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Volumn 49, Issue 21, 2010, Pages 4466-4475

CYP3A4-mediated oxygenation versus dehydrogenation of raloxifene

Author keywords

[No Author keywords available]

Indexed keywords

ARENE OXIDES; BREAST CANCER; CHEMOPREVENTION; CYTOCHROME P450-3A4; NOVEL ROUTE; POSTMENOPAUSAL WOMEN; REACTIVE INTERMEDIATE; TAMOXIFEN;

EID: 77952806659     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi902213r     Document Type: Article
Times cited : (24)

References (36)
  • 2
    • 0032569831 scopus 로고    scopus 로고
    • Tamoxifen in the treatment of breast cancer
    • Osborne, C. K. (1998) Tamoxifen in the treatment of breast cancer N. Engl. J. Med. 339, 1609-1618
    • (1998) N. Engl. J. Med. , vol.339 , pp. 1609-1618
    • Osborne, C.K.1
  • 3
    • 0032189117 scopus 로고    scopus 로고
    • Treatment of breast cancer
    • Hortobagyi, G. N. (1998) Treatment of breast cancer N. Engl. J. Med. 339, 974-984
    • (1998) N. Engl. J. Med. , vol.339 , pp. 974-984
    • Hortobagyi, G.N.1
  • 5
    • 0027412216 scopus 로고
    • High-grade endometrial carcinoma in tamoxifen-treated breast cancer patients
    • Magriples, U., Naftolin, F., Schwartz, P. E., and Carcangiu, M. L. (1993) High-grade endometrial carcinoma in tamoxifen-treated breast cancer patients J. Clin. Oncol. 11, 485-490
    • (1993) J. Clin. Oncol. , vol.11 , pp. 485-490
    • Magriples, U.1    Naftolin, F.2    Schwartz, P.E.3    Carcangiu, M.L.4
  • 6
    • 0028208456 scopus 로고
    • Endometrial cancer in tamoxifen-treated breast cancer patients: Findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14
    • Fisher, B., Costantino, J. P., Redmond, C. K., Fisher, E. R., Wickerham, D. L., and Cronin, W. M. (1994) 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 (Pubitemid 24111008)
    • (1994) Journal of the National Cancer Institute , vol.86 , Issue.7 , pp. 527-537
    • Fisher, B.1    Costantino, J.P.2    Redmond, C.K.3    Fisher, E.R.4    Wickerham, D.L.5    Cronin, W.M.6
  • 8
    • 14544270313 scopus 로고    scopus 로고
    • Tamoxifen treatment for breast cancer and risk of endometrial cancer: A case-control study
    • Swerdlow, A. J. and Jones, M. E. (2005) Tamoxifen treatment for breast cancer and risk of endometrial cancer: A case-control study J. Natl. Cancer Inst. 97, 375-384
    • (2005) J. Natl. Cancer Inst. , vol.97 , pp. 375-384
    • Swerdlow, A.J.1    Jones, M.E.2
  • 9
    • 0026606580 scopus 로고
    • Induction of covalent DNA adducts in rodents by tamoxifen
    • Han, X. L. and Liehr, J. G. (1992) Induction of covalent DNA adducts in rodents by tamoxifen Cancer Res. 52, 1360-1363
    • (1992) Cancer Res. , vol.52 , pp. 1360-1363
    • Han, X.L.1    Liehr, J.G.2
  • 10
    • 0028172454 scopus 로고
    • 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
    • 32P-postlabeling and use of metabolic inhibitors for two distinct pathways leading to mouse hepatic DNA adduct formation and identification of 4-hydroxytamoxifen as a proximate metabolite Carcinogenesis 15, 2087-2094
    • (1994) Carcinogenesis , vol.15 , pp. 2087-2094
    • Randerath, K.1    Moorthy, B.2    Mabon, N.3    Sriram, P.4
  • 11
    • 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
  • 12
    • 0031416520 scopus 로고    scopus 로고
    • Identification of tamoxifen-DNA adducts formed by 4-hydroxytamoxifen quinone methide
    • Marques, M. M. and Beland, F. A. (1997) Identification of tamoxifen-DNA adducts formed by 4-hydroxytamoxifen quinone methide Carcinogenesis 18, 1949-1954
    • (1997) Carcinogenesis , vol.18 , pp. 1949-1954
    • Marques, M.M.1    Beland, F.A.2
  • 13
    • 0033065364 scopus 로고    scopus 로고
    • Comparison of the DNA adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo
    • Beland, F. A., McDaniel, L. P., and Marques, M. M. (1999) Comparison of the DNA adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo Carcinogenesis 20, 471-477
    • (1999) Carcinogenesis , vol.20 , pp. 471-477
