Δ9-tetrahydrocannabinol disrupts estrogen-signaling through up-regulation of estrogen receptor β (ERβ)

Chemical Research in Toxicology

Volumn 26, Issue 7, 2013, Pages 1073-1079

  Takeda, Shuso ^a,e   Yoshida, Kazutaka ^a   Nishimura, Hajime ^a   Harada, Mari ^a   Okajima, Shunsuke ^a   Miyoshi, Hiroko ^a   Okamoto, Yoshiko ^a   Amamoto, Toshiaki ^b   Watanabe, Kazuhito ^c   Omiecinski, Curtis J ^d   Aramaki, Hironori ^a  

^a DAIICHI UNIVERSITY OF PHARMACY   (Japan)

^b NEUES Corporation   (Japan)

^c HOKURIKU UNIVERSITY   (Japan)

^d PENNSYLVANIA STATE UNIVERSITY   (United States)

^e HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DRONABINOL; ESTRADIOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTROGEN; ESTROGEN RECEPTOR ALPHA, HUMAN; LIGAND;

ARTICLE; BREAST CANCER; CELL GROWTH; CELL LINE; CELL PROLIFERATION; CELL STRAIN MCF 7; CELL STRUCTURE; CHEMICAL ANALYSIS; CONTROLLED STUDY; DIMERIZATION; ESTROGEN RECEPTOR POSITIVE BREAST CANCER; HUMAN; HUMAN CELL; IN VITRO STUDY; LIGAND BINDING; PROTEIN BINDING; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION; UPREGULATION; ANTAGONISTS AND INHIBITORS; BIOSYNTHESIS; CELL SURVIVAL; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MCF 7 CELL LINE; METABOLISM; STRUCTURE ACTIVITY RELATION; TUMOR CELL CULTURE;

CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRONABINOL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; ESTROGENS; HUMANS; LIGANDS; MCF-7 CELLS; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; UP-REGULATION;

EID: 84880291490     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx4000446     Document Type: Article

References (29)

