메뉴 건너뛰기




Volumn 109, Issue 1-3, 1998, Pages 221-235

Bioactivation of benzylic and allylic alcohols via sulfo-conjugation

Author keywords

Allylic alcohols; Benzylic alcohols; Bioactivation; Carcinogenicity and mutagenity; Sulfotransferase; Sulfuric acid esters

Indexed keywords

ADENOSINE 3' PHOSPHATE 5' PHOSPHOSULFATE; ALLYL COMPOUND; BENZO[A]PYRENE DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; CARCINOGEN; MUTAGENIC AGENT; POLYCYCLIC AROMATIC HYDROCARBON; SULFATE; SULFOTRANSFERASE;

EID: 0032548978     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(97)00134-8     Document Type: Conference Paper
Times cited : (33)

References (71)
  • 1
    • 0028247286 scopus 로고
    • Sulfonation in chemical carcinogenesis
    • Miller J.A. Sulfonation in chemical carcinogenesis. Chem.-Biol. Interact. 92:1994;329-341.
    • (1994) Chem.-Biol. Interact. , vol.92 , pp. 329-341
    • Miller, J.A.1
  • 2
    • 0030054952 scopus 로고    scopus 로고
    • Sulphation catalyzed by the human cytosolic sulphotransferases - Chemical defense or molecular terrorism?
    • Coughtrie M.W.H. Sulphation catalyzed by the human cytosolic sulphotransferases - chemical defense or molecular terrorism? Hum. Exp. Toxicol. 15:1996;547-555.
    • (1996) Hum. Exp. Toxicol. , vol.15 , pp. 547-555
    • Coughtrie, M.W.H.1
  • 4
    • 0010592932 scopus 로고
    • Hydroxylation and conjugation at the benzylic carbon atom: A possible mechanism of carcinogenic activation for some methyl-substituted aromatic hydrocarbons
    • P.W. Jones, & P. Leber. Ann Arbor, MI: Ann Arbor publishers
    • Cavalieri E.L., Roth R.W., Rogan E.G. Hydroxylation and conjugation at the benzylic carbon atom: A possible mechanism of carcinogenic activation for some methyl-substituted aromatic hydrocarbons. Jones P.W., Leber P. Polynuclear Aromatic Hydrocarbons. 1979;517-529 Ann Arbor publishers, Ann Arbor, MI.
    • (1979) Polynuclear Aromatic Hydrocarbons , pp. 517-529
    • Cavalieri, E.L.1    Roth, R.W.2    Rogan, E.G.3
  • 5
    • 0018141358 scopus 로고
    • Reactions of the carcinogens 7-hydroxymethyl-12-methylbenz[a]anthracene and 7-acetoxymethyl-12-methylbenz[a]anthracene with DNA
    • Flesher J.W., Tay L.K. Reactions of the carcinogens 7-hydroxymethyl-12-methylbenz[a]anthracene and 7-acetoxymethyl-12-methylbenz[a]anthracene with DNA. Res. Commun. Chem. Pathol. Pharmacol. 22:1978;345-355.
    • (1978) Res. Commun. Chem. Pathol. Pharmacol. , vol.22 , pp. 345-355
    • Flesher, J.W.1    Tay, L.K.2
  • 6
    • 0018766288 scopus 로고
    • Binding of 6-hydroxymethylbenzo[a]pyrene and 6-acetoxymethylbenzo[a]pyrene to DNA
    • Tay L.K., Sydnor K.L., Flesher J.W. Binding of 6-hydroxymethylbenzo[a]pyrene and 6-acetoxymethylbenzo[a]pyrene to DNA. Chem.-Biol. Interact. 25:1979;35-44.
    • (1979) Chem.-Biol. Interact. , vol.25 , pp. 35-44
    • Tay, L.K.1    Sydnor, K.L.2    Flesher, J.W.3
  • 7
    • 0000073503 scopus 로고
    • One-electron oxidation of polycyclic aromatics as a model for the metabolic activation of carcinogenic hydrocarbons
    • P.O.P. Ts'o, & J.A. DiPalo. New York: Marcel Dekker
    • Fried J. One-electron oxidation of polycyclic aromatics as a model for the metabolic activation of carcinogenic hydrocarbons. Ts'o P.O.P., DiPalo J.A. Chemical Carcinogenesis (Part I). 1974;197-215 Marcel Dekker, New York.
    • (1974) Chemical Carcinogenesis (Part I) , pp. 197-215
    • Fried, J.1
  • 8
    • 0020044747 scopus 로고
    • A 7-hydroxymethyl sulfate ester as an active metabolite of 7,12-dimethylbenz[a]anthracene
    • Watabe T., Ishizuka T., Isobe M., Ozawa N. A 7-hydroxymethyl sulfate ester as an active metabolite of 7,12-dimethylbenz[a]anthracene. Science. 215:1982;403-405.
