References
- Anonymous. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Some Pharmaceutical Drugs. IARC Press, 1996; Vol. 66, Lyon, France
- Bedford G. R., Richardson D. N. Preparation and identification cis and trans isomers of a substituted triarylethylene. Nature 1966; 212: 733–734
- Beland F. A., McDaniel L. P., Marques M. M. Comparison of the DNA adducts formed by tamoxifen and 4‐hydroxytamoxifen in vivo. Carcinogenesis 1999; 20: 471–477, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Bernstein L., Deapen D., Cerhan J. R., Schwartz S. M., Liff J., McGann‐Maloney E., Perlman J. A., Ford L. Tamoxifen therapy for breast cancer and endometrial cancer risk. J. Natl. Cancer Inst. 1999; 91: 1654–1662, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Berthou F., Dreano Y., Belloc C., Kangas L., Gautier J. C., Beaune P. Involvement of cytochrome P450 3A enzyme family in the major metabolic pathways of toremifene in human liver microsomes. Biochem. Pharmacol. 1994; 47: 1883–1895, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Boocock D. J., Maggs J. L., White I. N., Park B. K. α‐Hydroxytamoxifen, a genotoxic metabolite of tamoxifen in the rat: identification and quantification in vivo and in vitro. Carcinogenesis 1999; 20: 153–160, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Boocock D. J., Maggs J. L., Brown K., White I. N., Park B. K. Major inter‐species differences in the rates of O‐sulphonation and O‐glucuronylation of α‐hydroxytamoxifen in vitro: a metabolic disparity protecting human liver from the formation of tamoxifen‐DNA adducts. Carcinogenesis 2000; 21: 1851–1858, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Boocock D. J., Brown K., Gibbs A. H., Sanchez E., Turteltaub K. W., White I. N. Identification of human CYP forms involved in the activation of tamoxifen and irreversible binding to DNA. Carcinogenesis 2002; 23: 1897–1901, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Brown K., Brown J. E., Martin E. A., Smith L. L., White I. N. Determination of DNA damage in F344 rats induced by geometric isomers of tamoxifen and analogues. Chem. Res. Toxicol. 1998; 11: 527–534, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Buzdar A., Hortobagyi G. N. Tamoxifen and toremifene in breast cancer comparison of safety and efficacy. J. Clin. Oncol. 1998; 16: 348–353, [PUBMED], [INFOTRIEVE]
- Carmichael P. L., Ugwumadu A. H., Neven P., Hewer A. J., Poon G. K., Phillips D. H. Lack of genotoxicity of tamoxifen in human endometrium. Cancer Res. 1996; 56: 1475–1479, [PUBMED], [INFOTRIEVE]
- Carmichael P. L., Sardar S., Crooks N., Neven P., Van Hoof I., Ugwumadu A., Bourne T., Tomas E., Hellberg P., Hewer A. J., Phillips D. H. Lack of evidence from HPLC 32P‐post‐labelling for tamoxifen‐DNA adducts in the human endometrium. Carcinogenesis 1999; 20: 339–342, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Crewe H. K., Ellis S. W., Lennard M. S., Tucker G. T. Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4‐hydroxylation of tamoxifen by human liver microsomes. Biochem. Pharmacol. 1997; 53: 171–178, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Daniel P., Gaskell S. J., Bishop H., Campbell C., Nicholson R. I. Determination of tamoxifen and biologically active metabolites in human breast tumours and plasma. Eur. J. Cancer Clin. Oncol. 1981; 17: 1183–1189, [PUBMED], [INFOTRIEVE]
- Dasaradhi L., Shibutani S. Identification of tamoxifen‐DNA adducts formed by α‐sulfate tamoxifen and α‐acetoxytamoxifen. Chem. Res. Toxicol. 1997; 10: 189–196, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Davies R., Oreffo V. I., Martin E. A., Festing M. F., White I. N., Smith L. L., Styles J. A. Tamoxifen causes gene mutations in the livers of λ/lacI transgenic rats. Cancer Res. 1997; 57: 1288–1293, [PUBMED], [INFOTRIEVE]
