DNA cleavage and 8-hydroxydeoxyguanosine formation caused by tamoxifen derivatives in vitro

Cancer Letters

Volumn 122, Issue 1-2, 1998, Pages 9-15

  Okubo, Tomoko ^a   Nagai, Fumiko ^a   Ushiyama, Keiko ^a   Yokoyama, Yoshiko ^b   Ozawa, Satoshi ^c   Kano, Kazutaka ^c   Tomita, Shunnro ^d   Kubo, Hirotaka ^d   Kano, Itsu ^a  

^a TOKYO METROPOLITAN INSTITUTE OF PUBLIC HEALTH   (Japan)

^b WASEDA UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d JIKEI UNIVERSITY SCHOOL OF MEDICINE   (Japan)

Author keywords

hydroxytoremifene; 4 Hydroxytamoxifen; DNA damage; N desmethyltamoxifen; Tamoxifen; Toremifene

Indexed keywords

4 HYDROXYTAMOXIFEN; 8 HYDROXYDEOXYGUANOSINE; ALPHA HYDROXYTOREMIFENE; CATALASE; DITHIOTHREITOL; DROLOXIFENE; EDETIC ACID; HYDROXYTAMOXIFEN; MANNITOL; MERCAPTOETHANOL; METHIONINE; N DESMETHYLTOREMIFENE; NORTAMOXIFEN; PLASMID DNA; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; REDUCING AGENT; SODIUM AZIDE; SUPEROXIDE DISMUTASE; TAMOXIFEN; TAMOXIFEN DERIVATIVE; TOREMIFENE; UNCLASSIFIED DRUG;

AGAR GEL ELECTROPHORESIS; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA CLEAVAGE; DNA CONFORMATION; DNA DAMAGE; DRUG MECHANISM; DRUG METABOLISM; NONHUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; PRIORITY JOURNAL;

ANIMALS; CATTLE; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DNA DAMAGE; ESTROGEN ANTAGONISTS; TAMOXIFEN;

EID: 0032498329     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(97)00359-5     Document Type: Article

References (31)

