David Kupfer and the Metabolism Connection: On Aromatase Inhibitors and Tamoxifen

REFERENCES

• ATAC Trialists’ Group. Pharmacokinetics of anastrozole and tamoxifen alone, and in combination, during adjuvant endocrine therapy for early breast cancer in postmenopausal women: a sub-protocol of the ‘arimidex and tamoxifen alone or in combination’ (ATAC) trial. Br. J. Cancer 2001; 85(3)317–324, [CSA]
   PubMed Web of Science ®Google Scholar
• Borgna J. L., Rochefort H. Hydroxylated metabolites of tamoxifen are formed in vivo and bound to estrogen receptor in target tissues. J. Biol. Chem 1981; 256: 859–868, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Brodie A. Aromatase inhibitor development and hormone therapy: a perspective. Sem. in Oncol 2003; 30: 12–22, [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Brodie A. M. H., Marsh D. A., Brodie H. J. Aromatase inhibitors IV. Regression of estrogen-dependent mammary tumors in the rat with 4-acetoxy-4-androstene-3,17-dione. J. Steroid. Biochem 1979; 10: 423–429, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMedGoogle Scholar
• Brodie A. M. H., Schwarzel W. C., Shaikh A. A., Brodie H. J. The effect of an aromatase inhibitor, 4-hydroxy-4-androstene-3,17-dione, on estrogen dependent processes in reproduction and breast cancer. Endocrinology 1977; 100: 1684–1695, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Cavalieri E., Rogan E., Chakravarti D. The role of endogenous catachol quinines in the initiation of cancer and neurodegenerative diseases. Methods Enzymol 2004; 382: 293–319, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Chakravarti D., Mailander P. C., Li K.-M. Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and forms mutations in the H-ras gene. Oncogene 2001; 20: 7945–7953, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Coombs C. R., Goss P., Dowsett M., Gazet J. C., Brodie A. 4-Hydroxyandostenedione in treatment of postmenopausal patients with advanced breast cancer. The Lancet 1984; 2: 1237–1239, [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Crewe H. K., Ellis S. W., Lennard M. S., Tucker G. T. Variable contribution of cytochrome P-450 2D6, 2C9, and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes. Biochem. Pharmacol 1997; 53: 171–178, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Dehal S. S., Brodie A. M. H., Kupfer D. The aromatase inactivator 4-hydroxyandrostenedione (4-OHA) inhibits tamoxifen metabolism by rat hepatic cytochrome P450 3A: potential for drug-drug interaction of tamoxifen and 4-OHA in combined anti-breast cancer therapy. Drug Metab. Dispos 1999; 27: 389–394, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Dehal S. S., Kupfer D. Evidence that catechol 3,4-dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Cancer Res 1996; 56: 1283–1290, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Dehal S. S., Kupfer D. CPY2D6 catalyzes tamoxifen-4-hydroxylation in human liver. Cancer Res 1997; 57: 3402–3406, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Dowsett M., Pfister C., Johnston S. R., Miles D. W., Houston S. J., Verbeek J. A. Impact of tamoxifen on the pharmacokinetics and endocrine effects of the aromatase inhibitor letrozole in postmenopausal women with breast cancer. Clin. Cancer Res 1999; 5: 2338–2343, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Dowsett M., Cuzick J., Howell A., Jackson I., ATAC Trialists’ Group. Pharmacokinetics of anastrozole and tamoxifen alone, and in combination, during adjuvant endocrine therapy for early breast cancer in postmenopausal women: a sub-protocol of the ‘Arimidex and tamoxifen alone or in combination’ (ATAC) trial. Br. J. Cancer 2001; 85: 317–324, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Fendel K. C., Zimniski S. J. Role of tamoxifen in the induction of hormone-independent rat mammary tumors. Cancer Res 1992; 52: 235–237, [CSA]
   PubMed Web of Science ®Google Scholar
