1(2H) -carbox-amide), a novel, orally-effective vanilloid receptor 1 antagonist with analgesic properties: I. In vitro characterization and pharmacokinetic properties. J Pharmacol Exp Ther 306:377-386.
35. Wahl P, Foged C, Tullin S, and Thomsen C (2001) Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Mol Pharmacol 59:9-15.
36. 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.
37. Walpole CSJ, Wrigglesworth R, Bevan S, Campbell EA, Dray A, James IF, Masdin KJ, Perkins MN, and Winter J (1993a) Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 2. The amide bond "B-region". J Med Chem 36:2373-2380.
38. Walpole CSJ, Wrigglesworth R, Bevan S, Campbell EA, Dray A, James IF, Masdin KJ, Perkins MN, and Winter J (1993b) Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region". J Med Chem 36:2381-2389.
39. Walpole CSJ, Wrigglesworth R, Bevan S, Campbell EA, Dray A, James IF, Perkins MN, Reid DJ, and Winter J (1993c) Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 1. The aromatic "A-region". J Med Chem 36:2362-2372.
40. 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. [published erratum appears in Mol Pharmacol 63:958, 2003]. Mol Pharmacol 62:947-956.
41. 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. [published erratum appears in Mol Pharmacol 63:958, 2003]. Mol Pharmacol 62:947-956.
42. Wang Y, Toth A, Tran R, Szabo T, Welter JD, Blumberg PM, Lee J, Kang SU, Lim JO, and Lee J (2003) High affinity partial agonists of the vanilloid receptor Mol Pharmacol 64:325-333.
43. Welch JM, Simon SA, and Reinhart PH (2000) The activation mechanism of rat vanilloid receptor 1 by capsaicin involves the pore domain and differs from the activation by either acid or heat. Proc Natl Acad Sci USA 97:13889-138984.
44. 2+ entry. Biochem J 372:517-528.
45. Yoon JW, Choi HY, Lee HJ, Ryu CH, Park HG, Suh YG, Oh U, Jeong YS, Choi JK, Park YH, et al. (2003) Chain-branched acyclic phenethylthiocarbamates as vanilloid receptor antagonists. Bioorg Med Chem Lett 13:1549-1552.
46. Zygmunt PM, Petersson J, Andersson DA, Chuang H, Sorgard M, DiMarzo V, Julius D, and Hogestatt ED (1999) Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature (Lond) 400:452-457.