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Volumn 19, Issue 9, 2006, Pages 1125-1137

Bioactivation of selective estrogen receptor modulators (SERMs)

Author keywords

[No Author keywords available]

Indexed keywords

2 QUINONE; 3,4 DIHYDROXYTAMOXIFEN; 4 [4 METHYL 2 [4 [2 (1 PIPERIDINYL)ETHOXY]PHENYL] 7 PIVALOYLOXY 2H 1 BENZOPYRAN 3 YLPHENYL] PIVALATE; 4 FLUORONORARZOXIFENE; 4 HYDROXYEQUILENIN; ACOLBIFENE; ARZOXIFENE; BENZOPYRAN DERIVATIVE; BENZOTHIOPHENE DERIVATIVE; CARBOCATION; CARBON; CARCINOGEN; CATION; CYTOCHROME P450 2C9; DROLOXIFENE; DRUG METABOLITE; EQUILENIN; ESTROGEN RECEPTOR; FULVESTRANT; IDOXIFENE; LSN 2120310; LUCIFERASE; LY 2066948; NORARZOXIFENE; QUINONE DERIVATIVE; QUINONE METHIDE; RALOXIFENE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; TAMOXIFEN; TAMOXIFEN CITRATE; TOREMIFENE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 33748994836     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx060126v     Document Type: Review
Times cited : (59)

References (143)
  • 1
    • 0032490068 scopus 로고    scopus 로고
    • Breast Cancer Prevention Trial shows major benefit, some risk
    • Smigel, K. (1998) Breast Cancer Prevention Trial shows major benefit, some risk. J. Natl. Cancer Inst. 90, 647-648.
    • (1998) J. Natl. Cancer Inst. , vol.90 , pp. 647-648
    • Smigel, K.1
  • 3
    • 0033304703 scopus 로고    scopus 로고
    • Tamoxifen, raloxifene, and the prevention of breast cancer
    • Jordan, V. C., and Morrow, M. (1999) Tamoxifen, raloxifene, and the prevention of breast cancer. Endocr. Rev. 20, 253-278.
    • (1999) Endocr. Rev. , vol.20 , pp. 253-278
    • Jordan, V.C.1    Morrow, M.2
  • 4
    • 0023836871 scopus 로고
    • Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal Foundation award lecture
    • Henderson, B. E., Ross, R., and Bernstein, L. (1988) Estrogens as a cause of human cancer: The Richard and Hinda Rosenthal Foundation award lecture. Cancer Res. 48, 246-253.
    • (1988) Cancer Res. , vol.48 , pp. 246-253
    • Henderson, B.E.1    Ross, R.2    Bernstein, L.3
  • 5
    • 0028100979 scopus 로고
    • What do we know and what don't we know about tamoxifen in the human uterus
    • Friedl, A., and Jordan, V. C. (1994) What do we know and what don't we know about tamoxifen in the human uterus. Breast Cancer Res. Treat. 31, 27-39.
    • (1994) Breast Cancer Res. Treat. , vol.31 , pp. 27-39
    • Friedl, A.1    Jordan, V.C.2
  • 6
    • 0028158119 scopus 로고
    • Endometrial changes with tamoxifen: Comparison between tamoxifen-treated and nontreated asymptomatic, postmenopausal breast cancer patients
    • Cohen, I., Rosen, D. J., Shapira, J., Cordoba, M., Gilboa, S., Altaras, M. M., Yigael, D., and Beyth, Y. (1994) Endometrial changes with tamoxifen: Comparison between tamoxifen-treated and nontreated asymptomatic, postmenopausal breast cancer patients. Gynecol. Oncol. 52, 185-190.
    • (1994) Gynecol. Oncol. , vol.52 , pp. 185-190
    • Cohen, I.1    Rosen, D.J.2    Shapira, J.3    Cordoba, M.4    Gilboa, S.5    Altaras, M.M.6    Yigael, D.7    Beyth, Y.8
  • 7
    • 0034713769 scopus 로고    scopus 로고
    • Effect of tamoxifen treatment on the endometrial expression of human insulin-like growth factors and their receptor mRNAs
    • Roy, R. N., Gerulath, A. H., Cecutti, A., and Bhavnani, B. R. (2000) Effect of tamoxifen treatment on the endometrial expression of human insulin-like growth factors and their receptor mRNAs. Mol. Cell. Endocrinol. 165, 173-178.
    • (2000) Mol. Cell. Endocrinol. , vol.165 , pp. 173-178
    • Roy, R.N.1    Gerulath, A.H.2    Cecutti, A.3    Bhavnani, B.R.4
  • 10
    • 0033970909 scopus 로고    scopus 로고
    • Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4-Dihydroxytamoxifen-o-quinone
    • Zhang, F., Fan, P. W., Liu, X., Shen, L., van Breeman, R. B., and Bolton, J. L. (2000) Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4-Dihydroxytamoxifen-o-quinone. Chem. Res. Toxicol. 13, 53-62.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 53-62
    • Zhang, F.1    Fan, P.W.2    Liu, X.3    Shen, L.4    Van Breeman, R.B.5    Bolton, J.L.6
  • 11
    • 0033958868 scopus 로고    scopus 로고
    • 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremitene are metabolized to unusually stable quinone methides
    • Fan, P. W., Zhang, F., and Bolton, J. L. (2000) 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremitene are metabolized to unusually stable quinone methides. Chem. Res. Toxicol. 13, 45-52.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 45-52
    • Fan, P.W.1    Zhang, F.2    Bolton, J.L.3
  • 12
    • 0036680017 scopus 로고    scopus 로고
    • Quinoids, quinoid radicals, and phenoxyl radicals formed from estrogens and antiestrogens
    • Bolton, J. L. (2002) Quinoids, quinoid radicals, and phenoxyl radicals formed from estrogens and antiestrogens. Toxicology 177, 55-65.
    • (2002) Toxicology , vol.177 , pp. 55-65
    • Bolton, J.L.1
  • 14
    • 3042653655 scopus 로고    scopus 로고
    • Genotoxic mechanism of tamoxifen in developing endometrial cancer
    • Kim, S. Y., Suzuki, N., Laxmi, Y. R., and Shibutani, S. (2004) Genotoxic mechanism of tamoxifen in developing endometrial cancer. Drug Metab. Rev. 36, 199-218.
    • (2004) Drug Metab. Rev. , vol.36 , pp. 199-218
    • Kim, S.Y.1    Suzuki, N.2    Laxmi, Y.R.3    Shibutani, S.4
  • 16
    • 0035680322 scopus 로고    scopus 로고
    • Structure-function relationships in estrogen receptors and the characterization of novel selective estrogen receptor modulators with unique pharmacological profiles
    • Katzenellenbogen, B. S., Sun, J., Harrington, W. R., Kraichely, D. M., Ganessunker, D., and Katzenellenbogen, J. A. (2001) Structure-function relationships in estrogen receptors and the characterization of novel selective estrogen receptor modulators with unique pharmacological profiles. Ann. N. Y. Acad. Sci. 949, 6-15.
