메뉴 건너뛰기




Volumn , Issue , 2009, Pages 329-356

Formation and Reactions of Xenobiotic Quinone Methides in Biology

Author keywords

Alkylphenols BHT and related alkylphenols; Formation and reactions of xenobiotic quinone methides in biology; Methoxyphenols and catechols

Indexed keywords


EID: 84889320965     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470452882.ch10     Document Type: Chapter
Times cited : (9)

References (101)
  • 2
    • 0024662764 scopus 로고
    • Chemical modifications of bio-polymers by quinones and quinone methides
    • Peter,M.G. Chemical modifications of bio-polymers by quinones and quinone methides. Angew. Chem. Int. Ed. 1989, 28, 555-570.
    • (1989) Angew. Chem. Int. Ed. , vol.28 , pp. 555-570
    • Peter, M.G.1
  • 3
    • 0035996571 scopus 로고    scopus 로고
    • The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers
    • Monks, T. J.; Jones, D. C. The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. Curr. Drug Metab. 2002, 3, 425-438.
    • (2002) Curr. Drug Metab. , vol.3 , pp. 425-438
    • Monks, T.J.1    Jones, D.C.2
  • 5
    • 0001466726 scopus 로고
    • The effect of beta-fluorine substituents on the rate and equilibrium-constants for the reactions of alpha-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide
    • Richard, J. P.; Amyes, T. L.; Bei, L.; Stubblefield, V. The effect of beta-fluorine substituents on the rate and equilibrium-constants for the reactions of alpha-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide. J. Am. Chem. Soc. 1990, 112, 9513-9519.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9513-9519
    • Richard, J.P.1    Amyes, T.L.2    Bei, L.3    Stubblefield, V.4
  • 6
    • 0021021388 scopus 로고
    • Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides
    • Hulbert, P. B.; Grover, P. L. Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides. Biochem. Biophys. Res. Commun. 1983, 117, 129-134.
    • (1983) Biochem. Biophys. Res. Commun. , vol.117 , pp. 129-134
    • Hulbert, P.B.1    Grover, P.L.2
  • 7
    • 33748994836 scopus 로고    scopus 로고
    • Bioactivation of selective estrogen receptor modulators (SERMs)
    • Dowers, T. S.; Qin, Z. H.; Thatcher,G. R.; Bolton, J. L. Bioactivation of selective estrogen receptor modulators (SERMs). Chem. Res. Toxicol. 2006, 19, 1125-1137.
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 1125-1137
    • Dowers, T.S.1    Qin, Z.H.2    Thatcher, G.R.3    Bolton, J.L.4
  • 8
    • 0028285123 scopus 로고
    • Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactivation mechanism for the hepatocarcinogen safrole
    • Bolton, J. L.; Acay, N. M.; Vukomanovic, V. Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactivation mechanism for the hepatocarcinogen safrole. Chem. Res. Toxicol. 1994, 7, 443-450.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 443-450
    • Bolton, J.L.1    Acay, N.M.2    Vukomanovic, V.3
  • 9
    • 0029061720 scopus 로고
    • The influence of the para-alkyl substituent on the isomerization of o-quinones to p-quinone methides: potential bioactivation mechanism for catechols
    • Iverson, S. L.; Hu, L. Q.; Vukomanovic, V.; Bolton, J. L. The influence of the para-alkyl substituent on the isomerization of o-quinones to p-quinone methides: potential bioactivation mechanism for catechols. Chem. Res. Toxicol. 1995, 8, 537-544.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 537-544
    • Iverson, S.L.1    Hu, L.Q.2    Vukomanovic, V.3    Bolton, J.L.4
  • 10
    • 38949118229 scopus 로고    scopus 로고
    • Potential mechanisms of estrogen quinone carcinogenesis
    • Bolton, J. L.; Thatcher, G. R. Potential mechanisms of estrogen quinone carcinogenesis. Chem. Res. Toxicol. 2008, 21, 93-101.
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 93-101
    • Bolton, J.L.1    Thatcher, G.R.2
  • 11
    • 0028863679 scopus 로고
    • 4-(Fluoromethyl)phenyl phosphate acts as a mechanism-based inhibitor of calcineurin
    • Born, T. L.; Myers, J. K.;Widlanski, T. S.; Rusnak, F. 4-(Fluoromethyl)phenyl phosphate acts as a mechanism-based inhibitor of calcineurin. J. Biol. Chem. 1995, 270, 25651-25655.
    • (1995) J. Biol. Chem. , vol.270 , pp. 25651-25655
    • Born, T.L.1    Myers, J.K.2    Widlanski, T.S.3    Rusnak, F.4
  • 12
    • 0034647001 scopus 로고    scopus 로고
    • Spontaneous hydrolysis of 4-trifluoromethylphenol to a quinone methide and subsequent protein alkylation
    • Thompson, D. C.; Perera, K.; London, R. Spontaneous hydrolysis of 4-trifluoromethylphenol to a quinone methide and subsequent protein alkylation. Chem.-Biol. Interact. 2000, 126, 1-14.
    • (2000) Chem.-Biol. Interact. , vol.126 , pp. 1-14
    • Thompson, D.C.1    Perera, K.2    London, R.3
  • 13
    • 0017862850 scopus 로고
    • Toxicity of butylated hydroxytoluene in mouse following oral administration
    • Witschi, H.; Lock, S. Toxicity of butylated hydroxytoluene in mouse following oral administration. Toxicology 1978, 9, 137-146.
    • (1978) Toxicology , vol.9 , pp. 137-146
    • Witschi, H.1    Lock, S.2
  • 14
    • 0024560701 scopus 로고
    • Metabolism and pulmonary toxicity of butylated hydroxytoluene (BHT)
    • Witschi, H.; Malkinson, A. M.; Thompson, J. A. Metabolism and pulmonary toxicity of butylated hydroxytoluene (BHT). Pharmacol. Ther. 1989, 42, 89-113.
