Kinetics of penetration influence the apparent potency of vanilloids on TRPV1

Molecular Pharmacology

Volumn 69, Issue 4, 2006, Pages 1166-1173

  Lazar, Jozsef ^a,c   Braun, Derek C ^a,b   Tóth, Attila ^a,d   Wang, Yun ^a,e   Pearce, Larry V ^a   Pavlyukovets, Vladimir A ^a   Blumberg, Peter M ^a   Garfield, Susan H ^a   Wincovitch, Stephen ^a   Choi, Hyun Kyung ^c   Lee, Jeewoo ^c  

^a NATIONAL CANCER INSTITUTE   (United States)

^b GALLAUDET UNIVERSITY   (United States)

^c Seoul National University   (South Korea)

^d UNIVERSITY OF DEBRECEN   (Hungary)

^e PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

5 IODO RESINIFERATOXIN; CALCIUM; CAPSAICIN DERIVATIVE; CHK 884; OLVANIL; RESINIFERATOXIN; UNCLASSIFIED DRUG; VANILLOID RECEPTOR; VANILLOID RECEPTOR 1;

ANIMAL CELL; ARTICLE; CELL MEMBRANE; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; ENDOPLASMIC RETICULUM; GOLGI COMPLEX; INCUBATION TIME; KINETICS; LIPOPHILICITY; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TIMED DRUG RELEASE;

ANIMALS; BENZALDEHYDES; CHO CELLS; CRICETINAE; MICROSCOPY, CONFOCAL; MOLECULAR STRUCTURE; TRPV CATION CHANNELS;

EID: 33645103126     PISSN: 0026895X     EISSN: 15210111     Source Type: Journal    
DOI: 10.1124/mol.105.019158     Document Type: Article

References (38)

