α-hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts

Cancer Research

Volumn 58, Issue 4, 1998, Pages 647-653

  Shibutani, Shinya ^a   Dasaradhi, Lakkaraju ^a   Terashima, Isamu ^a   Banoglu, Erden ^b   Duffel, Michael W ^b  

^a STONY BROOK UNIVERSITY   (United States)

^b UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYSTEROID; HYDROXYTAMOXIFEN; SULFOTRANSFERASE;

ANIMAL CELL; ARTICLE; BREAST CANCER; DNA ADDUCT; ENZYME INHIBITION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; GENE DELETION; GENE MUTATION; HYDROXYLATION; LIVER MICROSOME; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; SULFATION;

ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA ADDUCTS; FEMALE; MODELS, CHEMICAL; RATS; RATS, SPRAGUE-DAWLEY; SULFOTRANSFERASES; TAMOXIFEN;

EID: 0032519594     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 Treleaven, 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, 83: 1450-1459, 1991.
4. 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.
5. Greaves, P., Goonetilleke, R., Nunn, G., Topham, J., and Orion, T. Two-year carcinogenicity study of tamoxifen in Alderley Park Wister-derived rats. Cancer Res., 53: 3919-3924, 1993.
6. 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.
7. 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 lambda/LacI transgenic rats. Cancer Res., 57: 1288-1293, 1997.
8. 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.
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., 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. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 66, Some Pharmaceutical Drugs. Lyon: IARC, 1996.
13. 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.
14. Pathak, D. N., Pongracz, K., and Bodell, W. J. Microsomal and peroxidase activation of 4-hydroxy-tamoxifen to form DNA adducts: comparison with DNA adducts formed in Sprague-Dawley rats treated with tamoxifen. Carcinogenesis (Lond.), 16: 11-15, 1995.
15. Hemminki, K., Widlak, P., and Hou, S. M. DNA adducts caused by tamoxifen and toremifene in human microsomal system and lymphocyte in vitro. Carcinogenesis (Lond.), 16: 1661-1664, 1995.
16. Han, X., and Liehr, J. G. Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res., 52: 1360-1363, 1992.
17. 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.
18. Hemminki, K., Rajaniemi, H., Lindahl, B., and Moberger, B. Tamoxifen-induced DNA adducts in endometrial samples from breast cancer patients. Cancer Res., 56: 4374-4377, 1996.
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. Poon, G. K., Walter, B., Lønning, P. E., Horton, M. N., and McCague, R. Identification of tamoxifen metabolites in human Hep G2 cell line, human liver homogenate, and in patients on long-term therapy for breast cancer. Drug Metab. Dispos., 23: 377-382, 1995.
21. 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.
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. 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.
25. 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.
26. 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.
27. 2-deoxyguanosinyl)tamoxifen. Biochemistry, 36: 13010-13017, 1997.
28. Lyon, E. S., Marcus, C. J., Wang, J-L., and Jakoby, W. B. Hydroxysteroid sulfotransferase. Methods Enzymol., 77: 206-213, 1981.
29. Watabe, T., Ishizuka, T., Isobe, M., and Ozawa, N. A 7-hydroxy-methyl sulfate ester as an active metabolite of 7,12-dimethyl-benz[a]anthracene. Science (Washington DC), 215: 403-405, 1982.
30. Surh, Y-J., Liem, A., Miller, E. C., and Miller, J. A. Metabolic activation of the carcinogen 6-hydroxymethylbenzo[a]pyrene: formation of an electrophilic sulfuric acid ester and benzylic DNA adducts in rat liver in vivo and in reactions in vitro. Carcinogenesis (Lond.), 10: 1519-1528, 1989.
31. Chen, G., Banoglu, E., and Duffel, M. W. Influence of substrate structure on the catalytic efficiency of hydroxysteroid sulfotransferase STa in the sulfation of alcohols. Chem. Res. Toxicol., 9: 67-74, 1996.
32. Ogura, K., Sohtome, T., Sugiyama, A., Okuda, H., Hiratsuka, A., and Watabe, T. Rat liver cytosolic hydroxysteroid sulfotransferase (sulfotransferase a) catalyzing the formation of reactive sulfate esters from carcinogenic polycyclic hydroxymethylarenes. Mol. Pharmacol., 37: 848-854, 1990.
33. Watabe, T., Ogura, K., Satsukawa, H., Okuda, H., and Hiratsuka, A. Molecular cloning and functions of rat liver hydroxysteroid sulfotransferases catalysing covalent binding of carcinogenic polycyclic arylmethanols to DNA. Chem. Biol. Interact., 92: 87-105, 1994.
34. Bensadoum, A., and Weinstein, D. Assay of proteins in the presence of interfering materials. Anal. Biochem., 70: 241-250, 1976.
35. Foster, A. B., Jarman, M., Leung, O-T., McCague, R., Leclercq, G., and Devleeschouwer, N. Hydroxy derivatives of tamoxifen. J. Med. Chem., 28: 1491-1497, 1985.
36. Sekura, R. D. Adenosine 3′-phosphate 5′-phosphosulfate. Methods Enzymol., 77: 413-415, 1981.
37. Duffel, M. W., Binder, T. P., and Rao, S. I. Assay of purified aryl sulfotransferase suitable for reactions yielding unstable sulfuric acid esters. Anal. Biochem., 183: 320-324, 1989.
38. Perella, F. W. EZ-FIT: a practical curve-fitting microcomputer program for the analysis of enzyme kinetic data on IBM-PC compatible computers. Anal. Biochem., 174: 437-447, 1988.
39. 2-AAF and oxidation products of dG-C8-AF. Carcinogenesis (Lond.), 12: 813-818, 1991.
40. Umemoto, A., Kajikawa, A., Tanaka, M., Hamada, K., Seraj, M. J., Kubota, A., Nakayama, M., Kinouchi, T., Ohnishi, Y., Yamashita, K., and Monden, Y. Presence of mucosa-specific DNA adduct in human colon: possible implication for colorectal cancer. Carcinogenesis (Lond.), 15: 901-905, 1994.
41. 32P-postlabeling. Carcinogenesis (Lond.), 12: 1181-1186, 1991.
42. Maniatis, T., Fritsch, E. F., and Sambrook, J. Molecular Cloning: A Laboratory Manual. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory, 1982.
43. Poon, G. K., Walter, B., Lønning, P. E., Horton, M. N., and McCague, R. Identification of tamoxifen metabolites in human Hep G2 cell line, human liver homogenate, and patients on long-term therapy for breast cancer. Drug. Metab. Dispos., 23: 377-382, 1995.
44. Falany, C. N. Enzymology of human cytosolic sulfotransferases. FASEB J., 11: 206-216, 1997.
45. Glatt, H., Pauly, K., Czich, A., Falany, J. L., and Falany, C. N. Activation of benzylic alcohols to mutagens by rat and human sulfotransferases expressed in Escherichia coli. Eur. J. Pharmacol., 293: 173-181, 1995.