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Volumn 107, Issue 3, 1997, Pages 185-200

Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: Studies utilizing amino acid and peptide models

Author keywords

Adduct; Butylated hydroxytoluene; Electrophile; Protein binding; Quinone methide

Indexed keywords

1,4 BENZOQUINONE; BUTYLCRESOL; THIOL GROUP;

EID: 0031434490     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(97)00079-3     Document Type: Article
Times cited : (95)

References (38)
  • 1
    • 0024662764 scopus 로고
    • Chemical modifications of biopolymers by quinones and quinone methides
    • Peter M.G. Chemical modifications of biopolymers by quinones and quinone methides. Angew. Chem. Int. Ed. Engl. 28:1989;555-570.
    • (1989) Angew. Chem. Int. Ed. Engl. , vol.28 , pp. 555-570
    • Peter, M.G.1
  • 3
    • 0001623803 scopus 로고
    • Quinone methides
    • in: S. Patai (Ed.), Wiley-Interscience, New York
    • H.-U. Wagner, R. Gompper, Quinone methides, in: S. Patai (Ed.), The Chemistry of the Quinonoid Compounds, Part 2, Wiley-Interscience, New York, 1974, pp. 1145-1175.
    • (1974) The Chemistry of the Quinonoid Compounds , Issue.PART 2 , pp. 1145-1175
    • Wagner, H.-U.1    Gompper, R.2
  • 4
    • 0001466726 scopus 로고
    • The effect of β-fluorine substituents on the rate and equilibrium constants for the reactions of α-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 β-fluorine substituents on the rate and equilibrium constants for the reactions of α-substituted 4-methoxybenzyl carbocations and on the reactivity of a simple quinone methide. J. Am. Chem. Soc. 112:1990;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
  • 5
    • 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. 96:1995;279-290.
    • (1995) Chem. -Biol. Interact. , vol.96 , pp. 279-290
    • Bolton, J.L.1    Comeau, E.2    Vukomanovic, V.3
  • 6
    • 0027092534 scopus 로고
    • The enzymatic and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes
    • Bolton J.L., Valerio L.G., Thompson J.A. The enzymatic and chemical reactivity of quinone methides correlate with alkylphenol-induced toxicity in rat hepatocytes. Chem. Res. Toxicol. 5:1992;816-822.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 816-822
    • Bolton, J.L.1    Valerio, L.G.2    Thompson, J.A.3
  • 7
    • 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. 3:1990;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
  • 10
    • 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. 8:1995;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
  • 12
    • 0027422011 scopus 로고
    • Role of quinone methide in the in vitro toxicity of the skin tumor promoter butylated hydroxytoluene hydroperoxide
    • Gyton 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. 6:1993;731-738.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 731-738
    • Gyton, K.Z.1    Thompson, J.A.2    Kensler, T.W.3
  • 13
    • 0023792356 scopus 로고
    • 2,6-di-tert-Butyl-4-methylene-2,5-cyclohexadienone (BHT quinone methide): An active metabolite of BHT causing haemorrhages in rats
    • Takahashi O. 2,6-di-tert-Butyl-4-methylene-2,5-cyclohexadienone (BHT quinone methide): an active metabolite of BHT causing haemorrhages in rats. Arch. Toxicol. 62:1988;325-327.
    • (1988) Arch. Toxicol. , vol.62 , pp. 325-327
    • Takahashi, O.1
  • 14
    • 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. Pharmacol. 69:1983;283-290.
    • (1983) Toxicol. Appl. Pharmacol. , vol.69 , pp. 283-290
    • Mizutani, T.1    Yamamoto, K.2    Tajima, K.3
