Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells

Carcinogenesis

Volumn 29, Issue 2, 2008, Pages 363-370

  Lehmann, Leane ^a   Jiang, Ling ^a   Wagner, Jörg ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYESTRADIOL; CATECHOL DERIVATIVE; CATECHOL METHYLTRANSFERASE; DAIDZEIN; ESTROGEN RECEPTOR; FULVESTRANT; GENISTEIN; ISOFLAVONE DERIVATIVE; QUERCETIN;

ARTICLE; BREAST CARCINOGENESIS; CELL STRAIN MCF 7; CHEMOPROPHYLAXIS; CONTROLLED STUDY; DETOXIFICATION; DOWN REGULATION; ENZYME ACTIVITY; GENE EXPRESSION; GENETIC POLYMORPHISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; METHYLATION; PRIORITY JOURNAL; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

BREAST NEOPLASMS; CATECHOL O-METHYLTRANSFERASE; CELL LINE, TUMOR; CELL PROLIFERATION; DIET; ESTRADIOL; ESTROGENS, CATECHOL; FEMALE; GENE EXPRESSION REGULATION, NEOPLASTIC; HUMANS; MODELS, BIOLOGICAL; MODELS, CHEMICAL; RECEPTORS, ESTROGEN; SOYBEANS;

EID: 40549126274     PISSN: 01433334     EISSN: 14602180     Source Type: Journal    
DOI: 10.1093/carcin/bgm235     Document Type: Article

References (52)