- Davis W., Venitt S., Phillips D. H. The metabolic activation of tamoxifen and alpha‐hydroxytamoxifen to DNA‐binding species in rat hepatocytes proceeds via sulphation. Carcinogenesis 1998; 19: 861–866, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Dehal S. S., Kupfer D. CYP2D6 catalyzes tamoxifen 4‐hydroxylation in human liver. Cancer Res. 1997; 57: 3402–3406, [PUBMED], [INFOTRIEVE]
- Dehal S. S., Kupfer D. Cytochrome P‐450 3A and 2D6 catalyze ortho hydroxylation of 4‐hydroxytamoxifen and 3‐hydroxytamoxifen (droloxifene) yielding tamoxifen catechol: involvement of catechols in covalent binding to hepatic proteins. Drug Metab. Dispos. 1999; 27: 681–688, [PUBMED], [INFOTRIEVE], [CSA]
- Divi R. L., Osborne M. R., Hewer A., Phillips D. H., Poirier M. C. Tamoxifen‐DNA adduct formation in rat liver determined by immunoassay and 32P‐postlabeling. Cancer Res. 1999; 59: 4829–4833, [PUBMED], [INFOTRIEVE]
- Divi R. L., Schild L. J., Phillips D. H., Carmichael P. L., Poirier M. C. Examination of human endometrial DNA samples for the presence of tamoxifen‐DNA adducts by tamoxifen‐DNA immunoassay. Genotoxicity of Tamoxifen: Extent and Consequences. January 23, 2003, Waikoloa, Hawaii
- Dragan Y. P., Fahey S., Street K., Vaughan J., Jordan V. C., Pitot H. C. Studies of tamoxifen as a promoter of hepatocarcinogenesis in female Fisher F344 rats. Breast Cancer Res. Treat. 1994; 31: 11–25, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Early Breast Cancer Trialists' Collaborative Group. Tamoxifen for early breast cancer: an overview of the randomized trials. Lancet 1998; 351: 1451–1467, [CROSSREF]
- Fischer 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. 1994; 86: 527–537
- Fisher B., Costantino J. P., Wickerham D. 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. Tamoxifen for prevention of breast cancer: report of the National Surgical Adjuvant Breast and Bowel Project P‐1 Study. J. Natl. Cancer Inst. 1998; 90: 1371–1388, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Furr B. J.A., Jordan V. C. The pharmacology and clinical uses of tamoxifen. Pharmacol. Ther. 1984; 25: 127–205, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Gamboa da Costa G., Hamilton L. P., Beland F. A., Marques M. M. Characterization of the major DNA adduct formed by α‐hydroxy‐N‐desmethyltamoxifen in vitro and in vivo. Chem. Res. Toxicol. 2000; 13: 200–207, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Glatt H., Davis W., Meinl W., Hermersdorfer H., Venitt S., Phillips D. Rat, but not human, sulfotransferase activates a tamoxifen metabolite to produce DNA adducts and gene mutations in bacteria and mammalian cells in culture. Carcinogenesis 1998; 19: 1709–1713, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Greaves P., Goonetilleke R., Nunn G., Topham J., Orton T. Two‐year carcinogenicity study of tamoxifen in Alderley Park Wister‐derived rats. Cancer Res. 1993; 53: 3919–3924, [PUBMED], [INFOTRIEVE]
- Hachisuga T., Miyakawa T., Tsujioka H., Horiuchi S., Emoto M., Kawarabayashi T. K‐ras mutation in tamoxifen‐related endometrial polyps. Cancer 2003; 98: 1890–1897, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Han X., Liehr J. G. Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res. 1992; 52: 1360–1363, [PUBMED], [INFOTRIEVE]
- Hard G. C., Iatropoulos M. J., Jordan K., Radi L., Kaltenberg O. P., Imondi A. R., 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. 1993; 53: 4534–4541, [PUBMED], [INFOTRIEVE]
