Antioxidant inhibits tamoxifen-DNA adducts in endometrial explant culture

Biochemical and Biophysical Research Communications

Volumn 307, Issue 1, 2003, Pages 157-164

  Sharma, Minoti ^a   Shubert, David E ^a   Sharma, Moheswar ^a   Rodabaugh, Kerry J ^a   McGarrigle, Barbara P ^b   Vezina, Chad M ^b   Bofinger, Diane P ^c   Olson, James R ^b  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

^b UNIVERSITY AT BUFFALO   (United States)

^c UNIVERSITY AT BUFFALO   (United States)

Author keywords

Antioxidant; Explant culture; Human endometrial tissue; Tamoxifen metabolites; Tamoxifen DNA adducts

Indexed keywords

4 HYDROXYTAMOXIFEN; ALCOHOL; ALPHA HYDROXYTAMOXIFEN; ALPHA(DEOXYGUANOSYL N 2)TAMOXIFEN; ANTIOXIDANT; ASCORBIC ACID; DNA; DRUG METABOLITE; NORTAMOXIFEN; NUCLEOTIDE; TAMOXIFEN; TAMOXIFEN DERIVATIVE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CULTURE MEDIUM; DNA ADDUCT; DNA DETERMINATION; DNA DRUG COMPLEX; DRUG EFFECT; DRUG EXPOSURE; DRUG OXIDATION; DRUG TRANSFORMATION; ENDOMETRIUM; EXPLANT; FEMALE; GENOTOXICITY; HUMAN; HUMAN TISSUE; INCUBATION TIME; PRIORITY JOURNAL; STANDARD; TEMPERATURE;

EID: 0038387788     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-291X(03)01134-3     Document Type: Article

References (50)

