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Volumn 32, Issue 12, 2004, Pages 1501-1508

Interactions of the stereoisomers of α-hydroxytamoxifen with human hydroxysteroid sulfotransferase SULT2A1 and rat hydroxysteroid sulfotransferase STa

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXYTAMOXIFEN; ANTIESTROGEN; DRUG METABOLITE; HYDROXYSTEROID SULFOTRANSFERASE; HYDROXYSTEROID SULFOTRANSFERASE STA; HYDROXYSTEROID SULFOTRANSFERASE SULT2A1; TAMOXIFEN; UNCLASSIFIED DRUG;

EID: 9444291414     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.104.000919     Document Type: Article
Times cited : (27)

References (55)
  • 1
    • 0010169673 scopus 로고    scopus 로고
    • A realistic clinical perspective of tamoxifen and endometrial carcinogenesis
    • Assikis VJ, Neven P, Jordan VC, and Vergote I (1996) A realistic clinical perspective of tamoxifen and endometrial carcinogenesis. Eur J Cancer 32A:1464-1476.
    • (1996) Eur J Cancer , vol.32 A , pp. 1464-1476
    • Assikis, V.J.1    Neven, P.2    Jordan, V.C.3    Vergote, I.4
  • 2
    • 0030711756 scopus 로고    scopus 로고
    • Studies on the interactions of chiral secondary alcohols with rat hydroxysteroid sulfotransferase STa
    • Banoglu E and Duffel MW (1997) Studies on the interactions of chiral secondary alcohols with rat hydroxysteroid sulfotransferase STa. Drug Metab Dispos 25:1304-1310.
    • (1997) Drug Metab Dispos , vol.25 , pp. 1304-1310
    • Banoglu, E.1    Duffel, M.W.2
  • 3
    • 0032977147 scopus 로고    scopus 로고
    • Importance of peri-interactions on the stereospecificity of rat hydroxysteroid sulfotransferase STa with 1-arylethanols
    • Banoglu E and Duffel MW (1999) Importance of peri-interactions on the stereospecificity of rat hydroxysteroid sulfotransferase STa with 1-arylethanols. Chem Res Toxicol 12:278-285.
    • (1999) Chem Res Toxicol , vol.12 , pp. 278-285
    • Banoglu, E.1    Duffel, M.W.2
  • 4
    • 0017277818 scopus 로고
    • Assay of proteins in the presence of interfering materials
    • Bensadoun A and Weinstein D (1976) Assay of proteins in the presence of interfering materials. Anal Biochem 70:241-250.
    • (1976) Anal Biochem , vol.70 , pp. 241-250
    • Bensadoun, A.1    Weinstein, D.2
  • 7
    • 0033790789 scopus 로고    scopus 로고
    • Major inter-species differences in the rates of O-sulphonation and O-glucuronylation of alpha-hydroxytamoxifen in vitro: A metabolic disparity protecting human liver from the formation of tamoxifen-DNA adducts
    • Boocock DJ, Maggs JL, Brown K, White INH, and Park BK (2000) Major inter-species differences in the rates of O-sulphonation and O-glucuronylation of alpha-hydroxytamoxifen in vitro: a metabolic disparity protecting human liver from the formation of tamoxifen-DNA adducts. Carcinogenesis 21:1851-1858.
    • (2000) Carcinogenesis , vol.21 , pp. 1851-1858
    • Boocock, D.J.1    Maggs, J.L.2    Brown, K.3    White, I.N.H.4    Park, B.K.5
  • 9
    • 0035001144 scopus 로고    scopus 로고
    • Human dehydroepiandrosterone sulfotransferase: Purification and characterization of a recombinant protein
    • Chang HJ, Zhou M, and Lin SX (2001) Human dehydroepiandrosterone sulfotransferase: purification and characterization of a recombinant protein. J Steroid Biochem Mol Biol 77:159-165.
    • (2001) J Steroid Biochem Mol Biol , vol.77 , pp. 159-165
    • Chang, H.J.1    Zhou, M.2    Lin, S.X.3
  • 11
    • 0036325773 scopus 로고    scopus 로고
    • Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: Formation of the 4-hydroxy, 4′-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen
    • Crewe HK, Notley LM, Wunsch RM, Lennard MS, and Gillam EMJ (2002) Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4′-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos 30:869-874.
    • (2002) Drug Metab Dispos , vol.30 , pp. 869-874
    • Crewe, H.K.1    Notley, L.M.2    Wunsch, R.M.3    Lennard, M.S.4    Gillam, E.M.J.5
  • 12
    • 0031054835 scopus 로고    scopus 로고
    • Identification of tamoxifen-DNA adducts formed by alpha-sulfate tamoxifen and alpha-acetoxy tamoxifen
    • Dasaradhi L and Shibutani S (1997) Identification of tamoxifen-DNA adducts formed by alpha-sulfate tamoxifen and alpha-acetoxy tamoxifen. Chem Res Toxicol 10:189-196.