    • (2001) Ann. N. Y. Acad. Sci. , vol.949 , pp. 6-15
    • Katzenellenbogen, B.S.1    Sun, J.2    Harrington, W.R.3    Kraichely, D.M.4    Ganessunker, D.5    Katzenellenbogen, J.A.6
  • 17
    • 0033835083 scopus 로고    scopus 로고
    • An issue of tissues: Divining the split personalities of selective estrogen receptor modulators
    • McKenna, N. J., and O'Malley, B. W. (2000) An issue of tissues: divining the split personalities of selective estrogen receptor modulators. Nat. Med. 6, 960-962.
    • (2000) Nat. Med. , vol.6 , pp. 960-962
    • McKenna, N.J.1    O'Malley, B.W.2
  • 19
    • 33749024584 scopus 로고    scopus 로고
    • STAR results: Raloxifene as effective as tamoxifen, better safety profile
    • Phillips, C. (2006) STAR results: Raloxifene as effective as tamoxifen, better safety profile. NCI Cancer Bulletin 3, 1-2.
    • (2006) NCI Cancer Bulletin , vol.3 , pp. 1-2
    • Phillips, C.1
  • 20
    • 0037204724 scopus 로고    scopus 로고
    • Connections and regulation of the human estrogen receptor
    • McDonnell, D. P., and Morris, J. D. (2002) Connections and regulation of the human estrogen receptor. Science 296, 1642-1644,
    • (2002) Science , vol.296 , pp. 1642-1644
    • McDonnell, D.P.1    Morris, J.D.2
  • 21
    • 0033305547 scopus 로고    scopus 로고
    • Nuclear receptor coregulators: Cellular and molecular biology
    • McKenna, N. J., Lanz, R. B., and O'Malley, B. W. (1999) Nuclear receptor coregulators: Cellular and molecular biology. Endocr. Rev. 20, 321-344.
    • (1999) Endocr. Rev. , vol.20 , pp. 321-344
    • McKenna, N.J.1    Lanz, R.B.2    O'Malley, B.W.3
  • 25
    • 0026735224 scopus 로고
    • Mechanism of estrogen activation of c-myc oncogene expression
    • Dubik, D., and Shiu, R. P. (1992) Mechanism of estrogen activation of c-myc oncogene expression. Oncogene 7, 1587-1594.
    • (1992) Oncogene , vol.7 , pp. 1587-1594
    • Dubik, D.1    Shiu, R.P.2
  • 27
    • 0033637703 scopus 로고    scopus 로고
    • Cofactor dynamics and sufficiency in estrogen receptor-regulated transcription
    • Shang, Y., Hu, X., DiRenzo, J., Lazar, M. A., and Brown, M. (2000) Cofactor dynamics and sufficiency in estrogen receptor-regulated transcription. Cell 103, 843-852.
    • (2000) Cell , vol.103 , pp. 843-852
    • Shang, Y.1    Hu, X.2    DiRenzo, J.3    Lazar, M.A.4    Brown, M.5
  • 28
    • 1442351143 scopus 로고    scopus 로고
    • Coregulator function: A key to understanding tissue specificity of selective receptor modulators
    • Smith, C. L., and O'Malley, B. W. (2004) Coregulator function: a key to understanding tissue specificity of selective receptor modulators. Endocr. Rev. 25, 45-71.
    • (2004) Endocr. Rev. , vol.25 , pp. 45-71
    • Smith, C.L.1    O'Malley, B.W.2
  • 29
    • 0037192501 scopus 로고    scopus 로고
    • Molecular determinants for the tissue specificity of SERMs
    • Shang, Y., and Brown, M. (2002) Molecular determinants for the tissue specificity of SERMs. Science 295, 2465-2468.
    • (2002) Science , vol.295 , pp. 2465-2468
    • Shang, Y.1    Brown, M.2
  • 30
    • 0028283503 scopus 로고
    • Molecular mechanisms of action of steroid/thyroid receptor superfamily members
    • Tsai, M. J., and O'Malley, B. W. (1994) Molecular mechanisms of action of steroid/thyroid receptor superfamily members. Annu. Rev. Biochem. 63, 451-486.
    • (1994) Annu. Rev. Biochem. , vol.63 , pp. 451-486
    • Tsai, M.J.1    O'Malley, B.W.2
  • 31
    • 0029618368 scopus 로고
    • Steroid hormone receptors: Many actors in search of a plot
    • Beato, M., Herrlich, P., and Schutz, G. (1995) Steroid hormone receptors: Many actors in search of a plot. Cell 83, 851-857.
    • (1995) Cell , vol.83 , pp. 851-857
    • Beato, M.1    Herrlich, P.2    Schutz, G.3
  • 32
    • 0031039888 scopus 로고    scopus 로고
    • Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta
    • Kuiper, G. G., Carlsson, B., Grandien, K., Enmark, E., Haggblad, J., Nilsson, S., and Gustafsson, J. A. (1997) Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 138, 863-870.
    • (1997) Endocrinology , vol.138 , pp. 863-870
    • Kuiper, G.G.1    Carlsson, B.2    Grandien, K.3    Enmark, E.4    Haggblad, J.5    Nilsson, S.6    Gustafsson, J.A.7
  • 33
    • 0028625491 scopus 로고
    • Insights from the study of animals lacking functional estrogen receptor
    • Korach, K. S. (1994) Insights from the study of animals lacking functional estrogen receptor. Science 266, 1524-1527.
    • (1994) Science , vol.266 , pp. 1524-1527
    • Korach, K.S.1
  • 35
    • 0031026744 scopus 로고    scopus 로고
    • Clinical potential of new antiestrogens
    • Gradishar, W. J., and Jordan, V. C. (1997) Clinical potential of new antiestrogens. J. Clin. Oncol. 15, 840-852.
    • (1997) J. Clin. Oncol. , vol.15 , pp. 840-852
    • Gradishar, W.J.1    Jordan, V.C.2
  • 36
    • 0032126882 scopus 로고    scopus 로고
    • Antiestrogenic action of raloxifene and tamoxifen: Today and tomorrow
    • Jordan, V. C. (1998) Antiestrogenic action of raloxifene and tamoxifen: Today and tomorrow. J. Natl. Cancer Inst. 90, 967-971.
    • (1998) J. Natl. Cancer Inst. , vol.90 , pp. 967-971
    • Jordan, V.C.1
  • 41
    • 33646371740 scopus 로고    scopus 로고
    • Molecular mechanisms of oestrogen and SERMs in endometrial carcinogenesis
    • Shang, Y. (2006) Molecular mechanisms of oestrogen and SERMs in endometrial carcinogenesis. Nat. Rev. Cancer 6, 360-368.