    • (1989) Pharmacol. Ther. , vol.42 , pp. 89-113
    • Witschi, H.1    Malkinson, A.M.2    Thompson, J.A.3
  • 15
    • 0030745488 scopus 로고    scopus 로고
    • Butylated hydroxytoluene exposure is necessary to induce lung tumors in BALB mice treated with 3-methylcholanthrene
    • Malkinson, A. M.; Koski, K. M.; Evans,W. A.; Festing, M. F. Butylated hydroxytoluene exposure is necessary to induce lung tumors in BALB mice treated with 3-methylcholanthrene. Cancer Res. 1997, 57, 2832-2834.
    • (1997) Cancer Res. , vol.57 , pp. 2832-2834
    • Malkinson, A.M.1    Koski, K.M.2    Evans, W.A.3    Festing, M.F.4
  • 16
    • 0035080008 scopus 로고    scopus 로고
    • Butylated hydroxytoluene (BHT) induction of pulmonary inflammation: a role in tumor promotion
    • Bauer, A. K.; Dwyer-Nield, L. D.; Keil, K.; Koski, K.; Malkinson, A. M. Butylated hydroxytoluene (BHT) induction of pulmonary inflammation: a role in tumor promotion. Exp. Lung Res. 2001, 27, 197-216.
    • (2001) Exp. Lung Res. , vol.27 , pp. 197-216
    • Bauer, A.K.1    Dwyer-Nield, L.D.2    Keil, K.3    Koski, K.4    Malkinson, A.M.5
  • 17
    • 0035499381 scopus 로고    scopus 로고
    • The lung tumor promoter, butylated hydroxytoluene (BHT), causes chronic inflammation in promotion-sensitive BALB/cByJ mice but not in promotion-resistant CXB4 mice
    • Bauer, A. K.; Dwyer-Nield, L. D.; Hankin, J. A.; Murphy, R. C.; Malkinson, A. M. The lung tumor promoter, butylated hydroxytoluene (BHT), causes chronic inflammation in promotion-sensitive BALB/cByJ mice but not in promotion-resistant CXB4 mice. Toxicology 2001, 169, 1-15.
    • (2001) Toxicology , vol.169 , pp. 1-15
    • Bauer, A.K.1    Dwyer-Nield, L.D.2    Hankin, J.A.3    Murphy, R.C.4    Malkinson, A.M.5
  • 18
    • 0026652576 scopus 로고
    • Primary lung tumors in mice: an experimentally manipulable model of human adenocarcinoma
    • Malkinson, A. M. Primary lung tumors in mice: an experimentally manipulable model of human adenocarcinoma. Cancer Res. 1992, 52, 2670s-2676s.
    • (1992) Cancer Res. , vol.52
    • Malkinson, A.M.1
  • 19
    • 0019309778 scopus 로고
    • Effects of drug metabolism inhibitors on butylated hydroxytoluene- induced pulmonary toxicity in mice
    • Kehrer, J. P.; Witschi, H. Effects of drug metabolism inhibitors on butylated hydroxytoluene- induced pulmonary toxicity in mice. Toxicol. Appl. Pharmacol. 1980, 53, 333-342.
    • (1980) Toxicol. Appl. Pharmacol. , vol.53 , pp. 333-342
    • Kehrer, J.P.1    Witschi, H.2
  • 20
    • 0018640331 scopus 로고
    • 2,6-Di-tert-butyl-4-methylene-2,5-cyclohexadienone: a hepatic metabolite of butylated hydroxytoluene in rats
    • Takahashi, O.; Hiraga, K. 2,6-Di-tert-butyl-4-methylene-2,5-cyclohexadienone: a hepatic metabolite of butylated hydroxytoluene in rats. Food Cosmet. Toxicol. 1979, 17, 451-454.
    • (1979) Food Cosmet. Toxicol. , vol.17 , pp. 451-454
    • Takahashi, O.1    Hiraga, K.2
  • 21
    • 0025236999 scopus 로고
    • Formation and reactivity of alternative quinone methides from butylated hydroxytoluene: possible explanation for species-specific pneumotoxicity
    • Bolton, J. L.; Sevestre, H.; Ibe, B. O.; Thompson, J. A. Formation and reactivity of alternative quinone methides from butylated hydroxytoluene: possible explanation for species-specific pneumotoxicity. Chem. Res. Toxicol. 1990, 3, 65-70.
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 65-70
    • Bolton, J.L.1    Sevestre, H.2    Ibe, B.O.3    Thompson, J.A.4
  • 22
    • 0025972135 scopus 로고
    • Oxidation of butylated hydroxytoluene to toxic metabolites: factors influencing hydroxylation and quinone methide formation by hepatic and pulmonary microsomes
    • Bolton, J. L.; Thompson, J. A. Oxidation of butylated hydroxytoluene to toxic metabolites: factors influencing hydroxylation and quinone methide formation by hepatic and pulmonary microsomes. Drug Metab. Dispos. 1991, 19, 467-472.
    • (1991) Drug Metab. Dispos. , vol.19 , pp. 467-472
    • Bolton, J.L.1    Thompson, J.A.2
  • 23
    • 0020522963 scopus 로고
    • Isotope effects on the metabolism and pulmonary toxicity of butylated hydroxytoluene in mice by deuteration of the 4-methyl group
    • Mizutani, T.;Yamamoto, K.; Tajima, K. Isotope effects on the metabolism and pulmonary toxicity of butylated hydroxytoluene in mice by deuteration of the 4-methyl group. Toxicol. Appl. Pharm. 1983, 69, 283-290.
