Tamoxifen metabolic activation: Comparison of DNA adducts formed by microsomal and chemical activation of tamoxifen and 4-hydroxytamoxifen with DNA adducts formed in vivo

Cancer Research

Volumn 56, Issue 1, 1996, Pages 53-57

  Moorthy, Bhagavatula ^a   Sriram, Padmavathi ^a   Pathak, Deena N ^b   Bodell, William J ^b   Randerath, Kurt ^a  

^a BAYLOR COLLEGE OF MEDICINE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYTAMOXIFEN; DNA; TAMOXIFEN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHEMICAL CARCINOGENESIS; CHEMICAL LABELING; CONTROLLED STUDY; DNA ADDUCT; DNA DETERMINATION; DRUG CARCINOGENICITY; DRUG MECHANISM; DRUG METABOLISM; FEMALE; LIVER CARCINOGENESIS; LIVER MICROSOME; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; ANTINEOPLASTIC AGENTS, HORMONAL; BENZENE DERIVATIVES; DNA; DNA ADDUCTS; FEMALE; MICE; MICE, INBRED ICR; MICROSOMES, LIVER; RATS; TAMOXIFEN;

EID: 0030069966     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Early Breast Cancer Trialist's Collaborative Group Systemic treatment of early breast cancer by hormonal, cytotoxic, or immune therapy 133 randomised trials involving 31,000 recurrences and 24,000 deaths among 75,000 women. Lancet, 339: 1-15, 71-85, 1992.
2. Jordan, V. C. Tamoxifen for breast cancer prevention. Proc Soc Exp. Biol. Med., 208: 144-149, 1995.
3. King, C. M. Tamoxifen and induction of cancer. Carcinogenesis (Lond), 16: 1449-1454, 1995
4. Fisher, 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, 86 527-537, 1994
5. Magriples, U., Naftolin, F., Schwartz, P E., and Carcangiu, M. L High-grade endometrial carcinoma in tamoxifen-treated breast cancer patients J. Clin. Oncol., 11: 485-490, 1993.
6. Han, X. L, and Liehr, J. G. Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res., 52: 1360-1363, 1992.
7. 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.
8. Randerath, K., Jia, B., Mabon, N., Sriram, P, and Moorthy, B. Strong intensification of mouse hepatic tamoxifen DNA adduct formation by pretreatment with the sulfotransferase inhibitor and ubiquitous environmental pollutant pentachlorophenol. Carcinogenesis (Lond.), 15: 797-800, 1994
9. 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 (Lond.), 15: 2087-2094, 1994
10. Pathak, D. N., Pongracz, K., and Bodell, W. J. Microsomal and peroxidase activation of 4-hydroxytamoxifen to form DNA adducts: comparison with DNA adducts formed in Sprague-Dawley rats treated with tamoxifen. Carcinogenesis (Lond), 16, 11-15, 1994.
11. Pongracz, K., Pathak, D. N., Nakamura, T, Burlingame, A. L., and Bodell, W. J. 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, 1995.
12. Pathak, D. N., and Bodell, W. J DNA adduct formation by tamoxifen with rat and human liver microsomal activation systems. Carcinogenesis (Lond.), 15, 529-532, 1994.
13. Lim, C K., Yuan, Z-X., Lamb, J. H, White, I. N. H., De Matteis, F., and Smith, L. L. A comparative study of tamoxifen metabolism in female rat, mouse, and human liver microsomes. Carcinogenesis (Lond.), 15. 589-593, 1994.
14. 5-ethyl]tamoxifen. Carcinogenesis (Lond), 16: 683-688, 1995
15. Phillips, D. H., Carmichael, P. L., Hewer, A., Cole, K. J., and Poon, G K. α-Hydroxytamoxifen, a metabolite with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res., 54. 5518-5522, 1994.
16. Murphy, C., Fotsis, T., Pantzar, P., Adlercreutz, H., and Martin, F. Analysis of tamoxifen and its metabolites in human plasma by gas chromatography-mass spectrometry (GC-MS) using selected ion monitoring (SIM). J. Steroid Biochem., 26: 547-555, 1987.
17. Furr, B J. A., and Jordan, V. C. The pharmacology and clinical uses of tamoxifen Pharmacol. Ther., 25: 127-205, 1984.
18. 12P-postlabeling assay based on the specific enzymatic conversion of bulky DNA lesions to radiolabeled dinucleotides and nucleoside 5′-monophosphates. Carcinogenesis (Lond.), 10: 1231-1239, 1989.
19. Gladek, A, and Liehr, J G. Mechanism of genotoxicity of diethylstilbestrol in vivo. J. Biol. Chem., 264: 16847-16852, 1989.
20. 32P-postlabeling and use of pentachlorophenol for a novel metabolic activation pathway of diechylstilbestrol (DES) and its dimethyl ether m mouse liver likely α-hydroxylation of ethyl group(s) followed by sulfate conjugation. Carcinogenesis, 16: 2643-2648, 1995
21. Ross, D., Mehlhorn, R. J., Moldeus, P, and Smith, M. T. Metabolism of diethylstilbestrol by horseradish peroxidase and prostaglandin-H synthase. J. Biol. Chem, 260. 16210-16214, 1985.
22. Cavalieri, E. L., and Rogan, E G. The approach to understanding aromatic hydrocarbon carcinogenesis: the central role of radical cations in metabolic activation. Pharmacol Ther., 55: 183-199, 1992.
23. Zanarotti, A. Synthesis and reactivity of vinyl quinone methides. J. Org. Chem., 50: 941-945, 1985.
24. Porter, G. A., McCague, R., and Jarman, M. A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism. Carcinogenesis (Lond.), 15: 439-442, 1994.
25. Holinka, C. F, and Gurpide, E Peroxidase activity in glands and stroma of human endometrium. Am. J. Obstet Gynecol., 138: 599-603, 1980.
26. Borgna, J-L., and Rochefort. H Hydroxylated metabolites of tamoxifen are formed in vivo and bound to the estrogen receptor in target tissue. J. Biol. Chem, 256: 859-868, 1981.
27. Robinson, S. P., Langan-Fahey, S. M., Johnson, D. A., and Jordan, V. C. Metabolites, pharmacodynamics, and pharmacokinetics of tamoxifen in rats and mice compared to the breast cancer patient. Drug Metab. Dispos., 19: 36-43, 1991.
28. Osborne, C. K, Wiebe, V J, McGuire, W L., Ciocca, D. R., and DeGregorio, M. W. Tamoxifen and the isomers of 4-hydroxytamoxifen in tamoxifen-resistant tumors from breast cancer patients. J. Clin. Oncol., 10: 304-310, 1992.
29. Bolton, J. L., Corneau, E., and Vukomanovic, V The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides, evidence that extended π-conjugation dramatically stabilizes the quinone methide formed from eugenol. Chem. Biol. Interact, 95: 279-290, 1995.