    • (2006) Nat. Rev. Cancer , vol.6 , pp. 360-368
    • Shang, Y.1
  • 42
    • 0032446607 scopus 로고    scopus 로고
    • The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen
    • Shiau, A. K., Barstad, D., Loria, P. M., Cheng, L., Kushner, P. J., Agard, D. A., and Greene, G. L. (1998) The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95, 927-937.
    • (1998) Cell , vol.95 , pp. 927-937
    • Shiau, A.K.1    Barstad, D.2    Loria, P.M.3    Cheng, L.4    Kushner, P.J.5    Agard, D.A.6    Greene, G.L.7
  • 45
    • 0023663885 scopus 로고
    • Functional domains of the human estrogen receptor
    • Kumar, V., Green, S., Stack, G., Berry, M., Jin, J. R., and Chambon, P. (1987) Functional domains of the human estrogen receptor. Cell 51, 941-951.
    • (1987) Cell , vol.51 , pp. 941-951
    • Kumar, V.1    Green, S.2    Stack, G.3    Berry, M.4    Jin, J.R.5    Chambon, P.6
  • 46
    • 0031833450 scopus 로고    scopus 로고
    • The nuclear receptor ligand-binding domain: Structure and function
    • Moras, D., and Gronemeyer, H. (1998) The nuclear receptor ligand-binding domain: structure and function. Curr. Opin. Cell Biol. 10, 384-391.
    • (1998) Curr. Opin. Cell Biol. , vol.10 , pp. 384-391
    • Moras, D.1    Gronemeyer, H.2
  • 51
    • 0030986236 scopus 로고    scopus 로고
    • A signature motif in transcriptional co-activators mediates binding to nuclear receptors
    • Heery, D. M., Kalkhoven, E., Hoare, S., and Parker, M. G. (1997) A signature motif in transcriptional co-activators mediates binding to nuclear receptors. Nature 387, 733-736.
    • (1997) Nature , vol.387 , pp. 733-736
    • Heery, D.M.1    Kalkhoven, E.2    Hoare, S.3    Parker, M.G.4
  • 52
    • 0030912539 scopus 로고    scopus 로고
    • The transcriptional co-activator p/CIP binds CBP and mediates nuclear-receptor function
    • Torchia, J., Rose, D. W., Inostroza, J., Kamei, Y., Westin, S., Glass, C. K., and Rosenfeld, M. G. (1997) The transcriptional co-activator p/CIP binds CBP and mediates nuclear-receptor function. Nature 387, 677-684.
    • (1997) Nature , vol.387 , pp. 677-684
    • Torchia, J.1    Rose, D.W.2    Inostroza, J.3    Kamei, Y.4    Westin, S.5    Glass, C.K.6    Rosenfeld, M.G.7
  • 53
    • 0032230231 scopus 로고    scopus 로고
    • Nuclear receptor-binding sites of coactivators glucocorticoid receptor interacting protein 1 (GRIP1) and steroid receptor coactivator 1 (SRC-1): Multiple motifs with different binding specificities
    • Ding, X. F., Anderson, C. M., Ma, H., Hong, H., Uht, R. M., Kushner, P. J., and Stallcup, M. R. (1998) Nuclear receptor-binding sites of coactivators glucocorticoid receptor interacting protein 1 (GRIP1) and steroid receptor coactivator 1 (SRC-1): Multiple motifs with different binding specificities. Mol. Endocrinol. 12, 302-313.
    • (1998) Mol. Endocrinol. , vol.12 , pp. 302-313
    • Ding, X.F.1    Anderson, C.M.2    Ma, H.3    Hong, H.4    Uht, R.M.5    Kushner, P.J.6    Stallcup, M.R.7
  • 54
    • 0029841744 scopus 로고    scopus 로고
    • A possible involvement of TIF1 alpha and TIF1 beta in the epigenetic control of transcription by nuclear receptors
    • Le Douarin, B., Nielsen, A. L., Garnier, J. M., Ichinose, H., Jeanmougin, F., Losson, R., and Chambon, P. (1996) A possible involvement of TIF1 alpha and TIF1 beta in the epigenetic control of transcription by nuclear receptors. EMBO J. 15, 6701-6715.
    • (1996) EMBO J. , vol.15 , pp. 6701-6715
    • Le Douarin, B.1    Nielsen, A.L.2    Garnier, J.M.3    Ichinose, H.4    Jeanmougin, F.5    Losson, R.6    Chambon, P.7
  • 55
    • 0037192485 scopus 로고    scopus 로고
    • Biomedicine. Defining the "S" in SERMs
    • Katzenellenbogen, B. S., and Katzenellenbogen, J. A. (2002) Biomedicine. Defining the "S" in SERMs. Science 295, 2380-2381.
    • (2002) Science , vol.295 , pp. 2380-2381
    • Katzenellenbogen, B.S.1    Katzenellenbogen, J.A.2
  • 56
    • 27144503005 scopus 로고    scopus 로고
    • Tamoxifen-DNA adduct formation in human endometrium. Chem
    • author reply 1509-1511
    • Beland, F. A., Marques, M. M., Gamboa da Costa, G., and Phillips, D. H. (2005) Tamoxifen-DNA adduct formation in human endometrium. Chem. Res. Toxicol. 18, 1507-1509; author reply 1509-1511.
    • (2005) Res. Toxicol. , vol.18 , pp. 1507-1509
    • Beland, F.A.1    Marques, M.M.2    Gamboa Da Costa, G.3    Phillips, D.H.4
  • 59
    • 13844264457 scopus 로고    scopus 로고
    • Bioactivation of the selective estrogen receptor modulator acolbifene to quinone methides
    • Liu, J., Liu, H., van Breemen, R. B., Thatcher, G. R., and Bolton, J. L. (2005) Bioactivation of the selective estrogen receptor modulator acolbifene to quinone methides. Chem. Res. Toxicol. 18, 174-182.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 174-182
    • Liu, J.1    Liu, H.2    Van Breemen, R.B.3    Thatcher, G.R.4    Bolton, J.L.5
  • 61
    • 13844269367 scopus 로고    scopus 로고
    • Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4′-Fluoro substitution prevents quinoid formation
    • Liu, H., Liu, J., van Breemen, R. B., Thatcher, G. R., and Bolton, J. L. (2005) Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4′-Fluoro substitution prevents quinoid formation. Chem. Res. Toxicol. 18, 162-173.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 162-173
    • Liu, H.1    Liu, J.2    Van Breemen, R.B.3    Thatcher, G.R.4    Bolton, J.L.5
  • 62
    • 25444462779 scopus 로고    scopus 로고
    • Analysis of protein covalent modification by xenobiotics using a covert oxidatively activated tag: Raloxifene proof-of-principle study
    • Liu, J., Li, Q., Yang, X., van Breemen, R. B., Bolton, J. L., and Thatcher, G. R. (2005) Analysis of protein covalent modification by xenobiotics using a covert oxidatively activated tag: Raloxifene proof-of-principle study. Chem. Res. Toxicol. 18, 1485-1496.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1485-1496
    • Liu, J.1    Li, Q.2    Yang, X.3    Van Breemen, R.B.4    Bolton, J.L.5    Thatcher, G.R.6
  • 64
    • 0033017135 scopus 로고    scopus 로고
    • Cytochrome P-450 3A and 2D6 catalyze ortho hydroxylation of 4-hydroxytamoxifen and 3-hydroxytamoxifen (droloxifene) yielding tamoxifen catechoh Involvement of catechols in covalent binding to hepatic proteins
    • Dehal, S. S., and Kupfer, D. (1999) Cytochrome P-450 3A and 2D6 catalyze ortho hydroxylation of 4-hydroxytamoxifen and 3-hydroxytamoxifen (droloxifene) yielding tamoxifen catechoh Involvement of catechols in covalent binding to hepatic proteins. Drug Metab. Dispos. 27, 681-688.