    • (1983) Toxicol. Appl. Pharm. , vol.69 , pp. 283-290
    • Mizutani, T.1    Yamamoto, K.2    Tajima, K.3
  • 24
    • 0029898605 scopus 로고    scopus 로고
    • Studies on the mechanism of hepatotoxicity of 4-methylphenol(p-cresol)-effects of deuterium labeling and ring substitution
    • Thompson, D. C.; Perera, K.; London, R. Studies on the mechanism of hepatotoxicity of 4-methylphenol(p-cresol)-effects of deuterium labeling and ring substitution. Chem.-Biol. Interact. 1996, 101, 1-11.
    • (1996) Chem.-Biol. Interact. , vol.101 , pp. 1-11
    • Thompson, D.C.1    Perera, K.2    London, R.3
  • 25
    • 0026099878 scopus 로고
    • Free radical-derived quinone methide mediates skin tumor promotion by butylated hydroxytoluene hydroperoxide: expanded role for electrophiles in multistage carcinogenesis
    • Guyton, K. Z.; Bhan, P.; Kuppusamy, P.; Zweier, J. L.; Trush, M. A.; Kensler, T.W. Free radical-derived quinone methide mediates skin tumor promotion by butylated hydroxytoluene hydroperoxide: expanded role for electrophiles in multistage carcinogenesis. Proc. Natl. Acad. Sci. USA 1991, 88, 946-950.
    • (1991) Proc. Natl. Acad. Sci. USA , vol.88 , pp. 946-950
    • Guyton, K.Z.1    Bhan, P.2    Kuppusamy, P.3    Zweier, J.L.4    Trush, M.A.5    Kensler, T.W.6
  • 26
    • 50549179309 scopus 로고
    • Preparation and behavior of simple quinone methides
    • Filar, L. J.; Winstein, S. Preparation and behavior of simple quinone methides. Tetrahedron Lett. 1960, 25, 9-16.
    • (1960) Tetrahedron Lett. , vol.25 , pp. 9-16
    • Filar, L.J.1    Winstein, S.2
  • 27
    • 0020067060 scopus 로고
    • Pulmonary toxicity of butylated hydroxytoluene and related alkylphenols: structural requirements for toxic potency in mice
    • Mizutani, T.; Ishida, I.; Yamamoto, K.; Tajima, K. Pulmonary toxicity of butylated hydroxytoluene and related alkylphenols: structural requirements for toxic potency in mice. Toxicol. Appl. Pharmacol. 1982, 62, 273-281.
    • (1982) Toxicol. Appl. Pharmacol. , vol.62 , pp. 273-281
    • Mizutani, T.1    Ishida, I.2    Yamamoto, K.3    Tajima, K.4
  • 28
    • 0027092534 scopus 로고
    • The enzymatic formation and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes
    • Bolton, J. L.; Valerio, L. G. J.; Thompson, J. A. The enzymatic formation and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes. Chem. Res. Toxicol. 1992, 5, 816-822.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 816-822
    • Bolton, J.L.1    Valerio, L.G.J.2    Thompson, J.A.3
  • 29
    • 0035819930 scopus 로고    scopus 로고
    • Studies using structural analogs and inbred strain differences to support a role for quinone methide metabolites of butylated hydroxytoluene (BHT) in mouse lung tumor promotion
    • Thompson, J. A.; Carlson, T. J.; Sun, Y.; Dwyer-Nield, L. D.; Malkinson, A. M. Studies using structural analogs and inbred strain differences to support a role for quinone methide metabolites of butylated hydroxytoluene (BHT) in mouse lung tumor promotion. Toxicology 2001, 160, 197-205.
    • (2001) Toxicology , vol.160 , pp. 197-205
    • Thompson, J.A.1    Carlson, T.J.2    Sun, Y.3    Dwyer-Nield, L.D.4    Malkinson, A.M.5
  • 30
    • 0037422402 scopus 로고    scopus 로고
    • Responses of tumorigenic and non-tumorigenic mouse lung epithelial cell lines to electrophilic metabolites of the tumor promoter butylated hydroxytoluene
    • Sun,Y.; Dwyer-Nield, L. D.; Malkinson, A. M.; Zhang,Y. L.; Thompson, J. A. Responses of tumorigenic and non-tumorigenic mouse lung epithelial cell lines to electrophilic metabolites of the tumor promoter butylated hydroxytoluene. Chem.-Biol. Interact. 2003, 145, 41-51.
    • (2003) Chem.-Biol. Interact. , vol.145 , pp. 41-51
    • Sun, Y.1    Dwyer-Nield, L.D.2    Malkinson, A.M.3    Zhang, Y.L.4    Thompson, J.A.5
  • 31
    • 0036667463 scopus 로고    scopus 로고
    • Lung toxicity and tumor promotion by hydroxylated derivatives of 2,6-di-tert-butyl-4-methylphenol (BHT) and 2-tert-butyl-4-methyl-6-iso-propylphenol: correlation with quinone methide reactivity
    • Kupfer, R.; Dwyer-Nield, L. D.; Malkinson, A. M.; Thompson, J. A. Lung toxicity and tumor promotion by hydroxylated derivatives of 2,6-di-tert-butyl-4-methylphenol (BHT) and 2-tert-butyl-4-methyl-6-iso-propylphenol: correlation with quinone methide reactivity. Chem. Res. Toxicol. 2002, 15, 1106-1112.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1106-1112
    • Kupfer, R.1    Dwyer-Nield, L.D.2    Malkinson, A.M.3    Thompson, J.A.4
  • 32
    • 0028179722 scopus 로고
    • Quinone methide mediates in vitro induction of ornithine decarboxylase by the tumor promoter butylated hydroxytoluene hydroperoxide
    • Guyton, K.; Dolan, P. M.; Kensler, T.W. Quinone methide mediates in vitro induction of ornithine decarboxylase by the tumor promoter butylated hydroxytoluene hydroperoxide. Carcinogenesis 1994, 15, 817-821.