1. Early Breast Cancer Trialists' Collaborative Group, Tamoxifen for early breast cancer: an overview of the randomized trials, Lancet 351 (1998) 1451-1467.
2. B. Fisher, J.P. Costantino, D.L. Wickerham, C.K., Redmond, M. Kavanah, W.M. Cronin, V. Vogel, A. Robidoux, N. Dimitrov, J. Atkins, M. Daly, S. Wieand, E., Tan-Chiu, L. Ford, N. Wolmark, and others, National Surgical Adjuvant Breast and Bowel Project Investigators, Tamoxifen for prevention of breast cancer. Report of the National Surgical Adjuvant Breast and Bowel Project P-1 Study, J. Natl. Cancer Inst. 90 (1998) 1371-1388.
3. L. Bergman, M.L.R. Beelen, M.P.W. Galle, H. Hollema, J. Benraadt, F.E. van Leeuwen and the Comprehensive Cancer Centers' ALERT Group, Risk and prognosis of endometrial cancer after tamoxifen for breast cancer, Lancet 356 (2000) 881-887.
4. Deligdisch L., Kalir T., Cohen C.J., de Larour M., Le Bouedec G., Penault-Llorca F. Enodmetiral histopathology in 700 patients treated with tamoxifen for breast cancer. Gynecol. Oncol. 78:2000;181-186.
5. Mantyla E., Karlsson S., Nieminen L. Induction of endometrial cancer by tamoxifen in the rat. Li J.J., Li S.A., Gustafsson J.A., Nandi N., Sekely L.I. Hormonal Carcinogenesis II. 1996;442-445 Springer, New York.
6. Hirsimaki P., Hirsimaki Y., Nieminen L., Karlsson S., Mantyla E. On the safety studies of the antiestrogens toremifine and tamoxifen. Scand. J. Lab. Anim. Sci. 23:1996;147-1543.
7. Lim C.K., Yuan Z.-X., Lamb J.H., White I.N.H., Matteis F.D., Smith L.L. A comparative study of tamoxifen metabolism in female rat, mouse and human liver microsomes. Carcinogenesis. 15:1994;589-593.
8. IARC, Monographs on the evolution of carcinogenic risks to humans, vol. 66, Some Pharmaceutical Drugs, IARC, Lyon, France, 1996, pp. 253-365.
9. Phillips D.H. Understanding the genotoxicity of tamoxifen. Carcinogenesis. 22:2001;839-861.
10. Potter G.A., McCague R., Jarman M. A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism. Carcinogenesis. 15:1994;439-442.
11. Shibutani S., Dasardhi L., Terashima I., Banoglu E., Duffel M.W. α-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfortransferase, resulting in tamoxifen DNA adducts. Cancer Res. 58:1998;647-653.
12. Glatt H., Davis W., Meinl W., Hermesdorfer H., Venitt S., Phillips D.H. Rat, but not human, sulfotransferase activates a tamoxifen metabolite to produce DNA adducts and gene mutations in bacteria and mammalian cells in culture. Carcinogenesis. 19:1998;1709-1713.
13. Shibutani S., Shaw P.M., Suzuki N., Dasaradhi L., Duffel M.W., Terashima I. Sulfation of α-hydroxytamoxifen catalyzed by human hydroxysteroid sulfotransferase results in tamoxifen-DNA adducts. Carcinogenesis. 19:1998;2007-2011.
14. Glatt H., Bartsch I., Cristoph S., Coughtrie M.W.H., Falany C.N., Hagen M., Landsiedel R., Pabel U., Phillips D.H., Seidel A., Yamazoe Y. Suofotransferase-mediated activation of mutagens studied using heterologous expression systems. Chem. Biol. Interact. 109:1998;195-219.
15. Osborne M.R., Hewer A., Hardcastle I.R., Carmichael P.L., Phillips D.H. Identification of the major tamoxifen-deoxyguanosine adducts formed in the liver DNA of rats treated with tamoxifen. Cancer Res. 56:1996;66-71.
16. Gambos da Costa G., McDaniel-Hamilton L.P., Heflich R.H., Marques M.M., Beland F.A. DNA adduct formation and mutant induction in Sprague-Dawley rats treated with tamoxifen and its derivatives. Carcinogenesis. 22:2001;1307-1315.
17. Hemminki K., Rajaniemi H., Lindahl B., Moberger B. Tamoxifen-induced DNA adducts in endometrial samples from breast cancer patients. Cancer Res. 56:1996;4374-4377.
18. Shibutani S., Suzuki N., Terashima I., Sugarman S.M., Grollman A.P., Pearl M.L. Tamoxifen-DNA adducts detected in the enodmetrium of women treated with tamoxifen. Chem. Res. Toxicol. 12:1999;546-653.
19. Shibutani S., Ravindernath A., Suzuki N., Terashima I., Sugarman S.M., Grollman A.P., Pearl M.L. Identification of tamoxifen-DNA adducts in the endometrium of women treated with tamoxifen. Carcinogenesis. 21:2000;1461-1467.
20. Carmichael P.L., Ugwumadu A.H.N., Neven P., Hewer A.J., Poon G.K., Phillips D.H. Lack of genotoxicity of tamoxifen in human enodmetrium. Cancer Res. 56:1996;1475-1479.
21. 32-postlabeling for tamoxifen-DNA adducts in the human endometrium. Carcinogenesis. 20:1999;339-342.
22. Gamboa da Costa G., Marques M.M., Beland F.A., Freeman J.P., Churchwell M.I., Doerge D.R. Quantification of tamoxifen DNA adducts using on-line sample preparation and HPLC-electrospray ionization tandem mass spectrometry. Chem. Res. Toxicol. 16:2003;357-366.
23. Grady D., Gebretsadik T., Kerlikowske K., Emster V., Petitti D. Hormone replacement therapy and endometrial cancer risk: a meta-analysis. Obstet. Gynecol. 85:1995;304-313.
24. J.G. Liehr, M.J. Ricci, C.R. Jefcoate, E.V. Hannigan, J.A. Hokanson, B.T. Zhu, 4-Hydroxylation of estradiol by human uterine myometrium and myoma microsomes: implications for the mechanism of uterine tumorigenesis, Proc. Natl. Acad. Sci. USA 92 (1995) 9220-9224.