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 681-688
    • Dehal, S.S.1    Kupfer, D.2
  • 65
    • 0029866506 scopus 로고    scopus 로고
    • Evidence that the catechol 3,4-Dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins
    • Dehal, S. S., and Kupfer, D. (1996) Evidence that the catechol 3,4-Dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Cancer Res. 56, 1283-1290.
    • (1996) Cancer Res. , vol.56 , pp. 1283-1290
    • Dehal, S.S.1    Kupfer, D.2
  • 66
    • 0025770020 scopus 로고
    • New perspective on cancer of the contralateral breast: A marker for assessing tamoxifen as a preventive agent
    • Fisher, B., and Redmond, C. (1991) New perspective on cancer of the contralateral breast: A marker for assessing tamoxifen as a preventive agent. J. Natl. Cancer Inst. 83, 1278-1280.
    • (1991) J. Natl. Cancer Inst. , vol.83 , pp. 1278-1280
    • Fisher, B.1    Redmond, C.2
  • 67
    • 0021960977 scopus 로고
    • Endometrial adenocarcinoma in breast cancer patients receiving antiestrogens
    • Killackey, M. A., Hakes, T. B., and Pierce, V. K. (1985) Endometrial adenocarcinoma in breast cancer patients receiving antiestrogens. Cancer Treat. Rep. 69, 237-238.
    • (1985) Cancer Treat. Rep. , vol.69 , pp. 237-238
    • Killackey, M.A.1    Hakes, T.B.2    Pierce, V.K.3
  • 69
    • 0028804312 scopus 로고
    • Endometrial cancer. Management of high risk and recurrence including the tamoxifen controversy
    • Cohen, C. J., and Rahaman, J. (1995) Endometrial cancer. Management of high risk and recurrence including the tamoxifen controversy. Cancer 76, 2044-2052.
    • (1995) Cancer , vol.76 , pp. 2044-2052
    • Cohen, C.J.1    Rahaman, J.2
  • 70
    • 0029123403 scopus 로고
    • The decision to enter a randomized trial of tamoxifen for the prevention of breast cancer in healthy women: An analysis of the tradeoffs
    • Nease, R. F., Jr., and Ross, J. M. (1995) The decision to enter a randomized trial of tamoxifen for the prevention of breast cancer in healthy women: an analysis of the tradeoffs. Am. J. Med. 99, 180-189.
    • (1995) Am. J. Med. , vol.99 , pp. 180-189
    • Nease Jr., R.F.1    Ross, J.M.2
  • 71
    • 0029012731 scopus 로고
    • Tamoxifen and the induction of cancer
    • King, C. M. (1995) Tamoxifen and the induction of cancer. Carcinogenesis 16, 1449-1454.
    • (1995) Carcinogenesis , vol.16 , pp. 1449-1454
    • King, C.M.1
  • 72
    • 0027930072 scopus 로고
    • Frequent and specific mutations of the rat p53 gene in hepatocarcinomas induced by tamoxifen
    • Vancutsem, P. M., Lazarus, P., and Williams, G. M. (1994) Frequent and specific mutations of the rat p53 gene in hepatocarcinomas induced by tamoxifen. Cancer Res. 54, 3864-3867.
    • (1994) Cancer Res. , vol.54 , pp. 3864-3867
    • Vancutsem, P.M.1    Lazarus, P.2    Williams, G.M.3
  • 73
    • 0026575696 scopus 로고
    • Role of tamoxifen in the induction of hormone-independent rat mammary tumors
    • Fendel, K. C. Z. S. J. (1992) Role of tamoxifen in the induction of hormone-independent rat mammary tumors. Cancer Res. 235-237.
    • (1992) Cancer Res. , pp. 235-237
    • Fendel, K.C.Z.S.J.1
  • 74
    • 0020506431 scopus 로고
    • Antiestrogenic action of 3-hydroxytamoxifen in the human breast cancer cell line MCF-7
    • Roos, W., Oeze, L., Loser, R., and Eppenberger, U. (1983) Antiestrogenic action of 3-hydroxytamoxifen in the human breast cancer cell line MCF-7. J. Natl. Cancer Inst. 71, 55-59.
    • (1983) J. Natl. Cancer Inst. , vol.71 , pp. 55-59
    • Roos, W.1    Oeze, L.2    Loser, R.3    Eppenberger, U.4
  • 75
    • 0027054733 scopus 로고
    • Genotoxic potential of tamoxifen and analogues in female Fischer F344/n rats, DBA/2 and C57BL/6 mice and in human MCL-5 cells
    • White, I. N., de Matteis, F., Davies, A., Smith, L. L., Crofton-Sleigh, C., Venitt, S., Hewer, A., and Phillips, D. H. (1992) 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, 2197-2203.
    • (1992) Carcinogenesis , vol.13 , pp. 2197-2203
    • White, I.N.1    De Matteis, F.2    Davies, A.3    Smith, L.L.4    Crofton-Sleigh, C.5    Venitt, S.6    Hewer, A.7    Phillips, D.H.8
  • 76
    • 0030750807 scopus 로고    scopus 로고
    • Idoxifene is equipotent to tamoxifen in inhibiting mammary carcinogenesis but forms lower levels of hepatic DNA adducts
    • Pace, P., Jarman, M., Phillips, D., Hewer, A., Bliss, J., and Coombes, R. C. (1997) Idoxifene is equipotent to tamoxifen in inhibiting mammary carcinogenesis but forms lower levels of hepatic DNA adducts. Br. J. Cancer 76, 700-704.
