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Volumn 27, Issue 4, 2012, Pages 453-462

Identification of human and murine sulfotransferases able to activate hydroxylated metabolites of methyleugenol to mutagens in Salmonella typhimurium and detection of associated DNA adducts using UPLC-MS/MS methods

Author keywords

[No Author keywords available]

Indexed keywords

1' HYDROXYMETHYLEUGENOL; 3' HYDROXYMETHYLISOEUGENOL; ALKENYLBENZENE DERIVATIVE; BENZENE DERIVATIVE; CARCINOGEN; METHYLEUGENOL; MUTAGENIC AGENT; N2 (METHYLISOEUGENOL 3' YL) 2' DEOXYGUANOSINE; N6 (METHYLISOEUGENOL 3' YL) 2' DEOXYADENOSINE; SULFOTRANSFERASE; SULFOTRANSFERASE 1A1; SULFOTRANSFERASE 1A2; SULFOTRANSFERASE 1A3; SULFOTRANSFERASE 1C1; SULFOTRANSFERASE 1C2; SULFOTRANSFERASE 1C3; SULFOTRANSFERASE 1D1; SULFOTRANSFERASE 1E1; SULFOTRANSFERASE 2A1; SULFOTRANSFERASE 2B1B; UNCLASSIFIED DRUG;

EID: 84863458837     PISSN: 02678357     EISSN: 14643804     Source Type: Journal    
DOI: 10.1093/mutage/ges004     Document Type: Article
Times cited : (63)

