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Volumn 9, Issue 4, 1996, Pages 713-721

Immunochemical detection of covalently modified protein adducts in livers of rats treated with methyleugenol

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIMETHOXYCINNAMIC ACID; EUGENOL; FLAVORING AGENT; POLYCLONAL ANTIBODY; SERUM ALBUMIN; SODIUM CARBONATE;

EID: 0029897470     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950211v     Document Type: Article
Times cited : (37)

References (32)
  • 1
    • 0012092005 scopus 로고
    • The metabolic activation and carcinogenicity of alkenylbenzenes that occur naturally in many spices
    • Miller, J. A., Miller, E. C., and Phillips, D. H. (1982) The metabolic activation and carcinogenicity of alkenylbenzenes that occur naturally in many spices. Carcinog. Mutagens Environ. 1, 83-97.
    • (1982) Carcinog. Mutagens Environ. , vol.1 , pp. 83-97
    • Miller, J.A.1    Miller, E.C.2    Phillips, D.H.3
  • 2
    • 0020692513 scopus 로고
    • Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring 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 synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res. 43, 1124-1134.
    • (1983) Cancer Res. , vol.43 , pp. 1124-1134
    • Miller, E.C.1    Swanson, A.B.2    Phillips, D.H.3    Fletcher, T.L.4    Liem, A.5    Miller, J.A.6
  • 5
    • 0019798592 scopus 로고
    • The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes
    • Swanson, A. B., Miller, E. C., and Miller, J. A. (1981) The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes. Biochim. Biophys. Acta 673, 504-515.
    • (1981) Biochim. Biophys. Acta , vol.673 , pp. 504-515
    • Swanson, A.B.1    Miller, E.C.2    Miller, J.A.3
  • 6
    • 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.
    • (1983) Cancer Res. , vol.43 , pp. 5163-5173
    • Boberg, E.W.1    Miller, E.C.2    Miller, J.A.3    Poland, A.4    Liem, A.5
  • 7
    • 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.
    • (1981) Cancer Res. , vol.41 , pp. 176-186
    • Phillips, D.H.1    Miller, J.A.2    Miller, E.C.3    Adams, B.4
  • 8
    • 0019395284 scopus 로고
    • N2 atom of guanine and N6 atom of adenine residues as sites for covalent binding of metabolically activated 1′-hydroxysafrole to mouse liver DNA in vivo
    • Phillips, D. H., Miller, J. A., Miller, E. C., and Adams, B. (1981) N2 atom of guanine and N6 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
  • 9
    • 0017194810 scopus 로고
    • The metabolic activation of the carcinogen 1′-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens
    • Wislocki, P. G., Borchert, P., Miller, J. A., and Miller, E. C. (1976) The metabolic activation of the carcinogen 1′-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens. Cancer Res. 36, 1686-1695.
    • (1976) Cancer Res. , vol.36 , pp. 1686-1695
    • Wislocki, P.G.1    Borchert, P.2    Miller, J.A.3    Miller, E.C.4
  • 10
    • 0017405097 scopus 로고
    • Carcinogenic and mutagenic activities of safrole, 1′-hydroxysafrole and some known or possible metabolites
    • Wislocki, P. G., Miller, E. C., Miller, J. A., McCoy, E. C., and Rosenkranz, H. S. (1977) Carcinogenic and mutagenic activities of safrole, 1′-hydroxysafrole and some known or possible metabolites. Cancer Res. 37, 1883-1891.
    • (1977) Cancer Res. , vol.37 , pp. 1883-1891
    • Wislocki, P.G.1    Miller, E.C.2    Miller, J.A.3    McCoy, E.C.4    Rosenkranz, H.S.5
  • 11
    • 0019210482 scopus 로고
    • Biotransformation of allylbenzene analogues in vivo and in vitro through the epoxide-diol pathway
    • Delaforge, M., Janiaud, P., Levi, P., and Morizot, J. P. (1980) Biotransformation of allylbenzene analogues in vivo and in vitro through the epoxide-diol pathway. Xenobiotica 10, 737-744.
    • (1980) Xenobiotica , vol.10 , pp. 737-744
    • Delaforge, M.1    Janiaud, P.2    Levi, P.3    Morizot, J.P.4
  • 12
    • 0025262274 scopus 로고