1. Jordan V.C. A current review of tamoxifen for the treatment and prevention of breast cancer. Br. J. Pharmacol. 110:1993;507-517.
2. Jordan V.C. Tamoxifen for breast cancer prevention. Proc. Soc. Exp. Biol. Med. 208:1995;144-149.
3. Hard G.C., Iatropoulos M.J., Jordan K., Radi L., Kaltenberg O.P., Imondi A.R., Williams G.M. Major differences in the hepatocarcinogenicity and DNA adduct forming ability between toremifene and tamoxifen in female Crl:CD(BR) rats. Cancer Res. 53:1993;4534-4541.
4. Williams G.M., Iatropoulos M.J., Djordjevic M.V., Kaltenberg O.P. The triphenylene drug tamoxifen is a strong liver carcinogen in the rat. Carcinogenesis. 14:1993;315-317.
5. Hirsmaki P., Hirsmaki Y., Nieminen L., Payne B.J. Tamoxifen induces hepatocellular carcinoma in rat liver: a one-year study with two antiestrogens. Arch. Toxicol. 67:1993;49-54.
6. Fornander T., Hellström A.C., Moberger B. Descriptive clinicopathologic study of 17 patients with endometrial cancer during or after adjuvant tamoxifen in early breast cancer. J. Natl. Cancer Inst. 85:1993;1850-1855.
7. Fisher B., Costantino J.P., Redmond C.K., Fisher E.R., Wickerham D.L., 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. 86:1994;527-537.
8. Lien E.A., Solheim E., Ureland P.M. Distribution of tamoxifen and its metabolites in rat and human tissues during steady state treatment. Cancer Res. 51:1991;4837-4844.
9. White I.N.H., De Matteis F., Davies A., Smith L.L., Crofton-Sleigh C., Venitt S., Hewer A., Phillips D.H. 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. 13:1992;2197-2203.
10. Styles J.A., Davies A., Lim C.K., De Matteis F., Stanley L.A., White I.N.H., Yuan Z.-X., Smith L.L. Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 15:1994;5-9.
11. Styles J.A., Davies A., Davies R., White I.N.H., Smith L.L. Clastogenic and aneugenic effects of tamoxifen and some of its analogues in hepatocytes from dosed rats and in human lymphoblastoid cells transfected with human P450 cDNAs (MCL-5 cells). Carcinogenesis. 18:1997;303-313.
12. Pathak D.N., Bodell W.J. DNA adduct formation by tamoxifen with rat and human liver microsomal activation systems. Carcinogenesis. 15:1994;529-532.
13. 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. 15:1994;2087-2094.
14. Moorthy B., Sriram P., Pathak D.K., Bodell W.J., Randerath K. Tamoxifen metabolic activation: comparison of DNA adducts formed by microsomal and chemical activation of tamoxifen and 4-hydroxytamoxifen with DNA adduct formed in vivo. Cancer Res. 56:1996;53-57.
15. Pathak D.N., Pongracz K., Bodell W.J. Activation of 4-hydroxytamoxifen and the tamoxifen derivative metabolite E by uterine peroxidase to form DNA adducts: comparison with DNA adducts formed in the uterus of Sprague-Dawley rats treated with tamoxifen. Carcinogenesis. 17:1996;1785-1790.
16. Pongracz K., Pathak D.N., Nakamura T., Burlingame A.L., 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. 55:1995;3012-3015.
17. Phillips D.H., Carmichael P.L., Hewer A., Cole K.J., Poon G.K. α-Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res. 54:1994;5518-5522.
18. Phillips D.H., Carmichael P.L., Hewer A., Cole K.J., Hardcastle I.R., Poon G.K., Keogh A., Strain A.J. Activation of tamoxifen and its metabolite α-hydroxytamoxifen to DNA-binding products: comparisons between human, rat and mouse hepatocytes. Carcinogenesis. 17:1996;89-94.
19. 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.
20. Osborne M.R., Hewer A., Hardcastle I.R., Carmichael P.L., Phillips D.H. Identification of the major tamoxifen-deoxyguanosine adduct formed in the liver DNA of rats treated with tamoxifen. Cancer Res. 56:1996;66-71.
21. Kuramochi H. Conformational studies and electronic structures of tamoxifen and toremifene and their allylic carbocations propose as reactive intermediates leading to DNA adduct formation. J. Medicin. Chem. 39:1996;2877-2886.
22. Davies A.M., Martin E.A., Jones R.M., Lim C.K., Smith L.L., White I.N.H. Peroxidase activation of tamoxifen and toremifene resulting in DNA damage and covalently bound protein adducts. Carcinogenesis. 16:1995;539-545.
23. Davies A.M., Malone M.E., Martin E.A., Jones R.M., Jukes R., Lim C.-K., Smith L.L., White I.N.H. Peroxidase activation of 4-hydroxytamoxifen to free radicals detected by EPR spectroscopy. Free Rad. Biol. Med. 22:1997;423-431.
24. Ye Q., Bodell W.J. Production of 8-hydroxy-2′-deoxyguanosine in DNA by microsomal activation of tamoxifen and 4-hydroxytamoxifen. Carcinogenesis. 17:1996;1747-1750.
25. T. Maniatis, E.F. Fritsch, J. Sambrook, Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, 1982, pp. 88-94.
26. Okubo T., Nagai F., Ushiyama K., Kano I. Contribution of oxygen radicals to DNA cleavage by quinone compounds derived from phenolic antioxidants, tert-butylhydroquinone and 2,5-di-tert-butylhydroquinone. Toxicol. Lett. 90:1997;11-18.
27. Nagai F., Ushiyama K., Satoh K., Kasai H., Kano I. Formation of 8-hydroxydeoxyguanosine in calf thymus DNA treated in vitro with phenyl hydroquinone, the major metabolite of o-phenylphenol. Carcinogenesis. 16:1995;837-840.
28. Nagai F., Ushiyama K., Satoh K., Kano I. DNA cleavage by phenylhydroquinone: the major metabolite of a fungicide o-phenylphenol. Chem.-Biol. Interact. 76:1990;163-179.
29. Lerner L.J., Jordan V.C. Development of antiestrogens and their use in breast cancer: Eighth Cain Memorial Award Lecture. Cancer Res. 50:1990;4177-4189.
30. Li D., Dragan Y., Jordan V.C., Wang M., Pitot H.C. Effects of chronic administration of tamoxifen and toremifene on DNA adducts in rat liver, kidney, and uterus. Cancer Res. 57:1997;1438-1441.
31. Cunningham A., Klopman G., Rosenkranz H.S. A study of the structural basis of the carcinogenicity of tamoxifen, toremifene and their metabolites. Mutat. Res. 349:1996;85-94.