    • (1994) Carcinogenesis , vol.15 , pp. 817-821
    • Guyton, K.1    Dolan, P.M.2    Kensler, T.W.3
  • 33
    • 0029945349 scopus 로고    scopus 로고
    • Mitogen-activated protein kinase (MAPK) activation by butylated hydroxytoluene hydroperoxide: implications for cellular survival and tumor promotion
    • Guyton, K. Z.; Gorospe, M.; Kensler, T. W.; Holbrook, N. J. Mitogen-activated protein kinase (MAPK) activation by butylated hydroxytoluene hydroperoxide: implications for cellular survival and tumor promotion. Cancer Res. 1996, 56, 3480-3485.
    • (1996) Cancer Res. , vol.56 , pp. 3480-3485
    • Guyton, K.Z.1    Gorospe, M.2    Kensler, T.W.3    Holbrook, N.J.4
  • 34
    • 0031755839 scopus 로고    scopus 로고
    • Transcriptional activity of quinone methides derived from the tumor promoter butylated hydroxytoluene in HepG2 cells
    • Desjardins, J. P.; Beard, S. E.; Mapoles, J. E.; Gee, P.; Thompson, J. A. Transcriptional activity of quinone methides derived from the tumor promoter butylated hydroxytoluene in HepG2 cells. Cancer Lett. 1998, 131, 201-207.
    • (1998) Cancer Lett. , vol.131 , pp. 201-207
    • Desjardins, J.P.1    Beard, S.E.2    Mapoles, J.E.3    Gee, P.4    Thompson, J.A.5
  • 35
    • 0031434490 scopus 로고    scopus 로고
    • Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models
    • Bolton, J. L.; Turnipseed, S. B.; Thompson, J. A. Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models. Chem.-Biol. Interact. 1997, 107, 185-200.
    • (1997) Chem.-Biol. Interact. , vol.107 , pp. 185-200
    • Bolton, J.L.1    Turnipseed, S.B.2    Thompson, J.A.3
  • 36
    • 0027422011 scopus 로고
    • Role of quinone methide in the in vitro toxicity of the skin tumor promoter butylated hydroxytoluene hydroperoxide
    • Guyton, K. Z.; Thompson, J. A.; Kensler, T. W. Role of quinone methide in the in vitro toxicity of the skin tumor promoter butylated hydroxytoluene hydroperoxide. Chem. Res. Toxicol. 1993, 6, 731-738.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 731-738
    • Guyton, K.Z.1    Thompson, J.A.2    Kensler, T.W.3
  • 37
    • 0027703513 scopus 로고
    • Reaction of quinone methides with proteins: analysis of myoglobin adduct formation by electrospray mass spectrometry
    • Bolton, J. L.; Le Blanc, J. C.Y.; Siu, K.W. M. Reaction of quinone methides with proteins: analysis of myoglobin adduct formation by electrospray mass spectrometry. Biol. Mass Spectrom. 1993, 22, 666-668.
    • (1993) Biol. Mass Spectrom. , vol.22 , pp. 666-668
    • Bolton, J.L.1    Le Blanc, J.C.Y.2    Siu, K.W.M.3
  • 38
    • 0000101446 scopus 로고    scopus 로고
    • Covalent modification of proteins and peptides by the quinone methide from 2-tert-butyl-4,6-dimethylphenol: selectivity and reactivity with respect to competitive hydration
    • McCracken, P.G.; Bolton, J. L.; Thatcher, G. R. J. Covalent modification of proteins and peptides by the quinone methide from 2-tert-butyl-4,6-dimethylphenol: selectivity and reactivity with respect to competitive hydration. J. Org. Chem. 1997, 62, 1820-1825.
    • (1997) J. Org. Chem. , vol.62 , pp. 1820-1825
    • McCracken, P.G.1    Bolton, J.L.2    Thatcher, G.R.J.3
  • 39
    • 27144456873 scopus 로고    scopus 로고
    • Immunochemical and proteomic analysis of covalent adducts formed by quinone methide tumor promoters in mouse lung epithelial cell lines
    • Meier, B.W.; Gomez, J. D.; Zhou, A.; Thompson, J. A. Immunochemical and proteomic analysis of covalent adducts formed by quinone methide tumor promoters in mouse lung epithelial cell lines. Chem. Res. Toxicol. 2005, 18, 1575-1585.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1575-1585
    • Meier, B.W.1    Gomez, J.D.2    Zhou, A.3    Thompson, J.A.4
  • 40
    • 33947096960 scopus 로고    scopus 로고
    • Mechanistic basis for inflammation and tumor promotion in lungs of 2,6-di-tert-butyl-4-methylphenol-treated mice: electrophilic metabolites alkylate and inactivate antioxidant enzymes
    • Meier, B. W.; Gomez, J. D.; Kirichenko, O. V.; Thompson, J. A. Mechanistic basis for inflammation and tumor promotion in lungs of 2,6-di-tert-butyl-4-methylphenol-treated mice: electrophilic metabolites alkylate and inactivate antioxidant enzymes. Chem. Res. Toxicol. 2007, 20, 199-207.