1. Badawi,A.F. et al. (2001) Role of human cytochrome P450 1A1, 1A2, 1B1, and 3A4 in the 2, 4-, and 16alpha-hydroxylation of 17beta-estradiol. Metabolism, 50, 1001-1003.
2. Zhu,B.T. et al. (1998) Functional role of estrogen metabolism in target cells: Review and perspectives. Carcinogenesis, 19, 1-27.
3. Ball,P. et al. (1980) Catecholoestrogens (2-and 4-hydroxyoestrogens): Chemistry, biogenesis, metabolism, occurrence and physiological significance. Acta Endocrinol. Suppl. (Copenh), 232, 1-127.
4. Dawling,S. et al. (2001) Catechol-O-methyltransferase (COMT)-mediated metabolism of catechol estrogens: Comparison of wild-type and variant COMT isoforms. Cancer Res., 61, 6716-6722.
5. Klauber,N. et al. (1997) Inhibition of angiogenesis and breast cancer in mice by the microtubule inhibitors 2-methoxyestradiol and taxol. Cancer Res., 57, 81-86.
6. Cheng,Y. et al. (2007) 4-Methoxyestradiol-induced oxidative injuries in human lung epithelial cells. Toxicol. Appl. Pharmacol. 220, 271-277.
7. Cavalieri,E. et al. (2006) Catechol estrogen quinones as initiators of breast and other human cancers: Implications for biomarkers of susceptibility and cancer prevention. Biochim. Biophys. Acta, 1766, 63-78.
8. Rogan,E.G. et al. (2003) Relative imbalances in estrogen metabolism and conjugation in breast tissue of women with carcinoma: potential biomarkers of susceptibility to cancer. Carcinogenesis, 24, 697-702.
9. Singh,S. et al. (2005) Relative imbalances in the expression of estrogen-metabolizing enzymes in the breast tissue of women with breast carcinoma. Oncol. Rep., 14, 1091-1096.
10. Wen,W. et al. (2007) Expression of cytochrome P450 1B1 and catechol-O-methyltransferase in breast tissue and their associations with breast cancer risk. Cancer Epidemiol. Biomarkers Prev., 16 917-920.
11. Mitrunen,K. et al. (2003) Molecular epidemiology of sporadic breast cancer. The role of polymorphic genes involved in oestrogen biosynthesis and metabolism. Mutat. Res., 544, 9-41.
12. Zhu,B.T. et al. (1996) Inhibition of catechol O-methyltransferase-catalyzed O-methylation of 2- and 4-hydroxyestradiol by quercetin. Possible role in estradiol-induced tumorigenesis. J. Biol. Chem., 271, 1357-1363.
13. Adlercreutz,H. et al. (2004) Phytoestrogens, cancer and coronary heart disease. Biofactors, 22, 229-236.
14. Lamartiniere,C.A. et al. (2002) Genistein chemoprevention: Timing and mechanisms of action in murine mammary and prostate. J. Nutr., 132, 552S-558S.
15. Allred,C.D. et al. (2001) Dietary genistein stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein. Carcinogenesis, 22, 1667-1673.
16. Day,J.K. et al. (2001) Dietary genistein increased DMBA-induced mammary adenocarcinoma in wild-type, but not ER alpha KO, mice. Nutr. Cancer, 39, 226-232.
17. Hsieh,C.Y. et al. (1998) Estrogenic effects of genistein on the growth of estrogen receptor-positive human breast cancer (MCF-7) cells in vitro and in vivo. Cancer Res., 58, 3833-3838.
18. Messina,M. et al. (2006) Addressing the soy and breast cancer relationship: Review, commentary, and workshop proceedings. J. Natl Cancer Inst., 98, 1275-1284.
19. Stopper,H. et al. (2005) Genotoxicity of phytoestrogens. Mutat. Res., 574, 139-155.
20. van Duursen,M.B. et al. (2004) Phytochemicals inhibit catechol-O-methyltransferase activity in cytosolic fractions from healthy human mammary tissues: Implications for cateehol estrogen-induced DNA damage. Toxicol. Sci., 81, 316-324.
21. Boudikova,B. et al. (1990) Human liver catechol-O-methyltransferase pharmacogenetics. Clin. Pharmacol. Ther. 48, 381-389.
22. Jori,A. et al. (1973) Homovanillic acid levels in rat striatum during the oestrous cycle. J. Endocrinol., 58, 341-342.
23. Parvez,S. et al. (1978) Activity of catechol-o-methyltransferase in brain regions and adrenal gland during the oestrus cycle. J. Neural Transm., 42, 305-312.
24. Xie,T. et al. (1999) Characterization and implications of estrogenic down-regulation of human catechol-O-methyltransferase gene transcription. Mol. Pharmacol., 56, 31-38.
25. Jiang,H. et al. (2003) Human catechol-O-methyltransferase down-regulation by estradiol. Neuropharmacology, 45, 1011-1018.
26. Anderson,K.M. et al. (1997) Rapid generation of homologous internal standards and evaluation of data for quantitation of messenger RNA by competitive polymerase chain reaction. J. Pharmacol. Toxicol. Methods, 38, 133-140.
