메뉴 건너뛰기




Volumn 35, Issue 11, 2007, Pages 2006-2014

Glucuronidation of active tamoxifen metabolites by the human UDP glucuronosyltransferases

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYTAMOXIFEN; DRUG METABOLITE; ENDOXIFEN; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 2B7; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 34748901348     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.017145     Document Type: Article
Times cited : (79)

References (39)
  • 2
    • 0034626064 scopus 로고    scopus 로고
    • Risk and prognosis of endometrial cancer after tamoxifen for breast cancer. Comprehensive Cancer Centres' ALERT Group. Assessment of liver and endometrial cancer risk following tamoxifen
    • Bergman L, Beelen ML, Gallee MP, Hollema H, Benraadt J, and van Leeuwen FE (2000) Risk and prognosis of endometrial cancer after tamoxifen for breast cancer. Comprehensive Cancer Centres' ALERT Group. Assessment of liver and endometrial cancer risk following tamoxifen. Lancet 356:881-887.
    • (2000) Lancet , vol.356 , pp. 881-887
    • Bergman, L.1    Beelen, M.L.2    Gallee, M.P.3    Hollema, H.4    Benraadt, J.5    van Leeuwen, F.E.6
  • 3
    • 1242273824 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of doxorubicin-formaldehyde conjugates targeted to breast cancer cells
    • Burke PJ and Koch TH (2004) Design, synthesis, and biological evaluation of doxorubicin-formaldehyde conjugates targeted to breast cancer cells. J Med Chem 47:1193-1206.
    • (2004) J Med Chem , vol.47 , pp. 1193-1206
    • Burke, P.J.1    Koch, T.H.2
  • 4
    • 29144448312 scopus 로고    scopus 로고
    • Extended adjuvant endocrine therapy of early breast cancer
    • Chowdhury S and Ellis P (2005) Extended adjuvant endocrine therapy of early breast cancer. Curr Med Res Opin 21:1985-1995.
    • (2005) Curr Med Res Opin , vol.21 , pp. 1985-1995
    • Chowdhury, S.1    Ellis, P.2
  • 5
    • 0022873553 scopus 로고
    • A general assay for UDPglucuronosyltransferase activity using polar amino-cyano stationary phase HPLC and UDP[U-14C]glucuronic acid
    • Coughtrie MW, Burchell B, and Bend JR (1986) A general assay for UDPglucuronosyltransferase activity using polar amino-cyano stationary phase HPLC and UDP[U-14C]glucuronic acid. Anal Biochem 159:198-205.
    • (1986) Anal Biochem , vol.159 , pp. 198-205
    • Coughtrie, M.W.1    Burchell, B.2    Bend, J.R.3
  • 9
    • 0032537396 scopus 로고    scopus 로고
    • Tamoxifen for early breast cancer: An overview of the randomised trials
    • Early Breast Cancer Trialists' Collaborative Group
    • [EBCTCG] Early Breast Cancer Trialists' Collaborative Group (1998) Tamoxifen for early breast cancer: an overview of the randomised trials. Lancet 351:1451-1467.
    • (1998) Lancet , vol.351 , pp. 1451-1467
  • 10
    • 0036532140 scopus 로고    scopus 로고
    • Characterization of benzo(a)pyrene-trans-7,8-dihydrodiol glucuronidation by human tissue microsomes and overexpressed UDP-glucuronosyltransferase enzymes
    • Fang JL, Beland FA, Doerge DR, Wiener D, Guillemette C, Marques MM, and Lazarus P (2002) Characterization of benzo(a)pyrene-trans-7,8-dihydrodiol glucuronidation by human tissue microsomes and overexpressed UDP-glucuronosyltransferase enzymes. Cancer Res 62:1978-1986.
    • (2002) Cancer Res , vol.62 , pp. 1978-1986
    • Fang, J.L.1    Beland, F.A.2    Doerge, D.R.3    Wiener, D.4    Guillemette, C.5    Marques, M.M.6    Lazarus, P.7
  • 11
    • 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 JP, Redmond CK, Fisher ER, Wickerham DL, and Cronin WM (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.
    • (1994) J Natl Cancer Inst , vol.86 , 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
  • 13
    • 0031706608 scopus 로고    scopus 로고
    • Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins
    • Green MD and Tephly TR (1998) Glucuronidation of amine substrates by purified and expressed UDP-glucuronosyltransferase proteins. Drug Metab Dispos 26:860-867.
