Mutagenic potential of α-(N2-deoxyguanosinyl)tamoxifen lesions, the major DNA adducts detected in endometrial tissues of patients treated with tamoxifen

Cancer Research

Volumn 59, Issue 9, 1999, Pages 2091-2095

  Terashima, Isamu ^a   Suzuki, Naomi ^a   Shibutani, Shinya ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAMOXIFEN;

ARTICLE; BREAST CANCER; CANCER RISK; CARCINOGENICITY; DNA SEQUENCE; DRUG STRUCTURE; ENDOMETRIUM CANCER; HUMAN; HUMAN TISSUE; MUTAGENICITY; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

ANIMALS; ANTINEOPLASTIC AGENTS, HORMONAL; BASE SEQUENCE; BREAST NEOPLASMS; COS CELLS; DNA ADDUCTS; ENDOMETRIUM; FEMALE; GENETIC VECTORS; HUMANS; ISOMERISM; MOLECULAR SEQUENCE DATA; MOLECULAR STRUCTURE; MUTAGENESIS; MUTAGENICITY TESTS; OLIGODEOXYRIBONUCLEOTIDES; POINT MUTATION; TAMOXIFEN;

EID: 0033135051     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (45)

1. Jordan, V. C. A current view of tamoxifen for the treatment and prevention of breast cancer. Br. J. Pharmacol., 110: 507-517, 1993.
2. Powles, T. J., Hardy, J. R., Ashley, S. E., Farrington, G. H., Cosgrove, D., Davey, J. R., Dowsett, M., McKinna, J. A., Wash, A. G., Sennet, H. D., Tillyer, C. R., and Treleavan, J. G. A pilot trial to evaluate the acute toxicology and feasibility of tamoxifen for the prevention of breast cancer. Br. J. Cancer, 60: 126-131, 1993.
3. Nayfield, S. G., Karp, J. E., Ford, L. G., Dorr, F. A., and Kramer, B. S. Potential role of tamoxifen in prevention of breast cancer. J. Natl. Cancer Inst. (Bethesda), 83: 1450-1459, 1991.
4. Fisher, B., Costantino, J. P., Wickerham, L., Redmond, C. K., Kavanah, M., Cronin, W. M., Vogel, V., Robidoux, A., Dimitrov, N., Atkins, J., Daly, M., Wieand, S., Tan-Chiu, E., Ford, L., Wolmark, N., and other NSABP Investigators. Tamoxifen for prevention of breast cancer: report of the National Surgical Adjuvant Breast and Bowel Project P-1 study. J. Natl. Cancer Inst. (Bethesda), 90: 1371-1388, 1998.
5. Powles, T., Eeles, R., Ashley, S., Easton, D., Chang, J., Dowsett, M., Tidy, A., Viggers, J., and Davey, J. Interim analysis of the incidence of breast cancer in the Royal Marsden Hospital tamoxifen randomised chemoprevention trial. Lancet, 352: 98-101, 1998.
6. Jordan, V. C. Tamoxifen for breast cancer prevention. Proc. Soc. Exp. Biol. Med., 208: 144-149, 1995.
7. Powles, T. J., Jones, A. L., Ashley, S. E., O'Brien, M. E. R., Tidy, V. A., Treleavan, J., Cosgrove, D., Nash, A. G., Sacks, N., Baum, M., McKinna, J. A., and Davey, J. B. The Royal Marsden Hospital pilot tamoxifen chemoprevention trial. Breast Cancer Res. Treat., 31: 73-82, 1994.
8. Vanchieri, C. Breast cancer prevention study initiated in Italy. J. Natl. Cancer Inst. (Bethesda), 84: 1555-1556, 1992.
9. Seoud, M. A-F., Johnson, J., and Weed, J. C. Gynecologic tumors in tamoxifen-treated women with breast cancer. Obstet. Gynecol., 82: 165-169, 1993.
10. Fischer, B., Costantino, J. P., Redmond, C. K., Fisher, E. R., Wickerham, D. L., and Cronin, W. M. Endometrial cancer in tamoxifen-treated breast cancer patients: findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14. J. Natl. Cancer Inst. (Bethesda), 86: 527-537, 1994.