1. 2 Pharmacol. Rev. 62, 588-631
2. Guindon, J. and Hohmann, A. G. (2011) The endocannabinoid system and cancer: therapeutic implication Br. J. Pharmacol. 163, 1447-1463
3. 9- tetrahydrocannabinol-11-oic acid as 15-lipoxygenase inhibitors J. Pharm. Sci. 100, 1206-1211
4. 9-tetrahydrocannabinol in human breast cancer cells J. Toxicol. Sci. 38, 305-308
5. Ruh, M. F., Taylor, J. A., Howlett, A. C., and Welshons, W. V. (1997) Failure of cannabinoid compounds to stimulate estrogen receptors Biochem. Pharmacol. 53, 35-41
6. Stella, N. (2001) How might cannabinoids influence sexual behavior? Proc. Natl. Acad. Sci. U.S.A. 98, 793-795
7. Kuiper, G. G., Enmark, E., Pelto-Huikko, M., Nilsson, S., and Gustafsson, J. A. (1996) Cloning of a novel receptor expressed in rat prostate and ovary Proc. Natl. Acad. Sci. U.S.A. 93, 5925-5930
8. Cowley, S. M., Hoare, S., Mosselman, S., and Parker, M. G. (1997) Estrogen receptors α and β form heterodimers on DNA J. Biol. Chem. 272, 19858-19862
9. 2 cell cycle arrest Cancer Res. 64, 423-428
10. Powell, E. and Xu, W. (2008) Intermolecular interactions identify ligand-selective activity of estrogen receptor α/β dimers Proc. Natl. Acad. Sci. U.S.A. 105, 19012-19017
11. Powell, E., Huang, S. X., Xu, Y., Rajski, S. R., Wang, Y., Peters, N., Guo, S., Xu, H. E., Hoffmann, F. M., Shen, B., and Xu, W. (2010) Identification and characterization of a novel estrogenic ligand actinopolymorphol A Biochem. Pharmacol. 80, 1221-1229
12. Powell, E., Shanle, E., Brinkman, A., Li, J., Keles, S., Wisinski, K. B., Huang, W., and Xu, W. (2012) PLoS One 7, e30993
13. Lin, C. Y., Ström, A., Li Kong, S., Kietz, S., Thomsen, J. S., Tee, J. B., Vega, V. B., Miller, L. D., Smeds, J., Bergh, J., Gustafsson, J. A., and Liu, E. T. (2007) Inhibitory effects of estrogen receptor beta on specific hormone-responsive gene expression and association with disease outcome in primary breast cancer Breast Cancer Res. 9, R25
14. 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
15. 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 GADD45γ and stimulates caspase-independent cell death in human breast cancer MDA-MB-231 cells Chem. Res. Toxicol. 24, 855-865
16. Takeda, S., Noguchi, M., Matsuo, K., Yamaguchi, Y., Kudo, T., Nishimura, H., Okamoto, Y., Amamoto, T., Shindo, M., Omiecinski, C. J., and Aramaki, H. (2013) (-)-Xanthatin up-regulation of the GADD45γ tumor suppressor gene in MDA-MB-231 breast cancer cells: Role of topoisomerase IIα inhibition and reactive oxygen species Toxicology 305, 1-9
17. Takeda, S., Ishii, Y., Iwanaga, M., Nurrochmad, A., Ito, Y., Mackenzie, P. I., Nagata, K., Yamazoe, Y., Oguri, K., and Yamada, H. (2009) Interaction of cytochrome P450 3A4 and UDP-glucuronosyltransferase 2B7: evidence for protein-protein association and possible involvement of CYP3A4 J-helix in the interaction Mol. Pharmacol. 75, 956-964
18. von Bueren, A. O., Schlumpf, M., and Lichtensteiger, W. (2008) Delta(9)-tetrahydrocannabinol inhibits 17β-estradiol-induced proliferation and fails to activate androgen and estrogen receptors in MCF7 human breast cancer cells Anticancer Res. 28, 85-89
19. Anderson, W. F., Chatterjee, N., Ershler, W. B., and Brawley, O. W. (2002) Estrogen receptor breast cancer phenotypes in the Surveillance, Epidemiology, and End Results database Breast Cancer Res. Treat. 76, 27-36
20. Urruticoechea, A., Smith, I. E., and Dowsett, M. (2005) Proliferation marker Ki-67 in early breast cancer J. Clin. Oncol. 23, 7212-7220
21. Huang, R. P., Fan, Y., de Belle, I., Niemeyer, C., Gottardis, M. M., Mercola, D., and Adamson, E. D. (1997) Decreased Egr-1 expression in human, mouse and rat mammary cells and tissues correlates with tumor formation Int. J. Cancer 72, 102-109
22. Comitato, R., Nesaretnam, K., Leoni, G., Ambra, R., Canali, R., Bolli, A., Marino, M., and Virgili, F. (2009) A novel mechanism of natural vitamin E tocotrienol activity: involvement of ERβ signal transduction Am. J. Physiol. Endocrinol. Metab. 297, E427-E437
23. Barkhem, T., Carlsson, B., Nilsson, Y., Enmark, E., Gustafsson, J., and Nilsson, S. (1998) Differential response of estrogen receptor α and estrogen receptor β to partial estrogen agonists/antagonists Mol. Pharmacol. 54, 105-112
24. Pettersson, K., Delaunay, F., and Gustafsson, J. A. (2000) Estrogen receptor β acts as a dominant regulator of estrogen signaling Oncogene 19, 4970-4978
25. Lazennec, G., Bresson, D., Lucas, A., Chauveau, C., and Vignon, F. (2001) ERβ inhibits proliferation and invasion of breast cancer cells Endocrinology 142, 4120-4130
26. Powell, E., Wang, Y., Shapiro, D. J., and Xu, W. (2010) Differential requirements of Hsp90 and DNA for the formation of estrogen receptor homodimers and heterodimers J. Biol. Chem. 285, 16125-16134
27. Schwope, D. M., Karschner, E. L., Gorelick, D. A., and Huestis, M. A. (2011) Identification of recent cannabis use: whole-blood and plasma free and glucuronidated cannabinoid pharmacokinetics following controlled smoked cannabis administration Clin. Chem. 57, 1406-1414
28. 9- tetrahydrocannabinol content and number of puffs J. Pharmacol. Exp. Ther. 261, 114-122
29. 1-tetrahydrocannabinol in human fat biopsies from marihuana users by gas chromatography-mass spectrometry Biomed. Chromatogr. 3, 35-38