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 199-207
    • Meier, B.W.1    Gomez, J.D.2    Kirichenko, O.V.3    Thompson, J.A.4
  • 41
    • 0029850686 scopus 로고    scopus 로고
    • Alkylation of 20-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol
    • Lewis, M. A.; Yoerg, D. G.; Bolton, J. L.; Thompson, J. A. Alkylation of 20-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol. Chem. Res. Toxicol. 1996, 9, 1368-1374.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1368-1374
    • Lewis, M.A.1    Yoerg, D.G.2    Bolton, J.L.3    Thompson, J.A.4
  • 42
    • 0030821682 scopus 로고    scopus 로고
    • Immunochemical visualization and identification of rat liver proteins adducted by 2,6-di-tert-butyl-4-methylphenol (BHT)
    • Reed, M.; Thompson, D. C. Immunochemical visualization and identification of rat liver proteins adducted by 2,6-di-tert-butyl-4-methylphenol (BHT). Chem. Res. Toxicol. 1997, 10, 1109-1117.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1109-1117
    • Reed, M.1    Thompson, D.C.2
  • 43
    • 10844243976 scopus 로고    scopus 로고
    • Inhibition of glutathione S-transferase P1-1 in mouse lung epithelial cells by the tumor promoter 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone (BHT-quinone methide): protein adducts investigated by electrospray mass spectrometry
    • Lemercier, J. N.; Meier, B. W.; Gomez, J. D.; Thompson, J. A. Inhibition of glutathione S-transferase P1-1 in mouse lung epithelial cells by the tumor promoter 2,6-di-tert-butyl-4-methylene-2,5-cyclohexadienone (BHT-quinone methide): protein adducts investigated by electrospray mass spectrometry. Chem. Res. Toxicol. 2004, 17, 1675-1683.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 1675-1683
    • Lemercier, J.N.1    Meier, B.W.2    Gomez, J.D.3    Thompson, J.A.4
  • 45
    • 0035847194 scopus 로고    scopus 로고
    • Alkylation of amino acids and glutathione in water by o-quinone methide. Reactivity and selectivity
    • Modica, E.; Zanaletti, R.; Freccero, M.; Mella, M. Alkylation of amino acids and glutathione in water by o-quinone methide. Reactivity and selectivity. J. Org. Chem. 2001, 66, 41-52.
    • (2001) J. Org. Chem. , vol.66 , pp. 41-52
    • Modica, E.1    Zanaletti, R.2    Freccero, M.3    Mella, M.4
  • 46
    • 17744394481 scopus 로고    scopus 로고
    • Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission
    • Kassahun, K.; Pearson, P. G.; Tang, W.; McIntosh, I.; Leung, K.; Elmore, C.; Dean, D.; Wang, R.; Doss, G.; Baillie, T. A. Studies on the metabolism of troglitazone to reactive intermediates in vitro and in vivo. Evidence for novel biotransformation pathways involving quinone methide formation and thiazolidinedione ring scission. Chem. Res. Toxicol. 2001, 14, 62-70.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 62-70
    • Kassahun, K.1    Pearson, P.G.2    Tang, W.3    McIntosh, I.4    Leung, K.5    Elmore, C.6    Dean, D.7    Wang, R.8    Doss, G.9    Baillie, T.A.10
  • 47
    • 84889281474 scopus 로고
    • IARC Monographs; International Agency for Research on Cancer: Lyon, France
    • IARC Monographs; International Agency for Research on Cancer: Lyon, France, 1985; Vol. 36, pp 75-97.
    • (1985) , vol.36 , pp. 75-97
  • 48
    • 0026068803 scopus 로고
    • Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes
    • Thompson, D. C.; Constantin, T. D.; Moldeus, P. Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes. Chem.-Biol. Interact. 1991, 77, 137-147.
    • (1991) Chem.-Biol. Interact. , vol.77 , pp. 137-147
    • Thompson, D.C.1    Constantin, T.D.2    Moldeus, P.3
  • 49
    • 0031878397 scopus 로고    scopus 로고
    • Oxidation of eugenol to form DNA adducts and 8-hydroxy-20-deoxyguanosine: role of quinone methide derivative in DNA adduct formation
    • Bodell, W. J.; Ye, Q.; Pathak, D. N.; Pongracz, K. Oxidation of eugenol to form DNA adducts and 8-hydroxy-20-deoxyguanosine: role of quinone methide derivative in DNA adduct formation. Carcinogenesis 1998, 19, 437-443.
    • (1998) Carcinogenesis , vol.19 , pp. 437-443
    • Bodell, W.J.1    Ye, Q.2    Pathak, D.N.3    Pongracz, K.4
  • 50
    • 0028899066 scopus 로고
    • The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended p-conjugation dramatically stabilizes the quinone methide formed from eugenol
    • Bolton, J. L.; Comeau, E.; Vukomanovic, V. The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended p-conjugation dramatically stabilizes the quinone methide formed from eugenol. Chem.-Biol. Interact. 1995, 95, 279-290.
    • (1995) Chem.-Biol. Interact. , vol.95 , pp. 279-290
    • Bolton, J.L.1    Comeau, E.2    Vukomanovic, V.3
  • 51
    • 0026403946 scopus 로고
    • Hepatotoxicity of eugenol and related compounds in mice depleted of glutathione: structural requirements for toxic potency
    • Mizutani, T.; Satoh, K.; Nomura, H. Hepatotoxicity of eugenol and related compounds in mice depleted of glutathione: structural requirements for toxic potency. Res. Commun. Chem. Pathol. Pharmacol. 1991, 73, 87-95.
    • (1991) Res. Commun. Chem. Pathol. Pharmacol. , vol.73 , pp. 87-95
    • Mizutani, T.1    Satoh, K.2    Nomura, H.3
  • 52
    • 0026071584 scopus 로고
    • Hepatotoxicity of eugenol in mice depleted of glutathione by treatment with DL-buthionine sulfoximine
    • Mizutani, T.; Satoh, K.; Nomura, H.; Nakanishi, K. Hepatotoxicity of eugenol in mice depleted of glutathione by treatment with DL-buthionine sulfoximine. Res. Commun. Chem. Pathol. Pharmacol. 1991, 71, 219-230.