    • (1982) Science , vol.215 , pp. 403-405
    • Watabe, T.1    Ishizuka, T.2    Isobe, M.3    Ozawa, N.4
  • 9
    • 0023017244 scopus 로고
    • A 7-hydroxymethyl sulfate ester as an active metabolite of the carcinogen, 7-hydroxymethylbenz[a]anthracene
    • Watabe T., Hakamata Y., Hiratsuka A., Ogura K. A 7-hydroxymethyl sulfate ester as an active metabolite of the carcinogen, 7-hydroxymethylbenz[a]anthracene. Carcinogenesis. 7:1986;207-214.
    • (1986) Carcinogenesis , vol.7 , pp. 207-214
    • Watabe, T.1    Hakamata, Y.2    Hiratsuka, A.3    Ogura, K.4
  • 10
    • 0023235214 scopus 로고
    • Sulfotransferase-mediated covalent binding of the carcinogen 7,12-dihydroxymethylbenz[a]anthracene to calf thymus DNA and its inhibition by glutathione transferase
    • Watabe T., Hiratsuka A., Ogura K. Sulfotransferase-mediated covalent binding of the carcinogen 7,12-dihydroxymethylbenz[a]anthracene to calf thymus DNA and its inhibition by glutathione transferase. Carcinogenesis. 8:1987;445-453.
    • (1987) Carcinogenesis , vol.8 , pp. 445-453
    • Watabe, T.1    Hiratsuka, A.2    Ogura, K.3
  • 11
    • 0022614236 scopus 로고
    • A hydroxymethyl sulphate ester as an active metabolite of the carcinogen, 5-hydroxymethylchrysene
    • Okuda H., Hiratsuka A., Nojima H., Watabe T. A hydroxymethyl sulphate ester as an active metabolite of the carcinogen, 5-hydroxymethylchrysene. Biochem. Pharmacol. 35:1986;535-538.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 535-538
    • Okuda, H.1    Hiratsuka, A.2    Nojima, H.3    Watabe, T.4
  • 12
    • 0010630607 scopus 로고
    • Hydroxymethyl sulfate esters as reactive metabolites of the carcinogen, 7-methyl- and 7,12-dimethylbenz[a]anthracene and 5-methylchrysene
    • R. Kato, R.W. Estabrook, & M.N. Cayen. London: Taylor and Francis
    • Watabe T., Ogura K., Okuda H., Hiratsuka A. Hydroxymethyl sulfate esters as reactive metabolites of the carcinogen, 7-methyl- and 7,12-dimethylbenz[a]anthracene and 5-methylchrysene. Kato R., Estabrook R.W., Cayen M.N. Xenobiotic Metabolism and Disposition. 1989;393-400 Taylor and Francis, London.
    • (1989) Xenobiotic Metabolism and Disposition , pp. 393-400
    • Watabe, T.1    Ogura, K.2    Okuda, H.3    Hiratsuka, A.4
  • 13
    • 0022446954 scopus 로고
    • Inhibition of the mutagenicity and metabolism of 6-methylbenzo[a]pyrene and 6-hydroxymethylbenzo[a]pyrene
    • Bayless J.H., Jablonski J.E., Roach S.M., Sullivan P.D. Inhibition of the mutagenicity and metabolism of 6-methylbenzo[a]pyrene and 6-hydroxymethylbenzo[a]pyrene. Biochem. Pharmacol. 35:1986;2313-2322.
    • (1986) Biochem. Pharmacol. , vol.35 , pp. 2313-2322
    • Bayless, J.H.1    Jablonski, J.E.2    Roach, S.M.3    Sullivan, P.D.4
  • 14
    • 0024374662 scopus 로고
    • Metabolic activation of the carcinogen 6-hydroxymethylbenzo[a]pyrene: Formation of an electrophilic sulfuric acid ester and benzylic DNA adducts in rat liver in vivo and in reactions in vitro
    • Surh Y.-J., Liem A., Miller E.C., Miller J.A. Metabolic activation of the carcinogen 6-hydroxymethylbenzo[a]pyrene: Formation of an electrophilic sulfuric acid ester and benzylic DNA adducts in rat liver in vivo and in reactions in vitro. Carcinogenesis. 10:1989;1519-1528.