    • (1998) Drug Metab Dispos , vol.26 , pp. 860-867
    • Green, M.D.1    Tephly, T.R.2
  • 14
    • 0042827285 scopus 로고    scopus 로고
    • New approaches to the endocrine prevention and treatment of breast cancer
    • Howell A, Howell SJ, and Evans DG (2003) New approaches to the endocrine prevention and treatment of breast cancer. Cancer Chemother Pharmacol 52 (Suppl 1):S39-S44.
    • (2003) Cancer Chemother Pharmacol , vol.52 , Issue.SUPPL. 1
    • Howell, A.1    Howell, S.J.2    Evans, D.G.3
  • 15
    • 0017665570 scopus 로고
    • A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity
    • Jordan VC, Collins MM, Rowsby L, and Prestwich G (1977) A monohydroxylated metabolite of tamoxifen with potent antioestrogenic activity. J Endocrinol 75:305-316.
    • (1977) J Endocrinol , vol.75 , pp. 305-316
    • Jordan, V.C.1    Collins, M.M.2    Rowsby, L.3    Prestwich, G.4
  • 16
    • 2342572781 scopus 로고    scopus 로고
    • Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4
    • Kaku T, Ogura K, Nishiyama T, Ohnuma T, Muro K, and Hiratsuka A (2004) Quaternary ammonium-linked glucuronidation of tamoxifen by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochem Pharmacol 67:2093-2102.
    • (2004) Biochem Pharmacol , vol.67 , pp. 2093-2102
    • Kaku, T.1    Ogura, K.2    Nishiyama, T.3    Ohnuma, T.4    Muro, K.5    Hiratsuka, A.6
  • 18
    • 6344248683 scopus 로고    scopus 로고
    • Specificity and regioselectivity of the conjugation of estradiol, estrone, and their catecholestrogen and methoxyestrogen metabolites by human uridine diphosphoglucuronosyltransferases expressed in endometrium
    • Lepine J, Bernard O, Plante M, Tetu B, Pelletier G, Labrie F, Belanger A, and Guillemette C (2004) Specificity and regioselectivity of the conjugation of estradiol, estrone, and their catecholestrogen and methoxyestrogen metabolites by human uridine diphosphoglucuronosyltransferases expressed in endometrium. J Clin Endocrinol Metab 89:5222-5232.
    • (2004) J Clin Endocrinol Metab , vol.89 , pp. 5222-5232
    • Lepine, J.1    Bernard, O.2    Plante, M.3    Tetu, B.4    Pelletier, G.5    Labrie, F.6    Belanger, A.7    Guillemette, C.8
  • 19
    • 0024584001 scopus 로고
    • Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment
    • Lien EA, Solheim E, Lea OA, Lundgren S, Kvinnsland S, and Ueland PM (1989) Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res 49:2175-2183.
    • (1989) Cancer Res , vol.49 , pp. 2175-2183
    • Lien, E.A.1    Solheim, E.2    Lea, O.A.3    Lundgren, S.4    Kvinnsland, S.5    Ueland, P.M.6
  • 20
    • 17644387537 scopus 로고    scopus 로고
    • Endoxifen (4-hydroxy-N-desmethyltamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxytamoxifen
    • Lim YC, Desta Z, Flockhart DA, and Skaar TC (2005) Endoxifen (4-hydroxy-N-desmethyltamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxytamoxifen. Cancer Chemother Pharmacol 55:471-478.
    • (2005) Cancer Chemother Pharmacol , vol.55 , pp. 471-478
    • Lim, Y.C.1    Desta, Z.2    Flockhart, D.A.3    Skaar, T.C.4
  • 21
    • 0025833585 scopus 로고
    • Fatal myocardial infarction in the Scottish adjuvant tamoxifen trial. The Scottish Breast Cancer Committee
    • McDonald CC and Stewart HJ (1991) Fatal myocardial infarction in the Scottish adjuvant tamoxifen trial. The Scottish Breast Cancer Committee. BMJ 303:435-437.