    • (1997) Br. J. Cancer , vol.76 , pp. 700-704
    • Pace, P.1    Jarman, M.2    Phillips, D.3    Hewer, A.4    Bliss, J.5    Coombes, R.C.6
  • 77
    • 0031039798 scopus 로고    scopus 로고
    • The novel anti-oestrogen idoxifene inhibits the growth of human MCF-7 breast cancer xenografts and reduces the frequency of acquired anti-oestrogen resistance
    • Johnston, S. R., Riddler, S., Haynes, B. P., A'Hern, R., Smith, I. E., Jarman, M., and Dowsett, M. (1997) The novel anti-oestrogen idoxifene inhibits the growth of human MCF-7 breast cancer xenografts and reduces the frequency of acquired anti-oestrogen resistance. Br. J. Cancer 75, 804-809.
    • (1997) Br. J. Cancer , vol.75 , pp. 804-809
    • Johnston, S.R.1    Riddler, S.2    Haynes, B.P.3    A'Hern, R.4    Smith, I.E.5    Jarman, M.6    Dowsett, M.7
  • 78
    • 0030613674 scopus 로고    scopus 로고
    • Comparisons of the binding of [14C]-radiolabelled tamoxifen or toremifene to rat DNA using accelerator mass spectrometry
    • White, I. N., Martin, E. A., Mauthe, R. J., Vogel, J. S., Turteltaub, K. W., and Smith, L. L. (1997) Comparisons of the binding of [14C]-radiolabelled tamoxifen or toremifene to rat DNA using accelerator mass spectrometry. Chem.-Biol. Interact. 106, 149-160.
    • (1997) Chem.-Biol. Interact. , vol.106 , pp. 149-160
    • White, I.N.1    Martin, E.A.2    Mauthe, R.J.3    Vogel, J.S.4    Turteltaub, K.W.5    Smith, L.L.6
  • 79
    • 3042653655 scopus 로고    scopus 로고
    • Genotoxic mechanism of tamoxifen in developing endometrial cancer
    • Kim, S. Y., Suzuki, N., Laxmi, Y. R., and Shibutani, S. (2004) Genotoxic mechanism of tamoxifen in developing endometrial cancer. Drug Metab. Rev. 36, 199-218.
    • (2004) Drug Metab. Rev. , vol.36 , pp. 199-218
    • Kim, S.Y.1    Suzuki, N.2    Laxmi, Y.R.3    Shibutani, S.4
  • 80
    • 0035661144 scopus 로고    scopus 로고
    • Endocrine manipulation in advanced breast cancer: Recent advances with SERM therapies
    • discussion 4411s-4412s
    • Johnston, S. R. (2001). Endocrine manipulation in advanced breast cancer: Recent advances with SERM therapies. Clin. Cancer Res. 7, 4376s-4387s; discussion 4411s-4412s.
    • (2001) Clin. Cancer Res. , vol.7
    • Johnston, S.R.1
  • 81
    • 0034193122 scopus 로고    scopus 로고
    • Effects of high dose raloxifene in selected patients with advanced breast carcinoma
    • Gradishar, W., Glusman, J., Lu, Y., Vogel, C., Cohen, F. J., and Sledge, G. W., Jr. (2000) Effects of high dose raloxifene in selected patients with advanced breast carcinoma. Cancer 88, 2047-2053.
    • (2000) Cancer , vol.88 , pp. 2047-2053
    • Gradishar, W.1    Glusman, J.2    Lu, Y.3    Vogel, C.4    Cohen, F.J.5    Sledge Jr., G.W.6
  • 83
    • 0035671943 scopus 로고    scopus 로고
    • Effects of the new selective estrogen receptor modulator LY353381.HCl (Arzoxifene) on human endometrial cancer growth in athymic mice
    • Dardes, R. C., Bentrem, D., O'Regan, R. M., Schafer, J. M., and Jordan, V. C. (2001) Effects of the new selective estrogen receptor modulator LY353381.HCl (Arzoxifene) on human endometrial cancer growth in athymic mice. Clin. Cancer Res. 7, 4149-4155.
    • (2001) Clin. Cancer Res. , vol.7 , pp. 4149-4155
    • Dardes, R.C.1    Bentrem, D.2    O'Regan, R.M.3    Schafer, J.M.4    Jordan, V.C.5
  • 84
    • 0037824471 scopus 로고    scopus 로고
    • A phase II trial of arzoxifene, a selective estrogen response modulator, in patients with recurrent or advanced endometrial cancer
    • McMeekin, D. S., Gordon, A., Fowler, J., Melemed, A., Buller, R., Burke, T., Bloss, J., and Sabbatini, P. (2003) A phase II trial of arzoxifene, a selective estrogen response modulator, in patients with recurrent or advanced endometrial cancer. Gynecol. Oncol. 90, 64-69.
    • (2003) Gynecol. Oncol. , vol.90 , pp. 64-69
    • McMeekin, D.S.1    Gordon, A.2    Fowler, J.3    Melemed, A.4    Buller, R.5    Burke, T.6    Bloss, J.7    Sabbatini, P.8
  • 86
    • 0036754189 scopus 로고    scopus 로고
    • Arzoxifene in breast cancer
    • Chan, S. (2002) Arzoxifene in breast cancer. Eur. J. Cancer. 38 (Suppl. 6), S55-S56.
    • (2002) Eur. J. Cancer , vol.38 , Issue.SUPPL. 6
    • Chan, S.1
  • 87
    • 0025177927 scopus 로고
    • Experimental endometriosis in laboratory animals as a research model
    • Vernon, M. W. (1990) Experimental endometriosis in laboratory animals as a research model. Prog. Clin. Biol. Res. 323, 49-60.
    • (1990) Prog. Clin. Biol. Res. , vol.323 , pp. 49-60
    • Vernon, M.W.1
  • 88
    • 13844286452 scopus 로고    scopus 로고
    • Arzoxifene as therapy for endometrial cancer
    • Thomas, W., Burke, M. D., and Walker, C. L. (2003) Arzoxifene as therapy for endometrial cancer. Gynecol. Oncol. 90, S40-S46.
    • (2003) Gynecol. Oncol. , vol.90
    • Thomas, W.1    Burke, M.D.2    Walker, C.L.3
  • 89
    • 33644775813 scopus 로고    scopus 로고
    • Arzoxifene: The development and clinical outcome of an ideal SERM
    • Munster, P. N. (2006) Arzoxifene: The development and clinical outcome of an ideal SERM. Exp. Opin. Invest. Drugs 15, 317-326.
