Furanocoumarins are a novel class of modulators for the transient receptor potential vanilloid type 1 (TRPV1) channel

Journal of Biological Chemistry

Volumn 289, Issue 14, 2014, Pages 9600-9610

  Chen, Xingjuan ^a   Sun, Weiyang ^a,b   Gianaris, Nicholas G ^a   Riley, Ashley M ^a   Cummins, Theodore R ^a   Fehrenbacher, Jill C ^a   Obukhov, Alexander G ^a  

^a INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b SHANDONG UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY;

ACID ACTIVATION; ACTIVE COMPONENTS; CURRENT AMPLITUDE; DRUG DISCOVERY PROCESS; EFFECTIVE CONCENTRATION; FURANOCOUMARINS; SITE DIRECTED MUTAGENESIS; TRANSIENT RECEPTOR POTENTIAL VANILLOID;

BIOLOGY;

4 [3 (TRIFLUOROMETHYL) 2 PYRIDINYL] N [5 (TRIFLUOROMETHYL) 2 PYRIDINYL] 1 PIPERAZINECARBOXAMIDE; CAPSAICIN; FORMALDEHYDE; PENTOSALEN; SODIUM CHANNEL NAV1.7; VANILLOID RECEPTOR 1;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; BINDING SITE; CALCIUM TRANSPORT; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DESENSITIZATION; DRUG POTENCY; DRUG POTENTIATION; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INACTIVATION; HUMAN; HUMAN CELL; IN VIVO STUDY; NOCICEPTION; NONHUMAN; PRIORITY JOURNAL; RAT; SENSITIZATION; SITE DIRECTED MUTAGENESIS;

CALCIUM; CALCIUM IMAGING; CALCIUM SIGNALING; ION CHANNELS; TRP CHANNELS;

ANALGESICS; ANGELICA; ANIMALS; DERMATOLOGIC AGENTS; HEK293 CELLS; HUMANS; MICE; MICE, KNOCKOUT; NAV1.7 VOLTAGE-GATED SODIUM CHANNEL; NOCICEPTION; PAIN MANAGEMENT; PAIN MEASUREMENT; PSORALENS; RATS; TRPV CATION CHANNELS;

EID: 84898075354     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M113.536862     Document Type: Article

References (44)