    • (1991) Res. Commun. Chem. Pathol. Pharmacol. , vol.71 , pp. 219-230
    • Mizutani, T.1    Satoh, K.2    Nomura, H.3    Nakanishi, K.4
  • 53
    • 0028930981 scopus 로고
    • O-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices
    • Thompson, D. C.; Perera, K.; Krol, E. S.; Bolton, J. L. O-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. Chem. Res. Toxicol. 1995, 8, 323-327.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 323-327
    • Thompson, D.C.1    Perera, K.2    Krol, E.S.3    Bolton, J.L.4
  • 54
    • 0000359187 scopus 로고
    • Betel-Quid and Areca Nut Chewing (IARC Monograph)
    • International Agency for Research on Cancer: Lyon, France
    • Betel-Quid and Areca Nut Chewing (IARC Monograph); International Agency for Research on Cancer: Lyon, France, 1985; Vol. 37, pp 141-291.
    • (1985) , vol.37 , pp. 141-291
  • 55
    • 0017365837 scopus 로고
    • Absorption, metabolism and excretion of safrole in the rat and man
    • Benedetti, M. S.; Malnoe, A.; Broillet, A. L. Absorption, metabolism and excretion of safrole in the rat and man. Toxicology 1977, 7, 69-83.
    • (1977) Toxicology , vol.7 , pp. 69-83
    • Benedetti, M.S.1    Malnoe, A.2    Broillet, A.L.3
  • 56
    • 9644268948 scopus 로고    scopus 로고
    • Copper-mediated oxidative DNA damage induced by eugenol: possible involvement of O-demethylation
    • Sakano, K.; Inagaki, Y.; Oikawa, S.; Hiraku, Y.; Kawanishi, S. Copper-mediated oxidative DNA damage induced by eugenol: possible involvement of O-demethylation. Mutat. Res. 2004, 565, 35-44.
    • (2004) Mutat. Res. , vol.565 , pp. 35-44
    • Sakano, K.1    Inagaki, Y.2    Oikawa, S.3    Hiraku, Y.4    Kawanishi, S.5
  • 57
    • 0030693983 scopus 로고    scopus 로고
    • The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkylcatechol-induced toxicity in human melanoma cells
    • Bolton, J. L.; Pisha, E.; Shen, L.; Krol, E. S.; Iverson, S. L.; Huang, Z.; van Breemen, R. B.; Pezzuto, J. M. The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkylcatechol-induced toxicity in human melanoma cells. Chem.-Biol. Interact. 1997, 106, 133-148.
    • (1997) Chem.-Biol. Interact. , vol.106 , pp. 133-148
    • Bolton, J.L.1    Pisha, E.2    Shen, L.3    Krol, E.S.4    Iverson, S.L.5    Huang, Z.6    Van Breemen, R.B.7    Pezzuto, J.M.8
  • 58
    • 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 1994, 5, 439-442.
    • (1994) Carcinogenesis , vol.5 , pp. 439-442
    • Potter, G.A.1    McCague, R.2    Jarman, M.3
  • 59
    • 0033958868 scopus 로고    scopus 로고
    • 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremifene are metabolized to unusually stable quinone methides
    • Fan, P. W.; Zhang, F.; Bolton, J. L. 4-Hydroxylated metabolites of the antiestrogens tamoxifen and toremifene are metabolized to unusually stable quinone methides. Chem. Res. Toxicol. 2000, 13, 45-52.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 45-52
    • Fan, P.W.1    Zhang, F.2    Bolton, J.L.3
  • 60
    • 0028899066 scopus 로고
    • The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended piconjugation dramatically stabilizes the quinone methide formed from eugenol
    • Bolton, J. L.; Comeau, E.; Vukomanovic, V. The influence of 4-alkyl substituents on the formation and reactivity of 2-methoxy-quinone methides: evidence that extended piconjugation dramatically stabilizes the quinone methide formed from eugenol. Chem.-Biol. Interact. 1995, 95, 279-290.
    • (1995) Chem.-Biol. Interact. , vol.95 , pp. 279-290
    • Bolton, J.L.1    Comeau, E.2    Vukomanovic, V.3
  • 61
    • 0037118685 scopus 로고    scopus 로고
    • DNA adducts formed from 4-hydroxytamoxifen are more mutagenic than those formed by alpha-acetoxytamoxifen in a shuttle vector target gene replicated in human Ad293 cells
    • McLuckie, K. I.; Routledge, M. N.; Brown, K.; Gaskell, M.; Farmer, P. B.; Roberts, G. C.; Martin, E. A. DNA adducts formed from 4-hydroxytamoxifen are more mutagenic than those formed by alpha-acetoxytamoxifen in a shuttle vector target gene replicated in human Ad293 cells. Biochemistry 2002, 41, 8899-8906.
    • (2002) Biochemistry , vol.41 , pp. 8899-8906
    • McLuckie, K.I.1    Routledge, M.N.2    Brown, K.3    Gaskell, M.4    Farmer, P.B.5    Roberts, G.C.6    Martin, E.A.7
  • 62
    • 0033065364 scopus 로고    scopus 로고
    • Comparison of the DNA adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo
    • Beland, F. A.; McDaniel, L. P.; Marques, M.M. Comparison of the DNA adducts formed by tamoxifen and 4-hydroxytamoxifen in vivo. Carcinogenesis 1999, 20, 471-477.
    • (1999) Carcinogenesis , vol.20 , pp. 471-477
    • Beland, F.A.1    McDaniel, L.P.2    Marques, M.M.3
  • 63
    • 0031416520 scopus 로고    scopus 로고
    • Identification of tamoxifen-DNA adducts formed by 4-hydroxytamoxifen quinone methide
    • Marques, M. M.; Beland, F. A. Identification of tamoxifen-DNA adducts formed by 4-hydroxytamoxifen quinone methide. Carcinogenesis 1997, 18, 1949-1954.