• Fisher B., Constantino J. P., Wickerham D. L., Redmond C. K., Fisher E. R., 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, [PUBMED], [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Fornander T., Cedermark B., Matteson A., Skoog L., Theve T., Askergren J., Rutqvist L. E., Glas U., Silljverswaard C., Somell A., Wilking N., Hjolmar M. J. Adjuvant tamoxifen in early breast cancer: occurrence of new primary cancer. Lancet 1989; 1: 117–120, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Geisler J., Haynes B., Anker G., Dowsett M., Lonning P. E. Influence of letrozole and anastrozole on total body aromatization and plasma estrogen levels in postmenopausal breast cancer patients evaluated in a randomized, cross-over study. J. Clin. Oncol 2002; 20: 751–757, [PUBMED], [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Goss P. E., Coombes R. L., Powles T. J., Dowsett M., Brodie A. M. H. Treatment of advanced postmenopausal breast cancer with aromatase inhibitor, 4-hydroxyandrostenedione- phase 2 report. Cancer Res 1986; 46: 4823–4826, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Han X. L., Liehr J. G. Induction of covalent DNA adducts in rodents by tamoxifen. Cancer Res 1992; 52: 1360–1363, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Ingle J. N., Suman V. J., Johnson P. A., Krook J. E., Mailliard J. A., Wheeler R. H. Evaluation of tamoxifen plus letrozole with assessment of pharmacokinetic interaction in postmenopausal women with metastatic breast cancer. Clin. Cancer Res 1999; 5: 1642–1649, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Jacolot F., Simon I., Dreano Y., Beaune P., Riche C., Berthou F. Identification of the cytochrome P-450 IIIA family as enzymes involved in the N-demethylation of tamoxifen in human liver microsomes. Biochem. Pharmacol 1991; 41: 1911–1919, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Jordan V. C. Tamoxifen for the Treatment and Prevention of Breast Cancer. PRR Inc, Melville, NY 1999
   Google Scholar
• Jordan V. C., Collins M. M., Rowsby L., Prestwich G. A monohydroxylated metabolite of tamoxifen with potent antiestrogenic activity. J. Endocrinol 1977; 75: 305–316, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Killakey M. A., Hakes T. B., Price V. K. Endometrial adenocarcinoma in breast cancer patients receiving antiestrogens. Cancer Treat Rep 1985; 69: 237–238, [CSA]
   PubMedGoogle Scholar
• Kupfer D. The covalent binding of tamoxifen to proteins and DNA. Tamoxifen: Beyond the Antiestrogen, J.A. Kellen. Birkhauser, Boston 1996; 201–230
   Google Scholar
• Kupfer D., Bulger W. H., Theoharides A. D. Metabolism of methoxychlor by hepatic P-450 monooxygenases in rat and human. I. Characterization of a novel catechol metabolite. Chem. Res. Toxicol 1990; 3: 8–16, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Kupfer D., Mani C., Lee C. A., Rifkind A. B. Induction of tamoxifen-4-hydroxylation by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), β-naphthoflavone (βNF), and phenbarbital (PB) in avian liver: identification of P450 TCDDAA as catalyst of 4-hydroxylation induced by TCDD and βNF. Cancer Res 1994; 54: 3140–3144, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Li S. A., Purdy R. H., Li J. J. Variations in catechol O-methyltransferase inrodent tissues: possible role in estrogen carcinogenicity. Carcinogenesis (Lond.) 1989; 10: 63–67, [CSA]
   PubMed Web of Science ®Google Scholar
• Lim C. K., Yuan Z. X., Lamb J. H., White I. N. H., DeMatteis F., Smith L. L. A comparative study of tamoxifen metabolism in female rat, mouse, and human liver microsomes. Carcinogenesis (Oxf) 1994; 15: 589–593, [CSA]
   PubMed Web of Science ®Google Scholar
• Long B. J., Jelovac D., Handratta V., Thiantanawat A., MacPherson N., Ragaz J., Goloubeva O., Brodie A. M. Therapeutic strategies using the aromatase inhibitor letrozole and tamoxifen in a breast cancer model. J. Natl. Cancer Inst 2004; 96: 456–465, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Lu Q., Liu Y., Long B. J., Grigoryev D., Gimbel M., Brodie A. The effect of combining aromatase inhibitors with antiestrogens on tumor growth in a nude mouse model for breast cancer. Br. Cancer Res. Treat 1999; 57: 183–192, [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Lu Q., Yue W., Wang J., Liu Y., Long B. J., Brodie A. The effect of aromatase inhibitors and antiestrogens in the nude mouse model. Br. Cancer Res. Treat 1998; 50: 63–71, [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Mani C., Gelboin H. V., Park S. S., Pierce 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, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• 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, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• 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, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Mani C., Pierce R., Parkinson A., Kupfer D. Involvement of cytochrome P-450A in catalysis of tamoxifen activation and covalent binding to rat and human liver microsomes. Carcinogenesis (Oxf) 1994; 15: 2715–2720, [CSA]