- Hardcastle I. R., Horton M. N., Osborne M. R., Hewer A., Jarman M., Phillips D. H. Synthesis and DNA reactive of α‐hydroxylated metabolites of nonsteroidal antiestrogens. Chem. Res. Toxicol. 1998; 11: 369–374, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Harper M. J., Walpole A. L. Contrasting endocrine activities of cis and trans isomers in a series of substituted triphenylethylenes. Nature 1966; 212: 87, [PUBMED], [INFOTRIEVE]
- Harper M. J., Walpole A. L. A new derivative of triphenylethylene: effect on implantation and mode of action in rats. J. Reprod. Fertil. 1967; 13: 101–119, [PUBMED], [INFOTRIEVE]
- Hellriegel E. T., Matwyshyn G. A., Fei P., Dragnev K. H., Nims R. W., Lubet R. A., Kong A. N. Regulation of gene expression of various phase I and phase II drug‐metabolizing enzymes by tamoxifen in rat liver. Biochem. Pharmacol. 1996; 52: 1561–1568, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Hemminki K., Rajaniemi H., Lindahl B., Moberger B. Tamoxifen‐induced DNA adducts in endometrial samples from breast cancer patients. Cancer Res. 1996; 56: 4374–4377, [PUBMED], [INFOTRIEVE]
- Hengstler J. G., van der Burg B., Steinberg P., Oesch F. Interspecies differences in cancer susceptibility and toxicity. Drug Metab. Rev. 1999; 31: 917–970, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Hukkanen J., Mantyla M., Kangas L., Wirta P., Hakkola J., Paakki P., Evisalmi S., Pelkonen O., Raunio H. Expression of cytochrome P450 genes encoding enzymes active in the metabolism of tamoxifen in human uterine endometrium. Pharmacol. Toxicol. 1998; 82: 93–97, [PUBMED], [INFOTRIEVE], [CSA]
- Jacolot F., Simon I., Dreano Y., Beaune P., Riche C., Berthou F. Identification of the cytochrome P‐450 IIIA family as the enzymes involved in the N‐demethylation of tamoxifen in human liver microsomes. Biochem. Pharmacol. 1991; 41: 1911–1919, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Jarman M., Poon G. K., Rowlands G., Grimshaw R. M., Horton M. N., Potter G. A., McCague R. The deuterium isotope effect for the α‐hydroxylation of tamoxifen by rat liver microsomes accounts for the reduced genotoxicity of [D5‐ethyl]tamoxifen. Carcinogenesis 1995; 16: 683–688, [PUBMED], [INFOTRIEVE]
- Jones R. M., Lim C. K. Toremifene metabolism in rat, mouse and human liver microsomes: identification of α‐hydroxytoremifene by LC‐MS. Biomed. Chromatogr. 2002; 16: 361–363, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Jordan V. C. Metabolites of tamoxifen in animals and man: identification, pharmacology and significance. Breast Cancer Res. Treat. 1982; 2: 123–128, [PUBMED], [INFOTRIEVE]
- Jordan V. C. The development of tamoxifen for breast cancer therapy: a tribute to the late Arthur L. Walpole. Breast Cancer Res. Treat. 1988; 11: 197–209, [PUBMED], [INFOTRIEVE]
- Jordan V. C., Koch R., Langan S., McCague R. Ligand interaction at the estrogen receptor to program antiestrogen action: a study with nonsteroidal compounds in vitro. Endocrinology 1988; 122: 1449–1454, [PUBMED], [INFOTRIEVE], [CSA]
- Kangas L. Review of the pharmacological properties of toremifene. J. Steroid Biochem. 1990; 36: 191–195, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Kasahara T., Hashiba M., Harada T., Degawa M. Change in the gene expression of hepatic tamoxifen‐metabolizing enzymes during the process of tamoxifen‐induced hepatocarcinogenesis in female rats. Carcinogenesis 2002; 3: 491–498, [CROSSREF]
- Killackey M., Hakes T. B., Pierce V. K. Endometrial adenocarcinoma in breast cancer patients receiving antiestrogens. Cancer Treat. Rep. 1985; 69: 237–238, [PUBMED], [INFOTRIEVE], [CSA]
