150
Views
25
CrossRef citations to date
0
Altmetric
Original Articles

2-HYDROXYESTRADIOL INDUCES OXIDATIVE DNA DAMAGE AND APOPTOSIS IN HUMAN MAMMARY EPITHELIAL CELLS

, , , &
Pages 1939-1953 | Published online: 12 Aug 2010

REFERENCES

  • Bernstein , L. and Ross , R. K. 1993 . Endogenous hormones and breast cancer risk . Epidemiol. Rev. , 15 : 48 – 65 .
  • Cavalieri , E. L. , Stack , D. E. , Devanesan , P. D. , Todorovic , R. , Dwivedy , I. , Higginbotham , S. , Johansson , S. L. , Patil , K. D. , Gross , M. L. , Gooden , J. K. , Ramanathan , R. , Cerny , R. L. and Rogan , E. G. 1997 . Molecular origin of cancer: Catechol estrogen-3,4-quinones as endogenous tumor initiators . Proc. Natl. Acad. Sci. USA , 94 : 10937 – 10942 .
  • Cavalieri , E. L. , Frenkel , K. , Liehr , J. G. , Rogan , E. and Roy , D. 2000 . Estrogens as endogenous genotoxic agents—DNA adducts and mutations . J. Natl. Cancer. Inst. Monogr. , 27 : 75 – 93 .
  • Cavalieri , E. L. , Devanesan , P. , Bosland , M. C. , Badawi , A. F. and Rogan , E. G. 2002 . Catechol estrogen metabolites and conjugates in different regions of the prostate of Noble rats treated with 4-hydroxyestradiol: implications for estrogen-induced initiation of prostate cancer . Carcinogenesis , 23 : 329 – 333 .
  • Chen , Z.-H. , Hurh , Y.-J. , Na , H.-K. , Kim , J.-H. , Chun , Y.-J. , Kim , D.-H. , Kang , K.-S. , Cho , M.-H. and Surh , Y.-J. 2004 . “ Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells ” . In Carcinogenesis , (In press) .
  • Convert , O. , Aerden , C. , Debrauwer , L. , Rathahao , E. , Molines , H. , Fournier , F. , Tabet , J. C. and Paris , A. 2002 . Reactions of estradiol-2,3-quinone with deoxyribonucleosides: Possible insights in the reactivity of estrogen quinones with DNA . Chem. Res. Toxicol. , 15 : 754 – 764 .
  • Hayes , C. L. , Spink , D. C. , Spink , B. C. , Cao , J. Q. , Walker , N. J. and Sutter , T. R. 1996 . 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1B1 . Proc. Natl. Acad. Sci. USA , 93 : 9776 – 9781 .
  • Henderson , B. E. and Feigelson , H. S. 2000 . Hormonal carcinogenesis . Carcinogenesis , 21 : 427 – 433 .
  • Henderson , B. E. , Ross , R. K. , Pike , M. C. and Casagrande , J. T. 1982 . Endogenous hormones as a major factor in human cancer . Cancer Res. , 42 : 3232 – 3239 .
  • Hiraku , Y. , Yamashita , N. , Nishiguchi , M. and Kawanishi , S. 2001 . Catechol estrogens induce oxidative DNA damage and estradiol enhances cell proliferation . Int. J. Cancer , 92 : 333 – 337 .
  • Huseby , R. A. 1980 . Demonstration of a direct carcinogenic effect of estradiol on Leydig cells of the mouse . Cancer Res. , 40 : 1006 – 1013 .
  • Jang , J.-H. and Surh , Y.-J. 2003 . Protective effect of resveratrol on beta-amyloid-induced oxidative PC12 cell death . Free Radical Biol. Med. , 34 : 1100 – 1110 .
  • Kang , C. D. , Jang , J. H. , Kim , K. W. , Lee , H. J. , Jeong , C. S. , Kim , C. M. , Kim , S. H. and Chung , B. S. 1998 . Activation of c-jun N-terminal kinase/stress-activated protein kinase and the decreased ratio of Bcl-2 to Bax are associated with the autoxidized dopamine-induced apoptosis in PC12 cells . Neurosci. Lett. , 25 : 37 – 40 .
  • Kang , H. J. , Soh , Y. , Kim , M. S. , Lee , E. J. , Surh , Y.-J. , Kim , H. R. , Kim , S. H. and Moon , A. 2003 . Roles of JNK-1 and p38 in selective induction of apoptosis by capsaicin in ras-transformed human breast epithelial cells . Int. J. Cancer , 103 : 475 – 482 .
  • Kuchino , Y. , Mori , F. , Kasai , H. , Inoue , H. , Iwai , S. , Miura , K. , Ohtsuka , E. and Nishimura , S. 1987 . Misreading of DNA templates containing 8-hydroxydeoxyguanosine at the modified base and at adjacent residues . Nature , 327 : 77 – 79 .