    • (1989) Carcinogenesis , vol.10 , pp. 1519-1528
    • Surh, Y.-J.1    Liem, A.2    Miller, E.C.3    Miller, J.A.4
  • 15
    • 0025147564 scopus 로고
    • The strong hepatocarcinogenicity of the elctrophilic and mutagenic metabolite 6-sulfooxymethylbenzo[a]pyrene and its formation of benzylic DNA adducts in the livers of infant male B6C3F1 mice
    • Surh Y.-J., Liem A., Miller E.C., Miller J.A. The strong hepatocarcinogenicity of the elctrophilic and mutagenic metabolite 6-sulfooxymethylbenzo[a]pyrene and its formation of benzylic DNA adducts in the livers of infant male B6C3F1 mice. Biochem. Biophys. Res. Commun. 172:1990;85-91.
    • (1990) Biochem. Biophys. Res. Commun. , vol.172 , pp. 85-91
    • Surh, Y.-J.1    Liem, A.2    Miller, E.C.3    Miller, J.A.4
  • 16
    • 0025090958 scopus 로고
    • Metabolic activation of 9-hydroxymethyl-10-methylanthracene and 1-hydroxymethylpyrene to electrophilic, mutagenic, and tumorigenic sulfuric acid esters by rat hepatic sulfotransferase activity
    • Surh Y.-J., Blomquist J.C., Liem A., Miller J.A. Metabolic activation of 9-hydroxymethyl-10-methylanthracene and 1-hydroxymethylpyrene to electrophilic, mutagenic, and tumorigenic sulfuric acid esters by rat hepatic sulfotransferase activity. Carcinogenesis. 11:1990;1451-1460.
    • (1990) Carcinogenesis , vol.11 , pp. 1451-1460
    • Surh, Y.-J.1    Blomquist, J.C.2    Liem, A.3    Miller, J.A.4
  • 18
    • 0028090022 scopus 로고
    • Substance-dependent sex differences in the activation of benzylic alcohols to mutagens by hepatic sulfotransferases of the rat
    • Glatt H., Pauly K., Frank H., Seidel A., Oesch F., Harvey R.G., Werle-Schneider G. Substance-dependent sex differences in the activation of benzylic alcohols to mutagens by hepatic sulfotransferases of the rat. Carcinogenesis. 15:1994;2605-2611.
    • (1994) Carcinogenesis , vol.15 , pp. 2605-2611
    • Glatt, H.1    Pauly, K.2    Frank, H.3    Seidel, A.4    Oesch, F.5    Harvey, R.G.6    Werle-Schneider, G.7
  • 19
    • 0030934879 scopus 로고    scopus 로고
    • Bioactivation of mutagens via sulfation
    • Glatt H. Bioactivation of mutagens via sulfation. FASEB J. 11:1997;314-321.
    • (1997) FASEB J. , vol.11 , pp. 314-321
    • Glatt, H.1
  • 20
    • 0023190875 scopus 로고
    • Hepatic DNA and RNA adduct formation from 7-hydroxymethyl-12-methylbenz[a]anthracene and its electrophilic sulfuric acid ester metabolite in preweanling rats and mice
    • Surh Y.-J., Liem A., Lai C.-C., Miller J.A., Miller E.C. Hepatic DNA and RNA adduct formation from 7-hydroxymethyl-12-methylbenz[a]anthracene and its electrophilic sulfuric acid ester metabolite in preweanling rats and mice. Biochem. Biophys. Res. Commun. 144:1987;576-582.
    • (1987) Biochem. Biophys. Res. Commun. , vol.144 , pp. 576-582
    • Surh, Y.-J.1    Liem, A.2    Lai, C.-C.3    Miller, J.A.4    Miller, E.C.5
  • 21
    • 0026074791 scopus 로고
    • Age- and sex-related differences in activation of the carcinogen 7-hydroxymethyl-12-methylbenz[a]anthracene to an electyrophilic sulfuric acid ester metabolite in rats: Possible involvement of hydroxysteroid sulfotransferase activity
    • Surh Y.-J., Liem A., Miller E.C., Miller J.A. Age- and sex-related differences in activation of the carcinogen 7-hydroxymethyl-12-methylbenz[a]anthracene to an electyrophilic sulfuric acid ester metabolite in rats: possible involvement of hydroxysteroid sulfotransferase activity. Biochem. Pharmacol. 41:1991;213-221.
    • (1991) Biochem. Pharmacol. , vol.41 , pp. 213-221
    • Surh, Y.-J.1    Liem, A.2    Miller, E.C.3    Miller, J.A.4
  • 23
    • 0025291487 scopus 로고
    • Rat liver cytosolic hydroxysteroid sulfotransferase (sulfotransferase a) catalyzing the formation of reactive sulfate esters from carcinogenic polycyclic hydroxymethylarenes
    • Ogura K., Sohotome T., Sugiyama A., Okuda H., Hiratsuka A., Watabe T. Rat liver cytosolic hydroxysteroid sulfotransferase (sulfotransferase a) catalyzing the formation of reactive sulfate esters from carcinogenic polycyclic hydroxymethylarenes. Mol. Pharmacol. 37:1990;848-854.