    • (1997) Chem Res Toxicol , vol.10 , pp. 189-196
    • Dasaradhi, L.1    Shibutani, S.2
  • 13
    • 0031867191 scopus 로고    scopus 로고
    • The metabolic activation of tamoxifen and alpha-hydroxytamoxifen to DNA-binding species in rat hepatocytes proceeds via sulphation
    • Davis W, Venitt S, and Phillips DH (1998) The metabolic activation of tamoxifen and alpha-hydroxytamoxifen to DNA-binding species in rat hepatocytes proceeds via sulphation. Carcinogenesis 19:861-866.
    • (1998) Carcinogenesis , vol.19 , pp. 861-866
    • Davis, W.1    Venitt, S.2    Phillips, D.H.3
  • 14
    • 0024790344 scopus 로고
    • Assay of purified aryl sulfotransferase suitable for reactions yielding unstable sulfuric acid esters
    • Duffel MW, Binder TP, and Rao SI (1989) Assay of purified aryl sulfotransferase suitable for reactions yielding unstable sulfuric acid esters. Anal Biochem 183:320-324.
    • (1989) Anal Biochem , vol.183 , pp. 320-324
    • Duffel, M.W.1    Binder, T.P.2    Rao, S.I.3
  • 16
    • 0035020110 scopus 로고    scopus 로고
    • Bioactivation of tamoxifen to metabolite E quinone methide: Reaction with glutathione and DNA
    • Fan PW and Bolton JL (2001) Bioactivation of tamoxifen to metabolite E quinone methide: reaction with glutathione and DNA. Drug Metab Dispos 29:891-896.
    • (2001) Drug Metab Dispos , vol.29 , pp. 891-896
    • Fan, P.W.1    Bolton, J.L.2
  • 17
    • 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 Nat Cancer Inst 86:527-537.
    • (1994) J Nat 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
  • 20
    • 0031670051 scopus 로고    scopus 로고
    • Rat, but not human, sulfotransferase activates a tamoxifen metabolite to produce DNA adducts and gene mutations in bacteria and mammalian cells in culture
    • Glatt H, Davis W, Meinl W, Hermersdorfer H, Venitt S, and Phillips DH (1998) Rat, but not human, sulfotransferase activates a tamoxifen metabolite to produce DNA adducts and gene mutations in bacteria and mammalian cells in culture. Carcinogenesis 19:1709-1713.
    • (1998) Carcinogenesis , vol.19 , pp. 1709-1713
    • Glatt, H.1    Davis, W.2    Meinl, W.3    Hermersdorfer, H.4    Venitt, S.5    Phillips, D.H.6
  • 21
    • 0028981772 scopus 로고
    • Activation of benzylic alcohols to mutagens by rat and human sulfotransferases expressed in Escherichia coli
    • Glatt H, Pauly K, Czich A, Falany JL, and Falany CN (1995) Activation of benzylic alcohols to mutagens by rat and human sulfotransferases expressed in Escherichia coli. Eur J Pharmacol 293:173-181.
    • (1995) Eur J Pharmacol , vol.293 , pp. 173-181
    • Glatt, H.1    Pauly, K.2    Czich, A.3    Falany, J.L.4    Falany, C.N.5
  • 23
    • 0037364074 scopus 로고    scopus 로고
    • Tamoxifen: A most unlikely pioneering medicine
    • Jordan VC (2003a) Tamoxifen: a most unlikely pioneering medicine. Nature Rev 2:205-213.
    • (2003) Nature Rev , vol.2 , pp. 205-213
    • Jordan, V.C.1
  • 24
    • 0037435046 scopus 로고    scopus 로고
    • Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions
    • Jordan VC (2003b) Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions. J Med Chem 46:883-908.
    • (2003) J Med Chem , vol.46 , pp. 883-908
    • Jordan, V.C.1
  • 25
    • 0037468902 scopus 로고    scopus 로고
    • Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 2. Clinical considerations and new agents
    • Jordan VC (2003c) Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 2. Clinical considerations and new agents. J Med Chem 46:1081-1111.
    • (2003) J Med Chem , vol.46 , pp. 1081-1111
    • Jordan, V.C.1
  • 26
    • 0029758139 scopus 로고    scopus 로고
    • Tamoxifen metabolism by microsomal cytochrome P450 and flavin-containing monooxygenase
    • Kupfer D and Dehal S (1996) Tamoxifen metabolism by microsomal cytochrome P450 and flavin-containing monooxygenase. Methods Enzymol 272:152-162.