    • (1997) Carcinogenesis , vol.18 , pp. 1949-1954
    • Marques, M.M.1    Beland, F.A.2
  • 64
    • 13844264457 scopus 로고    scopus 로고
    • Bioactivation of the selective estrogen receptor modulator acolbifene to quinone methides
    • Liu, J.; Liu, H.; van Breemen, R. B.; Thatcher, G. R.; Bolton, J. L. Bioactivation of the selective estrogen receptor modulator acolbifene to quinone methides. Chem. Res. Toxicol. 2005, 18, 174-182.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 174-182
    • Liu, J.1    Liu, H.2    Van Breemen, R.B.3    Thatcher, G.R.4    Bolton, J.L.5
  • 65
    • 30944469849 scopus 로고    scopus 로고
    • Estrogen carcinogenesis in breast cancer
    • Yager, J. D.; Davidson, N. E. Estrogen carcinogenesis in breast cancer. N. Engl. J. Med. 2006, 354, 270-282.
    • (2006) N. Engl. J. Med. , vol.354 , pp. 270-282
    • Yager, J.D.1    Davidson, N.E.2
  • 66
    • 0033649417 scopus 로고    scopus 로고
    • Developmental, cellular, and molecular basis of human breast cancer
    • Russo, J.; Hu,Y. F.;Yang, X.; Russo, I. H. Developmental, cellular, and molecular basis of human breast cancer. J. Natl. Cancer Inst. Monogr. 2000, 27, 17-37.
    • (2000) J. Natl. Cancer Inst. Monogr. , vol.27 , pp. 17-37
    • Russo, J.1    Hu, Y.F.2    Yang, X.3    Russo, I.H.4
  • 69
    • 33750975372 scopus 로고    scopus 로고
    • The role of estrogen in the initiation of breast cancer
    • Russo, J.; Russo, I. H. The role of estrogen in the initiation of breast cancer. J. Steroid Biochem. Mol. Biol. 2006, 102, 89-96.
    • (2006) J. Steroid Biochem. Mol. Biol. , vol.102 , pp. 89-96
    • Russo, J.1    Russo, I.H.2
  • 72
    • 0029036480 scopus 로고
    • Hormones and mammary carcinogenesis in mice, rats, and humans: a unifying hypothesis
    • Nandi, S.; Guzman, R. C.; Yang, J. Hormones and mammary carcinogenesis in mice, rats, and humans: a unifying hypothesis. Proc. Natl. Acad. Sci. USA 1995, 92, 3650-3657.
    • (1995) Proc. Natl. Acad. Sci. USA , vol.92 , pp. 3650-3657
    • Nandi, S.1    Guzman, R.C.2    Yang, J.3
  • 74
    • 0029924611 scopus 로고    scopus 로고
    • Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes
    • Iverson, S. L.; Shen, L.; Anlar, N.; Bolton, J. L. Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes. Chem. Res. Toxicol. 1996, 9, 492-499.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 492-499
    • Iverson, S.L.1    Shen, L.2    Anlar, N.3    Bolton, J.L.4
  • 75
    • 0029949969 scopus 로고    scopus 로고
    • P-Quinone methides are the major decomposition products of catechol estrogen o-quinones
    • Bolton, J. L.; Shen, L. p-Quinone methides are the major decomposition products of catechol estrogen o-quinones. Carcinogenesis 1996, 17, 925-929.
    • (1996) Carcinogenesis , vol.17 , pp. 925-929
    • Bolton, J.L.1    Shen, L.2
  • 76
    • 0029680465 scopus 로고    scopus 로고
    • Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides
    • Stack, D. E.; Byun, J.; Gross, M. L.; Rogan, E. G.; Cavalieri, E. L. Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides. Chem. Res. Toxicol. 1996, 9, 851-859.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 851-859
    • Stack, D.E.1    Byun, J.2    Gross, M.L.3    Rogan, E.G.4    Cavalieri, E.L.5
  • 77
    • 3042794987 scopus 로고    scopus 로고
    • Quinoids formed from estrogens and antiestrogens
    • Bolton, J. L.; Yu, L.; Thatcher, G. R. Quinoids formed from estrogens and antiestrogens. Methods Enzymol. 2004, 378, 110-123.
    • (2004) Methods Enzymol. , vol.378 , pp. 110-123
    • Bolton, J.L.1    Yu, L.2    Thatcher, G.R.3
  • 78
    • 25144479866 scopus 로고
    • Impact of metabolism on the safety of estrogen therapy
    • Prokai-Tatrai, K.; Prokai, L. Impact of metabolism on the safety of estrogen therapy. Ann. N.Y. Acad. Sci. 1052, 2005, 243-257.
    • (1052) Ann. N.Y. Acad. Sci. , vol.2005 , pp. 243-257
    • Prokai-Tatrai, K.1    Prokai, L.2
  • 79
    • 0034473063 scopus 로고    scopus 로고
    • Role of DNA adducts in hormonal carcinogenesis
    • Liehr, J. G. Role of DNA adducts in hormonal carcinogenesis. Regul. Toxicol. Pharmacol. 2000, 32, 276-282.
    • (2000) Regul. Toxicol. Pharmacol. , vol.32 , pp. 276-282
    • Liehr, J.G.1
  • 80
    • 3042632995 scopus 로고    scopus 로고
    • Genotoxicity of steroidal estrogens
    • Russo, J.; Russo, I. H. Genotoxicity of steroidal estrogens. Trends Endocrinol. Metab. 2004, 15, 211-214.
    • (2004) Trends Endocrinol. Metab. , vol.15 , pp. 211-214
    • Russo, J.1    Russo, I.H.2
  • 84
    • 33947151051 scopus 로고    scopus 로고
    • Formation of depurinating N3-adenine and N7-guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol
    • Saeed, M.; Rogan, E.; Fernandez, S. V.; Sheriff, F.; Russo, J.; Cavalieri, E. Formation of depurinating N3-adenine and N7-guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol. Int. J. Cancer 2007, 120, 1821-1824.