    • (1990) Mol. Pharmacol. , vol.37 , pp. 848-854
    • Ogura, K.1    Sohotome, T.2    Sugiyama, A.3    Okuda, H.4    Hiratsuka, A.5    Watabe, T.6
  • 25
    • 0027027396 scopus 로고
    • Bioactivation of 7-hydroxymethyl-12-methylbenz[a]anthracene by rat liver bile acid sulfotransferase I
    • C.N. Falany, J. Wheeler, L. Coward, D. Keehan, J.L. Falany, S. Barnes, Bioactivation of 7-hydroxymethyl-12-methylbenz[a]anthracene by rat liver bile acid sulfotransferase I, J. Biochem. Toxicol. (1992) 241-248.
    • (1992) J. Biochem. Toxicol. , pp. 241-248
    • Falany, C.N.1    Wheeler, J.2    Coward, L.3    Keehan, D.4    Falany, J.L.5    Barnes, S.6
  • 26
    • 0028171481 scopus 로고
    • Activation of benzylic alcohols to mutagens by human hepatic sulphotransferases
    • Glatt H., Seidel A., Harvey R.G., Coughtrie M.W.H. Activation of benzylic alcohols to mutagens by human hepatic sulphotransferases. Mutagenesis. 9:1994;553-557.
    • (1994) Mutagenesis , vol.9 , pp. 553-557
    • Glatt, H.1    Seidel, A.2    Harvey, R.G.3    Coughtrie, M.W.H.4
  • 27
    • 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 J.L., Falany C.N. Activation of benzylic alcohols to mutagens by rat and human sulfotransferases expressed in Escherichia coli. Eur. J. Pharmacol. 293:1995;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
  • 28
    • 0028301393 scopus 로고
    • Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures
    • Glatt H., Pauly K., Piee-Staffa A., Seidel A., Hornhardt S., Czich A. Activation of promutagens by endogenous and heterologous sulfotransferases expressed in continuous cell cultures. Toxicol. Lett. 72:1994;13-21.
    • (1994) Toxicol. Lett. , vol.72 , pp. 13-21
    • Glatt, H.1    Pauly, K.2    Piee-Staffa, A.3    Seidel, A.4    Hornhardt, S.5    Czich, A.6
  • 29
    • 0028245971 scopus 로고
    • Stable heterologous expression of hydroxysteroid sulphotransferase in Chinese hamster V79 cells and their use for toxicological investigations
    • Czich A., Bartsch I., Dogra S., Hornhardt S., Glatt H.R. Stable heterologous expression of hydroxysteroid sulphotransferase in Chinese hamster V79 cells and their use for toxicological investigations. Chem.-Biol. Interact. 92:1994;119-128.
    • (1994) Chem.-Biol. Interact. , vol.92 , pp. 119-128
    • Czich, A.1    Bartsch, I.2    Dogra, S.3    Hornhardt, S.4    Glatt, H.R.5
  • 32
    • 0030598140 scopus 로고    scopus 로고
    • Chemopreventive effect of chlorophyllin on mutagenicity and cytotoxicity of 6-sulfooxymethylbenzo[a]pyrene
    • Cho Y.S., Kim B.-Y., Lee S.-T., Surh Y.-J., Chung A.-S. Chemopreventive effect of chlorophyllin on mutagenicity and cytotoxicity of 6-sulfooxymethylbenzo[a]pyrene. Cancer Lett. 107:1996;223-228.
    • (1996) Cancer Lett. , vol.107 , pp. 223-228
    • Cho, Y.S.1    Kim, B.-Y.2    Lee, S.-T.3    Surh, Y.-J.4    Chung, A.-S.5
  • 33
    • 0029738020 scopus 로고    scopus 로고
    • Sulfotransferase-mediated activation of some benzylic and allylic alcohols
    • R. et al. Snyder. New York: Plenum
    • Surh Y.-J. Sulfotransferase-mediated activation of some benzylic and allylic alcohols. Snyder R. et al. Biological Reactive Intermediates V. 1996;339-345 Plenum, New York.