    • (1996) Methods Enzymol , vol.272 , pp. 152-162
    • Kupfer, D.1    Dehal, S.2
  • 27
    • 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
  • 29
    • 0019274413 scopus 로고
    • The identity of alcohol sulfotransferases with hydroxysteroid sulfotransferases
    • Lyon ES and Jakoby WB (1980) The identity of alcohol sulfotransferases with hydroxysteroid sulfotransferases. Arch Biochem Biophys 202:474-481.
    • (1980) Arch Biochem Biophys , vol.202 , pp. 474-481
    • Lyon, E.S.1    Jakoby, W.B.2
  • 30
    • 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
  • 31
    • 0025944433 scopus 로고
    • Electrophilic sulfuric acid ester metabolites of hydroxy-methyl aromatic hydrocarbons as precursors of hepatic benzylic DNA adducts in vivo
    • (Witmer CM ed), Plenum Press, New York
    • Miller JA, Surh Y-J, Liem A, and Miller EC (1990) Electrophilic sulfuric acid ester metabolites of hydroxy-methyl aromatic hydrocarbons as precursors of hepatic benzylic DNA adducts in vivo, in Biological Reactive Intermediates IV (Witmer CM ed), pp 555-567, Plenum Press, New York.
    • (1990) Biological Reactive Intermediates IV , pp. 555-567
    • Miller, J.A.1    Surh, Y.-J.2    Liem, A.3    Miller, E.C.4
  • 32
  • 34
    • 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
  • 36
    • 0025291487 scopus 로고
    • Rat liver cytosolic hydroxysteroid sulfotransferase (sulfotransferase a) catalyzing the formation of reactive sulfate esters from carcinogenic polycyclic hydroxymethylarenes
    • Ogura K, Sohtome T, Sugiyama A, Okuda H, Hiratsuka A, and Watabe T (1990) Rat liver cytosolic hydroxysteroid sulfotransferase (sulfotransferase a) catalyzing the formation of reactive sulfate esters from carcinogenic polycyclic hydroxymethylarenes. Mol Pharmacol 37:848-854.
    • (1990) Mol Pharmacol , vol.37 , pp. 848-854
    • Ogura, K.1    Sohtome, T.2    Sugiyama, A.3    Okuda, H.4    Hiratsuka, A.5    Watabe, T.6
  • 38
    • 0034942563 scopus 로고    scopus 로고
    • Resolution of alpha-hydroxytamoxifen: R-isomer forms more DNA adducts in rat liver cells
    • Osborne MR, Hewer A, and Phillips DH (2001) Resolution of alpha-hydroxytamoxifen: R-isomer forms more DNA adducts in rat liver cells. Chem Res Toxicol 14:888-893.
    • (2001) Chem Res Toxicol , vol.14 , pp. 888-893
    • Osborne, M.R.1    Hewer, A.2    Phillips, D.H.3
  • 39
    • 0028172242 scopus 로고
    • Alpha-hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes
    • Phillips DH, Carmichael PL, Hewer A, Cole KJ, and Poon GK (1994) Alpha-hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res 54:5518-5522.
    • (1994) Cancer Res , vol.54 , pp. 5518-5522
    • Phillips, D.H.1    Carmichael, P.L.2    Hewer, A.3    Cole, K.J.4    Poon, G.K.5
  • 41
    • 0028326053 scopus 로고
    • A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism
    • Potter GA, 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
  • 42
    • 0028226088 scopus 로고
    • Strong intensification of mouse hepatic tamoxifen-DNA adduct formation by pretreatment with the sulfotransferase inhibitor and ubiquitous environmental pollutant pentachlorophenol
    • Randerath K, Bi J, Mabon N, Sriram P, and Moorthy B (1994) Strong intensification of mouse hepatic tamoxifen-DNA adduct formation by pretreatment with the sulfotransferase inhibitor and ubiquitous environmental pollutant pentachlorophenol. Carcinogenesis 15:797-800.
    • (1994) Carcinogenesis , vol.15 , pp. 797-800
    • Randerath, K.1    Bi, J.2    Mabon, N.3    Sriram, P.4    Moorthy, B.5
  • 43
    • 0000196638 scopus 로고
    • Adenosine 3′-phosphate 5′-phosphosulfate
    • Sekura R (1981) Adenosine 3′-phosphate 5′-phosphosulfate. Methods Enzymol 77:413-415.
    • (1981) Methods Enzymol , vol.77 , pp. 413-415
    • Sekura, R.1
  • 44
    • 0034952130 scopus 로고    scopus 로고
    • Bacterial expression, purification and characterization of rat hydroxysteroid sulfotransferase STa
    • Sheng JJ and Duffel MW (2001) Bacterial expression, purification and characterization of rat hydroxysteroid sulfotransferase STa. Protein Expression Purif 21:235-242.