References (29)
  • 1
    • 0020692513 scopus 로고
    • Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole
    • Miller, E. C., Swanson, A. B., Phillips, D. H., Fletcher, T. L., Liem, A. and Miller, J. A. (1983) Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res., 43, 1124-1134. (Pubitemid 13160033)
    • (1983) Cancer Research , vol.43 , Issue.3 , pp. 1124-1134
    • Miller, E.C.1    Swanson, A.B.2    Phillips, D.H.3
  • 2
    • 21244492084 scopus 로고    scopus 로고
    • Toxicology and carcinogenesis studies of methyleugenol
    • NTP
    • NTP (2000) Toxicology and carcinogenesis studies of methyleugenol. Natl Toxicol. Program Tech. Rep. Ser., 491, 1-420.
    • (2000) Natl Toxicol. Program Tech. Rep. Ser. , vol.491 , pp. 1-420
  • 3
    • 0019378206 scopus 로고
    • Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1'-hydroxyestragole
    • Phillips, D. H., Miller, J. A., Miller, E. C. and Adams, B. (1981) Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1′-hydroxyestragole. Cancer Res., 41, 176-186. (Pubitemid 11218813)
    • (1981) Cancer Research , vol.41 , Issue.1 , pp. 176-186
    • Phillips, D.H.1    Miller, J.A.2    Miller, E.C.3    Adams, B.4
  • 4
    • 0019395284 scopus 로고
    • 6 atom of adenine residues as sites for covalent binding of metabolically activated 1′-hydroxysafrole to mouse liver DNA in vivo
    • 6 atom of adenine residues as sites for covalent binding of metabolically activated 1′-hydroxysafrole to mouse liver DNA in vivo. Cancer Res., 41, 2664-2671.
    • (1981) Cancer Res. , vol.41 , pp. 2664-2671
    • Phillips, D.H.1    Miller, J.A.2    Miller, E.C.3    Adams, B.4
  • 5
    • 0021856770 scopus 로고
    • Further characterization of the DNA adducts formed by electrophilic esters of the hepatocarcinogens 1'-hydroxysafrole and 1'-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues
    • Wiseman, R. W., Fennell, T. R., Miller, J. A. and Miller, E. C. (1985) Further characterization of DNA adducts formed by electrophilic esters of the hepatocarcinogens 1′-hydroxysafrole and 1′-hydroxyestragole in vitro and in mouse liver in vivo, including new adducts at C-8 and N-7 of guanine residues. Cancer Res., 45, 3096-3105. (Pubitemid 15007179)
    • (1985) Cancer Research , vol.45 , Issue.7 , pp. 3096-3105
    • Wiseman, R.W.1    Fennell, T.R.2    Miller, J.A.3    Miller, E.C.4
  • 6
    • 0021646473 scopus 로고
    • 32P-Post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes: I. Adult female CD-1 mice
    • 32P-Post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes: I. Adult female CD-1 mice. Carcinogenesis, 5, 1613-1622.
    • (1984) Carcinogenesis , vol.5 , pp. 1613-1622
    • Randerath, K.1    Haglund, R.E.2    Phillips, D.H.3    Reddy, M.V.4
  • 7
    • 0021054404 scopus 로고
    • Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1'-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1'-hydroxysafrole in mouse liver
    • Boberg, E. W., Miller, E. C., Miller, J. A., Poland, A. and Liem, A. (1983) Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1′-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1′-hydroxysafrole in mouse liver. Cancer Res., 43, 5163-5173. (Pubitemid 14227494)
    • (1983) Cancer Research , vol.43 , Issue.11 , pp. 5163-5173
    • Boberg, E.W.1    Miller, E.C.2    Miller, J.A.3
  • 8
    • 0023224579 scopus 로고
    • Inhibition by pentachlorophenol of the initiating and promoting activities of 1'-hydroxysafrole for the formation of enzyme-altered foci and tumors in rat liver
    • Boberg, E. W., Liem, A., Miller, E. C. and Miller, J. A. (1987) Inhibition by pentachlorophenol of the initiating and promoting activities of 1′-hydroxysafrole for the formation of enzyme-altered foci and tumors in rat liver. Carcinogenesis, 8, 531-539. (Pubitemid 17127671)
    • (1987) Carcinogenesis , vol.8 , Issue.4 , pp. 531-539
    • Boberg, E.W.1    Liem, A.2    Miller, E.C.3    Miller, J.A.4
  • 9
    • 0031424256 scopus 로고    scopus 로고
    • Inhibition of sulfotransferase affecting in vivo genotoxicity and DNA adducts induced by safrole in rat liver
    • DOI 10.1002/(SICI)1520-6866(1997)17:6<327::AID-TCM3>3.0.CO;2-J
    • Daimon, H., Sawada, S., Asakura, S. and Sagami, F. (1997) Inhibition of sulfotransferase affecting in vivo genotoxicity and DNA adducts induced by safrole in rat liver. Teratog. Carcinog. Mutagen., 17, 327-337. (Pubitemid 28076173)
    • (1997) Teratogenesis Carcinogenesis and Mutagenesis , vol.17 , Issue.6 , pp. 327-337
    • Daimon, H.1    Sawada, S.2    Asakura, S.3    Sagami, F.4
  • 10