25. Hayes C.L., Spink D.C., Spink B.C., Cao B.C., Walker N., Sutter R. 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1B1. Proc. Natl. Acad. Sci. USA. 93:1996;9776-9781.
26. Hukkanen J., Mantyla M., Kangas L., Wirta P., Hakkola J., Paakki P., Evisalmi S., Pelkonen O., Raunio H. Expression of cytochrome P450 genes encoding enzymes active in the metabolism of tamoxifen in human uterine endometrium. Pharmacol. Toxicol. 82:1998;93-97.
27. Sharma M., Lewis J., Sharma M., McGarrigle B.P., Shubert D.E., Bofinger D.P., Olson J.R. Biotransformation of tamoxifen in a human endometrial explant culture model. Int. J. Cancer. S13:2002;18 M. Sharma, D.E. Shubert, M. Sharma, J. Lewis, B.P. McGarrigle, D.P. Bofinger, J.R. Olson, Biotransformation of tamoxifen in a human endometrial explant culture model, Chem.-Biol. Interact., in press.
28. Foster A.B., Jarman M., Leung O.-T., McCague R., Leclercq G., Devleeschouwer N. Hydroxy derivatives of tamoxifen. J. Med. Chem. 28:1985;1491-1497.
29. Brown K., Heydon R.T., Jukes R., White I.N.H., Martin E.A. Further characterization of the DNA adducts formed in rat liver after the administration of tamoxifen, N-desmethyltamoxifen or N,N-didesmethyltamoxifen. Carcinogenesis. 20:1999;2061-2066.
30. Osteen K.G., Rodgers W.H., Gaire M., Hargrove J.T., Gorstein F., Matrisian L.M. Stromal-epithelial interaction mediated steroidal regulation of metalloproteinase expression in human endometrium. Proc. Natl. Acad. Sci. USA. 91:1994;10129-10133.
31. Bofinger D.P., Feng L., Chi L.-H., Love J., Stephen F.D., Sutter T.R., Osteen K.G., Coslich T.G., Batt R.E., Koury S.T., Olson J.R. Effect of TCDD exposure on CYP1A1 and CYP1B1 in explant cultures of human endometrium. Toxicol. Sci. 62:2001;299-314.
32. Sharma M., Slocum H.K. Prevention of quinone-mediated DNA arylation by antioxidants. Biochem. Biophys. Res. Commun. 262:1999;769-774.
33. Fried K.M., Wainer I.W. Direct determination of tamoxifen and its four major metabolites in plasma using coupled column high-performance liquid chromatography. J. Chromatogr. B. 655:1994;261-268.
34. Merle O., Guitton J., Burke M.D., Ollagnier M. Rapid and simple method to determine tamoxifen and its major metabolites in human liver microsomes by high performance liquid chromatography with fluorescence detection. Anal. Lett. 31:1998;2067-2076.
35. Brown R.R., Bain R., Jordan V.C. Determination of tamoxifen and metabolites in human serum by high-performance liquid chromatography with post-column fluorescence activation. J. Chromatogr. 272:1983;351-358.
36. Lien E.A., Soleim E., Ueland P.M. Distribution of tamoxifen and its metabolites in rat and human tissues during steady-state treatment. Cancer Res. 51:1991;4837-4844.
37. Giorda G., Franceschi L., Crivellari D., Magri M.D., Veronesi A., Scarabelli C., Furlanut M. Determination of tamoxifen and its metabolites in the endometrial tissue of long-term treated women. Eur. J. Cancer. 36:2000;S81-S91.
38. 32P-Labeling test for DNA damage. Proc. Natl. Acad. Sci. USA. 78:1981;6126-6129.
39. 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis. 7:1986;1543-1551.
40. Sharma M., Freund H.G. Development of laser-induced fluorescence detection to assay DNA damage. Fearey B.L. Optical Methods for Ultrasensitive Detection and Analysis: Techniques and Applications. Proc. SPIE. 1435:1991;280-291.
41. Jain R., Sharma M. Fluorescence postlableling assay of DNA damage induced by N-methyl-N-nitrosourea. Cancer Res. 53:1993;2771-2774.
42. Sharma M., Jain R., Campbell R.B., Ionescu E., Slocum H.K. Nonisotopic detection of 5-fluorouracil incorporation into nucleic acids of exposed human ileocecal adenocarcinoma (HCT-8) cells. Rao R.S., Deo M.G., Sanghvi L.D. Proc. XVI Int. Cancer Congr., New Delhi, India, 30 October-5 November. 3:1994;1885-1889.
43. ′ -deoxythymidine incorporation in DNA of human colon tumor cells Bioconjug. Chem. 6:1995;536-540.
44. Sharma M. Analysis of tamoxifen-DNA adducts by high-performance liquid chromatography using postcolumn online photochemical activation. Biochem. Biophys. Res. Commun. 273:2000;40-44.
45. Ames B.N. Micronutrients prevent cancer and delay aging. Toxcicol. Lett. 102-103:1998;5-18.
46. Head K.A. Ascorbic acid in the prevention and treatment of cancer. Altern. Med. Rev. 3:1998;174-186.
47. Jordan C.G.M., Brown K., Beedham C., Brown J.E. Effects of inhibitors on the biotransformation of tamoxifen by female rat and mouse liver slices and homogenates. Drug Metab. Drug Interact. 15:1999;239-258.
48. Holinka C.F., Gurpide E. Peroxidase activity in glands and stroma of human endometrium. Am. J. Obstet. Gynecol. 1:1980;599-603.
49. Glascott P.A., Gilfor E. Jr., Farber J.L. Relationship of metabolism of vitamins C and E in cultured hepatocytes treated with tert-butylhydroperoxide. Mol. Pharmacol. 48:1995;80-88.
50. Niki E. Vitamin C as an antioxidant. World. Rev. Nutr. Diet. 64:1991;1-30.