    • Beland, F.A.1    McDaniel, L.P.2    Marques, M.M.3
  • 14
    • 3042794987 scopus 로고    scopus 로고
    • Quinoids formed from estrogens and antiestrogens
    • Bolton, J. L., Yu, L., and Thatcher, G. R. (2004) Quinoids formed from estrogens and antiestrogens Methods Enzymol. 378, 110-123
    • (2004) Methods Enzymol. , vol.378 , pp. 110-123
    • Bolton, J.L.1    Yu, L.2    Thatcher, G.R.3
  • 15
    • 0021201213 scopus 로고
    • Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[ b ]thiophene derivatives leading to [6-hydroxy-2-(4- hydroxyphenyl)benzo[ b ]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity
    • Jones, C. D., Jevnikar, M. G., Pike, A. J., Peters, M. K., Black, L. J., Thompson, A. R., Falcone, J. F., and Clemens, J. A. (1984) Antiestrogens. 2. Structure-activity studies in a series of 3-aroyl-2-arylbenzo[ b ]thiophene derivatives leading to [6-hydroxy-2-(4-hydroxyphenyl)benzo[ b ]thien-3-yl] [4-[2-(1-piperidinyl)ethoxy]-phenyl]methanone hydrochloride (LY156758), a remarkably effective estrogen antagonist with only minimal intrinsic estrogenicity J. Med. Chem. 27, 1057-1066
    • (1984) J. Med. Chem. , vol.27 , pp. 1057-1066
    • Jones, C.D.1    Jevnikar, M.G.2    Pike, A.J.3    Peters, M.K.4    Black, L.J.5    Thompson, A.R.6    Falcone, J.F.7    Clemens, J.A.8
  • 16
    • 0033864535 scopus 로고    scopus 로고
    • Raloxifene: A review of its use in postmenopausal osteoporosis
    • Clemett, D. and Spencer, C. M. (2000) Raloxifene: A review of its use in postmenopausal osteoporosis Drugs 60, 379-411
    • (2000) Drugs , vol.60 , pp. 379-411
    • Clemett, D.1    Spencer, C.M.2
  • 18
    • 61449444415 scopus 로고    scopus 로고
    • The NSABP study of tamoxifen and raloxifene (STAR) trial
    • Vogel, V. G. (2009) The NSABP study of tamoxifen and raloxifene (STAR) trial Expert Rev. Anticancer Ther. 9, 51-60
    • (2009) Expert Rev. Anticancer Ther. , vol.9 , pp. 51-60
    • Vogel, V.G.1
  • 22
    • 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
  • 23
    • 34447133553 scopus 로고    scopus 로고
    • Time-dependent inactivation of P450 3A4 by raloxifene: Identification of Cys239 as the site of apoprotein alkylation
    • Baer, B. R., Wienkers, L. C., and Rock, D. A. (2007) Time-dependent inactivation of P450 3A4 by raloxifene: Identification of Cys239 as the site of apoprotein alkylation Chem. Res. Toxicol. 20, 954-964
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 954-964
    • Baer, B.R.1    Wienkers, L.C.2    Rock, D.A.3
  • 24
    • 38149048655 scopus 로고    scopus 로고
    • Differential time-dependent inactivation of P450 3A4 and P450 3A5 by raloxifene: A key role for C239 in quenching reactive intermediates
    • Pearson, J. T., Wahlstrom, J. L., Dickmann, L. J., Kumar, S., Halpert, J. R., Wienkers, L. C., Foti, R. S., and Rock, D. A. (2007) Differential time-dependent inactivation of P450 3A4 and P450 3A5 by raloxifene: A key role for C239 in quenching reactive intermediates Chem. Res. Toxicol. 20, 1778-1786
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 1778-1786
    • Pearson, J.T.1    Wahlstrom, J.L.2    Dickmann, L.J.3    Kumar, S.4    Halpert, J.R.5    Wienkers, L.C.6    Foti, R.S.7    Rock, D.A.8
  • 25
    • 35848962726 scopus 로고    scopus 로고
    • Identification of cytochrome P450 3A4 modification site with reactive metabolite using linear ion trap-Fourier transform mass spectrometry
    • Yukinaga, H., Takami, T., Shioyama, S. H., Tozuka, Z., Masumoto, H., Okazaki, O., and Sudo, K. (2007) Identification of cytochrome P450 3A4 modification site with reactive metabolite using linear ion trap-Fourier transform mass spectrometry Chem. Res. Toxicol. 20, 1373-1378
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 1373-1378
    • Yukinaga, H.1    Takami, T.2    Shioyama, S.H.3    Tozuka, Z.4    Masumoto, H.5    Okazaki, O.6    Sudo, K.7
  • 26
    • 37249003946 scopus 로고    scopus 로고
    • Uterine peroxidase-catalyzed formation of diquinone methides from the selective estrogen receptor modulators raloxifene and desmethylated arzoxifene
