Minor products of reaction of DNA with α-acetoxytamoxifen

Carcinogenesis

Volumn 18, Issue 3, 1997, Pages 539-543

  Osborne, Martin R ^a   Hardcastle, Ian R ^a   Phillips, David H ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG METABOLITE; TAMOXIFEN; TAMOXIFEN DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CIS TRANS ISOMERISM; DNA ADDUCT; DNA ALKYLATION; DRUG DNA INTERACTION; GENOTOXICITY; LIVER CARCINOGENESIS; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RAT;

ANIMALS; BIOTRANSFORMATION; CARCINOGENS; DNA; DNA ADDUCTS; LIVER; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; RATS; SPECTROPHOTOMETRY, ULTRAVIOLET; TAMOXIFEN;

EID: 0031427032     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/18.3.539     Document Type: Article

References (28)

1. Powles, T.J. (1992) The case for clinical trials of tamoxifen for prevention of breast cancer. Lancet, 340, 1145-1147.
2. Nease, R.F. and Ross, J.M. (1995) The decision to enter a randomized trial of tamoxifen for the prevention of breast cancer in healthy women - an analysis of the tradeoffs. Am. J. Med., 99, 180-189.
3. Hard, G.C., Iatropoulos, M.J., Jordan, K., Radi, L., Kaltenberg, O.P., Imondi, A.R. and Williams, G.M. (1993) Major differences in the hepatocarcinogenicity and DNA adduct forming ability between toremifene and tamoxifen in female Crl:CD(BR) rats. Cancer Res., 53, 4534-4541.
4. Greaves, P., Goonetilleke, R., Nunn, G., Topham, J. and Orton, T. (1993) Two-year carcinogenicity study of tamoxifen in Alderley Park-Wistar derived rats. Cancer Res., 53, 3919-3924.
5. Williams, G.M., Iatropoulos, M.J., Djordjevic, M.V. and Kaltenberg, O.P. (1993) The triphenylethylene drug tamoxifen is a strong liver carcinogen in the rat. Carcinogenesis, 14, 315-317.
6. Sargent, L.M. et al. (1996) Induction of hepatic aneuploidy in vivo by tamoxifen, toremifene and idoxifene in female Sprague-Dawley rats. Carcinogenesis, 17, 1051-1056.
7. Vijayalaxmi, K.K. and Rai, S.P. (1996) Studies on the genotoxicity of tamoxifen citrate in mouse bone marrow cells. Mutat. Res., 368, 109-114.
8. White, I.N.H., de Matteis, F., Davies, A., Smith, L.L., Crofton-Sleigh, C., Venitt, S., Hewer, A. and Phillips, D.H. (1992) Genotoxic potential of tamoxifen and analogues in female Fischer F344/n rats, DBA/2 and C57Bl/ 6 mice and in human MCL-5 cells. Carcinogenesis, 13, 2197-2203.
9. Styles, J.A., Davies, A., Lim, C.K., de Matteis, F., Stanley, L.A., White, I.N.H., Yuan, Z.X. and Smith, L.L. (1994) Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis, 15, 5-9.
10. Han, X. and Liehr, J.G. (1992) Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res., 52, 1360-1363.
11. Seoud, M.A.-F., Johnson, J. and Weed, J.C. (1993) Gynecologic tumors in tamoxifen-treated women with breast cancer. Obstet. Gynecol., 82, 165-169.
12. Cook, L.S., Weiss, N.S., Schwartz, S.M., White, E., McKnight, B., Moore, D.E. and Daling, J.R. (1995) Population-based study of tamoxifen therapy and subsequent ovarian, endometrial and breast cancers. J. Natl Cancer Inst., 87, 1359-1364.
13. Cuenca, R.E., Giachino, J., Arrendondo, M.A., Hempling, R. and Edge, S.B. (1996) Endometrial carcinoma associated with breast carcinoma: low incidence with tamoxifen use. Cancer, 77, 2058-2063.
14. Curtis, R.E., Boice, J.D., Shriner, D.A., Hanley, B.F. and Fraumeni, J.F. (1996) Second cancers after adjuvant tamoxifen therapy for breast cancer. J. Natl Cancer Inst., 88, 832-834.
15. Carmichael, P.L., Ugwumadu, A.H.N., Neven, P., Hewer, A.J., Poon, G.K. and Phillips, D.H. (1996) Lack of genotoxicity of tamoxifen in human endometrium. Cancer Res., 56, 1475-1479.
16. Hemminki, K., Rajaniemi, H., Lindahl, B. and Moberger, B. (1996) Tamoxifen-induced DNA adducts in endometrial samples from breast cancer patients. Cancer Res., 56, 4374-4377.
17. 32P-Postlabelled DNA adducts in liver obtained from women treated with tamoxifen. Carcinogenesis, 16, 1651-1654.
18. Potter, G.A., McCague, R. and Jarman, M. (1994) A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism. Carcinogenesis, 15, 439-442.
19. 32P-postlabeling and use of metabolic inhibitors for two distinct pathways leading to mouse hepatic DNA adduct formation and identification of 4-hydroxytamoxifen as a proximate metabolite. Carcinogenesis, 15, 2087-2094.
20. Kuramochi, H. (1996) Conformational studies and electronic structures of tamoxifen and toremifene and their allylic carbocations proposed as reactive intermediates leading to DNA adduct formation. J. Med. Chem., 39, 2877-2886.
21. Phillips, D.H., Carmichael, P.L., Hewer, A., Cole, K.J. and Poon, G.K. (1994) α-Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res., 54, 5518-5522.
22. Phillips, D.H., Carmichael, P.L., Hewer, A., Cole, K.J., Hardcastle, I.R., Poon, G.K., Keogh, A. and Strain, A.J. (1996) Activation of tamoxifen and its metabolite α-hydroxytamoxifen to DNA-binding products: comparisons between human, rat and mouse hepatocytes. Carcinogenesis, 17, 89-94.
23. 5-ethyl]-tamoxifen implicates α-hydroxylation of the ethyl group as a major pathway of tamoxifen activation to a liver carcinogen. Carcinogenesis, 15, 1487-1492.
24. Osborne, M.R., Hewer, A., Hardcastle, I.R., Carmichael, P.L. and Phillips, D.H. (1996) Identification of the major tamoxifen-deoxyguanosine adduct formed in the liver DNA of rats treated with tamoxifen. Cancer Res., 56, 66-71.
25. Lawley, P.D. (1971) The spectra of purines. In Lister, J.H. (ed.), fused Pyrimidines. Part II: Purines. Wiley-Interscience, New York, NY, pp. 439-528.
26. Osborne, M.R. (1984) DNA interactions of reactive intermediates derived from carcinogens. In Searle, C.E. (ed.), Chemical Carcinogens. American Chemical Society, Washington, DC, ACS Monograph 182, Vol. 1, pp. 485-524.
27. Pathak, D.N., Pongracz, K. and Bodell, W.J. (1995) Microsomal and peroxidase activation of 4-hydroxytamoxifen to form DNA adducts: comparison with DNA adducts formed in Sprague-Dawley rats treated with tamoxifen. Carcinogenesis, 16, 11-15.
28. Pongracz, K., Pathak, D.N., Nakamura, T., Burlingame, A.L. and Bodell, W.J. (1995) Activation of the tamoxifen derivative metabolite E to form DNA adducts: comparison with the adducts formed by microsomal activation of tamoxifen. Cancer Res., 55, 3012-3015.