    • Formation of glutathione conjugates during oxidation of eugenol by microsomal fractions of rat liver and lung
    • Thompson, D. C., Teodosiu, D., Egestad, B., Mickos, H., and Moldeus, P. (1990) Formation of glutathione conjugates during oxidation of eugenol by microsomal fractions of rat liver and lung. Biochem. Pharmacol. 39, 1587-1595.
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 1587-1595
    • Thompson, D.C.1    Teodosiu, D.2    Egestad, B.3    Mickos, H.4    Moldeus, P.5
  • 13
    • 0026068803 scopus 로고
    • Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes
    • Thompson, D. C., Constantin, T. D., and Moldeus, P. (1991) Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes. Chem.-Biol. Interact. 77, 137-147.
    • (1991) Chem.-Biol. Interact. , vol.77 , pp. 137-147
    • Thompson, D.C.1    Constantin, T.D.2    Moldeus, P.3
  • 14
    • 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., and Bolton, J. (1995) o-Methoxy-4-alkylphenols that form quinone methides of intermediate reactivity are the most toxic in rat liver slices. Chem. Res. Toxicol. 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.4
  • 15
    • 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., and Vukomanovic, V. (1994) Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: potential bioactivation mechanism for the hepatocarcinogen safrole. Chem. Res. Toxicol. 7, 443-450.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 443-450
    • Bolton, J.L.1    Acay, N.M.2    Vukomanovic, V.3
  • 16
    • 0026459531 scopus 로고
    • Comparative induction of unscheduled DNA synthesis in cultured rat hepatocytes by allylbenzenes and their 1′-hydroxymetabolites
    • Chan, V. S. W., and Caldwell, J. (1992) Comparative induction of unscheduled DNA synthesis in cultured rat hepatocytes by allylbenzenes and their 1′-hydroxymetabolites. Food Chem. Toxicol. 30, 831-836.
    • (1992) Food Chem. Toxicol. , vol.30 , pp. 831-836
    • Chan, V.S.W.1    Caldwell, J.2
  • 17
    • 0025113923 scopus 로고
    • Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes
    • Howes, A. J., Chan, V. S. W., and Caldwell, J. (1990) Structure-specificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes. Food Chem. Toxicol. 28, 537-542.
    • (1990) Food Chem. Toxicol. , vol.28 , pp. 537-542
    • Howes, A.J.1    Chan, V.S.W.2    Caldwell, J.3
  • 18
    • 0017286721 scopus 로고
    • Metabolism of alkenylbenzene derivatives in the rat II eugenol and isoeugenolmethylether
    • Solheim, E. and Scheline, R. (1976) Metabolism of alkenylbenzene derivatives in the rat II eugenol and isoeugenolmethylether. Xenobiotica 6, 137-150.
    • (1976) Xenobiotica , vol.6 , pp. 137-150
    • Solheim, E.1    Scheline, R.2
  • 19
    • 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
  • 20
    • 0013889689 scopus 로고
    • Determination of free amino groups in proteins by trinitrobenzene sulfonic acid
    • Habeeb, A. F. S. A. (1966) Determination of free amino groups in proteins by trinitrobenzene sulfonic acid. Anal. Biochem. 14, 328-336.
    • (1966) Anal. Biochem. , vol.14 , pp. 328-336
    • Habeeb, A.F.S.A.1
  • 21
    • 0023253196 scopus 로고
    • Identification by immunoblotting of three halothane-induced liver microsomal polypeptide antigens recognized by antibodies in sera from patients with halothane associated hepatitis
    • Kenna, J. G., Neuberger, J., and Williams, R. (1987) Identification by immunoblotting of three halothane-induced liver microsomal polypeptide antigens recognized by antibodies in sera from patients with halothane associated hepatitis. J. Pharmacol. Exp. Ther. 242, 733-740.
    • (1987) J. Pharmacol. Exp. Ther. , vol.242 , pp. 733-740
    • Kenna, J.G.1    Neuberger, J.2    Williams, R.3
  • 22
    • 0020039866 scopus 로고
    • Isolation of intracellular membranes by means of sodium carbonate treatment: Application to endoplasmic reticulum
    • Fujiki, Y., Hubbard, A. L., Fowler, S., and Lazarow, P. B. (1982) Isolation of intracellular membranes by means of sodium carbonate treatment: application to endoplasmic reticulum. J. Cell Biol. 93, 97-102.