    • (1996) Biological Reactive Intermediates V , pp. 339-345
    • Surh, Y.-J.1
  • 34
    • 0027479544 scopus 로고
    • Sulfotransferase-mediated activation of 4-hydroxy- and 3,4-dihydroxy-3,4-dihydrocyclopenta[c,d]pyrene, major metabolites of cyclopenta[c,d]pyrene
    • Surh Y.-J., Kwon H., Tannenbaum S.R. Sulfotransferase-mediated activation of 4-hydroxy- and 3,4-dihydroxy-3,4-dihydrocyclopenta[c,d]pyrene, major metabolites of cyclopenta[c,d]pyrene. Cancer Res. 53:1993;1017-1022.
    • (1993) Cancer Res. , vol.53 , pp. 1017-1022
    • Surh, Y.-J.1    Kwon, H.2    Tannenbaum, S.R.3
  • 35
    • 0010631749 scopus 로고
    • Bioactivation of cyclopenta- and cyclohexa-fused polycyclic aromatic hydrocarbons via the formation of benzylic sulfuric acid esters
    • Surh Y.-J., Tannenbaum S.R. Bioactivation of cyclopenta- and cyclohexa-fused polycyclic aromatic hydrocarbons via the formation of benzylic sulfuric acid esters. Polycyclic Aromat. Compd. 7:1994;83-90.
    • (1994) Polycyclic Aromat. Compd. , vol.7 , pp. 83-90
    • Surh, Y.-J.1    Tannenbaum, S.R.2
  • 36
    • 0029550674 scopus 로고
    • Intrinsic mutagenicity and electrophilicity of 1-sulfooxy-3-methylcholanthrene: Implications for metabolic activation of the carcinogen 3-methylcholanthrene
    • Jeong H.-K., Shlyankevich M., Surh Y.-J. Intrinsic mutagenicity and electrophilicity of 1-sulfooxy-3-methylcholanthrene: Implications for metabolic activation of the carcinogen 3-methylcholanthrene. Biochem. Mol. Biol. Int. 37:1995;877-883.
    • (1995) Biochem. Mol. Biol. Int. , vol.37 , pp. 877-883
    • Jeong, H.-K.1    Shlyankevich, M.2    Surh, Y.-J.3
  • 37
    • 0029003187 scopus 로고
    • Sulfotransferase-mediated activation of 7,8,9,10-tetrahydro-7-ol, 7,8-dihydrodiol, 7,8,9,10-tetraol derivatives of benzo[a]pyrene
    • Surh Y.-J., Tannenbaum S.R. Sulfotransferase-mediated activation of 7,8,9,10-tetrahydro-7-ol, 7,8-dihydrodiol, 7,8,9,10-tetraol derivatives of benzo[a]pyrene. Chem. Res. Toxicol. 8:1995;693-698.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 693-698
    • Surh, Y.-J.1    Tannenbaum, S.R.2
  • 38
    • 0027287612 scopus 로고
    • Sulfotransferase-mediated mutagenicity of 1-hydroxymethylpyrene and 4H-cyclopenta[def]chrysen-4-ol and its enhancement by chloride ion
    • Glatt H., Henschler R., Frank H., Seidel A., Yang C., Abu-Shqara E., Harvey R.G. Sulfotransferase-mediated mutagenicity of 1-hydroxymethylpyrene and 4H-cyclopenta[def]chrysen-4-ol and its enhancement by chloride ion. Carcinogenesis. 14:1993;599-602.
    • (1993) Carcinogenesis , vol.14 , pp. 599-602
    • Glatt, H.1    Henschler, R.2    Frank, H.3    Seidel, A.4    Yang, C.5    Abu-Shqara, E.6    Harvey, R.G.7
  • 39
    • 0023870660 scopus 로고
    • Preparation and antischistosomal and antitumor activity of hycanthone and some of its congeners. Evidence for the mode of action of hycanthone
    • Archer S., Pica-Mattoccia L., Cioli D., Seyed-Mozaffari A., Zayed A.-H. Preparation and antischistosomal and antitumor activity of hycanthone and some of its congeners. Evidence for the mode of action of hycanthone. J. Med. Chem. 31:1988;254-260.
    • (1988) J. Med. Chem. , vol.31 , pp. 254-260
    • Archer, S.1    Pica-Mattoccia, L.2    Cioli, D.3    Seyed-Mozaffari, A.4    Zayed, A.-H.5
  • 40
    • 0024413050 scopus 로고
    • Early years of the Salmonella mutagen tester strains: Lessons from hycanthone
    • Hartman P.E. Early years of the Salmonella mutagen tester strains: Lessons from hycanthone. Environ. Mol. Mutagen. 16:1989;39-45.