1. 3H]resiniferatoxin binding to spinal cord and dorsal root ganglia of newborn and adult rats. Life Sci 54:1875-1882.
2. 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.
3. Brand L, Berman E, Schwen R, Loomans M, Janusz J, Bohne R, Maddin C, Gardner J, Lahann T, Farmer R, et al. (1987) NE-19550: a novel, orally active anti-inflammatory analgesic. Drugs Exp Clin Res 13:259-265.
4. Braun DC, Cao Y, Wang S, Garfield SH, Min Hur G, and Blumberg PM (2005a) Role of phorbol ester localization in determining protein kinase C or RasGRP3 translocation: real-time analysis using fluorescent ligands and proteins. Mol Cancer Ther 4:141-150.
5. Braun DC, Garfield SH, and Blumberg PM (2005b) Analysis by FRET of the interaction between ligands and protein kinase C delta in the intact cell. J Biol Chem 280:8164-8171.
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. Chou MZ, Mtui T, Gao Y-D, Kohler M, and Middleton RE (2004) Resiniferatoxin binds to the capsaicin receptor (TRPV1) near the extracellular side of the S4 transmembrane domain. Biochemistry 43:2501-2511.
8. Deng Y, Bennink JR, Kang HC, Haugland RP, and Yewdell JW (1995) Fluorescent conjugates of brefeldin A selectively stain the endoplasmic reticulum and Golgi complex of living cells. J Histochem Cytochem 43:907-915.
9. De Petrocellis L, Bisogno T, Maccarrone M, Davis JB, Finazzi-Agro A, and Di Marzo V (2001) The activity of anandamide at vanilloid VR1 receptors requires facilitated transport across the cell membrane and is limited by intracellular metabolism. J Biol Chem 276:12856-12863.
10. 2+ stores in the dorsal root ganglion cells of adult rats. Biochem Biophys Res Commun 285:1114-1120.
11. Gavva NR, Klionsky L, Qu Y, Shi L, Tamir R, Edenson S, Zhang TJ, Viswanadhan VN, Tóth A, Pearce LV, et al. (2004) Molecular determinants of vanilloid sensitivity in TRPV1. J Biol Chem 279:20283-20295.
12. Hwang SW, Cho H, Kwak J, Lee SY, Kang CJ, Jung J, Cho S, Min KH, Suh 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.
13. Iida T, Moriyama T, Kobata K, Morita A, Murayama N, Hashizume S, Fushiki T, Yazawa S, Watanabe T, and Tominaga M (2003) TRPV1 activation and induction of nociceptive response by a non-pungent capsaicin-like compound, capsiate. Neuropharmacology 44:958-967.
14. Jerman JC, Brough SJ, Prinjha R, Harries MH, Davis JB, and Smart D (2000) Characterization using FLIPR of rat vanilloid receptor (rVR1) pharmacology. Br J Pharmacol 130:916-922.
15. Jerman JC, Gray J, Brough SJ, Ooi L, Owen D, Davis JB, and Smart D (2002) Comparison of effects of anandamide at recombinant and endogenous rat vanilloid receptors. Br J Anaesth 89:882-887.
16. Jordt SE and Julius D (2002) Molecular basis for species-specific sensitivity to 'hot' chili peppers. Cell 108:421-430.
17. 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.
18. Liu L, Lo Y-C, Chen I-J, and Simon SA (1997) The responses of rat trigeminal ganglion neurons to capsaicin and two nonpungent vanilloid receptor agonists, olvanil and glyceryl nonamide. J Neurosci 17:4101-4111.
19. 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.
20. Meylan WM and Howard PH (1995) Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci 84:83-92.
21. Morice AH and Geppetti P (2004) Cough. 5: The type 1 vanilloid receptor: a sensory receptor for cough. Thorax 59:257-258.
22. Olah Z, Szabo T, Karai L, Hough C, Fields RD, Caudle RM, Blumberg PM, and Iadarola MJ (2001) Ligand-induced dynamic membrane changes and cell deletion conferred by vanilloid receptor 1. J Biol Chem 276:11021-11030.
23. Phillips E, Reeve A, Bevan S, and McIntyre P (2004) Identification of species-specific determinants of the action of the antagonist capsazepine and the agonist PPAHV on TRPV1. J Biol Chem 279:17165-17172.
24. Rami HK, Thompson M, Wyman P, Jerman JC, Egerton J, Brough S, Stevens AJ, Randall AD, Smart D, Gunthorpe MJ, et al. (2004) Discovery of small molecule antagonists of TRPV1. Bioorg Med Chem Lett 14:3631-3634.
25. Robbins W (2000) Clinical applications of capsaicinoids. Clin J Pain 16:S86-S89.
26. Seabrook GR, Sutton KG, Jarolimek W, Hollingworth GJ, Teague S, Webb J, Clark N, Boyce S, Kerby J, Ali Z, et al. (2002) Functional properties of the high-affinity TRPV1 (VR1) vanilloid receptor antagonist (4-hydroxy-5-iodo-3- methoxyphenylacetate ester) iodo-resiniferatoxin. J Pharmacol Exp Ther 303:1052-1060.
27. Shimizu I, Iida T, Horiuchi N, and Caterina MJ (2005) 5-Iodoresiniferatoxin evokes hypothermia in mice and is a partial transient receptor potential vanilloid 1 agonist in vitro. J Pharmacol Exp Ther 314:1378-1385.
28. 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.
29. 3H]resiniferatoxin binding to rat dorsal root ganglion membranes as a novel approach in evaluating compounds with capsaicin-like activity. Naunyn-Schmiedeberg's Arch Pharmacol 344:551-556.
30. Szallasi A, Lewin NE, and Blumberg PM (1992) Identification of alpha-1-acid glycoprotein (orosomucoid) as a major vanilloid binding protein in serum. J Pharmacol Exp Ther 262:883-888.
31. Tóth A, Wang Y, Kedei N, Tran R, Pearce LV, Kang SU, Jin MK, Choi HK, Lee J, and Blumberg PM (2005) Different vanilloid agonists cause different patterns of calcium response in CHO cells heterologously expressing rat TRPV1. Life Sci 76:2921-2932.
32. Valenzano KJ, Grant ER, Wu G, Hachicha M, Schmid L, Tafesse L, Sun Q, Rotshteyn Y, Francis J, Limberis J, et al. (2003) N-(4-Tertiarybutylphenyl)-4- (3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide (BCTC), 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.
33. Vyklicky L, Lyfenko A, Kuffler DP, and Vlachova V (2003) Vanilloid receptor TRPV1 is not activated by vanilloids applied intracellularly. Neuroreport 14:1061-1065.
34. Wahl P, Foged C, Tullin S, and Thomsen C (2001) Iodo-resiniferatoxin, a new potent vanilloid receptor antagonist. Mol Pharmacol 59:9-15.
35. Wang QJ, Fang TW, Fenick D, Garfield S, Bienfait B, Marquez VE, and Blumberg PM (2000) The lipophilicity of phorbol esters as a critical factor in determining the pattern of translocation of protein kinase C delta fused to green fluorescent protein. J Biol Chem 275:12136-12146.
36. Wang Y, Tóth A, Tran R, Szabo T, Welter JD, Blumberg PM, Lee J, Kang S-U, Lim J-O, and Lee J (2003) High-affinity partial agonists of the vanilloid receptor. Mol Pharmacol 64:325-333.
37. Wrigglesworth R, Walpole CSJ, Bevan S, Campbell EA, Dray A, Hughes GA, James I, Masdin KJ, and Winter J (1996) Analogues of capsaicin with agonist activity as novel analgesic agents: Structure-activity studies. 4. Potent, orally active analgesics. J Med Chem 39:4942-4951.
38. Zygmunt PM, Petersson J, Andersson DA, Chuang H, Sorgard M, Di Marzo V, Julius D, and Hogestatt ED (1999) Vanilloid receptors on sensory nerves mediate the vasodilator action of anandamide. Nature (Lond) 400:452-457.