  • 15
    • 0030069966 scopus 로고    scopus 로고
    • Tamoxifen metabolic activation: Comparison of DNA adducts formed by microsomal and chemical activation of tamoxifen and 4-hydroxytamoxifen with DNA adducts formed in vivo
    • Moorthy B., Sriram P., Pathak D.N., Bodell W.J., Randerath K. Tamoxifen metabolic activation: comparison of DNA adducts formed by microsomal and chemical activation of tamoxifen and 4-hydroxytamoxifen with DNA adducts formed in vivo. Cancer Res. 56:1996;53-57.
    • (1996) Cancer Res. , vol.56 , pp. 53-57
    • Moorthy, B.1    Sriram, P.2    Pathak, D.N.3    Bodell, W.J.4    Randerath, K.5
  • 16
    • 0025959672 scopus 로고
    • Relationship between the metabolism of butylated hydroxytoluene (BHT) and lung tumor promotion in mice
    • Thompson J.A., Bolton J.L., Malkinson A.M. Relationship between the metabolism of butylated hydroxytoluene (BHT) and lung tumor promotion in mice. Exp. Lung Res. 17:1991;439-453.
    • (1991) Exp. Lung Res. , vol.17 , pp. 439-453
    • Thompson, J.A.1    Bolton, J.L.2    Malkinson, A.M.3
  • 17
    • 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. 88:1991;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
  • 18
    • 0020560784 scopus 로고
    • On the mechanism of covalent binding of butylated hydroxytoluene to microsomal protein
    • Nakagawa Y., Hiraga K., Suga T. On the mechanism of covalent binding of butylated hydroxytoluene to microsomal protein. Biochem. Pharmacol. 32:1983;1417-1421.
    • (1983) Biochem. Pharmacol. , vol.32 , pp. 1417-1421
    • Nakagawa, Y.1    Hiraga, K.2    Suga, T.3
  • 19
    • 0029850686 scopus 로고    scopus 로고
    • Alkylation of 2′-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol
    • Lewis M.A., Graff D.A., Bolton J.L., Thompson J.A. Alkylation of 2′-deoxynucleosides and DNA by quinone methides derived from 2,6-di-tert-butyl-4-methylphenol. Chem. Res. Toxicol. 9:1996;1368-1374.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 1368-1374
    • Lewis, M.A.1    Graff, D.A.2    Bolton, J.L.3    Thompson, J.A.4
  • 20
    • 0028227732 scopus 로고
    • Suicide inactivation of human prostatic acid phosphatase and a phosphotyrosine phosphatase
    • Wang Q., Dechert U., Jirik F., Withers S.G. Suicide inactivation of human prostatic acid phosphatase and a phosphotyrosine phosphatase. Biochem. Biophys. Res. Commun. 200:1994;577-583.
    • (1994) Biochem. Biophys. Res. Commun. , vol.200 , pp. 577-583
    • Wang, Q.1    Dechert, U.2    Jirik, F.3    Withers, S.G.4
  • 21
    • 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. 270:1995;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
  • 22
    • 0018350430 scopus 로고
    • Biological fate of butylated hydroxytoluene (BHT): Binding in vivo of BHT to macromolecules of rat liver
    • Nakagawa Y., Hiraga K., Suga T. Biological fate of butylated hydroxytoluene (BHT): binding in vivo of BHT to macromolecules of rat liver. Chem. Pharm. Bull. 27:1979;442-446.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 442-446
    • Nakagawa, Y.1    Hiraga, K.2    Suga, T.3
  • 24
    • 0025262274 scopus 로고
    • Formation of glutathione conjugates during oxidation of eugenol by microsomal fractions of rat liver and lung
    • Thompson D., Constantin-Teodosiu D., Egestad B., Henrik M., Moldeus P. Formation of glutathione conjugates during oxidation of eugenol by microsomal fractions of rat liver and lung. Biochem. Pharmacol. 39:1990;1587-1595.
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 1587-1595