    • (1989) Environ. Mol. Mutagen. , vol.16 , pp. 39-45
    • Hartman, P.E.1
  • 41
    • 0017113491 scopus 로고
    • Long-term hepatocellular effects of hycanthone and of two other antischistosomal drugs in mice infected with Schistosoma mansoni
    • Haese W.H., Bueding E. Long-term hepatocellular effects of hycanthone and of two other antischistosomal drugs in mice infected with Schistosoma mansoni. J. Pharmacol. Exp. Ther. 197:1976;703-713.
    • (1976) J. Pharmacol. Exp. Ther. , vol.197 , pp. 703-713
    • Haese, W.H.1    Bueding, E.2
  • 42
    • 0016657212 scopus 로고
    • Genetic activity spectra of some antischistosomal compounds, with particular emphasis on thioxanthenones and benzothiopyranoindazoles
    • Hartman P.E., Hulbert P.B. Genetic activity spectra of some antischistosomal compounds, with particular emphasis on thioxanthenones and benzothiopyranoindazoles. J. Toxicol. Environ. Health. 1:1975;243-270.
    • (1975) J. Toxicol. Environ. Health , vol.1 , pp. 243-270
    • Hartman, P.E.1    Hulbert, P.B.2
  • 43
    • 0021792249 scopus 로고
    • Evidence for the mode of antischistosomal action of hycanthone
    • Cioli D., Pica-Mattoccia L., Rosenberg S., Archer S. Evidence for the mode of antischistosomal action of hycanthone. Life Sci. 37:1985;161-171.
    • (1985) Life Sci. , vol.37 , pp. 161-171
    • Cioli, D.1    Pica-Mattoccia, L.2    Rosenberg, S.3    Archer, S.4
  • 44
    • 0013844002 scopus 로고
    • Carcinogenicity of 'alderlin' (pronethalol) in mice
    • Howe R. Carcinogenicity of 'alderlin' (pronethalol) in mice. Nature. 207:1965;594-595.
    • (1965) Nature , vol.207 , pp. 594-595
    • Howe, R.1
  • 46
    • 0016330496 scopus 로고
    • Enzymatic aziridine synthesis from β aminoalcohols - A new example of endogenous carcinogen formation
    • Bicker U., Fischer W. Enzymatic aziridine synthesis from β aminoalcohols - a new example of endogenous carcinogen formation. Nature. 249:1974;344-345.
    • (1974) Nature , vol.249 , pp. 344-345
    • Bicker, U.1    Fischer, W.2
  • 47
    • 36949045654 scopus 로고
    • Metabolism of oestrone and oestradiol-17β in human liver in vitro
    • Breuer H., Knuppen R., Haupt M. Metabolism of oestrone and oestradiol-17β in human liver in vitro. Nature. 212:1966;76.
    • (1966) Nature , vol.212 , pp. 76
    • Breuer, H.1    Knuppen, R.2    Haupt, M.3
  • 48
    • 0026326830 scopus 로고
    • Synthesis and mechanism of hydrolysis of estrogen 6-sulfates: Model compounds for demonstrating the carcinogenesis of estrogen
    • Takagi H., Komatsu K.-I., Yoshizawa I. Synthesis and mechanism of hydrolysis of estrogen 6-sulfates: model compounds for demonstrating the carcinogenesis of estrogen. Steroids. 56:1991;173-179.
    • (1991) Steroids , vol.56 , pp. 173-179
    • Takagi, H.1    Komatsu, K.-I.2    Yoshizawa, I.3
  • 49
    • 0020030204 scopus 로고
    • Structure-mutagenicity relationship in α,β-unsaturated carbonyl compounds and their corresponding allylic alcohols
    • Lutz D., Eder E., Neudecker T., Henschler D. Structure-mutagenicity relationship in α,β-unsaturated carbonyl compounds and their corresponding allylic alcohols. Mutat. Res. 93:1982;305-315.
    • (1982) Mutat. Res. , vol.93 , pp. 305-315
    • Lutz, D.1    Eder, E.2    Neudecker, T.3    Henschler, D.4
  • 50
    • 0020446036 scopus 로고
    • Mutagenic properties of allylic and α,β-unsaturated compounds: Consideration of alkylating mechanisms
    • Eder E., Henschler D., Neudecker T. Mutagenic properties of allylic and α,β-unsaturated compounds: Consideration of alkylating mechanisms. Xenobiotica. 12:1982;831-848.
    • (1982) Xenobiotica , vol.12 , pp. 831-848
    • Eder, E.1    Henschler, D.2    Neudecker, T.3
  • 51
    • 0015829610 scopus 로고
    • Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein
    • Kaye C.M. Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein. Biochem. J. 134:1973;1093-1101.
