Lipophilicity of capsaicinoids and capsinoids influences the multiple activation process of rat TRPV1

Life Sciences

Volumn 79, Issue 24, 2006, Pages 2303-2310

  Morita, Akihito ^a   Iwasaki, Yusaku ^a   Kobata, Kenji ^a   Iida, Tohko ^b   Higashi, Tomohiro ^b   Oda, Kyoko ^a   Suzuki, Asami ^a   Narukawa, Masataka ^a   Sasakuma, Shiho ^a   Yokogoshi, Hidehiko ^a   Yazawa, Susumu ^c   Tominaga, Makoto ^b   Watanabe, Tatsuo ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b OKAZAKI INSTITUTE FOR INTEGRATIVE BIOSCIENCE   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

Capsaicinoids; Capsinoids; Intracellular calcium concentration; Lipophilicity; TRPV1

Indexed keywords

CALCIUM ION; CAPSAICIN; CAPSAICIN DERIVATIVE; CAPSAZEPINE; CAPSIATE; OLVANIL; OLVANILATE; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1;

AGONIST; ARTICLE; CALCIUM CELL LEVEL; CELL MEMBRANE; CELL STRAIN HEK293; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; EMBRYO; ENDOPLASMIC RETICULUM; EXTRACELLULAR CALCIUM; HETEROLOGOUS EXPRESSION; HUMAN; HUMAN CELL; LIPOPHILICITY; MEASUREMENT;

ANALGESICS, NON-NARCOTIC; ANIMALS; CALCIUM; CALCIUM SIGNALING; CAPSAICIN; CELL LINE; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MEMBRANE POTENTIALS; PATCH-CLAMP TECHNIQUES; RATS; SOLUBILITY; TRPV CATION CHANNELS;

EID: 33750529913     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2006.07.024     Document Type: Article

References (35)