27. de Kok,J.B. et al. (2005) Normalization of gene expression measurements in tumor tissues: Comparison of 13 endogenous control genes. Lab. Invest., 85, 154-159.
28. Rey,J.M. et al. (2000) Semiquantitative reverse transcription-polymerase chain reaction to evaluate the expression patterns of genes involved in the oestrogen pathway. J. Mol. Endocrinol., 24, 433-440.
29. Brogdon,W.G. et al. (1983) A microassay system for measuring esterase activity and protein concentration in small samples and in high-pressure liquid chromatography eluate fractions. Anal. Biochem. 131, 499-503.
30. Gugler,R. et al. (1973) Inhibition of human liver catechol-O-methyltransferase by flavonoids. Naunyn Schmiedebergs Arch. Pharmacol., 276, 223-233.
31. Nagai,M. et al. (2004) Strong inhibitory effects of common tea catechins and bioflavonoids on the O-methylation of catechol estrogens catalyzed by human liver cytosolic catechol-O-methyltransferase. Drug Metab. Dispos., 32, 497-504.
32. Kuiper,G.G. et al. (1998) Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology, 139 4252-4263.
33. Wakeling,A.E. et al. (1992) ICI 182,780, a new antioestrogen with clinical potential. J. Steroid Biochem. Mol. Biol., 43, 173-177.
34. Wakeling,A.E. et al. (1991) A potent specific pure antiestrogen with clinical potential. Cancer Res., 51, 3867-3873.
35. Lavigne,J.A. et al. (2007) Concentration-dependent effects of genistein on global gene expression in MCF-7 breast cancer cells: An oligo microarray study. Breast Cancer Res. Treat. in press.
36. Payne,J. et al. (2000) Improving the reproducibility of the MCF-7 cell proliferation assay for the detection of xenoestrogens. Sci. Total Environ., 248, 51-62.
37. Rasmussen,T.H. et al. (2002) Critical parameters in the MCF-7 cell proliferation bioassay (E-Screen). Biomarkers, 7, 322-336.
38. Kulling,S. et al. (2002) Oxidative metabolism and genotoxic potential of major isoflavone phytoestrogens. J. Chromatogr. B, 777, 211-218.
39. Lehmann,L. et al. (2005) Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of daidzein in cultured human Ishikawa cells. Toxicol. Lett., 158, 72-86.
40. Lavigne,J.A. et al. (2001) The effects of catechol-O-methyltransferase inhibition on estrogen metabolite and oxidative DNA damage levels in estradiol-treated MCF-7 cells. Cancer Res., 61, 7488-7494.
41. Hirose,Y. et al. (2007) Effects of a catechol-O-methyltransferase inhibitor on catechol estrogen-induced cellular transformation, chromosome aberrations and apoptosis in Syrian hamster embryo cells. Int. J. Cancer, 120, 1627-1633.
42. Zhu,B.T. et al. (1994) Quercetin increases the severity of estradiol-induced tumorigenesis in hamster kidney. Toxicol. Appl. Pharmacol., 125, 149-158.
43. Gaudet,M.M. et al. (2006) Catechol-O-methyltransferase haplotypes and breast cancer among women on Long Island, New York. Breast Cancer Res. Treat., 99, 235-240.
44. Gaudet,M.M. et al. (2006) Comprehensive asessment of genetic variation of catechol-o-methyltransferase and breast cancer risk. Cancer Res., 66, 9781-9785.
45. Huang,C.S. et al. (1999) Breast cancer risk associated with genotype polymorphism of the estrogen-metabolizing genes CYP17, CYP1A1, and COMT: A multigenic study on cancer susceptibility. Cancer Res. 59, 4870-4875.
46. Lavigne,J.A. et al. (1997) An association between the allele coding for a low activity variant of catechol-O-methyltransferase and the risk for breast cancer. Cancer Res., 57, 5493-5497.
47. Hamajima,N. et al. (2001) Limited association between a catechol-O-methyltransferase (COMT) polymorphism and breast cancer risk in Japan. Int. J. Clin. Oncol., 6, 13-18.
48. Hong,C.C. et al. (2003) Val158Met Polymorphism in catechol-O-methyltransferase gene associated with risk factors for breast cancer. Cancer Epidemiol. Biomarkers Prev., 12, 838-847.
49. Wen,W. et al. (2005) Cytochrome P450 1B1 and catechol-methyltransferase genetic polymorphisms and breast cancer risk in Chinese women: Results from the shanghai breast cancer study and a meta-analysis. Cancer Epidemiol. Biomarkers Prev., 14, 329-335.
50. Cassidy,A. et al. (1994) Biological effects of a diet of soy protein rich in isoflavones on the menstrual cycle of premenopausal women. Am. J. Clin. Nutr., 60, 333-340.
51. Watanabe,S. et al. (2000) Effects of isoflavone supplement on healthy women. Biofactors, 12, 233-241.
52. Zhu,G. et al. (2004) Differential expression of human COMT alleles in brain and lymphoblasts detected by RT-coupled 5′ nuclease assay. Psychopharmacology (Berl), 177, 178-184.