    • 0034534841 scopus 로고    scopus 로고
    • Sulfotransferases in the bioactivation of xenobiotics
    • Glatt, H. R. (2000) Sulfotransferases in the bioactivation of xenobiotics. Chem. Biol. Interact., 129, 141-170.
    • (2000) Chem. Biol. Interact. , vol.129 , pp. 141-170
    • Glatt, H.R.1
  • 11
    • 30144435525 scopus 로고    scopus 로고
    • Activation and inactivation of carcinogens by human sulfotransferases
    • Pacifici, G. M. and Coughtrie, M. W. H. (eds), Taylor & Francis, London
    • Glatt, H. R. (2005) Activation and inactivation of carcinogens by human sulfotransferases. In Pacifici, G. M. and Coughtrie, M. W. H. (eds), Human Sulphotransferases, Taylor & Francis, London, pp. 281-306.
    • (2005) Human Sulphotransferases , pp. 281-306
    • Glatt, H.R.1
  • 12
    • 80053160462 scopus 로고    scopus 로고
    • Hydroxymethyl-substituted furans: Mutagenicity in Salmonella typhimurium strains engineered for expression of various human and rodent sulphotransferases
    • Glatt, H. R., Schneider, H., Murkovic, M., Monien, B. H. and Meinl, W. (2012) Hydroxymethyl-substituted furans: mutagenicity in Salmonella typhimurium strains engineered for expression of various human and rodent sulphotransferases. Mutagenesis, 27, 41-48.
    • (2012) Mutagenesis , vol.27 , pp. 41-48
    • Glatt, H.R.1    Schneider, H.2    Murkovic, M.3    Monien, B.H.4    Meinl, W.5
  • 13
    • 31844448260 scopus 로고    scopus 로고
    • Human sulphotransferases are involved in the activation of aristolochic acids and are expressed in renal target tissue
    • DOI 10.1002/ijc.21480
    • Meinl, W., Pabel, U., Osterloh-Quiroz, M., Hengstler, J. G. and Glatt, H. R. (2006) Human sulfotransferases are involved in the activation of aristolochic acids and are expressed in renal target tissue. Int. J. Cancer, 118, 1090-1097. (Pubitemid 43185594)
    • (2006) International Journal of Cancer , vol.118 , Issue.5 , pp. 1090-1097
    • Meinl, W.1    Pabel, U.2    Osterloh-Quiroz, M.3    Hengstler, J.G.4    Glatt, H.5
  • 14
    • 4244160059 scopus 로고    scopus 로고
    • Enantioselective metabolic activation of safrole
    • Eisenbrand, G., Dayan, A. D., Elias, P. S., Grunow, W. and Schlatter, J. (eds), Wiley-VCH Verlag, Weinheim, Germany
    • Landsiedel, R., Andrae, U., Kuhlow, A., Scholtyssek, M., Engst, W. and Glatt, H. R. (2000) Enantioselective metabolic activation of safrole. In Eisenbrand, G., Dayan, A. D., Elias, P. S., Grunow, W. and Schlatter, J. (eds), Carcinogenic/Anticarcinogenic Factors in Food, Wiley-VCH Verlag, Weinheim, Germany, pp. 464-467.
    • (2000) Carcinogenic/Anticarcinogenic Factors in Food , pp. 464-467
    • Landsiedel, R.1    Andrae, U.2    Kuhlow, A.3    Scholtyssek, M.4    Engst, W.5    Glatt, H.R.6
  • 16
    • 0015593170 scopus 로고
    • The metabolism of the naturally occurring hepatocarcinogen safrole to 1′-hydroxysafrole and the electrophilic reactivity of 1′- acetoxysafrole
    • Borchert, P., Wislocki, P. G., Miller, J. A. and Miller, E. C. (1973) The metabolism of the naturally occurring hepatocarcinogen safrole to 1′-hydroxysafrole and the electrophilic reactivity of 1′- acetoxysafrole. Cancer Res., 33, 575-589.
    • (1973) Cancer Res. , vol.33 , pp. 575-589
    • Borchert, P.1    Wislocki, P.G.2    Miller, J.A.3    Miller, E.C.4
  • 17
    • 80052013370 scopus 로고    scopus 로고
    • Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin
    • Cartus, A. T., Merz, K. H. and Schrenk, D. (2011) Metabolism of methylisoeugenol in liver microsomes of human, rat, and bovine origin. Drug Metab. Dispos., 39, 1727-1733.
    • (2011) Drug Metab. Dispos. , vol.39 , pp. 1727-1733
    • Cartus, A.T.1    Merz, K.H.2    Schrenk, D.3
  • 18
    • 77952546103 scopus 로고    scopus 로고
    • A physiologically based biodynamic (PBBD) model for estragole DNA binding in rat liver based on in vitro kinetic data and estragole DNA adduct formation in primary hepatocytes
    • Paini, A., Punt, A., Viton, F., Scholz, G., Delatour, T., Marin-Kuan, M., Schilter, B., van Bladeren, P. J. and Rietjens, I. M. C. M. (2010) A physiologically based biodynamic (PBBD) model for estragole DNA binding in rat liver based on in vitro kinetic data and estragole DNA adduct formation in primary hepatocytes. Toxicol. Appl. Pharmacol., 245, 57-66.
    • (2010) Toxicol. Appl. Pharmacol. , vol.245 , pp. 57-66
    • Paini, A.1    Punt, A.2    Viton, F.3    Scholz, G.4    Delatour, T.5    Marin-Kuan, M.6    Schilter, B.7    Van Bladeren, P.J.8    Rietjens, I.M.C.M.9
  • 19
    • 34547641946 scopus 로고    scopus 로고
