메뉴 건너뛰기




Volumn 108, Issue 3, 1998, Pages 137-154

Reactions of halogen-substituted aziridinylbenzoquinones with glutathione: Formation of diglutathionyl conjugates and semiquinones

Author keywords

Azirinidylbenzoquinones; EPR; Glutathione; Glutathione conjugates; NAD(P)H:quinone oxidoreductase; Semiquinones

Indexed keywords

AZIRIDINYLBENZOQUINONE DERIVATIVE; DISULFIDE; GLUTATHIONE; GLUTATHIONE DISULFIDE; HALOGEN; SEMIQUINONE; SULFIDE;

EID: 0032579346     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(97)00104-X     Document Type: Article
Times cited : (4)

References (30)
  • 1
    • 0017239858 scopus 로고
    • Potential central nervous system anticancer agents Aziridinyl-benzoquinones
    • Khan A.H., Driscoll J.S. Potential central nervous system anticancer agents Aziridinyl-benzoquinones. J. Med. Chem. 19:1976;313-317.
    • (1976) J. Med. Chem. , vol.19 , pp. 313-317
    • Khan, A.H.1    Driscoll, J.S.2
  • 3
    • 0026612119 scopus 로고
    • DT-Diaphorase and cancer chemotherapy
    • Riley R.J., Workman P. DT-Diaphorase and cancer chemotherapy. Biochem. Pharmacol. 43:1992;1657-1669.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 1657-1669
    • Riley, R.J.1    Workman, P.2
  • 4
    • 0017397793 scopus 로고
    • Bioactivation as a model for drug design Bioreductive alkylation
    • Moore H.W. Bioactivation as a model for drug design Bioreductive alkylation. Science. 197:1977;527-532.
    • (1977) Science , vol.197 , pp. 527-532
    • Moore, H.W.1
  • 5
    • 0027048768 scopus 로고
    • Relationship between DT-diaphorase-mediated metabolism of a series of aziridinylbenzoquinones and DNA damage and cytotoxicity
    • Gibson N.W., Hartley J.A., Butler J., Siegel D., Ross D. Relationship between DT-diaphorase-mediated metabolism of a series of aziridinylbenzoquinones and DNA damage and cytotoxicity. Mol. Pharmacol. 42:1992;531-536.
    • (1992) Mol. Pharmacol. , vol.42 , pp. 531-536
    • Gibson, N.W.1    Hartley, J.A.2    Butler, J.3    Siegel, D.4    Ross, D.5
  • 6
    • 0027159001 scopus 로고
    • Two structurally related diaziridinylbenzoquinones preferentially cross-link DNA at different sites upon reduction with DT-diaphorase
    • Berardini M.D., Souhami R.L., Lee C.S., Gibson N.W., Butler J., Hartley J.A. Two structurally related diaziridinylbenzoquinones preferentially cross-link DNA at different sites upon reduction with DT-diaphorase. Biochemistry. 32:1993;3306-3312.
    • (1993) Biochemistry , vol.32 , pp. 3306-3312
    • Berardini, M.D.1    Souhami, R.L.2    Lee, C.S.3    Gibson, N.W.4    Butler, J.5    Hartley, J.A.6
  • 7
    • 0026589825 scopus 로고
    • Alteration in DNA cross-linking and sequence selectivity of a series of aziridinylbenzoquinones after enzymatic reduction by DT-diaphorase
    • Lee C.S., Hartley J.A., Berardini M.D., Butler J., Siegel D., Ross D., Gibson N.W. Alteration in DNA cross-linking and sequence selectivity of a series of aziridinylbenzoquinones after enzymatic reduction by DT-diaphorase. Biochemistry. 31:1992;3019-3025.
    • (1992) Biochemistry , vol.31 , pp. 3019-3025
    • Lee, C.S.1    Hartley, J.A.2    Berardini, M.D.3    Butler, J.4    Siegel, D.5    Ross, D.6    Gibson, N.W.7
  • 8
    • 0026348793 scopus 로고
    • Free radical formation and DNA strand breakage during metabolism of diaziquone by NAD(P)H quinone-acceptor oxidoreductase (DT-diaphorase) and NADPH cytochrome c reductase