    • (2006) Exp. Opin. Invest. Drugs , vol.15 , pp. 317-326
    • Munster, P.N.1
  • 92
    • 0030879732 scopus 로고    scopus 로고
    • Characterization of the effects of the novel non-steroidal antiestrogen EM-800 on basal and estrogen-induced proliferation of T-47D, ZR-75-1 and MCF-7 human breast cancer cells in vitro
    • Simard, J., Labrie, C., Belanger, A., Gauthier, S., Singh, S. M., Merand, Y., and Labrie, F. (1997) Characterization of the effects of the novel non-steroidal antiestrogen EM-800 on basal and estrogen-induced proliferation of T-47D, ZR-75-1 and MCF-7 human breast cancer cells in vitro. Int. J. Cancer 73, 104-112.
    • (1997) Int. J. Cancer , vol.73 , pp. 104-112
    • Simard, J.1    Labrie, C.2    Belanger, A.3    Gauthier, S.4    Singh, S.M.5    Merand, Y.6    Labrie, F.7
  • 93
    • 0030860885 scopus 로고    scopus 로고
    • Blockade of the stimulatory effect of estrogens. OH-tamoxifen, OH-toremifene, droloxifene, and raloxifene on alkaline phosphatase activity by the antiestrogen EM-800 in human endometrial adenocarcinoma Ishikawa cells
    • Simard, J., Sanchez, R., Poirier, D., Gauthier, S., Singh, S. M., Merand, Y., Belanger, A., Labrie, C., and Labrie, F. (1997) Blockade of the stimulatory effect of estrogens. OH-tamoxifen, OH-toremifene, droloxifene, and raloxifene on alkaline phosphatase activity by the antiestrogen EM-800 in human endometrial adenocarcinoma Ishikawa cells. Cancer Res. 57, 3494-3497.
    • (1997) Cancer Res. , vol.57 , pp. 3494-3497
    • Simard, J.1    Sanchez, R.2    Poirier, D.3    Gauthier, S.4    Singh, S.M.5    Merand, Y.6    Belanger, A.7    Labrie, C.8    Labrie, F.9
  • 94
    • 0031964105 scopus 로고    scopus 로고
    • Comparison of the effects of the antiestrogens EM-800 and tamoxifen on the growth of human breast ZR-75-1 cancer xenografts in nude mice
    • Couillard, S., Gutman, M., Labrie, C., Belanger, A., Candas, B., and Labrie, F. (1998) Comparison of the effects of the antiestrogens EM-800 and tamoxifen on the growth of human breast ZR-75-1 cancer xenografts in nude mice. Cancer Res. 58, 60-64.
    • (1998) Cancer Res. , vol.58 , pp. 60-64
    • Couillard, S.1    Gutman, M.2    Labrie, C.3    Belanger, A.4    Candas, B.5    Labrie, F.6
  • 95
    • 0030738259 scopus 로고    scopus 로고
    • Effect of dehydroepiandrosterone on bone mass, serum lipids, and dimethylbenz(a)anthracene-induced mammary carcinoma in the rat
    • Luo, S., Labrie, C., Belanger, A., and Labrie, F. (1997). Effect of dehydroepiandrosterone on bone mass, serum lipids, and dimethylbenz(a) anthracene-induced mammary carcinoma in the rat. Endocrinology 138, 3387-3394.
    • (1997) Endocrinology , vol.138 , pp. 3387-3394
    • Luo, S.1    Labrie, C.2    Belanger, A.3    Labrie, F.4
  • 96
    • 1642544604 scopus 로고    scopus 로고
    • Selective estrogen receptor modulation: Concept and consequences in cancer
    • Jordan, V. C. (2004) Selective estrogen receptor modulation: Concept and consequences in cancer. Cancer Cell 5, 207-213.
    • (2004) Cancer Cell , vol.5 , pp. 207-213
    • Jordan, V.C.1
  • 98
    • 27544464442 scopus 로고    scopus 로고
    • Formation of tamoxifen-DNA adducts via O-sulfonation, not O-acetylation of alpha-hydroxytamoxifen in rat and human livers
    • Kim, S. Y., Laxmi, Y. R., Suzuki, N., Ogura, K., Watabe, T., Duffel, M. W., and Shibutani, S. (2005) Formation of tamoxifen-DNA adducts via O-sulfonation, not O-acetylation of alpha-hydroxytamoxifen in rat and human livers. Drug Metab. Dispos. 33, 1673-1678.
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 1673-1678
    • Kim, S.Y.1    Laxmi, Y.R.2    Suzuki, N.3    Ogura, K.4    Watabe, T.5    Duffel, M.W.6    Shibutani, S.7
  • 100
    • 0141961680 scopus 로고    scopus 로고
    • Correspondence regarding M. Sharma et al., Antioxidant inhibits tamoxifen-DNA adducts in endometrial explant culture
    • Brown, K., and Carmichael, P. L. (2003) Correspondence regarding M. Sharma et al., Antioxidant inhibits tamoxifen-DNA adducts in endometrial explant culture. Biochem. Biophys. Res. Commun. 310, 1039.
    • (2003) Biochem. Biophys. Res. Commun. , vol.310 , pp. 1039
    • Brown, K.1    Carmichael, P.L.2
  • 101
    • 0028911210 scopus 로고
    • Identification of tamoxifen metabolites in human Hep G2 cell line, human liver homogenate, and patients on long-term therapy for breast cancer
    • Poon, G. K., Walter, B., Lonning, P. E., Horton, M. N., and McCague, R. (1995) 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) Drug Metab. Dispos. , vol.23 , pp. 377-382
    • Poon, G.K.1    Walter, B.2    Lonning, P.E.3    Horton, M.N.4    McCague, R.5
  • 103
    • 0141513744 scopus 로고    scopus 로고
    • Hydroxylation of tamoxifen and toremifene by human and rat cytochrome P450 3A subfamily enzymes
    • Kim, S. Y., Suzuki, N., Santosh Laxmi, Y. R., Rieger, R., and Shibutani, S. (2003) α-Hydroxylation of tamoxifen and toremifene by human and rat cytochrome P450 3A subfamily enzymes. Chem. Res. Toxicol. 16, 1138-1144.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1138-1144
    • Kim, S.Y.1    Suzuki, N.2    Santosh Laxmi, Y.R.3    Rieger, R.4    Shibutani, S.5
  • 105
    • 0030008422 scopus 로고    scopus 로고
    • Conformational studies and electronic structures of tamoxifen and toremifene and their allylic carbocations proposed as reactive intermediates leading to DNA adduct formation
    • Kuramochi, H. (1996) 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. 39, 2877-2886.
    • (1996) J. Med. Chem. , vol.39 , pp. 2877-2886
    • Kuramochi, H.1
  • 106
  • 107
    • 0028930981 scopus 로고
    • Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices
    • Thompson, D. C., Perera, K., Krol, E. S., and Bolton, J. L. (1995) o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. Chem. Res. Toxicol. 8, 323-327.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 323-327
    • Thompson, D.C.1    Perera, K.2    Krol, E.S.3    Bolton, J.L.4
  • 108
    • 0024662764 scopus 로고
    • Chemical modifications of bio-polymers by quinones and quinone methides
    • Peter, M. G. (1989) Chemical modifications of bio-polymers by quinones and quinone methides. Angew. Chem. Int. Ed. 28, 555-570.