1. Sarker, S. D., and Nahar, L. (2004) Natural medicine: the genus Angelica. Curr. Med. Chem. 11, 1479-1500
2. Lu, H. C. (2005) Chinese Natural Cures, Black Dog & Leventhal Publishers, Inc., New York
3. Liu, R., Li, A., and Sun, A. (2004) Preparative isolation and purification of coumarins from Angelica dahurica (Fisch. ex Hoffn) Benth, et Hook. f (Chinese traditional medicinal herb) by high-speed counter-current chro-matography. J. Chromatogr. A 1052, 223-227
4. Zhang, H., Gong, C., Lv, L., Xu, Y., Zhao, L., Zhu, Z., Chai, Y., and Zhang, G. (2009) Rapid separation and identification of furocoumarins in Angelica dahurica by high-performance liquid chromatography with diode-array detection, time-of-flight mass spectrometry and quadrupole ion trap mass spectrometry. Rapid Commun. Mass Spectrom. 23, 2167-2175
5. Salat, K., Moniczewski, A., and Librowski, T. (2013) Transient receptor potential channels: emerging novel drug targets for the treatment of pain. Curr. Med. Chem. 20, 1409-1436
6. v1.7 sodium channel: from molecule to man. Nat. Rev. Neurosci. 14, 49-62
7. Planells-Cases, R., Valente, P., Ferrer-Montiel, A., Qin, F., and Szallasi, A. (2011) Complex regulation of TRPV1 and related thermo-TRPs: implications for therapeutic intervention. Adv. Exp. Med. Biol. 704, 491-515
8. Cox, J. J., Reimann, F., Nicholas, A. K., Thornton, G., Roberts, E., Springell, K., Karbani, G., Jafri, H., Mannan, J., Raashid, Y., Al-Gazali, L., Hamamy, H., Valente, E. M., Gorman, S., Williams, R., McHale, D. P., Wood, J. N., Gribble, F. M., and Woods, C. G. (2006) An SCN9A channelopathy causes congenital inability to experience pain. Nature 444, 894-898
9. Dib-Hajj, S. D., Cummins, T. R., Black, J. A., and Waxman, S. G. (2010) Sodium channels in normal and pathological pain. Annu. Rev. Neurosci. 33, 325-347
10. Jordt, S. E., and Julius, D. (2002) Molecular basis for species-specific sensitivity to "hot" chili peppers. Cell 108, 421-430
11. Szallasi, A., Cortright, D.N., Blum, C. A., andEid, S.R. (2007) Thevanilloid receptor TRPV1: 10 years from channel cloning to antagonist proof-of-concept. Nat. Rev. Drug Discov. 6, 357-372
12. Brederson, J.D., Kym, P. R., and Szallasi, A. (2013) Targeting TRP channels for pain relief. Eur. J. Pharmacol. 716, 61-76
13. Cortright, D. N., and Szallasi, A. (2009) TRP channels and pain. Curr. Pharm. Des 15, 1736-1749
14. (2011) Capsaicin patch (Qutenza) for postherpetic neuralgia. Med. Lett. Drugs Ther. 53, 42-43
15. Reilly, R. M., McDonald, H. A., Puttfarcken, P. S., Joshi, S. K., Lewis, L., Pai, M., Franklin, P. H., Segreti, J. A., Neelands, T. R., Han, P., Chen, J., Mantyh, P. W., Ghilardi, J. R., Turner, T. M., Voight, E. A., Daanen, J. F., Schmidt, R. G., Gomtsyan, A., Kort, M. E., Faltynek, C. R., and Kym, P. R. (2012) Pharmacology of modality-specific transient receptor potential vanil-loid-1 antagonists that do not alter body temperature. J. Pharmacol. Exp. Ther. 342, 416-428
16. Hargreaves, K., Dubner, R., Brown, F., Flores, C, andJoris, J. (1988) Anew and sensitive method for measuring thermal nociception in cutaneous hyperalgesia. Pain 32, 77-88
17. 2+ channel complex. Nat. Med. 17, 822-829
18. 2+ and transient receptor potential canonical channels. J. Pharmacol. Exp. Ther. 339, 329-340
19. Xiao, Y., Bingham, J. P., Zhu, W., Moczydlowski, E., Liang, S., and Cummins, T. R. (2008) Tarantula huwentoxin-IV inhibits neuronal sodium channels by binding to receptor site 4 and trapping the domain ii voltage sensor in the closed configuration. J. Biol. Chem. 283, 27300-27313
20. Kumar, S., Chakraborty, S., Barbosa, C, Brustovetsky, T., Brustovetsky, N., and Obukhov, A. G. (2012) Mechanisms controlling neurite outgrowth in a pheochromocytoma cell line: The role of TRPC channels. J. Cell. Physiol. 227, 1408-1419
21. Guo, A., Vulchanova, L., Wang, J., Li, X., and Elde, R. (1999) Immunocy-tochemical localization of the vanilloid receptor 1 (VR1): relationship to neuropeptides, the P2X3 purinoceptor and IB4-binding sites. Eur. J. Neurosci. 11, 946-958
22. Nakamura, A., Hayakawa, T., Kuwahara, S., Maeda, S., Tanaka, K., Seki, M., and Mimura, O. (2007) Morphological and immunohistochemical characterization of the trigeminal ganglion neurons innervating the cornea and upper eyelid of the rat. J. Chem. Neuroanat. 34, 95-101
