Down-regulation of cyclooxygenase-2 (cox-2) by cannabidiolic acid in human breast cancer cells

Journal of Toxicological Sciences

Volumn 39, Issue 5, 2014, Pages 711-716

  Takeda, Shuso ^a,b   Okazaki, Hiroyuki ^a   Ikeda, Eriko ^a   Abe, Satomi ^a   Yoshioka, Yasushi ^a   Watanabe, Kazuhito ^c   Aramaki, Hironori ^a  

^a DAIICHI UNIVERSITY OF PHARMACY   (Japan)

^b HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

^c HOKURIKU UNIVERSITY   (Japan)

Author keywords

Cannabidiolic acid; Cyclooxygenase 2; Fiber type cannabis plant; Human breast cancer cells; Metastasis

Indexed keywords

CANNABIDIOL DERIVATIVE; CANNABIDIOLIC ACID; COMPLEMENTARY DNA; CYCLOOXYGENASE 2; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; BASIC HELIX LOOP HELIX TRANSCRIPTION FACTOR; BHLHE41 PROTEIN, HUMAN; CANNABINOID; CANNABIS; ENZYME INHIBITOR; PTGS2 PROTEIN, HUMAN;

ARTICLE; BREAST CANCER; CANCER CELL; CELL CULTURE; CONTROLLED STUDY; DNA MICROARRAY; ENZYME INHIBITION; GENE; GENE EXPRESSION; HUMAN; HUMAN CELL; IC50; METASTASIS; MICROARRAY ANALYSIS; PROTEIN EXPRESSION; REAL TIME POLYMERASE CHAIN REACTION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; RNA ANALYSIS; UPREGULATION; BREAST TUMOR; DOWN REGULATION; DRUG EFFECTS; ENZYMOLOGY; FEMALE; GENETICS; METABOLISM; PATHOLOGY; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BASIC HELIX-LOOP-HELIX TRANSCRIPTION FACTORS; BREAST NEOPLASMS; CANNABINOIDS; CANNABIS; CYCLOOXYGENASE 2; DOWN-REGULATION; ENZYME INHIBITORS; FEMALE; GENE EXPRESSION; HUMANS; NEOPLASM METASTASIS; REAL-TIME POLYMERASE CHAIN REACTION; TUMOR CELLS, CULTURED; UP-REGULATION;

EID: 84907557918     PISSN: 03881350     EISSN: 18803989     Source Type: Journal    
DOI: 10.2131/jts.39.711     Document Type: Article

References (41)