    • Liu, H., Qin, Z., Thatcher, G. R., and Bolton, J. L. (2007) Uterine peroxidase-catalyzed formation of diquinone methides from the selective estrogen receptor modulators raloxifene and desmethylated arzoxifene Chem. Res. Toxicol. 20, 1676-1684
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 1676-1684
    • Liu, H.1    Qin, Z.2    Thatcher, G.R.3    Bolton, J.L.4
  • 27
    • 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
  • 28
    • 53549100467 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose
    • Obach, R. S., Kalgutkar, A. S., Soglia, J. R., and Zhao, S. X. (2008) Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose Chem. Res. Toxicol. 21, 1814-1822
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 1814-1822
    • Obach, R.S.1    Kalgutkar, A.S.2    Soglia, J.R.3    Zhao, S.X.4
  • 29
    • 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
  • 30
    • 0031824305 scopus 로고    scopus 로고
    • Analysis of four residues within substrate recognition site 4 of human cytochrome P450 3A4: Role in steroid hydroxylase activity and alpha-naphthoflavone stimulation
    • Domanski, T. L., Liu, J., Harlow, G. R., and Halpert, J. R. (1998) Analysis of four residues within substrate recognition site 4 of human cytochrome P450 3A4: Role in steroid hydroxylase activity and alpha-naphthoflavone stimulation Arch. Biochem. Biophys. 350, 223-232
    • (1998) Arch. Biochem. Biophys. , vol.350 , pp. 223-232
    • Domanski, T.L.1    Liu, J.2    Harlow, G.R.3    Halpert, J.R.4
  • 31
    • 0024518203 scopus 로고
    • Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis
    • Shen, A. L., Porter, T. D., Wilson, T. E., and Kasper, C. B. (1989) Structural analysis of the FMN binding domain of NADPH-cytochrome P-450 oxidoreductase by site-directed mutagenesis J. Biol. Chem. 264, 7584-7589
    • (1989) J. Biol. Chem. , vol.264 , pp. 7584-7589
    • Shen, A.L.1    Porter, T.D.2    Wilson, T.E.3    Kasper, C.B.4
  • 32
    • 0000837057 scopus 로고
    • Least squares analysis and simplification of multi-isotope mass spectra
    • Brauman, J. I. (1966) Least squares analysis and simplification of multi-isotope mass spectra Anal. Chem. 38, 607-610
    • (1966) Anal. Chem. , vol.38 , pp. 607-610
    • Brauman, J.I.1
  • 33
    • 0025257457 scopus 로고
    • The use of Brauman's least squares approach for the quantification of deuterated chlorophenols
    • Korzekwa, K., Howald, W. N., and Trager, W. F. (1990) The use of Brauman's least squares approach for the quantification of deuterated chlorophenols Biomed. Environ. Mass Spectrom. 19, 211-217
    • (1990) Biomed. Environ. Mass Spectrom. , vol.19 , pp. 211-217
    • Korzekwa, K.1    Howald, W.N.2    Trager, W.F.3
  • 34
    • 0000392379 scopus 로고
    • Benzo[ a ]pyrene anti -diol epoxide covalently modifies human serum albumin carboxylate side chains and imidazole side chain of histidine(146)
    • Day, B. W., Skipper, P. L., Zaia, J., and Tannenbaum, S.R. (1991) Benzo[ a ]pyrene anti -diol epoxide covalently modifies human serum albumin carboxylate side chains and imidazole side chain of histidine(146) J. Am. Chem. Soc. 113, 8505-8509
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 8505-8509
    • Day, B.W.1    Skipper, P.L.2    Zaia, J.3    Tannenbaum, S.R.4
  • 36
    • 70349509736 scopus 로고    scopus 로고
    • Theoretical characterization of substrate access/exit channels in the human cytochrome P450 3A4 enzyme: Involvement of phenylalanine residues in the gating mechanism
    • Fishelovitch, D., Shaik, S., Wolfson, H. J., and Nussinov, R. (2009) Theoretical characterization of substrate access/exit channels in the human cytochrome P450 3A4 enzyme: Involvement of phenylalanine residues in the gating mechanism J. Phys. Chem. B 113, 13018-13025
    • (2009) J. Phys. Chem. B , vol.113 , pp. 13018-13025
    • Fishelovitch, D.1    Shaik, S.2    Wolfson, H.J.3    Nussinov, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.