    • Fisher G.R., Gutierrez P.L. Free radical formation and DNA strand breakage during metabolism of diaziquone by NAD(P)H quinone-acceptor oxidoreductase (DT-diaphorase) and NADPH cytochrome c reductase. Free Radical Biol. Med. 11:1991;597-607.
    • (1991) Free Radical Biol. Med. , vol.11 , pp. 597-607
    • Fisher, G.R.1    Gutierrez, P.L.2
  • 9
    • 0025799550 scopus 로고
    • The reductive metabolism of diaziquone (AZQ) in the S9 fraction of MCF-7 cells: Free radical formation and NAD(P)H:quinone-acceptor oxidoreductase (DT-diaphorase) activity
    • Fisher G.F., Gutierrez P.L. The reductive metabolism of diaziquone (AZQ) in the S9 fraction of MCF-7 cells: free radical formation and NAD(P)H:quinone-acceptor oxidoreductase (DT-diaphorase) activity. Free Radical Biol. Med. 10:1991;359-370.
    • (1991) Free Radical Biol. Med. , vol.10 , pp. 359-370
    • Fisher, G.F.1    Gutierrez, P.L.2
  • 10
    • 0026795829 scopus 로고
    • Thiol oxidation coupled to DT-diaphorase-catalysed reduction of diaziquone. Reductive and oxidative pathways of diaziquone semiquinone modulated by glutathione and superoxide dismutase
    • Ordonez I.D., Cadenas E. Thiol oxidation coupled to DT-diaphorase-catalysed reduction of diaziquone. Reductive and oxidative pathways of diaziquone semiquinone modulated by glutathione and superoxide dismutase. Biochem. J. 286:1992;481-490.
    • (1992) Biochem. J. , vol.286 , pp. 481-490
    • Ordonez, I.D.1    Cadenas, E.2
  • 11
    • 0029730636 scopus 로고
    • Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells
    • Qiu X., Schonthal A.H., Forman H.J., Cadenas E. Induction of p21 mediated by reactive oxygen species formed during the metabolism of aziridinylbenzoquinones by HCT116 cells. J. Biol. Chem. 271:1986;31915-31922.
    • (1986) J. Biol. Chem. , vol.271 , pp. 31915-31922
    • Qiu, X.1    Schonthal, A.H.2    Forman, H.J.3    Cadenas, E.4
  • 12
    • 0025082798 scopus 로고
    • Bioreductive activation of quinones: Redox properties and thiol reactivity
    • Wardman P. Bioreductive activation of quinones: redox properties and thiol reactivity. Free Radical Res. Comms. 8:1980;219-229.
    • (1980) Free Radical Res. Comms. , vol.8 , pp. 219-229
    • Wardman, P.1
  • 13
    • 0023214785 scopus 로고
    • Reactivity of thiols towards derivatives of 2- and 6- methyl-1,4-naphthoquinone bioreductive alkylating agents
    • Wilson I., Wardman P., Lin T.-S., Sartorelli A.C. Reactivity of thiols towards derivatives of 2- and 6- methyl-1,4-naphthoquinone bioreductive alkylating agents. Chem. Biol. Interact. 61:1987;229-240.
    • (1987) Chem. Biol. Interact. , vol.61 , pp. 229-240
    • Wilson, I.1    Wardman, P.2    Lin, T.-S.3    Sartorelli, A.C.4
  • 14
    • 0002387069 scopus 로고
    • The addition and substitution chemistry of quinones
    • In: S. Patai (Ed.) Wiley, London
    • K.T. Finley, The addition and substitution chemistry of quinones, In: S. Patai (Ed.), The Chemistry of Quinonoid Compounds, Wiley, London, 1974, 877-1144.
    • (1974) The Chemistry of Quinonoid Compounds , pp. 877-1144
    • Finley, K.T.1
  • 15
    • 0002394573 scopus 로고
    • Conjugation and oxidation of glutathione via thiyl free radicals
    • In: H. Sies, B. Ketterer (Eds.) Academic Press, London