    • (1989) Angew. Chem. Int. Ed. , vol.28 , pp. 555-570
    • Peter, M.G.1
  • 110
    • 0001466726 scopus 로고
    • The effect of β-fluorine substituents on the rate and equilibrium-constants for the reactions of α-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide
    • Richard, J. P., Amyes, T. L., Bei, L., and Stubblefield, V. (1990) The effect of β-fluorine substituents on the rate and equilibrium-constants for the reactions of α-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide. J. Am. Chem. Soc. 112, 9513-9519.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9513-9519
    • Richard, J.P.1    Amyes, T.L.2    Bei, L.3    Stubblefield, V.4
  • 111
    • 0021021388 scopus 로고
    • Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides
    • Hulbert, P. B., and Grover, P. L. (1983) Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides. Biochem. Biophys. Res. Commun. 117, 129-134.
    • (1983) Biochem. Biophys. Res. Commun. , vol.117 , pp. 129-134
    • Hulbert, P.B.1    Grover, P.L.2
  • 112
    • 0028326053 scopus 로고
    • A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism
    • Potter, G. A., McCague, R., and Jarman, M. (1994) A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism. Carcinogenesis 15, 439-442.
    • (1994) Carcinogenesis , vol.15 , pp. 439-442
    • Potter, G.A.1    McCague, R.2    Jarman, M.3
  • 113
    • 0028899066 scopus 로고
    • The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxyquinone methides: Evidence that extended pi-conjugation dramatically stabilizes the quinone methide formed from eugenol
    • Bolton, J. L., Comeau, E., and Vukomanovic, V. (1995) The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxyquinone methides: Evidence that extended pi-conjugation dramatically stabilizes the quinone methide formed from eugenol. Chem.-Biol. Interact. 95, 279-290.
    • (1995) Chem.-Biol. Interact. , vol.95 , pp. 279-290
    • Bolton, J.L.1    Comeau, E.2    Vukomanovic, V.3
  • 114
    • 0030812209 scopus 로고    scopus 로고
    • CYP2D6 catalyzes tamoxifen 4-hydroxylation in human liver
    • Dehal, S. S., and Kupfer, D. (1997) CYP2D6 catalyzes tamoxifen 4-hydroxylation in human liver. Cancer Res. 57, 3402-3406.
    • (1997) Cancer Res. , vol.57 , pp. 3402-3406
    • Dehal, S.S.1    Kupfer, D.2
  • 115
    • 0031031421 scopus 로고    scopus 로고
    • Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes
    • Crewe, H. K., Ellis, S. W., Lennard, M. S., and Tucker, G. T. (1997) Variable contribution of cytochromes P450 2D6, 2C9 and 3A4 to the 4-hydroxylation of tamoxifen by human liver microsomes. Biochem. Pharmacol. 53, 171-178.
    • (1997) Biochem. Pharmacol. , vol.53 , pp. 171-178
    • Crewe, H.K.1    Ellis, S.W.2    Lennard, M.S.3    Tucker, G.T.4
  • 116
    • 0029935962 scopus 로고    scopus 로고
    • The metabolism of tamoxifen by human cytochromes P450 is rationalized by molecular modelling of the enzyme-substrate interactions: Potential importance to its proposed anti-carcinogenic/carcinogenic actions
    • Wiseman, H., and Lewis, D. F. (1996) The metabolism of tamoxifen by human cytochromes P450 is rationalized by molecular modelling of the enzyme-substrate interactions: Potential importance to its proposed anti-carcinogenic/ carcinogenic actions. Carcinogenesis 17, 1357-1360.
    • (1996) Carcinogenesis , vol.17 , pp. 1357-1360
    • Wiseman, H.1    Lewis, D.F.2
  • 117
    • 0028997955 scopus 로고
    • "It's the genes, stupid". Molecular bases and clinical consequences of genetic cytochrome P450 2D6 polymorphism
    • Kroemer, H. K., and Eichelbaum, M. (1995) "It's the genes, stupid". Molecular bases and clinical consequences of genetic cytochrome P450 2D6 polymorphism. Life Sci. 56, 2285-2298.
    • (1995) Life Sci. , vol.56 , pp. 2285-2298
    • Kroemer, H.K.1    Eichelbaum, M.2
  • 118
  • 119
    • 0020003085 scopus 로고
    • Tamoxifen and metabolites in MCF7 cells: Correlation between binding to estrogen receptor and inhibition of cell growth
    • Coezy, E., Borgna, J. L., and Rochefort, H. (1982) Tamoxifen and metabolites in MCF7 cells: correlation between binding to estrogen receptor and inhibition of cell growth. Cancer Res. 42, 317-323.
    • (1982) Cancer Res. , vol.42 , pp. 317-323
    • Coezy, E.1    Borgna, J.L.2    Rochefort, H.3
  • 120
    • 0019411776 scopus 로고
    • Hydroxylated metabolites of tamoxifen are formed in vivo and bound to estrogen receptor in target tissues
    • Borgna, J. L., and Rochefort, H. (1981) Hydroxylated metabolites of tamoxifen are formed in vivo and bound to estrogen receptor in target tissues. J. Biol. Chem. 256, 859-868.
    • (1981) J. Biol. Chem. , vol.256 , pp. 859-868
    • Borgna, J.L.1    Rochefort, H.2
  • 121
  • 125
  • 126
    • 0036266936 scopus 로고    scopus 로고
    • Characterization of raloxifene glucuronidation in vitro: Contribution of intestinal metabolism to presystemic clearance
    • Kemp, D. C., Fan, P. W., and Stevens, J. C. (2002) Characterization of raloxifene glucuronidation in vitro: Contribution of intestinal metabolism to presystemic clearance. Drug Metab. Dispos. 30, 694-700.
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 694-700
    • Kemp, D.C.1    Fan, P.W.2    Stevens, J.C.3
  • 127
    • 0020402019 scopus 로고
    • Metabolites of tamoxifen in animals and man: Identification, pharmacology, and significance
    • Jordan, V. C. (1982) Metabolites of tamoxifen in animals and man: Identification, pharmacology, and significance. Breast Cancer Res. Treat. 2, 123-138.
    • (1982) Breast Cancer Res. Treat. , vol.2 , pp. 123-138
    • Jordan, V.C.1
  • 129
    • 0027198580 scopus 로고
    • Metabolism of the antimammary cancer antiestrogenic agent tamoxifen. II. Flavin-containing monooxygenase-mediated N-oxidation
    • Mani, C., Hodgson, E., and Kupfer, D. (1993) Metabolism of the antimammary cancer antiestrogenic agent tamoxifen. II. Flavin-containing monooxygenase-mediated N-oxidation. Drug Metab. Dispos. 21, 657-661.
