Estrogen carcinogenesis: Specific identification of estrogen-modified nucleobase in breast tissue from women

Chemical Research in Toxicology

Volumn 21, Issue 8, 2008, Pages 1509-1513

  Zhang, Qiang ^a   Aft, Rebecca L ^a   Gross, Michael L ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTROGEN; ESTRONE;

ARTICLE; BREAST CANCER; CARCINOGENESIS; CHEMICAL STRUCTURE; CLINICAL ARTICLE; FEMALE; HUMAN; HUMAN TISSUE; IMMUNOPRECIPITATION; LIQUID CHROMATOGRAPHY; RISK FACTOR; TANDEM MASS SPECTROMETRY;

ADENINE; BREAST; CARCINOGENS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESTROGENS; ESTRONE; FEMALE; HUMANS; POSTMENOPAUSE; PREDICTIVE VALUE OF TESTS; PREMENOPAUSE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 51449103374     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx8001737     Document Type: Article

References (21)

1. Yager, J. D., and Liehr, J. G. (1996) Molecular mechanisms of estrogen carcinogenesis. Annu. Rev. Pharmacol. Toxicol. 36, 203-232.
2. Clemons, M., and Goss, P. (2001) Mechanisms of disease - Estrogen and the risk of breast cancer. N. Engl. J. Med. 344, 276-285.
3. Santen, R. J. (2002) To block estrogen's synthesis or action: That is the question. J. Clin. Endocrinol. Metab. 87, 3007-3012.
4. Liehr, J. G., Avitts, T. A., Randerath, E., and Randerath, K. (1986) Estrogen-induced endogenous DNA adduction: Possible mechanism of hormonal cancer. Proc. Natl. Acad. Sci. U.S.A. 83, 5301-5305.
5. 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. U.S.A. 94, 10937-10942.
6. Yue, W., Santen, R. J., Wang, J. P., Li, Y., Verderame, M. F., Bocchinfuso, W. R., Korach, K. S., Devanesan, P., Todorovic, R., Rogan, E. G., and Cavalieri, E. L. (2003) Genotoxic metabolites of estradiol in breast: Potential mechanism of estradiol induced carcinogenesis. J. Steroid Biochem. Mol. Biol. 86, 477-486.
7. Li, K. M., Todorovic, R., Devanesan, P., Higginbotham, S., Kofeler, H., Ramanathan, R., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (2004) Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo. Carcinogenesis 25, 289-297.
8. Yager, J. D., and Davidson, N. E. (2006) Mechanisms of disease: Estrogen carcinogenesis in breast cancer. N. Engl. J. Med. 354, 270-282.
9. Zahid, M., Kohli, E., Saeed, M., Rogan, E., and Cavalieri, E. (2006) The greater reactivity of estradiol-3,4-quinone vs estradiol-2,3-quinone with DNA in the formation of depurinating adducts: Implications for tumor-initiating activity. Chem. Res. Toxicol. 19, 164-172.
10. Iverson, S. L., Shen, L., Anlar, N., and Bolton, J. L. (1996) Bioactivation of estrone and its catechol metabolites to quinoidglutathione conjugates in rat liver microsomes. Chem. Res. Toxicol. 9, 492-499.
11. Markushin, Y., Zhong, W., Cavalieri, E. L., Rogan, E. G., Small, G. J., Yeung, E. S., and Jankowiak, R. (2003) Spectral characterization of catechol estrogen quinone (CEQ)-derived DNA adducts and their identification in human breast tissue extract. Chem. Res. Toxicol. 16, 1107-1117.
12. Embrechts, J., Lemiere, F., Van Dongen, W., Esmans, E. L., Buytaert, P., Van Marck, E., Kockx, M., and Makar, A. (2003) Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 14, 482-491.
13. Markushin, Y., Gaikwad, N., Zhang, H., Kapke, P., Rogan, E. G., Cavalieri, E. L., Track, B. J., Pavlovich, C., and Jankowiak, R. (2006) Potential biomarker for early risk assessment of prostate cancer. Prostate 66, 1565-1571.
14. Gaikwad, N. W., Yang, L., Muti, P., Meza, J. L., Pruthi, S., Ingle, J. N., Rogan, E. G., and Cavalieri, E. L. (2008) The molecular etiology of breast cancer: Evidence from biomarkers of risk. Int. J. Cancer 122, 1949-1957.
15. Todorovic, R., Devanesan, P., Higginbotham, S., Zhao, J., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (2001) Analysis of potential biomarkers of estrogen-initiated cancer in the urine of Syrian golden hamsters treated with 4-hydroxyestradiol. Carcinogenesis 22, 905-911.
16. Zhang, Q., and Gross, M. L. (2008) Efficient synthesis, liquid-chromatography purification, and tandem mass spectrometric characterization of estrogen-modified DNA bases. Chem. Res. Toxicol. 21, 1244-1252.
17. Pasqualini, J. R., Chetrite, G., Blacker, C., Feinstein, M. C., Delalonde, L., Talbi, M., and Maloche, C. (1996) Concentrations of estrone, estradiol, and estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients. J. Clin. Endocrinol. Metab. 81, 1460-1464.
18. Frigerio, M., Santagostino, M., and Sputore, S. (1999) A user-friendly entry to 2-iodoxybenzoic acid (IBX). J. Org. Chem. 64, 4537-4538.
19. Belous, A. R., Hachey, D. L., Dawling, S., Roodi, N., and Parl, F. F. (2007) Cytochrome P4501B1-mediated estrogen metabolism results in estrogen-deoxyribonucleoside adduct formation. Cancer Res. 67, 812-817.
20. Saeed, M., Rogan, E., Fernandez, S. V., Sheriff, F., Russo, J., and Cavalieri, E. (2007) Formation of depurinating N3Adenine and N7Guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol. Int. J. Cancer 120, 1821-1824.
21. 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.