- Kim S. Y., Suzuki N., Santosh Laxmi Y. R., Rieger R., Shibutani S. α‐Hydroxylation of tamoxifen and toremifene by human and rat cytochrome P450 3A subfamily enzymes. Chem. Res. Toxicol. 2003; 16: 1138–1144, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Kitagawa M., Ravindernath A., Suzuki N., Rieger R., Terashima I., Umemoto A., Shibutani S. Identification of tamoxifen‐DNA adducts induced by α‐acetoxy‐N‐desmethyltamoxifen. Chem. Res. Toxicol. 2000; 13: 761–769, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Kuramochi H. 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. 1996; 39: 2877–2886, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Lien E. A., Solheim E., Ueland P. M. Distribution of tamoxifen and its metabolites in rat and human tissues during steady‐state treatment. Cancer Res. 1991; 51: 4837–4844, [PUBMED], [INFOTRIEVE]
- Lim C. K., Yuan Z. X., Lamb J. H., White I. N., De Matteis F., Smith L. L. A comparative study of tamoxifen metabolism in female rat, mouse and human liver microsomes. Carcinogenesis 1994; 15: 589–593, [PUBMED], [INFOTRIEVE]
- Lowes D. A., Brown K., Heydon R., Martin E. A., Gant T. W. Site‐specific tamoxifen‐DNA adduct formation: lack of correlation with mutational ability in Escherichia coli. Biochemistry 1999; 38: 10989–10996, [PUBMED], [INFOTRIEVE]
- Mäenpää J., Holli K., Pasanen T. Toremifene. Where do we stand?. Eur. J. Cancer 2000; 36(Suppl. 40)S61–S62
- Mani C., Kupfer D. Cytochrome P‐450‐mediated activation and irreversible binding of the antiestrogen tamoxifen to proteins in rat and human liver: possible involvement of flavin‐containing monooxygenases in tamoxifen activation. Cancer Res. 1991; 51: 6052–6058, [PUBMED], [INFOTRIEVE]
- Mani C., Gelboin H. V., Park S. S., Pearce R., Parkinson A., Kupfer D. Metabolism of the antimammary cancer antiestrogenic agent tamoxifen. I. Cytochrome P‐450‐catalyzed N‐demethylation and 4‐hydroxylation. Drug Metab. Dispos. 1993a; 21: 645–656, [PUBMED], [INFOTRIEVE]
- Mani C., Hodgson E., Kupfer D. Metabolism of the antimammary cancer antiestrogenic agent tamoxifen. II. Flavin‐containing monooxygenase‐mediated N‐oxidation. Drug Metab. Dispos. 1993b; 21: 657–661, [PUBMED], [INFOTRIEVE]
- Marques M. M., Beland F. A. Identification of tamoxifen‐DNA adducts formed by 4‐hydroxytamoxifen quinone methide. Carcinogenesis 1997; 18: 1949–1954, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Martin E. A., Rich K. J., White I. N., Woods K. L., Powles T. J., Smith L. L. 32P‐postlabelled DNA adducts in liver obtained from women treated with tamoxifen. Carcinogenesis 1995; 16: 1651–1654, [PUBMED], [INFOTRIEVE]
- Martin E. A., Heydon R. T., Brown K., Brown J. E., Lim C. K., White I. N., Smith L. L. Evaluation of tamoxifen and α‐hydroxytamoxifen 32P‐post‐labelled DNA adducts by the development of a novel automated on‐line solid‐phase extraction HPLC method. Carcinogenesis 1998; 19: 1061–1069, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Martin E. A., Gaskell M., Boocock D. J., Turteltaub K. W., Al‐Azzawi F., White I. N., Brown K. Detection of DNA and protein adducts in [14C]‐tamoxifen treated women by accelerator mass spectrometry (AMS). Mutat. Res. 2001; 483(Suppl. 1)S146
- Martin E. A., Brown K., Gaskell M., Al‐Azzawi F., Garner R. C., Boocock D. J., Mattock E., Pring D. W., Dingley K., Turteltaub K. W., Smith L. L., White I. N. Tamoxifen DNA damage detected in human endometrium using accelerator mass spectrometry. Cancer Res. 2003; 63: 8461–8465, [PUBMED], [INFOTRIEVE]