    • 2-(trans-isoestragol- 3′-yl)-2′-deoxyguanosine as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1′- hydroxyestragole
    • 2-(trans-isoestragol-3′-yl)-2′-deoxyguanosine as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1′-hydroxyestragole. Chem. Res. Toxicol., 20, 991-998.
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 991-998
    • Punt, A.1    Delatour, T.2    Scholz, G.3    Schilter, B.4    Van Bladeren, P.J.5    Rietjens, I.M.6
  • 20
    • 1642268315 scopus 로고    scopus 로고
    • A proposed nomenclature system for the cytosolic sulfotransferase (SULT) superfamily
    • DOI 10.1097/00008571-200403000-00009
    • Blanchard, R. L., Freimuth, R. R., Buck, J., Weinshilboum, R. M. and Coughtrie, M. H. (2004) A proposed nomenclature system for the cytosolic sulfotransferase (SULT) superfamily. Pharmacogenetics, 14, 199-211. (Pubitemid 38373115)
    • (2004) Pharmacogenetics , vol.14 , Issue.3 , pp. 199-211
    • Blanchard, R.L.1    Freimuth, R.R.2    Buck, J.3    Weinshilboum, R.M.4    Coughtrie, M.W.H.5
  • 21
    • 0020533372 scopus 로고
    • Revised methods for the Salmonella mutagenicity test
    • Maron, D. M. and Ames, B. N. (1983) Revised methods for the Salmonella mutagenicity test. Mutat. Res., 113, 173-215. (Pubitemid 13120319)
    • (1983) Mutation Research , vol.113 , Issue.3-4 , pp. 173-215
    • Maron, D.M.1    Ames, B.N.2
  • 23
    • 0027346285 scopus 로고
    • 32P-Postlabelling analysis of bulky aromatic adducts
    • 32P-Postlabelling analysis of bulky aromatic adducts. IARC Sci. Publ., 11-23.
    • (1993) IARC Sci. Publ. , pp. 11-23
    • Gupta, R.C.1
  • 25
    • 0032545405 scopus 로고    scopus 로고
    • Molecular cloning, expression, and characterization of novel human SULT1C sulfotransferases that catalyze the sulfonation of N-hydroxy-2- acetylaminofluorene
    • Sakakibara, Y., Yanagisawa, K., Katafuchi, J., Ringer, D. P., Takami, Y., Nakayama, T., Suiko, M. and Liu, M. C. (1998) Molecular cloning, expression, and characterization of novel human SULT1C sulfotransferases that catalyze the sulfonation of N-hydroxy-2-acetylaminofluorene. J. Biol. Chem., 273, 33929-33935.
    • (1998) J. Biol. Chem. , vol.273 , pp. 33929-33935
    • Sakakibara, Y.1    Yanagisawa, K.2    Katafuchi, J.3    Ringer, D.P.4    Takami, Y.5    Nakayama, T.6    Suiko, M.7    Liu, M.C.8
  • 26
    • 0034865895 scopus 로고    scopus 로고
    • Detection and characterization of DNA adducts of 3-methylindole
    • DOI 10.1021/tx0100237
    • Regal, K. A., Laws, G. M., Yuan, C., Yost, G. S. and Skiles, G. L. (2001) Detection and characterization of DNA adducts of 3-methylindole. Chem. Res. Toxicol., 14, 1014-1024. (Pubitemid 32800157)
    • (2001) Chemical Research in Toxicology , vol.14 , Issue.8 , pp. 1014-1024
    • Regal, K.A.1    Laws, G.M.2    Yuan, C.3    Yost, G.S.4    Skiles, G.L.5
  • 27
    • 80053149190 scopus 로고    scopus 로고
    • Furfuryl alcohol: Mutagenicity and DNA adducts in Salmonella typhimurium strains expressing human sulfotransferase 1A1 and formation of the same adducts in mouse tissues in vivo
    • Monien, B. H., Herrmann, K., Meinl, W. and Glatt, H. R. (2011) Furfuryl alcohol: mutagenicity and DNA adducts in Salmonella typhimurium strains expressing human sulfotransferase 1A1 and formation of the same adducts in mouse tissues in vivo. Carcinogenesis, 32, 1533-1539.
    • (2011) Carcinogenesis , vol.32 , pp. 1533-1539
    • Monien, B.H.1    Herrmann, K.2    Meinl, W.3    Glatt, H.R.4
  • 28
    • 33748750527 scopus 로고    scopus 로고
    • Tissue distribution and ontogeny of sulfotransferase enzymes in mice
    • DOI 10.1093/toxsci/kfl050
    • Alnouti, Y. and Klaassen, C. D. (2006) Tissue distribution and ontogeny of sulfotransferase enzymes in mice. Toxicol. Sci., 93, 242-255. (Pubitemid 44400443)
    • (2006) Toxicological Sciences , vol.93 , Issue.2 , pp. 242-255
    • Alnouti, Y.1    Klaassen, C.D.2
  • 29
    • 0022907909 scopus 로고
    • The metabolic sulfonation and side-chain oxidation of 3'-hydroxyisosafrole in the mouse and its inactivity as a hepatocarcinogen relative to 1'-hydroxysafrole
    • Boberg, E. W., Miller, E. C. and Miller, J. A. (1986) The metabolic sulfonation and side-chain oxidation of 3′-hydroxyisosafrole in the mouse and its inactivity as a hepatocarcinogen relative to 1′-hydroxysafrole. Chem. Biol. Interact., 59, 73-97. (Pubitemid 16030993)
    • (1986) Chemico-Biological Interactions , vol.59 , Issue.1 , pp. 73-97
    • Boberg, E.W.1    Miller, E.C.2    Miller, J.A.3


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