1. Appendino G., Minassi A., Morello A.S., De Petrocellis L., and Di Marzo V. N-Acylvanilylamides: development of an expeditious synthesis and discovery of new acyl templates for powerful activation of the vanilloid receptor. Journal of Medicinal Chemistry 45 17 (2002) 3739-3745
2. Bian J.H., Ghosh T.K., Wang J.C., and Gill D.L. Identification of intracellular calcium pools. Selective modification by tapsigargin. Journal of Biological Chemistry 266 14 (1991) 8801-8806
3. Bíró T., Brodie C., Modarres S., Lewin N.E., Ács P., and Blumberg P.M. Specific vanilloid responses in C6 rat glioma cells. Molecular Brain Research 56 1-2 (1998) 89-98
4. Caterina M.J., Schumacher M.A., Tominaga M., Rosen T.A., Levine J.D., and Julius D. The capsaicin receptor: a heat-activated ion channel in the pain pathway. Nature 389 6653 (1997) 816-824
5. Chou M.Z., Mtui T., Gao Y.D., Kohler M., and Middleton R.E. Resiniferatoxin binds to the capsaicin receptor (TRPV1) near the extracellular side of the S4 transmembrane domain. Biochemistry 43 9 (2004) 2501-2511
6. Chu C.J., Huang S.M., De Petrocellis L., Bisogno T., Ewing S.A., Miller J.D., Zipkin R.E., Daddario N., Appendino G., Di Marzo V., and Walker J.M. N-Oleoyldopamine: a novel endogenous capsaicin-like lipid that produces hyperalgesia. Journal of Biological Chemistry 278 16 (2003) 13633-13639
7. De Petrocellis L., Davis J.B., and Di Marzo V. Palmitoylethanolamide enhances anandamide stimulation of human vanilloid VR1 receptors. FEBS Letters 506 3 (2001) 253-256
8. 2+ stores in the dorsal root ganglion cells of adult rats. Biochemical and Biophysical Research Communications 285 5 (2001) 1114-1120
9. Gavva N.R., Klionsky L., Qu Y., Shi L., Tamir R., Edenson S., Zhang T.J., Viswanadhan V.N., Toth A., Pearce L.V., Vanderah T.W., Porreca F., Blumberg P.M., Lile J., Sun Y., Wild K., Louis J.C., and Treanor J.J. Molecular determinants of vanilloid sensitivity in TRPV1. Journal of Biological Chemistry 279 19 (2004) 20283-20295
10. 2+ indicators with greatly improved fluorescence properties. Journal of Biological Chemistry 260 6 (1985) 3440-3450
11. Hamilton J.A. Fatty acid transport: difficult or easy?. Journal of Lipid Research 39 3 (1998) 467-481
12. 2+]. Journal of Cell Biology 140 2 (1998) 325-334
13. Huang S.M., Bisogno T., Trevisani M., Al-Hayani A., De Petrocellis L., Fezza F., Tognetto M., Petros T.J., Krey J.F., Chu C.J., Miller J.D., Davies S.N., Geppetti P., Walker J.M., and Di Marzo V. An endogenous capsaicin-like substance with high potency at recombinant and native vanilloid VR1 receptors. Proceedings of the National Academy of Sciences of the United States of America 99 12 (2002) 8400-8405
14. Hui K., Liu B., and Qin F. Capsaicin activation of the pain receptor, VR1: multiple open states from both partial and full binding. Biophysical Journal 84 5 (2003) 2957-2968
15. Iida T., Moriyama T., Kobata K., Morita A., Murayama N., Hashizume S., Fushiki T., Yazawa S., Watanabe T., and Tominaga M. TRPV1 activation and induction of nociceptive response by a non-pungent capsaicin-like compound, capsiate. Neuropharmacology 44 7 (2003) 958-967
16. Jerman J.C., Brough S.J., Prinjha R., Harries M.H., Davis J.B., and Smart D. Characterization using FLIPR of rat vanilloid receptor (rVR1) pharmacology. British Journal of Pharmacology 130 4 (2000) 916-922
17. Jordt S.E., and Julius D. Molecular basis for species-specific sensitivity to "hot" chili peppers. Cell 108 3 (2002) 421-430
18. Jung J., Lee S.Y., Hwang S.W., Cho H., Shin J., Kang Y.S., Kim S., and Oh U. Agonist recognition sites in the cytosolic tails of vanilloid receptor 1. Journal of Biological Chemistry 277 46 (2002) 44448-44454
19. 2+-release in sensory neurons. Journal of Biological Chemistry 279 16 (2004) 16377-16387
20. Kobata K., Todo T., Yazawa S., Iwai K., and Watanabe T. Novel capsaicinoid-like substances, capsiate and dihydrocapsiate, from the fruits of a nonpungent cultivar, CH-19 sweet, of pepper (Capsicum annuum L.). Journal of Agricultural and Food Chemistry 46 5 (1998) 1695-1697
21. Kobata K., Sutoh K., Todo T., Yazawa S., Iwai K., and Watanabe T. Nordihydrocapsiate, a new capsinoid from the fruits of a nonpungent pepper, Capsicum annuum. Journal of Natural Products 62 2 (1999) 335-336
22. Kobata K., Kawaguchi M., and Watanabe T. Enzymatic synthesis of a capsinoid by the acylation of vanillyl alcohol with fatty acid derivatives catalyzed by lipases. Bioscience, Biotechnology, and Biochemistry 66 2 (2002) 319-327
23. Lytton J., Westlin M., and Hanley M.R. Thapsigargin inhibits the sarcoplasmic or endoplasmic reticulum Ca-ATPase family of calcium pumps. Journal of Biological Chemistry 266 26 (1991) 17067-17071
24. Marshall I.C., Owen D.E., Cripps T.V., Davis J.B., McNulty S., and Smart D. Activation of vanilloid receptor 1 by resiniferatoxin mobilizes calcium from inositol 1,4,5-trisphosphate-sensitive stores. British Journal of Pharmacology 138 1 (2003) 172-176
25. Olah Z., Szabo T., Karai L., Hough C., Fields R.D., Caudle R.M., Blumberg P.M., and Iadarola M.J. Ligand-induced dynamic membrane changes and cell deletion conferred by vanilloid receptor 1. Journal of Biological Chemistry 276 14 (2001) 11021-11030
26. Peters T. All About Albumin: Biochemistry, Genetics and Medical Applications (1996), Academic Press, San Diego Chapter 3
27. Phillips E., Reeve A., Bevan S., and McIntyre P. Identification of species-specific determinants of the action of the antagonist capsazepine and the agonist PPAHV on TRPV1. Journal of Biological Chemistry 279 17 (2004) 17165-17172
28. Rangoonwala G.W., and Seitz G. "cis-Capsaicin" Ein beitrag zur synthese, analytic und dem vermuteten vorkommen in capsicum-früchen. Deutsche Apotheker-Zeitung 110 50 (1970) 1946-1949
29. Sutoh K., Kobata K., and Watanabe T. Stability of capsinoid in various solvents. Journal of Agricultural and Food Chemistry 49 8 (2001) 4026-4030
30. Szallasi A., and Blumberg P.M. Vanilloid (capsaicin) receptors and mechanisms. Pharmacological Reviews 51 2 (1999) 159-212
31. Tominaga M., Caterina M.J., Malmberg A.B., Rosen T.A., Gilbert H., Skinner K., Raumann B.E., Basbaum A.I., and Julius D. The cloned capsaicin receptor integrates multiple pain-producing stimuli. Neuron 21 3 (1998) 531-543
32. Toth A., Wang Y., Kedei N., Tran R., Pearce L.V., Kang S.U., Jin M.K., Chol H.K., Lee J., and Blumberg P.M. Different vanilloid agonists cause different patterns of calcium response in CHO cells heterologously expressing rat TRPV1. Life Sciences 76 25 (2005) 2921-2932
33. 2+ influx via TRPV1 channels. EMBO Journal 24 17 (2005) 3026-3037
34. Walpole C.S., Wrigglesworth R., Bevan S., Campbell E.A., Dray A., James I.F., Masdin K.J., Perkins M.N., and Winter J. Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 3. The hydrophobic side-chain "C-region". Journal of Medicinal Chemistry 36 16 (1993) 2381-2389
35. Zhang F., Kamp F., and Hamilton J.A. Dissociation of long and very long chain fatty acids from phospholipid bilayers. Biochemistry 35 50 (1996) 16055-16060