- McLuckie K. I., Routledge M. N., Brown K., Gaskell M., Farmer P. B., Roberts G. C., Martin E. A. DNA adducts formed from 4‐hydroxytamoxifen are more mutagenic than those formed by α‐acetoxytamoxifen in a shuttle vector target gene replicated in human Ad293 cells. Biochemistry 2002; 41: 8899–8906, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Moorthy B., Sriram P., Pathak D. N., 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 adducts formed in vitro. Cancer Res. 1996; 56: 53–57, [PUBMED], [INFOTRIEVE]
- 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. U. S. A. 1993; 90: 1122–1126, [PUBMED], [INFOTRIEVE], [CSA]
- Murphy C., Fotsis T., Pantzar P., Adlercreutz H., Martin F. Analysis of tamoxifen, N‐desmethyltamoxifen and 4‐hydroxytamoxifen levels in cytosol and KCl‐nuclear extracts of breast tumours from tamoxifen treated patients by gas chromatography‐mass spectrometry (GC‐MS) using selected ion monitoring (SIM). J. Steroid Biochem. 1987; 28: 609–618, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Nicolò G., Pujic N., Ragni N., Gustavino C., Ferrara G. B., Pera C., Bertelli G. High frequency of K‐ras mutations in endometrial specimens from breast cancer patients treated with tamoxifen. Cancer Detection and Prevention 2000; 24(Suppl. 1)
- O'Regan R. M., Cisneros A., England G. M., MacGregor J. I., Muenzner H. D., Assikis V. J., Bilimoria M. M., Piette M., Dragan Y. P., Pitot H. C., Chatterton R., Jordan V. C. Effects of the antiestrogens tamoxifen, toremifene, and ICI 182,780 on endometrial cancer growth. J. Natl. Cancer Inst. 1998; 90: 1552–1558, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Osborne C. K. Tamoxifen in the treatment of breast cancer. New Engl. J. Med. 1998; 339: 1609–1617, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Osborne C. K., Wiebe V. J., McGuire W. L., Ciocca D. R., DeGregorio M. W. Tamoxifen and the isomers of 4‐hydroxytamoxifen in tamoxifen‐resistant tumors from breast cancer patients. J. Clin. Oncol. 1992; 10: 304–310, [PUBMED], [INFOTRIEVE]
- 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. 1996; 56: 66–71, [PUBMED], [INFOTRIEVE]
- Osborne M. R., Hardcastle I. R., Phillips D. H. Minor products of reaction of DNA with α‐acetoxytamoxifen. Carcinogenesis 1997; 18: 539–543, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Patterson J. S., Settatree R. S., Adam A. K., Kemp J. V. Serum concentrations of tamoxifen and major metabolites during long‐term Nolvadex therapy, correlated with clinical response. Breast Cancer: Experimental and Clinical Aspects, H. T. Mouridsen, T. Palshoff. Pergamon Press, New York 1980; 89
- Phillips D. H., Potter G. A., Horton M. N., Hewer A., Crofton‐Sleigh C., Jarman M., Venitt S. Reduced genotoxicity of [D5‐ethyl]‐tamoxifen implicates α‐hydroxylation of the ethyl group as a major pathway of tamoxifen activation to a liver carcinogen. Carcinogenesis 1994; 15: 1487–1492, [PUBMED], [INFOTRIEVE]
- Phillips D. H., Hewer A., Grover P. L., Poon G. K., Carmichael P. L. Tamoxifen does not form detectable adducts in white blood cells of breast cancer patients. Carcinogenesis 1996; 17: 1149–1152, [PUBMED], [INFOTRIEVE]
- Poirier M. C., Schild L. J. The genotoxicity of tainoxifen: extent and consequences. Mutagenesis 2003; 18: 395–399, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Poon G. K., Chui Y. C., McCague R., Lonning P. E., Feng R., Rowlands M. G., Jarman M. Analysis of phase I and phase II metabolites of tamoxifen in breast cancer patients. Drug Metab. Dispos. 1993; 21: 1119–1124, [PUBMED], [INFOTRIEVE], [CSA]
- Poon G. K., Walter B., Lonning P. E., Horton M. N., 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. 1995; 23: 377–382, [PUBMED], [INFOTRIEVE], [CSA]