    • (1973) Biochem. J. , vol.134 , pp. 1093-1101
    • Kaye, C.M.1
  • 52
    • 0019762671 scopus 로고
    • The Maillard reaction in food; A critical review from the nutritional standpoint
    • Mauron J. The Maillard reaction in food; a critical review from the nutritional standpoint. Prog. Food Nutr. 5:1981;5-35.
    • (1981) Prog. Food Nutr. , vol.5 , pp. 5-35
    • Mauron, J.1
  • 53
    • 0021722064 scopus 로고
    • A review of 5-hydroxymethylfurfural (HMF) in parentheral solutions
    • Ulbricht R.J., Northup S.J., Thomas J.A. A review of 5-hydroxymethylfurfural (HMF) in parentheral solutions. Fund. Appl. Toxicol. 4:1984;843-853.
    • (1984) Fund. Appl. Toxicol. , vol.4 , pp. 843-853
    • Ulbricht, R.J.1    Northup, S.J.2    Thomas, J.A.3
  • 54
    • 0027196817 scopus 로고
    • Initiation and promotion of colonic aberrant crypt foci in rats by 5-hydroxymethyl-2-furaldehyde in thermolyzed sucrose
    • Zhang X.-M., Chan C.C., Stamp D., Minkin S., Archer M.C., Bruce W.R. Initiation and promotion of colonic aberrant crypt foci in rats by 5-hydroxymethyl-2-furaldehyde in thermolyzed sucrose. Carcinogenesis. 14:1993;773-775.
    • (1993) Carcinogenesis , vol.14 , pp. 773-775
    • Zhang, X.-M.1    Chan, C.C.2    Stamp, D.3    Minkin, S.4    Archer, M.C.5    Bruce, W.R.6
  • 55
    • 0029049978 scopus 로고
    • Bioactivation of 5-hydroxymethyl-2-furaldehyde to an electrophilic and mutagenic allylic sulfuric acid ester
    • Lee Y.-C., Schlyankevich M., Jeong H.-K., Douglas J.S., Surh Y.-J. Bioactivation of 5-hydroxymethyl-2-furaldehyde to an electrophilic and mutagenic allylic sulfuric acid ester. Biochem. Biophys. Res. Commun. 209:1995;996-1002.
    • (1995) Biochem. Biophys. Res. Commun. , vol.209 , pp. 996-1002
    • Lee, Y.-C.1    Schlyankevich, M.2    Jeong, H.-K.3    Douglas, J.S.4    Surh, Y.-J.5
  • 56
    • 0028222204 scopus 로고
    • Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination
    • Surh Y.-J., Tannenbaum S.R. Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination. Chem. Res. Toxicol. 7:1994;313-318.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 313-318
    • Surh, Y.-J.1    Tannenbaum, S.R.2
  • 57
    • 0027973158 scopus 로고
    • 5-Sulfooxymethylfurfural as a possible ultimate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxymethylfurfural
    • Surh Y.-J., Liem A., Miller J.A., Tannenbaum S.R. 5-Sulfooxymethylfurfural as a possible ultimate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxymethylfurfural. Carcinogenesis. 15:1994;2375-2377.
    • (1994) Carcinogenesis , vol.15 , pp. 2375-2377
    • Surh, Y.-J.1    Liem, A.2    Miller, J.A.3    Tannenbaum, S.R.4
  • 58
    • 0027172047 scopus 로고
    • A current view of tamoxifen for the treatment and prevention of breast cancer
    • Jordan V.C. A current view of tamoxifen for the treatment and prevention of breast cancer. Br. J. Pharmacol. 110:1993;507-517.
    • (1993) Br. J. Pharmacol. , vol.110 , pp. 507-517
    • Jordan, V.C.1
  • 59
    • 0028331217 scopus 로고
    • Tamoxifen: New membrane-mediated mechanisms of action and therapeutic advances
    • Wiseman H. Tamoxifen: New membrane-mediated mechanisms of action and therapeutic advances. Trends Pharmacol. Sci. 15:1994;83-89.
    • (1994) Trends Pharmacol. Sci. , vol.15 , pp. 83-89
    • Wiseman, H.1
  • 60
    • 0029012731 scopus 로고
    • Tamoxifen and the induction of cancer
    • King C.M. Tamoxifen and the induction of cancer. Carcinogenesis. 16:1995;1449-1454.
    • (1995) Carcinogenesis , vol.16 , pp. 1449-1454
    • King, C.M.1
  • 62
    • 0028179723 scopus 로고
    • Co-chromatography of a tamoxifen epoxide-deoxyguanosine acid adduct with a major DNA adduct formed in the livers of tamoxifen-treated rats
    • D.H. Phillips, A. Hewer, I.N.H. White, P.B. Farmer, Co-chromatography of a tamoxifen epoxide-deoxyguanosine acid adduct with a major DNA adduct formed in the livers of tamoxifen-treated rats, Carcinogenesis (1994) 793-795.