    • Thompson, D.1    Constantin-Teodosiu, D.2    Egestad, B.3    Henrik, M.4    Moldeus, P.5
  • 25
    • 0021610533 scopus 로고
    • Effects of modifying structure on electrophilic reactions with biological nucleophiles
    • Coles B. Effects of modifying structure on electrophilic reactions with biological nucleophiles. Drug Metab. Rev. 15:1985;1307-1334.
    • (1985) Drug Metab. Rev. , vol.15 , pp. 1307-1334
    • Coles, B.1
  • 26
    • 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. 22:1993;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
  • 27
    • 0026508172 scopus 로고
    • A short, efficient synthesis of tert-butyl-hydroxylated di-tert-butylphenols
    • Miller J.A., Matthews R.S. A short, efficient synthesis of tert-butyl-hydroxylated di-tert-butylphenols. J. Org. Chem. 57:1992;2514-2516.
    • (1992) J. Org. Chem. , vol.57 , pp. 2514-2516
    • Miller, J.A.1    Matthews, R.S.2
  • 28
    • 0017168720 scopus 로고
    • Fluorescamine derivatives of histidine, distamine, and certain related imidazoles: Unique fluorescence after heating in acid
    • Nakamura H., Pisano J.J. Fluorescamine derivatives of histidine, distamine, and certain related imidazoles: unique fluorescence after heating in acid. Arch. Biochem. Biophys. 177:1976;334-335.
    • (1976) Arch. Biochem. Biophys. , vol.177 , pp. 334-335
    • Nakamura, H.1    Pisano, J.J.2
  • 31
    • 0026709939 scopus 로고
    • PH-Dependent stability and reactivity of a thiol-quinone methide adduct
    • Angle S.R., Yang W. pH-Dependent stability and reactivity of a thiol-quinone methide adduct. Tetrahedron Lett. 33:1992;6089-6092.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6089-6092
    • Angle, S.R.1    Yang, W.2
  • 33
    • 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. 62:1997;1820-1825.
    • (1997) J. Org. Chem. , vol.62 , pp. 1820-1825
    • McCracken, P.G.1    Bolton, J.L.2    Thatcher, G.R.J.3
  • 36
    • 0024208625 scopus 로고
    • Covalent binding of acetaminophen to mouse hemoglobin. Identification of major and minor adducts formed in vivo and implications for the nature of the arylating metabolites
    • Axworthy D.B., Hoffmann K.-J., Streeter A.J., Calleman C.J., Pascoe G.A., Baillie T.A. Covalent binding of acetaminophen to mouse hemoglobin. Identification of major and minor adducts formed in vivo and implications for the nature of the arylating metabolites. Chem. -Biol. Interact. 68:1988;99-116.
    • (1988) Chem. -Biol. Interact. , vol.68 , pp. 99-116
    • Axworthy, D.B.1    Hoffmann, K.-J.2    Streeter, A.J.3    Calleman, C.J.4    Pascoe, G.A.5    Baillie, T.A.6
  • 37
    • 0023734035 scopus 로고
    • Isolation and characterization of the major fluoranthene-hemoglobin adducts formed in vivo in the rat
    • Hutchins D.A., Skipper P.L., Naylor S., Tannenbaum S.R. Isolation and characterization of the major fluoranthene-hemoglobin adducts formed in vivo in the rat. Cancer Res. 48:1988;4756-4761.
    • (1988) Cancer Res. , vol.48 , pp. 4756-4761
    • Hutchins, D.A.1    Skipper, P.L.2    Naylor, S.3    Tannenbaum, S.R.4
  • 38
    • 0030004278 scopus 로고    scopus 로고
    • Analysis of hemoglobin adducts of benzene oxide by gas chromatography-mass spectrometry
    • Yeowell-O'Connell K., Macdonald T.A., Rappaport S.M. Analysis of hemoglobin adducts of benzene oxide by gas chromatography-mass spectrometry. Anal. Biochem. 237:1996;49-55.
    • (1996) Anal. Biochem. , vol.237 , pp. 49-55
    • Yeowell-O'Connell, K.1    Macdonald, T.A.2    Rappaport, S.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.