1. Appendino, G., Gibbons, S., Giana, A., Pagani, A., Grassi, G., Stavri, M., Smith, E. and Rahman, M.M. (2008): Antibacterial cannabinoids from Cannabis sativa: a structure-activity study. J. Nat. Prod., 71, 1427-1430.
2. 1A receptor activation. Br. J. Pharmacol., 168, 1456-1470.
3. Brueggemeier, R.W., Quinn, A.L., Parrett, M.L., Joarder, F.S., Harris, R.E. and Robertson, F.M. (1999): Correlation of aro-matase and cyclooxygenase gene expression in human breast cancer specimens. Cancer Lett., 140, 27-35.
4. Burstein, S.H. (1999): The cannabinoid acids: nonpsychoactive derivatives with therapeutic potential. Pharmacol. Ther., 82, 87-96.
5. Caffarel, M.M., Andradas, C., Pérez-Gómez, E., Guzmán, M. and Sánchez, C. (2012): Cannabinoids: a new hope for breast cancer therapy? Cancer Treat. Rev., 38, 911-918.
6. Davies, G., Martin, L.A., Sacks, N. and Dowsett, M. (2002): Cyclooxygenase-2 (COX-2), aromatase and breast cancer: a possible role for COX-2 inhibitors in breast cancer chemopreven-tion. Ann. Oncol., 13, 669-678.
7. Dikshit, P. and Jana, N.R. (2007): The co-chaperone CHIP is induced in various stresses and confers protection to cells. Biochem. Biophys. Res. Commun., 357, 761-765.
8. Dong, Z., Huang, C., Brown, R.E. and Ma, W.Y. (1997): Inhibition of activator protein 1 activity and neoplastic transformation by aspirin. J. Biol. Chem., 272, 9962-9970.
9. Fong, S., Itahana, Y., Sumida, T., Singh, J., Coppe, J.P., Liu, Y., Richards, P.C., Bennington, J.L., Lee, N.M., Debs, R.J. and Desprez, P.Y. (2003): Id-1 as a molecular target in therapy for breast cancer cell invasion and metastasis. Proc. Natl. Acad. Sci. USA, 100, 13543-13548.
10. Hanahan, D. and Weinberg, R.A. (2011): Hallmarks of cancer: the next generation. Cell, 144, 646-674.
11. Holmes, M.D., Chen, W.Y., Schnitt, S.J., Collins, L., Colditz, G.A., Hankinson, S.E. and Tamimi, R.M. (2011): COX-2 expression predicts worse breast cancer prognosis and does not modify the association with aspirin. Breast Cancer Res. Treat., 130, 657-662.
12. Hwang, G.W., Lee, J.Y., Ryoke, K., Matsuyama, F., Kim, J.M., Takahashi, T. and Naganuma, A. (2011): Gene expression profiling using DNA microarray analysis of the cerebellum of mice treated with methylmercury. J. Toxicol. Sci., 36, 389-391.
13. Izzo, A.A., Borrelli, F., Capasso, R., Di Marzo, V. and Mechoulam, R. (2009): Non-psychotropic plant cannabinoids: new therapeutic opportunities from an ancient herb. Trends Pharmacol. Sci., 30, 515-527 [Erratum in Trends Pharmacol. Sci., 30, 609 (2009)].
14. Kajiro, M., Hirota, R., Nakajima, Y., Kawanowa, K., So-ma, K., Ito, I., Yamaguchi, Y., Ohie, S.H., Kobayashi, Y., Seino, Y., Kawano, M., Kawabe, Y., Takei, H., Hayashi, S., Kurosumi, M., Murayama, A., Kimura, K. and Yanagisawa, J. (2009): The ubiquitin ligase CHIP acts as an upstream regulator of oncogenic pathways. Nat. Cell Biol., 11, 312-319.
15. Kopp, E. and Ghosh, S. (1994): Inhibition of NF-kappa B by sodium salicylate and aspirin. Science, 265, 956-959.
16. Ligresti, A., Moriello, A.S., Starowicz, K., Matias, I., Pisanti, S., De Petrocellis, L., Laezza, C., Portella, G., Bifulco, M. and Di Marzo, V. (2006): Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma. J. Pharmacol. Exp. Ther., 318, 1375-1387.
17. McAllister, S.D., Christian, R.T., Horowitz, M.P., Garcia, A. and Desprez, P.Y. (2007): Cannabidiol as a novel inhibitor of Id-1 gene expression in aggressive breast cancer cells. Mol. Cancer Ther., 6, 2921-2927.
18. Mishima, K., Hayakawa, K., Abe, K., Ikeda, T., Egashira, N., Iwasaki, K. and Fujiwara, M. (2005): Cannabidiol prevents cerebral infarction via a serotonergic 5-hydroxytryptamine1A receptor-dependent mechanism. Stroke, 36, 1077-1082.
19. Montagner, M., Enzo, E., Forcato, M., Zanconato, F., Parenti, A., Rampazzo, E., Basso, G., Leo, G., Rosato, A., Bicciato, S., Cordenonsi, M. and Piccolo, S. (2012): SHARP1 suppresses breast cancer metastasis by promoting degradation of hypoxia-inducible factors. Nature, 487, 380-384.
20. Price, J.E., Polyzos, A., Zhang, R.D. and Daniels, L.M. (1990): Tumorigenicity and metastasis of human breast carcinoma cell lines in nude mice. Cancer Res., 50, 717-721.