    • (1994) Carcinogenesis , pp. 793-795
    • Phillips, D.H.1    Hewer, A.2    White, I.N.H.3    Farmer, P.B.4
  • 63
    • 0028172242 scopus 로고
    • Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes
    • Phillips D.H., Carmichael P.L., Hewer A., Cole K.J., Poon G.K. Hydroxytamoxifen, a metabolite of tamoxifen with exceptionally high DNA-binding activity in rat hepatocytes. Cancer Res. 54:1994;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
  • 64
    • 0028326053 scopus 로고
    • A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism
    • Potter G.A., McCague R., Jarman M. A mechanistic hypothesis for DNA adduct formation by tamoxifen following hepatic oxidative metabolism. Carcinogenesis. 15:1994;439-442.
    • (1994) Carcinogenesis , vol.15 , pp. 439-442
    • Potter, G.A.1    McCague, R.2    Jarman, M.3
  • 65
    • 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., Moorthy B. Strong intensification of mouse hepatic tamoxifen DNA adduct formation by pretreatment with the sulfotransferase inhibitor and ubiquitous environmental pollutant pentachlorophenol. Carcinogenesis. 15:1994;797-800.
    • (1994) Carcinogenesis , vol.15 , pp. 797-800
    • Randerath, K.1    Bi, J.2    Mabon, N.3    Sriram, P.4    Moorthy, B.5
  • 66
    • 0027217590 scopus 로고
    • Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures
    • Topinka J., Andrae U., Schwarz L.R., Wolff T. Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures. Carcinogenesis. 14:1993;423-427.
    • (1993) Carcinogenesis , vol.14 , pp. 423-427
    • Topinka, J.1    Andrae, U.2    Schwarz, L.R.3    Wolff, T.4
  • 67
    • 0028864079 scopus 로고
    • Accumulation and persistence of DNA adducts of the synthetic steroid cyproterone acetate in rat liver
    • Werner S., Topinka J., Wolff T., Schwarz L.R. Accumulation and persistence of DNA adducts of the synthetic steroid cyproterone acetate in rat liver. Carcinogenesis. 16:1995;2369-2372.
    • (1995) Carcinogenesis , vol.16 , pp. 2369-2372
    • Werner, S.1    Topinka, J.2    Wolff, T.3    Schwarz, L.R.4
  • 68
    • 0028979550 scopus 로고
    • Identification of 3α-hydroxy-cyproterone acetate as a metabolite of cyproterone acetate in the bile of female rats and the potential of this and other already known or putative metabolites to form DNA adducts in vitro
    • Kerdar R.S., Baumann A., Brudny-Kloppel M., Biere H., Blode H., Kuhnz W. Identification of 3α-hydroxy-cyproterone acetate as a metabolite of cyproterone acetate in the bile of female rats and the potential of this and other already known or putative metabolites to form DNA adducts in vitro. Carcinogenesis. 16:1995;1835-1841.
    • (1995) Carcinogenesis , vol.16 , pp. 1835-1841
    • Kerdar, R.S.1    Baumann, A.2    Brudny-Kloppel, M.3    Biere, H.4    Blode, H.5    Kuhnz, W.6
  • 70
    • 0028030505 scopus 로고
    • Metabolic chiral inversion of stiripentol in the rat. II. Influence of route of administration
    • Tang C., Zhang K., Lepage F., Levy R.H., Baillie T.A. Metabolic chiral inversion of stiripentol in the rat. II. Influence of route of administration. Drug Metab. Dispos. 22:1994;554-560.
    • (1994) Drug Metab. Dispos. , vol.22 , pp. 554-560
    • Tang, C.1    Zhang, K.2    Lepage, F.3    Levy, R.H.4    Baillie, T.A.5
  • 71
    • 0025803794 scopus 로고
    • In vitro and in vivo investigations of dihydropyridine-based chemical delivery systems for anticonvulsants
    • Boddy A.V., Zhang K., Lepage F., Tombret F., Slatter J. G., Baillie T.A., Levy R.H. In vitro and in vivo investigations of dihydropyridine-based chemical delivery systems for anticonvulsants. Pharm. Res. 8:1991;690-697.
    • (1991) Pharm. Res. , vol.8 , pp. 690-697
    • Boddy, A.V.1    Zhang, K.2    Lepage, F.3    Tombret, F.4    Slatter, J.G.5    Baillie, T.A.6    Levy, R.H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.