  • Li , Y. and Trush , M. A. 1993a . DNA damage resulting from the oxidation of hydroquinone by copper: Role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation. . Carcinogenesis , 14 : 1303 – 1311 .
  • Li , Y. and Trush , M. A. 1993b . Oxidation of hydroquinone by copper: Chemical mechanism and biological effects. . Arch. Biochem. Biophys. , 300 : 346 – 355 .
  • Liehr , J. G. 2000 . Is estradiol a genotoxic mutagenic carcinogen? . Endocrin. Rev. , 21 : 40 – 54 .
  • Liehr , J. G. and Jones , J. S. 2001 . Role of iron in estrogen-induced cancer . Curr. Med. Chem. , 8 : 839 – 849 .
  • Liehr , J. G. and Ricci , M. J. 1996 . 4-Hydroxylation of estrogens as marker of human mammary tumors . Proc. Natl. Acad. Sci. USA , 93 : 3294 – 3926 .
  • Liehr , J. G. and Roy , D. 1990 . Free radical generation by redox cycling of estrogens . Free Radical Biol. Med. , 8 : 415 – 423 .
  • Lin , P.-H. , Nakamura , J. , Yamaguchi , S. , Asakkura , S. and Swenberg , J. A. 2003 . Aldehydic DNA lesions induced by catechol estrogens in calf thymus DNA . Carcinogenesis , 24 : 1133 – 1141 .
  • Mobley , J. A. , Bhat , A. S. and Brueggemeier , R. W. 1999 . Measurement of oxidative DNA damage by catechol estrogens and analogues in vitro . Chem. Res. Toxicol. , 12 : 270 – 277 .
  • Murray , G. I. , Taylor , M. C. , McFadyen , M. C. , McKay , J. A. , Greenlee , W. F. , Burke , M. D. and Melvin , W. T. 1997 . Tumor-specific expression of cytochrome P450 CYP1B1 . Cancer Res. , 57 : 3026 – 3031 .
  • Newbold , R. R. and Liehr , J. G. 2000 . Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens . Cancer Res. , 60 : 235 – 237 .
  • Rogan , E. G. , Badawi , A. F. , Devanesan , P. D. , Meza , J. L. , Edney , J. A. , West , W. W. , Higginbotham , S. M. and Cavalieri , E. L. 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 .
  • Roy , D. and Liehr , J. G. 1988 . Temporary decrease in renal quinone reductase activity induced by chronic administration of estradiol to male Syrian hamsters. Increased superoxide formation by redox cycling of estrogen . J. Biol. Chem. , 263 : 3646 – 3651 .
  • Roy , D. and Liehr , J. G. 1989 . Changes in activities of free radical detoxifying enzymes in kidneys of male Syrian hamsters treated with estradiol . Cancer Res. , 49 : 1475 – 1480 .
  • Sato , M. , Bagchi , D. , Tosaki , A. and Das , D. K. 2001 . Grape seed proanthocyanidin reduces cardiomyocyte apoptosis by inhibiting ischemia/reperfusion-induced activation of JNK-1 and c-JUN . Free Radical Biol. Med. , 31 : 729 – 737 .
  • Seacat , A. M. , Kuppusamy , P. , Zweier , J. L. and Yager , J. D. 1997 . ESR identification of free radicals formed from the oxidation of catechol estrogens by Cu2+ . Arch. Biochem. Biophys. , 347 : 45 – 52 .
  • Shin , M.-H. , Jang , J.-H. and Surh , Y.-J. 2004 . Potential roles of NF-κB and ERK1/2 in cytoprotection against oxidative cell death induced by tetrahydropapaveroline . Free Radical Biol. Med. , 36 : 1185 – 1194 .
  • Surh , Y.-J. , Jung , Y.-J. , Jang , J.-H. , Lee , J.-S. and Yoon , H.-R. 2002 . Iron enhancement of oxidative DNA damage and neuronal cell death induced by salsolinol . J. Toxicol. Environ. Health A , 65 : 473 – 488 .
  • Terashima , I. , Suzuki , N. and Shibutani , S. 2001 . Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells . Biochemistry , 40 : 166 – 172 .
  • Thibodeau , P. A. and Paquette , B. 1999 . DNA damage induced by catechol estrogens in the presence of copper(II): Generation of reactive oxygen species and enhancement by NADH . Free Radical Biol. Med. , 27 : 1367 – 1377 .
  • Yagi , E. , Barrett , J. C. and Tsutsui , T. 2001 . The ability of four catechol estrogens of 17β-estradiol and estrone to induce DNA adducts in Syrian hamster embryo fibroblasts . Carcinogenesis , 22 : 1505 – 1510 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.