    • (2007) Int. J. Cancer , vol.120 , pp. 1821-1824
    • Saeed, M.1    Rogan, E.2    Fernandez, S.V.3    Sheriff, F.4    Russo, J.5    Cavalieri, E.6
  • 85
    • 31844450313 scopus 로고    scopus 로고
    • The greater reactivity of estradiol-3,4-quinone vs. estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity
    • Zahid, M.; Kohli, E.; Saeed, M.; Rogan, E.; Cavalieri, E. The greater reactivity of estradiol-3,4-quinone vs. estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity. Chem. Res. Toxicol. 2006, 19, 164-172.
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 164-172
    • Zahid, M.1    Kohli, E.2    Saeed, M.3    Rogan, E.4    Cavalieri, E.5
  • 86
    • 0037975592 scopus 로고    scopus 로고
    • Investigation of the regio- and stereoselectivity of deoxyguanosine linkage to deuterated 2-hydroxyestradiol by using liquid chromatography/ESI-ion trap mass spectrometry
    • Debrauwer, L.; Rathahao, E.; Jouanin, I.; Paris, A.; Clodic, G.; Molines, H.; Convert, O.; Fournier, F.; Tabet, J. C. Investigation of the regio- and stereoselectivity of deoxyguanosine linkage to deuterated 2-hydroxyestradiol by using liquid chromatography/ESI-ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2003, 14, 364-372.
    • (2003) J. Am. Soc. Mass Spectrom. , vol.14 , pp. 364-372
    • Debrauwer, L.1    Rathahao, E.2    Jouanin, I.3    Paris, A.4    Clodic, G.5    Molines, H.6    Convert, O.7    Fournier, F.8    Tabet, J.C.9
  • 87
    • 0035830448 scopus 로고    scopus 로고
    • Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells
    • Terashima, I.; Suzuki, N.; Shibutani, S. Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells. Biochemistry 2001, 40, 166-172.
    • (2001) Biochemistry , vol.40 , pp. 166-172
    • Terashima, I.1    Suzuki, N.2    Shibutani, S.3
  • 88
    • 0029766576 scopus 로고    scopus 로고
    • Estrogen-induced cell transformation and DNA adduct formation in cultured Syrian hamster embryo cells
    • Hayashi, N.; Hasegawa, K.; Barrett, J. C.; Tsutsui, T. Estrogen-induced cell transformation and DNA adduct formation in cultured Syrian hamster embryo cells. Mol. Carcinog. 1996, 16, 149-156.
    • (1996) Mol. Carcinog. , vol.16 , pp. 149-156
    • Hayashi, N.1    Hasegawa, K.2    Barrett, J.C.3    Tsutsui, T.4
  • 89
    • 0037487092 scopus 로고    scopus 로고
    • Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry
    • Embrechts, J.; Lemiere, F.; Dongen, W. V.; Esmans, E. L.; Buytaert, P.; van Marck, E.; Kockx, M.; Makar, A. Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 2003, 14, 482-491.
    • (2003) J. Am. Soc. Mass Spectrom. , vol.14 , pp. 482-491
    • Embrechts, J.1    Lemiere, F.2    Dongen, W.V.3    Esmans, E.L.4    Buytaert, P.5    Van Marck, E.6    Kockx, M.7    Makar, A.8
  • 91
    • 0018079525 scopus 로고
    • Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium
    • MacGregor, J. T.; Jurd, L. Mutagenicity of plant flavonoids: structural requirements for mutagenic activity in Salmonella typhimurium. Mutat. Res. 1978, 54, 297-309.
    • (1978) Mutat. Res. , vol.54 , pp. 297-309
    • MacGregor, J.T.1    Jurd, L.2
  • 92
    • 0018854928 scopus 로고
    • A review of the genetic effects of naturally occurring flavonoids, anthraquinolines and related compounds
    • Brown, J. P. A review of the genetic effects of naturally occurring flavonoids, anthraquinolines and related compounds. Mutat. Res. 1980, 75, 243-277.
    • (1980) Mutat. Res. , vol.75 , pp. 243-277
    • Brown, J.P.1
  • 94
    • 0038730962 scopus 로고    scopus 로고
    • Evidence of covalent binding of the dietary flavonoid quercetin to DNA and protein in human intestinal and hepatic cells
    • Walle, T.; Vincent, T. S.; Walle, U. K. Evidence of covalent binding of the dietary flavonoid quercetin to DNA and protein in human intestinal and hepatic cells. Biochem. Pharmacol. 2003, 65, 1603-1610.
    • (2003) Biochem. Pharmacol. , vol.65 , pp. 1603-1610
    • Walle, T.1    Vincent, T.S.2    Walle, U.K.3
  • 96
    • 13844269367 scopus 로고    scopus 로고
    • Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 40-fluoro substitution prevents quinoid formation
    • Liu, H.; Liu, J.; van Breemen, R. B.; Thatcher, G. R.; Bolton, J. L. Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 40-fluoro substitution prevents quinoid formation. Chem. Res. Toxicol. 2005, 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
  • 99
    • 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.; Rock, D. A. Time-dependent inactivation of P450 3A4 by raloxifene: identification of Cys239 as the site of apoprotein alkylation. Chem. Res. Toxicol. 2007, 20, 954-964.
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 954-964
    • Baer, B.R.1    Wienkers, L.C.2    Rock, D.A.3
  • 100
    • 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.; Thatcher, G. R. Analysis of protein covalent modification by xenobiotics using a covert oxidatively activated tag: raloxifene proof-of-principle study. Chem. Res. Toxicol. 2005, 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
  • 101
    • 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.; Bolton, J. L. Uterine peroxidase-catalyzed formation of diquinone methides from the selective estrogen receptor modulators raloxifene and desmethylated arzoxifene. Chem. Res. Toxicol. 2007, 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.