    • (1993) Drug Metab. Dispos. , vol.21 , pp. 657-661
    • Mani, C.1    Hodgson, E.2    Kupfer, D.3
  • 130
    • 0027195827 scopus 로고
    • High-performance liquid chromatographic analysis of tamoxifen, toremifene and their major human metabolites
    • Berthou, F., and Dreano, Y. (1993) High-performance liquid chromatographic analysis of tamoxifen, toremifene and their major human metabolites. J. Chromatogr. 616, 117-127.
    • (1993) J. Chromatogr. , vol.616 , pp. 117-127
    • Berthou, F.1    Dreano, Y.2
  • 131
    • 0035663252 scopus 로고    scopus 로고
    • Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: Droloxifene and toremifene o-quinones
    • Yao, D., Zhang, F., Yu, L., Yang, Y., van Breemen, R. B., and Bolton, J. L. (2001) Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: Droloxifene and toremifene o-quinones. Chem. Res. Toxicol. 14, 1643-1653.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1643-1653
    • Yao, D.1    Zhang, F.2    Yu, L.3    Yang, Y.4    Van Breemen, R.B.5    Bolton, J.L.6
  • 132
    • 0343144815 scopus 로고    scopus 로고
    • Mechanism of cytochrome P450-catalyzed aromatic hydroxylation of estrogens
    • Sarabia, S. F., Zhu, B. T., Kurosawa, T., Tohma, M., and Liehr, J. G. (1997) Mechanism of cytochrome P450-catalyzed aromatic hydroxylation of estrogens. Chem. Res. Toxicol. 10, 767-771.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 767-771
    • Sarabia, S.F.1    Zhu, B.T.2    Kurosawa, T.3    Tohma, M.4    Liehr, J.G.5
  • 134
    • 0032973129 scopus 로고    scopus 로고
    • The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone
    • Zhang, F., Chen, Y., Pisha, E., Shen, L., Xiong, Y., van Breemen, R. B., and Bolton, J. L. (1999) The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Chem. Res. Toxicol. 12, 204-213.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 204-213
    • Zhang, F.1    Chen, Y.2    Pisha, E.3    Shen, L.4    Xiong, Y.5    Van Breemen, R.B.6    Bolton, J.L.7
  • 135
    • 0031426130 scopus 로고    scopus 로고
    • Bioreductive activation of catechol estrogen-ortho-quinones: Aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity
    • Shen, L., Pisha, E., Huang, Z., Pezzuto, J. M., Krol, E., Alam, Z., van Breemen, R. B., and Bolton, J. L. (1997) Bioreductive activation of catechol estrogen-ortho-quinones: Aromatization of the B ring in 4-hydroxyequilenin markedly alters quinoid formation and reactivity. Carcinogenesis 18, 1093-1101.
    • (1997) Carcinogenesis , vol.18 , pp. 1093-1101
    • Shen, L.1    Pisha, E.2    Huang, Z.3    Pezzuto, J.M.4    Krol, E.5    Alam, Z.6    Van Breemen, R.B.7    Bolton, J.L.8
  • 136
    • 0031692626 scopus 로고    scopus 로고
    • The equine estrogen metabolite 4-hydroxyequilenin causes DNA single-strand breaks and oxidation of DNA bases in vitro
    • Chen, Y., Shen, L., Zhang, F., Lau, S. S., van Breemen, R. B., Nikolic, D., and Bolton, J. L. (1998) The equine estrogen metabolite 4-hydroxyequilenin causes DNA single-strand breaks and oxidation of DNA bases in vitro. Chem. Res. Toxicol. 11, 1105-1111.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1105-1111
    • Chen, Y.1    Shen, L.2    Zhang, F.3    Lau, S.S.4    Van Breemen, R.B.5    Nikolic, D.6    Bolton, J.L.7
  • 137
    • 0031931940 scopus 로고    scopus 로고
    • Alkylation of 2′-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical
    • Shen, L., Qiu, S., Chen, Y., Zhang, F., van Breemen, R. B., Nikolic, D., and Bolton, J. L. (1998) Alkylation of 2′-deoxynucleosides and DNA by the Premarin metabolite 4-hydroxyequilenin semiquinone radical. Chem. Res. Toxicol. 11, 94-101.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 94-101
    • Shen, L.1    Qiu, S.2    Chen, Y.3    Zhang, F.4    Van Breemen, R.B.5    Nikolic, D.6    Bolton, J.L.7
  • 138
    • 0035659961 scopus 로고    scopus 로고
    • Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: Formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases
    • Zhang, F., Swanson, S. M., van Breemen, R. B., Liu, X., Yang, Y., Gu, C., and Bolton, J. L. (2001) Equine estrogen metabolite 4-hydroxyequilenin induces DNA damage in the rat mammary tissues: Formation of single-strand breaks, apurinic sites, stable adducts, and oxidized bases. Chem. Res. Toxicol. 14, 1654-1659.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1654-1659
    • Zhang, F.1    Swanson, S.M.2    Van Breemen, R.B.3    Liu, X.4    Yang, Y.5    Gu, C.6    Bolton, J.L.7
  • 139
    • 0035996332 scopus 로고    scopus 로고
    • Inhibition of cellular enzymes by equine catechol estrogens in human breast cancer cells: Specificity for glutathione S-transferase P1-1
    • Yao, J., Chang, M., Li, Y., Pisha, E., Liu, X., Yao, D., Elguindi, E. C., Blond, S. Y., and Bolton, J. L. (2002) Inhibition of cellular enzymes by equine catechol estrogens in human breast cancer cells: Specificity for glutathione S-transferase P1-1. Chem. Res. Toxicol. 15, 935-942.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 935-942
    • Yao, J.1    Chang, M.2    Li, Y.3    Pisha, E.4    Liu, X.5    Yao, D.6    Elguindi, E.C.7    Blond, S.Y.8    Bolton, J.L.9
  • 140
    • 1942518324 scopus 로고    scopus 로고
    • Equine catechol estrogen 4-hydroxyequilenin is a more potent inhibitor of the variant form of catechol-O-methyltransferase
    • Li, Y., Yao, J., Chang, M., Nikolic, D., Yu, L., Yager, J. D., Mesecar, A. D., van Breemen, R. B., and Bolton, J. L. (2004) Equine catechol estrogen 4-hydroxyequilenin is a more potent inhibitor of the variant form of catechol-O-methyltransferase. Chem. Res. Toxicol. 17, 512-520.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 512-520
    • Li, Y.1    Yao, J.2    Chang, M.3    Nikolic, D.4    Yu, L.5    Yager, J.D.6    Mesecar, A.D.7    Van Breemen, R.B.8    Bolton, J.L.9
  • 143


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