    • (1991) BMJ , vol.303 , pp. 435-437
    • McDonald, C.C.1    Stewart, H.J.2
  • 22
    • 0031811978 scopus 로고    scopus 로고
    • Tamoxifen and risk of idiopathic venous thromboembolism
    • Meier CR and Jick H (1998) Tamoxifen and risk of idiopathic venous thromboembolism. Br J Clin Pharmacol 45:608-612.
    • (1998) Br J Clin Pharmacol , vol.45 , pp. 608-612
    • Meier, C.R.1    Jick, H.2
  • 23
    • 0025200665 scopus 로고
    • Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro
    • Murphy CS, Langan-Fahey SM, McCague R, and Jordan VC (1990) Structure-function relationships of hydroxylated metabolites of tamoxifen that control the proliferation of estrogen-responsive T47D breast cancer cells in vitro. Mol Pharmacol 38:737-743.
    • (1990) Mol Pharmacol , vol.38 , pp. 737-743
    • Murphy, C.S.1    Langan-Fahey, S.M.2    McCague, R.3    Jordan, V.C.4
  • 24
    • 0036673215 scopus 로고    scopus 로고
    • Tamoxifen and breast cancer
    • 718-720, 761, 760.
    • Nechushtan H and Peretz T (2002) Tamoxifen and breast cancer. Harefuah 141:718-720, 761, 760.
    • (2002) Harefuah , vol.141
    • Nechushtan, H.1    Peretz, T.2
  • 25
    • 0037094334 scopus 로고    scopus 로고
    • Reverse geometrical selectivity in glucuronidation and sulfation of cis- and trans-4-hydroxytamoxifens by human liver UDP-glucuronosyltransferases and sulfotransferases
    • Nishiyama T, Ogura K, Nakano H, Ohnuma T, Kaku T, Hiratsuka A, Muro K, and Watabe T (2002) Reverse geometrical selectivity in glucuronidation and sulfation of cis- and trans-4-hydroxytamoxifens by human liver UDP-glucuronosyltransferases and sulfotransferases. Biochem Pharmacol 63:1817-1830.
    • (2002) Biochem Pharmacol , vol.63 , pp. 1817-1830
    • Nishiyama, T.1    Ogura, K.2    Nakano, H.3    Ohnuma, T.4    Kaku, T.5    Hiratsuka, A.6    Muro, K.7    Watabe, T.8
  • 27
    • 0025808718 scopus 로고
    • Synthesis and antiestrogenic activity of the compounds related to the metabolites of (E)-4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-(4- isopropylphenyl)-1-butenyl]phenyl monophosphate (TAT-59) [corrected]
    • Ogawa K, Matsushita Y, Yamawaki I, Kaneda M, Shibata J, Toko T, and Asao T (1991) Synthesis and antiestrogenic activity of the compounds related to the metabolites of (E)-4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-(4- isopropylphenyl)-1-butenyl]phenyl monophosphate (TAT-59) [corrected]. Chem Pharm Bull 39:911-916.
    • (1991) Chem Pharm Bull , vol.39 , pp. 911-916
    • Ogawa, K.1    Matsushita, Y.2    Yamawaki, I.3    Kaneda, M.4    Shibata, J.5    Toko, T.6    Asao, T.7
  • 28
    • 33645119456 scopus 로고    scopus 로고
    • Quaternary ammonium-linked glucuronidation of trans-4- hydroxytamoxifen, an active metabolite of tamoxifen, by human liver microsomes and UDP-glucuronosyltransferase 1A4
    • Ogura K, Ishikawa Y, Kaku T, Nishiyama T, Ohnuma T, Muro K, and Hiratsuka A (2006) Quaternary ammonium-linked glucuronidation of trans-4- hydroxytamoxifen, an active metabolite of tamoxifen, by human liver microsomes and UDP-glucuronosyltransferase 1A4. Biochem Pharmacol 71:1358-1369.
    • (2006) Biochem Pharmacol , vol.71 , pp. 1358-1369
    • Ogura, K.1    Ishikawa, Y.2    Kaku, T.3    Nishiyama, T.4    Ohnuma, T.5    Muro, K.6    Hiratsuka, A.7
  • 29
    • 0032569831 scopus 로고    scopus 로고
    • Tamoxifen in the treatment of breast cancer
    • Osborne CK (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
  • 31
    • 0032871069 scopus 로고    scopus 로고
    • Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanol (NNAL) by rat UDP-glucuronosyltransferase 2B1
    • Ren Q, Murphy SE, Dannenberg AJ, Park JY, Tephly TR, and Lazarus P (1999) Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanol (NNAL) by rat UDP-glucuronosyltransferase 2B1. Drug Metab Dispos 27:1010-1016.