    • P. Wardman, Conjugation and oxidation of glutathione via thiyl free radicals. In: H. Sies, B. Ketterer (Eds.), Glutathione Conjugation. Mechanisms and Biological Significance, Academic Press, London, 1988, pp. 44-72.
    • (1988) Glutathione Conjugation. Mechanisms and Biological Significance , pp. 44-72
    • Wardman, P.1
  • 16
    • 0021962271 scopus 로고
    • The formation of aminopyrine cation radical by the peroxidase activity of prostaglandin H synthase and subsequent reactions of the radical
    • Eling T.E., Mason R.P., Sivarajah K. The formation of aminopyrine cation radical by the peroxidase activity of prostaglandin H synthase and subsequent reactions of the radical. J. Biol. Chem. 260:1985;1601-1607.
    • (1985) J. Biol. Chem. , vol.260 , pp. 1601-1607
    • Eling, T.E.1    Mason, R.P.2    Sivarajah, K.3
  • 17
    • 0022548865 scopus 로고
    • One-electron reduction of 2- and 6-methyl-1,4-naphthoquinone bioreductive alkylating agents
    • Wilson I., Wardman P., Lin T.-S., Sartorelli A.C. One-electron reduction of 2- and 6-methyl-1,4-naphthoquinone bioreductive alkylating agents. J. Med. Chem. 29:1986;1381-1384.
    • (1986) J. Med. Chem. , vol.29 , pp. 1381-1384
    • Wilson, I.1    Wardman, P.2    Lin, T.-S.3    Sartorelli, A.C.4
  • 18
    • 0024989984 scopus 로고
    • Interactions between potential anti-tumour 2,5-bis(1-aziridinyl)-1,4-benzoquinone derivatives and glutathione: Reductive activation, conjugation and DNA damage
    • Lusthof K.J., de Mol N.J., Janssen L.H.M., Prins B., Verboom B.W., Reinhoudt D.N. Interactions between potential anti-tumour 2,5-bis(1-aziridinyl)-1,4-benzoquinone derivatives and glutathione: reductive activation, conjugation and DNA damage. Anti-Cancer Drug Design. 5:1990;283-290.
    • (1990) Anti-Cancer Drug Design , vol.5 , pp. 283-290
    • Lusthof, K.J.1    De Mol, N.J.2    Janssen, L.H.M.3    Prins, B.4    Verboom, B.W.5    Reinhoudt, D.N.6
  • 19
    • 0025776518 scopus 로고
    • Glutathionyl- and hydroxyl radical formation coupled to the redox transitions of 1,4-naphthoquinone bioreductive alkylating agents during glutathione two-electron reductive addition
    • Goin J., Gibson D.D., McCay P.B., Cadenas E. Glutathionyl- and hydroxyl radical formation coupled to the redox transitions of 1,4-naphthoquinone bioreductive alkylating agents during glutathione two-electron reductive addition. Arch. Biochem. Biophys. 288:1991;386-396.
    • (1991) Arch. Biochem. Biophys. , vol.288 , pp. 386-396
    • Goin, J.1    Gibson, D.D.2    McCay, P.B.3    Cadenas, E.4
  • 20
    • 0028966862 scopus 로고
    • Enzymic- and thiol-mediated activation of halogen-substituted diaziridinylbenzoquinones: Redox transitions of the semiquinone and semiquinone-thioether species
    • Goin J., Giulivi C., Butler J., Cadenas E. Enzymic- and thiol-mediated activation of halogen-substituted diaziridinylbenzoquinones: redox transitions of the semiquinone and semiquinone-thioether species. Free Rad. Biol. Med. 18:1995;525-536.
    • (1995) Free Rad. Biol. Med. , vol.18 , pp. 525-536
    • Goin, J.1    Giulivi, C.2    Butler, J.3    Cadenas, E.4
  • 21
    • 0028950763 scopus 로고
    • Diaziquone-glutathione conjugates: Characterization and mechanisms of formation
    • Gutierrez P.L., Siva S. Diaziquone-glutathione conjugates: characterization and mechanisms of formation. Chem. Res. Toxicol. 8:1995;455-464.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 455-464