- Rajaniemi H., Rasanen I., Koivisto P., Peltonen K., Hemminki K. Identification of the major tamoxifen‐DNA adducts in rat liver by mass spectroscopy. Carcinogenesis 1999; 20: 305–309, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Rubin G. L., Harrold A. J., Mills J. A., Falany C. N., Coughtrie M. W. Regulation of sulphotransferase expression in the endometrium during the menstrual cycle, by oral contraceptives and during early pregnancy. Mol. Hum. Reprod. 1999; 5: 995–1002, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Sanchez C., Shibutani S., Dasaradhi L., Bolton J. L., Fan P. W., McClelland R. A. Lifetime and reactivity of an ultimate tamoxifen carcinogen: the tamoxifen carbocation. J. Am. Chem. Soc. 1998; 120: 13513–13514, [CROSSREF]
- Schild L. J., Divi R. L., Beland F. A., Churchwell M. I., Doerge D. R., Gamboa da Costa G., Marques M. M., Poirier M. C. Formation of tamoxifen‐DNA adducts in multiple organs of adult female cynomolgus monkeys dosed with tamoxifen for 30 days. Cancer Res. 2003; 63: 5999–6003, [PUBMED], [INFOTRIEVE]
- Seoud M. A.‐F., Johnson J., Weed J. C. Gynecologic tumors in tamoxifen‐treated women with breast cancer. Obstet. Gynecol. 1993; 82: 165–169, [PUBMED], [INFOTRIEVE]
- Sharma M., Shubert D. E., Sharma M., Lewis J., McGarrigle B. P., Bofinger D. P., Olson J. R. Antioxidant inhibits tamoxifen‐DNA adducts in endometrial explant culture. Biochem. Biophys. Res. Commun. 2003a; 307: 157–164, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Sharma M., Shubert D. E., Sharma M., Lewis J., McGarrigle B. P., Bofinger D. P., Olson J. R. Biotransformation of tamoxifen in a human endometrial explant culture model. Chem. Biol. Interact. 2003b; 146: 237–249, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Shibutani S. Genotoxic mechanism of tamoxifen. Genotoxicity of Tamoxifen: Extent and Consequences. January 23, 2003, Waikoloa, Hawaii
- Shibutani S., Dasaradhi L. Miscoding potential of tamoxifen‐derived DNA adducts: α‐(N2‐deoxyguanosinyl) tamoxifen. Biochemistry 1997; 36: 13010–13017, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Shibutani S., Takeshita M., Grollman A. P. Insertion of specific bases during DNA synthesis past the oxidation‐damaged base 8‐oxodG. Nature 1991; 349: 431–434, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Shibutani S., Dasaradhi L., Terashima I., Banoglu E., Duffel M. W. α‐Hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts. Cancer Res. 1998a; 58: 647–653, [PUBMED], [INFOTRIEVE]
- Shibutani S., Shaw P., Suzuki N., Dasaradhi L., Duffel M. W., Terashima I. Sulfation of α‐hydroxytamoxifen catalyzed by human hydroxysteroid sulfotransferase results in tamoxifen DNA adducts. Carcinogenesis 1998b; 19: 2007–2011, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Shibutani S., Suzuki N., Terashima I., Sugarman M. S., Grollman A. P., Pearl M. L. Tamoxifen‐DNA adducts detected in the endometrium of women treated with tamoxifen. Chem. Res. Toxicol. 1999; 12: 646–653, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Shibutani S., Ravindernath A., Suzuki N., Terashima I., Sugarman S. M., Grollman A. P., Pearl M. L. Identification of tamoxifen‐DNA adducts in the endometrium of women treated with tamoxifen. Carcinogenesis 2000a; 21: 1461–1467, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Shibutani S., Reardon J. T., Suzuki N., Sancar A. Excision of tamoxifen‐DNA adducts by the human nucleotide excision repair system. Cancer Res. 2000b; 60: 2607–2610, [PUBMED], [INFOTRIEVE]
- Shibutani S., Ravindernath A., Terashima I., Suzuki N., Laxmi Y. R., Kanno Y., Suzuki M., Apak T. I., Sheng J. J., Duffel M. W. Mechanism of lower genotoxicity of toremifene compared with tamoxifen. Cancer Res. 2001; 61: 3925–3931, [PUBMED], [INFOTRIEVE]