11. van Leeuwen, F. E., Benraadt, J., Coebergh, J. W. W., Kiemeney, L. A. L. M., Diepenhorst, F. W., van den Belt-Dusebout, A. W., and van Tinteren, H. Risk of endometrial cancer after tamoxifen treatment of breast cancer. Lancet, 343: 448-452, 1994
12. Williams, G. M., Iatropoulos, M. J., Djordjevic, M. V., and Kaltenberg, O. P. The triphenylethylene drug tamoxifen is a strong liver carcinogen in the rat. Carcinogenesis (Lond.), 14: 315-317, 1993.
13. Greaves, P., Goonetilleke, R., Nunn, G., Topham, J., and Orton, T. Two-year carcinogenicity study of tamoxifen in Alderley Park Wister-derived rats. Cancer Res., 53: 3919-3924, 1993.
14. Hard, G. C., Iatropoulos, M. J., Jordan, K., Radi, L., Kaltenberg, O. P., Imondi, A. R., and Williams, G. M. Major difference in the hepatocarcinogenicity and DNA adduct forming ability between toremifene and tamoxifen in female Crl:CD(BR) rats. Cancer Res., 53: 4534-4541, 1993.
15. Davies, R., Oreffo, V. I. C., Martin, E. A., Festing, M. F. W., White, I. N. H., Smith, L. L., and Styles, J. A. Tamoxifen causes gene mutations in the livers of lamda/lacI transgenic rats. Cancer Res., 57: 1288-1293, 1997.
16. Vancutsem, P. M., Lazarus, P., and Williams, G. M. Frequent and specific mutations of the rat p53 gene in hepatocarcinomas induced by tamoxifen. Cancer Res., 54: 3864-3867, 1994.
17. Han, X., and Liehr, J. G. Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res., 52: 1360-1363, 1992.
18. White, I. N. H., de Matteis, F., Davies, A., Smith, L. L., Crofton-Sleigh, C., Venitt, S., Hewer, A., and Phillips, D. H. Genotoxic potential of tamoxifen and analogues in female Fischer F344/n rats, DBA/2 and C57B1/6 mice and in human MCL-5 cells. Carcinogenesis (Lond.), 13: 2197-2203, 1992.
19. Moorthy, B., Sriram, P., Pathak, D. N., Bodell, W. J., and Randerath, K. Tamoxifen metabolic activation: comparison of DNA adducts formed by microsomal and chemical activation of tamoxifen and 4-hydroxytamoxifen with DNA adducts formed in vitro. Cancer Res., 56: 53-57, 1996.
20. Marques, M. M., and Beland, F. A. Identification of tamoxifen-DNA adducts formed by 4-hydroxytamoxifen quinone methide. Carcinogenesis (Lond.), 18: 1949-1954, 1997.
21. Phillips, D. H., Hewer, A., White, I. N. H., and Farmer, P. B. Co-chromatography of a tamoxifen epoxide-deoxyguanylic acid adduct with a major DNA adduct formed in the livers of tamoxifen-treated rats. Carcinogenesis (Lond.), 15: 793-795, 1994.
22. Potter, G. A., McCague, R., and Jarman, M. A mechanism hypothesis for DNA adduct formation by tamoxifen hepatic oxidative metabolism. Carcinogenesis (Lond.), 15: 439-442, 1994.
23. 5-ethyl]-tamoxifen implicates α-hydroxylation of the ethyl group as a major pathway of tamoxifen activation to a liver carcinogen. Carcinogenesis (Lond.), 15: 1487-1492, 1994.
24. Phillips, D. H., Carmichael, P. L., Hewer, A., Cole, K. J., and Poon, G. K. α-Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res., 54: 5518-5522, 1994.
25. 5-ethyl]tamoxifen. Carcinogenesis (Lond.), 16: 683-688, 1995.
26. Shibutani, S., Dasaradhi, L., Terashima, I., Banoglu, E., and Duffel, M. W. α-Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts. Cancer Res., 58: 647-653, 1998.
27. Shibutani, S., Shaw, P. M., Suzuki, N., Dasaradhi, L., Duffel, M. W., and Terashima, I. Sulfation of α-hydroxytamoxifen catalyzed by human hydroxysteroid sulfotransferase results in tamoxifen-DNA adducts. Carcinogenesis (Lond.), 19: 2007-2011, 1998.