    • (1999) Drug Metab Dispos , vol.27 , pp. 1010-1016
    • Ren, Q.1    Murphy, S.E.2    Dannenberg, A.J.3    Park, J.Y.4    Tephly, T.R.5    Lazarus, P.6
  • 32
    • 0033783035 scopus 로고    scopus 로고
    • O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9
    • Ren Q, Murphy SE, Zheng Z, and Lazarus P (2000) O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9. Drug Metab Dispos 28:1352-1360.
    • (2000) Drug Metab Dispos , vol.28 , pp. 1352-1360
    • Ren, Q.1    Murphy, S.E.2    Zheng, Z.3    Lazarus, P.4
  • 33
    • 0020033521 scopus 로고
    • Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifen
    • Robertson DW, Katzenellenbogen JA, Long DJ, Rorke EA, and Katzenellenbogen BS (1982) Tamoxifen antiestrogens. A comparison of the activity, pharmacokinetics, and metabolic activation of the cis and trans isomers of tamoxifen. J Steroid Biochem 16:1-13.
    • (1982) J Steroid Biochem , vol.16 , pp. 1-13
    • Robertson, D.W.1    Katzenellenbogen, J.A.2    Long, D.J.3    Rorke, E.A.4    Katzenellenbogen, B.S.5
  • 34
    • 0027325734 scopus 로고
    • Cardiac and thromboembolic morbidity among postmenopausal women with early-stage breast cancer in a randomized trial of adjuvant tamoxifen. The Stockholm Breast Cancer Study Group
    • Rutqvist LE and Mattsson A (1993) Cardiac and thromboembolic morbidity among postmenopausal women with early-stage breast cancer in a randomized trial of adjuvant tamoxifen. The Stockholm Breast Cancer Study Group. J Natl Cancer Inst 85:1398-1406.
    • (1993) J Natl Cancer Inst , vol.85 , pp. 1398-1406
    • Rutqvist, L.E.1    Mattsson, A.2
  • 35
    • 0022397494 scopus 로고
    • Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent
    • Shani J, Gazit A, Livshitz T, and Biran S (1985) Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent. J Med Chem 28:1504-1511.
    • (1985) J Med Chem , vol.28 , pp. 1504-1511
    • Shani, J.1    Gazit, A.2    Livshitz, T.3    Biran, S.4
  • 36
    • 33748318005 scopus 로고    scopus 로고
    • Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants
    • Sun D, Chen G, Dellinger RW, Duncan K, Fang JL, and Lazarus P (2006) Characterization of tamoxifen and 4-hydroxytamoxifen glucuronidation by human UGT1A4 variants. Breast Cancer Res 8:R50.
    • (2006) Breast Cancer Res , vol.8
    • Sun, D.1    Chen, G.2    Dellinger, R.W.3    Duncan, K.4    Fang, J.L.5    Lazarus, P.6
  • 38
    • 1642457368 scopus 로고    scopus 로고
    • Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: Importance of UDP-glucuronosyltransferase 1A4
    • Wiener D, Doerge DR, Fang JL, Upadhyaya P, and Lazarus P (2004a) Characterization of N-glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human liver: importance of UDP-glucuronosyltransferase 1A4. Drug Metab Dispos 32:72-79.
    • (2004) Drug Metab Dispos , vol.32 , pp. 72-79
    • Wiener, D.1    Doerge, D.R.2    Fang, J.L.3    Upadhyaya, P.4    Lazarus, P.5
  • 39
    • 0842325733 scopus 로고    scopus 로고
    • Correlation between UDP-glucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone glucuronidation phenotype in human liver microsomes
    • Wiener D, Fang JL, Dossett N, and Lazarus P (2004b) Correlation between UDP-glucuronosyltransferase genotypes and 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone glucuronidation phenotype in human liver microsomes. Cancer Res 64:1190-1196.
    • (2004) Cancer Res , vol.64 , pp. 1190-1196
    • Wiener, D.1    Fang, J.L.2    Dossett, N.3    Lazarus, P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.