- Shibutani S., Santosh Laxmi Y. R., Suzuki N. Inter‐laboratory variation of detecting tamoxifen‐DNA adducts using 32P‐postlabeling analysis. Proc. Am. Assoc. Cancer Res. 2002; 43: 1042
- Shibutani S., Suzuki N., Laxmi Y. R., Schild L. J., Divi R. L., Grollman A. P., Poirier M. C. Identification of tamoxifen‐DNA adducts in monkeys treated with tamoxifen. Cancer Res. 2003; 63: 4402–4406, [PUBMED], [INFOTRIEVE]
- Sridar C., Kent U. M., Notley L. M., Gillam E. M., Hollenberg P. F. Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J. Pharmacol. Exp. Ther. 2002; 301: 945–952, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Stearns V., Gelman E. P. Does tamoxifen cause cancer in human?. J. Clin. Oncol. 1998; 16: 779–792, [PUBMED], [INFOTRIEVE]
- Tannenbaum S. R. Comparative metabolism of tamoxifen and DNA adduct formation and in vitro studies on genotoxicity. Semin. Oncol. 1997; 24: 81–86
- Terashima I., Suzuki N., Shibutani S. Mutagenic potential of α‐(N2‐deoxyguanosinyl)tamoxifen lesions, the major DNA adducts detected in endometrial tissues of patients treated with tamoxifen. Cancer Res. 1999; 59: 2091–2095, [PUBMED], [INFOTRIEVE]
- Tomas E., Kauppila A., Blanco G., Apaja‐Sarkkinen M., Laatikainen T. Comparison between the effects of tamoxifen and toremifene on the uterus in postmenopausal breast cancer patients. Gynecol. Oncol. 1995; 59: 261–266, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Umemoto A., Monden Y., Komaki K., Suwa M., Kanno Y., Suzuki M., Lin C. X., Ueyama Y., Momen M. A., Ravindernath A., Shibutani S. Tamoxifen‐DNA adducts formed by α‐acetoxytamoxifen N‐oxide. Chem. Res. Toxicol. 1999; 12: 1083–1089, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- Umemoto A., Monden Y., Suwa M., Kanno Y., Suzuki M., Lin C. X., Ueyama Y., Momen M. A., Ravindernath A., Shibutani S., Komaki K. Identification of hepatic tamoxifen‐DNA adducts in mice: α‐(N2‐deoxyguanosinyl)tamoxifen and α‐(N2‐deoxyguanosinyl)tamoxifen N‐oxide. Carcinogenesis 2000; 21: 1737–1744, [PUBMED], [INFOTRIEVE], [CROSSREF]
- Umemoto A., Komaki K., Monden Y., Suwa M., Kanno Y., Kitagawa M., Suzuki M., Lin C. X., Ueyama Y., Momen M. A., Ravindernath A., Shibutani S. Identification and quantification of tamoxifen‐DNA adducts in the liver of rats and mice. Chem. Res. Toxicol. 2001; 14: 1006–1013, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
- van Leeuwen F. E., Benraadt J., Coebergh J. W.W., Kiemeney L. A.L.M., Gimbrère C. H.F., Otter R., Schouten L. J., Damhuis R. A.M., Bontenbal M., Diepenhorst F. W., van den Belt‐Dusebout A. W., van Tinteren H. Risk of endometrial cancer after tamoxifen treatment of breast cancer. Lancet 1994; 343: 448–452, [PUBMED], [INFOTRIEVE]
- Watanabe N., Koyama M., Yamashita K., Tominaga T. Metabolism of toremifene in rat. Antibiot. Chemother. 1996; 12: 287–296
- White I. N., 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 C57B1/6 mice and in human MCL‐5 cells. Carcinogenesis 1992; 13: 2197–2203, [PUBMED], [INFOTRIEVE]
- Williams G. M., Iatropoulos M. J., Djordjevic M. V., Kaltenberg O. P. The triphenylethylene drug tamoxifen is a strong liver carcinogen in the rat. Carcinogenesis 1993; 14: 315–317, [PUBMED], [INFOTRIEVE]
- Wogan G. N. Review of the toxicology of tamoxifen. Semin. Oncol. 1997; 24(Suppl. 1)87–97
- Ye Q., Bodell W. J. Production of 8‐hydroxy‐2′‐deoxyguanosine in DNA by microsomal activation of tamoxifen and 4‐hydroxytamoxifen. Carcinogenesis 1996; 17: 1747–1750, [PUBMED], [INFOTRIEVE]
- Zhang F., Fan P. W., Liu X., Shen L., van Breemen R. B., Bolton J. L. Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4‐dihydroxytamoxifen‐o‐quinone. Chem. Res. Toxicol. 2000; 13: 53–62, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]