28. Dasaradhi, L., and Shibutani, S. Identification of tamoxifen-DNA adducts formed by α-sulfate tamoxifen and α-acetoxytamoxifen. Chem. Res. Toxicol., 10: 189-196, 1997.
29. Osborne, M. R., Hewer, A., Hardcastle, I. R., Carmichael, P. L., and Phillips, D. H. Identification of the major tamoxifen-deoxyguanosine adduct formed in the liver DNA of rats treated with tamoxifen. Cancer Res., 56: 66-71, 1996.
30. Sanchez, C., Shibutani, S., Dasaradhi, L., Bolton, J. L., Fan, P. W., and McClelland, R. A. Lifetime and reactivity of an ultimate tamoxifen carcinogen: the tamoxifen carbocation. J. Am. Chem. Soc., 120: 13513-13514, 1998.
31. 32P-post-labeled DNA adducts by the development of a novel automated on-line solid-phase extraction HPLC method. Carcinogenesis (Lond.), 19: 1061-1069, 1998.
32. 2-deoxyguanosinyl)tamoxifen. Biochemistry, 36: 13010-13017, 1997.
33. Shibutani, S. Genotoxicity of estrogen- and tamoxifen-derived DNA adducts in mammalian cells. Environ. Mutagen Res., 20: 201-211, 1998.
34. Maniatis, T., Fritsch, E. F., and Sambrook, J. Molecular Cloning. A Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory, 1982.
35. Moriya, M. Single strand shuttle phagemid for mutagenesis studies in mammalian cells: 8-oxoguanine in DNA induces targeted G:C→T:A transversion in simian kidney cells. Proc. Natl. Acad. Sci. USA, 90: 1122-1126, 1993.
36. Felgner, P. L., Gadek, T. R., Holm, M., Roman, R., Chan, H. W., Wenz, M., Northrop, J. P., Ringold, G. M., and Danielsen, M. Lipofection: a highly efficient, lipid-mediated DNA-transfection procedure. Proc. Natl. Acad. Sci. USA. 84: 7413-7417, 1987.
37. Hirt, B. Selective extraction of polyoma DNA from infected mouse cell cultures. J. Mol. Biol., 26: 365-369, 1967.
38. Inouye, S., and Inouye, M. In: S. Narang (ed.), Synthesis and Applications of DNA and RNA, pp. 181-206. New York: Academic Press, 1987.
39. Moriya, M., Takeshita, M., Johnson, K., Peden, K., Will, S., and Grollman, A. P. Targeted mutations induced by a single acetylaminofluorene DNA adduct in mammalian cells and bacteria. Proc. Natl. Acad. Sci. USA, 85: 1586-1589, 1988.
40. Sanger, F., Nicklen, S., and Coulson, A. R. DNA sequencing with chain-terminating inhibitors. Proc. Natl. Acad. Sci. USA, 74: 5463-5467, 1977.
41. Wang, T. S-F. Eukaryotic DNA polymerases. Annu. Rev. Biochem., 60: 513-552, 1991.
42. Osborne, M. R., Hardcastle, I. R., and Phillips, D. H. Minor products of reaction of DNA with α-acetoxytamoxifen. Carcinogenesis (Lond.), 18: 539-543, 1997.
43. Moriya, M., Spiegel, S., Fernandes, A., Amin, S., Liu, T., Geacintov, N. E., and Grollman, A. P. Fidelity of translesional synthesis past benzo[a]pyrene diol epoxide-2′-deoxyguanosine DNA adducts: marked effect of host cell, sequence context, and chirality. Biochemistry, 35: 16646-16651, 1996.
44. Shibutani, S., Suzuki, N., and Grollman, A. P. Mutagenic specificity of (acetylamino)fluorene-derived DNA adducts in mammalian cells. Biochemistry, 37: 12034-12041, 1998.
45. Terashima, I., Suzuki, N., Itoh, S., Yoshizawa, I., and Shibutani, S. Mutagenic specificity of model estrogen-DNA adducts in mammalian cells. Biochemistry, 37: 8803-8807, 1998.