21. Razdan, R.K. (1986): Structure-activity relationships in cannabi-noids. Pharmacol. Rev., 38, 75-149.
22. Rock, E.M. and Parker, L.A. (2013): Effect of low doses of can-nabidiolic acid and ondansetron on LiCl-induced conditioned gaping (a model of nausea-induced behaviour) in rats. Br. J. Pharmacol., 169, 685-692.
23. Roelofs, H.M., Te Morsche, R.H., van Heumen, B.W., Nagengast, F.M. and Peters, W.H. (2014): Over-expression of COX-2 mRNA in colorectal cancer. BMC. Gastroenterol., 14, 1.
24. Ruhaak, L.R., Felth, J., Karlsson, P.C., Rafter, J.J., Verpoorte, R. and Bohlin, L. (2011): Evaluation of the cyclooxygenase inhibiting effects of six major cannabinoids isolated from Cannabis sativa. Biol. Pharm. Bull., 34, 774-778.
25. Shigematsu, Y., Hanagiri, T., Kuroda, K., Baba, T., Mizukami, M., Ichiki, Y., Yasuda, M., Takenoyama, M., Sugio, K. and Yasumoto, K. (2009): Malignant mesothelioma-associated antigens recognized by tumor-infiltrating B cells and the clinical significance of the antibody titers. Cancer Sci., 100, 1326-1334.
26. Shrivastava, A., Kuzontkoski, P.M., Groopman, J.E. and Prasad, A. (2011): Cannabidiol induces programmed cell death in breast cancer cells by coordinating the cross-talk between apoptosis and autophagy Mol. Cancer Ther, 10, 1161-1172.
27. Singh, B., Berry, J.A., Shoher, A., Ayers, G.D., Wei, C. and Lucci, A. (2007): COX-2 involvement in breast cancer metastasis to bone. Oncogene, 26, 3789-3796.
28. Takeda, S., Misawa, K., Yamamoto, I. and Watanabe, K. (2008): Cannabidiolic acid as a selective cyclooxygenase-2 inhibitory component in cannabis. Drug Metab. Dispos., 36, 1917-1921.
29. Takeda, S., Usami, N., Yamamoto, I. and Watanabe, K. (2009): Can-nabidiol-2',6'-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor. Drug Metab. Dispos., 37, 1733-1737.
30. Takeda, S., Matsuo, K., Yaji, K., Okajima-Miyazaki, S., Harada, M., Miyoshi, H., Okamoto, Y, Amamoto, T., Shindo, M., Omiecinski, C.J. and Aramaki, H. (2011): (-)-Xanthatin selectively induces GADD45y and stimulates caspase-independent cell death in human breast cancer MDA-MB-231 cells. Chem. Res. Toxicol., 24, 855-865.
31. Takeda, S., Okajima, S., Miyoshi, H., Yoshida, K., Okamoto, Y, Okada, T., Amamoto, T., Watanabe, K., Omiecinski, C.J. and Aramaki, H. (2012): Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration. Toxicol. Lett., 214, 314-319.
32. Takeda, S. (2013): Medicinal chemistry and pharmacology focused on cannabidiol, a major component of the fiber-type cannabis. Yakugaku Zasshi, 133, 1093-1101.
33. 9-Tetrahydrocan-nabinol Disrupts Estrogen-Signaling through Up-Regulation of Estrogen Receptor P (ERP). Chem. Res. Toxicol., 26, 1073-1079.
34. 9-tetrahydrocannabinol in human breast cancer cells. J. Toxicol. Sci., 38, 305-308.
35. Taura, F., Sirikantaramas, S., Shoyama, Y, Shoyama, Y and Morimoto, S. (2007): Phytocannabinoids in Cannabis sativa: recent studies on biosynthetic enzymes. Chem. Biodivers, 4, 1649-1663.
36. Turner, C.E., Elsohly, M.A. and Boeren, E.G. (1980): Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J. Nat. Prod., 43, 169-234.
37. Toyama, T., Yoshida, E., Shinkai, Y and Kumagai, Y (2011): DNA microarray analysis of human neuroblastoma SH-SY5Y cells exposed to methylmercury. J. Toxicol. Sci., 36, 843-845.
38. Yamauchi, T., Shoyama, Y, Aramaki, H., Azuma, T. and Nishioka, I. (1967): Tetrahydrocannabinolic acid, a genuine substance of tetrahydrocannabinol. Chem. Pharm. Bull., 15, 1075-1076.
39. Yoshinaka, R., Shibata, M.A., Morimoto, J., Tanigawa, N. and Otsuki, Y. (2006): COX-2 inhibitor celecoxib suppresses tumor growth and lung metastasis of a murine mammary cancer. Anti-cancer Res., 26, 4245-4254.
40. Wu, J., Xia, H.H., Tu, S.P., Fan, D.M., Lin, M.C., Kung, H.F., Lam, S.K. and Wong, B.C. (2003): 15-Lipoxygenase-1 mediates cyclooxygenase-2 inhibitor-induced apoptosis in gastric cancer. Carcinogenesis, 24, 243-247.
41. Xu, X.M., Sansores-Garcia, L., Chen, X.M., Matijevic-Aleksic, N., Du, M. and Wu, K.K. (1999): Suppression of inducible cycloox-ygenase 2 gene transcription by aspirin and sodium salicylate. Proc. Natl. Acad. Sci. USA, 96, 5292-5297.