    • (2001) Protein Expression Purif , vol.21 , pp. 235-242
    • Sheng, J.J.1    Duffel, M.W.2
  • 45
    • 0037855908 scopus 로고    scopus 로고
    • Enantioselectivity of human hydroxysteroid sulfotransferase ST2A3 with naphthyl-1-ethanols
    • Sheng JJ and Duffel MW (2003) Enantioselectivity of human hydroxysteroid sulfotransferase ST2A3 with naphthyl-1-ethanols. Drug Metab Dispos 31:697-700.
    • (2003) Drug Metab Dispos , vol.31 , pp. 697-700
    • Sheng, J.J.1    Duffel, M.W.2
  • 46
    • 79952199079 scopus 로고    scopus 로고
    • Measurement of aryl and alcohol sulfotransferase activity
    • (Maines M, Costa LG, Hodgson E, Reed DJ, and Sipes IG eds), John Wiley & Sons, Inc., New York
    • Sheng JJ, Sharma V, and Duffel MW (2001) Measurement of aryl and alcohol sulfotransferase activity, in Current Protocols in Toxicology (Maines M, Costa LG, Hodgson E, Reed DJ, and Sipes IG eds), pp. 4.5.1-4.5.9, John Wiley & Sons, Inc., New York.
    • (2001) Current Protocols in Toxicology
    • Sheng, J.J.1    Sharma, V.2    Duffel, M.W.3
  • 47
    • 0032519594 scopus 로고    scopus 로고
    • Alpha-hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts
    • Shibutani S, Dasaradhi L, Terashima I, Banoglu E, and Duffel MW (1998a) Alpha-hydroxytamoxifen is a substrate of hydroxysteroid (alcohol) sulfotransferase, resulting in tamoxifen DNA adducts. Cancer Res 58:647-653.
    • (1998) Cancer Res , vol.58 , pp. 647-653
    • Shibutani, S.1    Dasaradhi, L.2    Terashima, I.3    Banoglu, E.4    Duffel, M.W.5
  • 48
    • 0031721571 scopus 로고    scopus 로고
    • Sulfation of alpha-hydroxytamoxifen catalyzed by human hydroxysteroid sulfotransferase results in tamoxifen-DNA adducts
    • Shibutani S, Shaw PM, Suzuki N, Dasaradhi L, Duffel MW, and Terashima I (1998b) Sulfation of alpha-hydroxytamoxifen catalyzed by human hydroxysteroid sulfotransferase results in tamoxifen-DNA adducts. Carcinogenesis 19:2007-2011.
    • (1998) Carcinogenesis , vol.19 , pp. 2007-2011
    • Shibutani, S.1    Shaw, P.M.2    Suzuki, N.3    Dasaradhi, L.4    Duffel, M.W.5    Terashima, I.6
  • 51
    • 0032548978 scopus 로고    scopus 로고
    • Bioactivation of benzylic and allylic alcohols via sulfo-conjugation
    • Surh YJ (1998) Bioactivation of benzylic and allylic alcohols via sulfo-conjugation. Chem Biol Interact 109:221-235.
    • (1998) Chem Biol Interact , vol.109 , pp. 221-235
    • Surh, Y.J.1
  • 52
    • 0033135051 scopus 로고    scopus 로고
    • 2-deoxyguanosinyl)tamoxifen lesions, the major DNA adducts detected in endometrial tissues of patients treated with tamoxifen
    • 2-deoxyguanosinyl)tamoxifen lesions, the major DNA adducts detected in endometrial tissues of patients treated with tamoxifen. Cancer Res 59:2091-2095.
    • (1999) Cancer Res , vol.59 , pp. 2091-2095
    • Terashima, I.1    Suzuki, N.2    Shibutani, S.3
  • 53
    • 0032808213 scopus 로고    scopus 로고
    • The tamoxifen dilemma
    • White INH (1999) The tamoxifen dilemma. Carcinogenesis 20:1153-1160.
    • (1999) Carcinogenesis , vol.20 , pp. 1153-1160
    • White, I.N.H.1
  • 54
    • 0027308685 scopus 로고
    • The triphenylethylene drug tamoxifen is a strong liver carcinogen in the rat
    • Williams G and Iatropoulos M (1993) The triphenylethylene drug tamoxifen is a strong liver carcinogen in the rat. Carcinogenesis 14:315-317.
    • (1993) Carcinogenesis , vol.14 , pp. 315-317
    • Williams, G.1    Iatropoulos, M.2


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