   PubMed Web of Science ®Google Scholar
• McCague R., Seago A. Aspects of metabolism of tamoxifen by rat liver microsomes. Biochem. Pharmacol 1986; 35: 827–834, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Pathak D. N., Bodell W. J. DNA adducts formation by tamoxifen with rat and human liver microsomal activation system. Carcinogenesis (Oxf) 1994; 15: 529–532, [CSA]
   PubMed Web of Science ®Google Scholar
• 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 1994; 54: 5518–5522, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• 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, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Randerath K., Bi J., Mabon N., Sriram P., Moorthy B. Strong intensification of mouse hepatic tamoxifen DNA adduct formation by pretreatment with sulfotranferase inhibitor and ubiquitous environmental pollutant pentachlorophenol. Carcinogenesis (Oxf) 1994; 15: 797–800, [CSA]
   PubMed Web of Science ®Google Scholar
• Reunitz P. C., Bagley J. R., Pape C. W. Some chemical and biochemical aspects of liver microsomal metabolism of tamoxifen. Drug Metab. Dispos 1984; 12: 478–483, [CSA]
   PubMed Web of Science ®Google Scholar
• Schwarzel W. C., Kruggel W., Brodie H. J. Studies on the mechanism of estrogen biosynthesis. VII. The development of inhibitors of the enzyme system in the human placenta. Endocrinology 1973; 92: 866–880, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Smith C. L., Nawaz Z., O'Malley B. W. Coactivator and corepressor regulation of the agonist/antagonist activity of the mixed antiestrogen, 4-hydroxytamoxifen. Mol. Endocrinol 1997; 11: 657–666, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Takimoto G. S., Graham J. D., Jackson T. A., Tung L., Powell R. L., Horwitz L. D. Tamoxifen resistant breast cancer: coregulators determine the direction of transcription by antagonist-occupied steroid receptors. J. Steroid. Biochem. Mol. Biol 1999; 69: 45–50, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Vancutsem P. M., Lazarus P., Williams G. M. Frequent and specific mutations of the rat p53 gene in hepatocarcinomas induced by tamoxifen. Cancer Res 1994; 54: 3864–3867, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Van Leeumne F. E., Benraadt J., Coebergh J. W. W., Kiemeney L. A. L. M., Gimbrere 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, [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• White I. N. H., deMatteis F, Davies A, Smith L.L, Crofton-Sleigh C, Venitt S, Hewer A, Phillips D.H. Genotoxic potential of tamoxifen and analogs in female Fischer F344/N rats, DBA/2 and C57B1/G mice and in human MCL-5 cells. Carcinogenesis (Oxf) 1992; 13: 2197–2203, [CSA]
   PubMed Web of Science ®Google Scholar
• Williams G. M., Iatropoulos M. J., Djordjevic M. W., Kaltenberg O. P. The triphenlyethylene drug tamoxifen is a strong carcinogen in the rat. Carcinogenesis (Oxf) 1993; 14: 315–317, [CSA]
   PubMed Web of Science ®Google Scholar
• Winer E. P., Hudis C., Bursein H. J., Chlebowski R. T., Ingle J. N., Edge S. B., Mamounas E. P., Gralow J., Goldstein L. J., Pritchard K. I., Braun S., Cobleigh M. A., Langer A. S., Perotti J., Powles T. J., Whelan T. J., Browman G. P. American Society of Clinical Oncology technology assessment on the use of aromatase inhibitors as adjuvant therapy for women with hormone receptor-positive breast cancer: status report 2002. J.Clin. Oncol 2002; 20: 3317–3327, [INFOTRIEVE], [CROSSREF], [CSA]
   PubMed Web of Science ®Google Scholar
• Yue W., Brodie A. M. H. A nude mouse model for postmenopausal breast cancer using MCF-7 cells transfected with the human aromatase gene. Cancer Res 1994; 54: 5092–5095, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Yue W., Wang J, Savinov A., Brodie A. Effect of aromatase inhibitors on growth of mammary tumors in a nude mouse model. Cancer Res 1995; 55: 3073–3077, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Yue W., Wang J-P., Li Y., Bocchinfuso W. P., Korach K. S., Devanesan P. D., Rogan E., Cavalieri E., Richard J., Santen R.J. Tamoxifen versus aromatase inhibitors for breast cancer prevention. Clin. Cancer Res 2005; 11: 925s–930s, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar
• Zhou D., Pompon D., Chen S. Stable expression of human aromatase complementary DNA in mammalian cells: a useful system for aromatase inhibitor screening. Cancer Res 1990; 50: 6949–6954, [INFOTRIEVE], [CSA]
   PubMed Web of Science ®Google Scholar