23. Diogenes, A., Patwardhan, A. M., Jeske, N. A., Ruparel, N. B., Goffin, V., Akopian, A. N., and Hargreaves, K. M. (2006) Prolactin modulates TRPV1 in female rat trigeminal sensory neurons. J. Neurosci. 26, 8126-8136
24. Farazifard, R., Safarpour, F., Sheibani, V., and Javan, M. (2005) Eye-wiping test: a sensitive animal model for acute trigeminal pain studies. Brain Res. Brain Res. Protoc. 16, 44-49
25. Szolcsányi, J., and Jancsó-Gábor, A. (1975) Sensory effects of capsaicin congeners I. Relationship between chemical structure and pain-producing potency of pungent agents. Arzneimittelforschung 25, 1877-1881
26. Dubuisson, D., and Dennis, S. G. (1977) The formalin test: a quantitative study of the analgesic effects of morphine, meperidine, and brain stem stimulation in rats and cats. Pain 4, 161-174
27. Hunskaar, S., and Hole, K. (1987) The formalin test in mice: dissociation between inflammatory and non-inflammatory pain. Pain 30, 103-114
28. Chung, M. K., Güler, A. D., and Caterina, M. J. (2008) TRPV1 shows dynamic ionic selectivity during agonist stimulation. Nat. Neurosci. 11, 555-564
29. Hou, X., Pedi, L., Diver, M. M., and Long, S. B. (2012) Crystal structure of the calcium release-activated calcium channel Orai. Science 338, 1308-1313
30. Rohacs, T. (2013) Regulation of transient receptor potential channels by the phospholipase C pathway. Adv. Biol. Regul. 53, 341-355
31. Lukacs, V., Rives, J. M., Sun, X., Zakharian, E., and Rohacs, T. (2013) Promiscuous activation of transient receptor potential vanilloid 1 channels by negatively charged intracellular lipids, the key role of endogenous phosphoinositides in maintaining channel activity. J. Biol. Chem. 288, 35003-35013
32. 2-mediated inhibition. Nature 411, 957-962
33. Premkumar, L. S., and Ahern, G. P. (2000) Induction of vanilloid receptor channel activity by protein kinase C. Nature 408, 985-990
34. Pabbidi, R. M., Yu, S. Q., Peng, S., Khardori, R., Pauza, M. E., and Premku-mar, L. S. (2008) Influence of TRPV1 on diabetes-induced alterations in thermal pain sensitivity. Mol. Pain 4, 9
35. Premkumar, L. S., and Abooj, M. (2013) TRP channels and analgesia. Life Sci. 92, 415-424
36. Mathie, A. (2010) Ion channels as novel therapeutic targets in the treatment of pain. J. Pharm. Pharmacol. 62, 1089-1095
37. McNamara, C. R., Mandel-Brehm, J., Bautista, D. M., Siemens, J., Dera-nian, K. L., Zhao, M., Hayward, N. J., Chong, J.A., Julius, D., Moran, M. M., and Fanger, C. M. (2007) TRPA1 mediates formalin-induced pain. Proc. Natl. Acad. Sci. U.S.A. 104, 13525-13530
38. Ruparel, N. B., Patwardhan, A. M., Akopian, A. N., and Hargreaves, K. M. (2008) Homologous and heterologous desensitization of capsaicin and mustard oil responses utilize different cellular pathways in nociceptors. Pain 135, 271-279
39. Btesh, J., Fischer, M. J., Stott, K., and McNaughton, P. A. (2013) Mapping the-binding site of TRPV1 on AKAP79: implications for inflammatory hyperalgesia. J. Neurosci. 33, 9184-9193
40. Huang, G. J., Deng, J. S., Liao, J. C., Hou, W. C., Wang, S. Y., Sung, P. J., and Kuo, Y. H. (2012) Inducible nitric oxide synthase and cyclooxygenase-2 participate in anti-inflammatory activity of imperatorin from Glehnia lit-toralis. J. Agric. Food Chem. 60, 1673-1681
41. Ban, H. S., Lim, S. S., Suzuki, K., Jung, S. H., Lee, S., Lee, Y. S., Shin, K. H., and Ohuchi, K.(2003) Inhibitory effects of furanocoumarins isolated from the roots of Angelica dahurica on prostaglandin E2 production. Planta Med. 69, 408-412
42. Luszczki, J. J., Wojda, E., Andres-Mach, M., Cisowski, W., Glensk, M., Glowniak, K., and Czuczwar, S. J. (2009) Anticonvulsant and acute neu-rotoxic effects of imperatorin, osthole and valproate in the maximal elec-troshock seizure and chimney tests in mice: a comparative study. Epilepsy Res. 85, 293-299
43. Lu, W., Zhang, T., Li, P., Wang, F., Pan, X., Wang, C., Hu, Z., and Zhang, J. (2013) Structural modeling and identification of imperatorin as novel L-type calcium channel blocker. Med. Chem. 9, 993-998
44. Wu, K. C., Chen, Y. H., Cheng, K. S., Kuo, Y. H., Yang, C. T., Wong, K. L., Tu, Y. K., Chan, P., and Leung, Y. M. (2013) Suppression of voltage-gated Na channels and neuronal excitability by imperatorin. Eur. J. Pharmacol. 721, 49-55