    • (1982) J. Cell Biol. , vol.93 , pp. 97-102
    • Fujiki, Y.1    Hubbard, A.L.2    Fowler, S.3    Lazarow, P.B.4
  • 24
    • 0026683699 scopus 로고
    • Hydrolysis of the 2′,3′-allylic epoxides of allylbenzene, estragole, eugenol and safrole by both microsomal and cytosolic epoxide hydrolases
    • Luo, G., Qato, M. K., and Guenther, T. M. (1992) Hydrolysis of the 2′,3′-allylic epoxides of allylbenzene, estragole, eugenol and safrole by both microsomal and cytosolic epoxide hydrolases. Drug Metab. Dispos. 20, 440-445.
    • (1992) Drug Metab. Dispos. , vol.20 , pp. 440-445
    • Luo, G.1    Qato, M.K.2    Guenther, T.M.3
  • 25
    • 0028123172 scopus 로고
    • Detoxication of the 2′,3′-epoxide metabolites of allylbenzene and estragole: Conjugation with glutathione
    • Luo, G., and Guenther, T. M. (1994) Detoxication of the 2′,3′-epoxide metabolites of allylbenzene and estragole: conjugation with glutathione. Drug Metab. Dispos. 22, 731-737.
    • (1994) Drug Metab. Dispos. , vol.22 , pp. 731-737
    • Luo, G.1    Guenther, T.M.2
  • 26
    • 0028861306 scopus 로고
    • Metabolism of allylbenzene 2′,3′-oxide and estragole 2′,3′-oxide in the isolated perfused rat liver
    • Luo, G., and Guenther, T. M. (1995) Metabolism of allylbenzene 2′,3′-oxide and estragole 2′,3′-oxide in the isolated perfused rat liver. J. Pharmacol. Exp. Ther. 272, 588-596.
    • (1995) J. Pharmacol. Exp. Ther. , vol.272 , pp. 588-596
    • Luo, G.1    Guenther, T.M.2
  • 27
    • 0026722898 scopus 로고
    • Influence of modulators of epoxide metabolism on the cytotoxicity of trans-anethole in freshly isolated rat hepatocytes
    • Marshall, A. D., and Caldwell, J. (1992) Influence of modulators of epoxide metabolism on the cytotoxicity of trans-anethole in freshly isolated rat hepatocytes. Food Chem. Toxicol. 30, 467-473.
    • (1992) Food Chem. Toxicol. , vol.30 , pp. 467-473
    • Marshall, A.D.1    Caldwell, J.2
  • 28
    • 8944252152 scopus 로고
    • Metabolism of phenols and ethers
    • (Scheline, R., Ed.) CRC Press, Boca Raton, FL
    • Scheline, R. (1991) Metabolism of phenols and ethers. In CRC Handbook of mammalian metabolism of plant compounds (Scheline, R., Ed.) pp 49-84, CRC Press, Boca Raton, FL.
    • (1991) CRC Handbook of Mammalian Metabolism of Plant Compounds , pp. 49-84
    • Scheline, R.1
  • 29
    • 0024447657 scopus 로고
    • Distribution of 2-naphthol sulphotransferase and its endogenous substrate adenosine 3′-phosphate 5′-phosphosulphate in human tissues
    • Cappiello, M., Frandii, M., Giulani, L., and Pacifici, G. M. (1989) Distribution of 2-naphthol sulphotransferase and its endogenous substrate adenosine 3′-phosphate 5′-phosphosulphate in human tissues. Eur. J. Clin. Pharmacol. 37, 317-320.
    • (1989) Eur. J. Clin. Pharmacol. , vol.37 , pp. 317-320
    • Cappiello, M.1    Frandii, M.2    Giulani, L.3    Pacifici, G.M.4
  • 30
    • 0012003976 scopus 로고
    • Isolation and characterization of membranes and cell organelles
    • (Rickwood, D., Hames, and B. D., Eds.) IRL Press, Oxford
    • Evans, W. H. (1992) Isolation and characterization of membranes and cell organelles. In Preparative centrifugation: a practical approach (Rickwood, D., Hames, and B. D., Eds.) pp 233-270, IRL Press, Oxford.
    • (1992) Preparative Centrifugation: A Practical Approach , pp. 233-270
    • Evans, W.H.1
  • 31
    • 0026640574 scopus 로고
    • The topography of trifluoroacetylated protein antigens in liver microsomal fractions from halothane treated rats
    • Kenna, J. G., Martin, J. L., and Pohl, L. R. (1992) The topography of trifluoroacetylated protein antigens in liver microsomal fractions from halothane treated rats. Biochem. Pharmacol. 44, 621-629.
    • (1992) Biochem. Pharmacol. , vol.44 , pp. 621-629
    • Kenna, J.G.1    Martin, J.L.2    Pohl, L.R.3


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