    • Gutierrez, P.L.1    Siva, S.2
  • 22
    • 0023079953 scopus 로고
    • High-performance liquid chromatography of thiols and distilfides: Dinitrophenol derivatives
    • Fariss M.W., Reed D.J. High-performance liquid chromatography of thiols and distilfides: dinitrophenol derivatives. Methods Enzymol. 143:1987;101-109.
    • (1987) Methods Enzymol. , vol.143 , pp. 101-109
    • Fariss, M.W.1    Reed, D.J.2
  • 23
    • 0021688435 scopus 로고
    • Free radicals in quinone-containing antitumor agents. Electrochemical reduction of diaziquone (2,5-diaziridine-3,6-bis(carboetho-xyamino)-1,4-benzoquinone) and two analogues
    • Gutierrez P.L., Fox B.M., Mossoba M.M., Bachur N.R. Free radicals in quinone-containing antitumor agents. Electrochemical reduction of diaziquone (2,5-diaziridine-3,6-bis(carboetho-xyamino)-1,4-benzoquinone) and two analogues. Mol. Pharmacol. 26:1984;582-586.
    • (1984) Mol. Pharmacol. , vol.26 , pp. 582-586
    • Gutierrez, P.L.1    Fox, B.M.2    Mossoba, M.M.3    Bachur, N.R.4
  • 24
    • 0020524131 scopus 로고
    • Free radicals in quinone-containing antitumor agents. The nature of the diaziquone (3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4- benzoquinone) free radical
    • Gutierrez P.L., Bachur N.R. Free radicals in quinone-containing antitumor agents. The nature of the diaziquone (3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4- benzoquinone) free radical. Biochim. Biophys. Acta. 758:1983;37-41.
    • (1983) Biochim. Biophys. Acta , vol.758 , pp. 37-41
    • Gutierrez, P.L.1    Bachur, N.R.2
  • 25
    • 0021790461 scopus 로고
    • Electron spin resonance of electrochemically generated free radicals from diaziquone and its derivatives
    • Gutierrez P.L., Fox B.M., Mossoba M.M., Egorin M.J., Nakazawa H., Bachur N.R. Electron spin resonance of electrochemically generated free radicals from diaziquone and its derivatives. Biophys. Chem. 22:1985;115-123.
    • (1985) Biophys. Chem. , vol.22 , pp. 115-123
    • Gutierrez, P.L.1    Fox, B.M.2    Mossoba, M.M.3    Egorin, M.J.4    Nakazawa, H.5    Bachur, N.R.6
  • 26
    • 0026537127 scopus 로고
    • Reactions of glutathione and glutathione radicals with benzoquinones
    • Butler J., Hoey B.M. Reactions of glutathione and glutathione radicals with benzoquinones. Free Radical Biol. Med. 12:1992;337-345.
    • (1992) Free Radical Biol. Med. , vol.12 , pp. 337-345
    • Butler, J.1    Hoey, B.M.2
  • 28
    • 0022502943 scopus 로고
    • Semiquinone anion radicals formed by the reaction of quinones with glutathione or amino acids
    • Gant T.W., d'Arcy Doherty M., Odowole D., Sales K.D., Cohen G.M. Semiquinone anion radicals formed by the reaction of quinones with glutathione or amino acids. FEBS Lett. 201:1986;296-300.
    • (1986) FEBS Lett. , vol.201 , pp. 296-300
    • Gant, T.W.1    D'Arcy Doherty, M.2    Odowole, D.3    Sales, K.D.4    Cohen, G.M.5
  • 29
    • 0023100690 scopus 로고
    • Formation of glutathione-conjugated semiquinones by the reaction of quinones with glutathione: An ESR study
    • Takahashi N., Schreiber J., Fisher V., Mason R.P. Formation of glutathione-conjugated semiquinones by the reaction of quinones with glutathione: an ESR study. Arch. Biochem. Biophys. 252:1987;41-48.
    • (1987) Arch. Biochem. Biophys. , vol.252 , pp. 41-48
    • Takahashi, N.1    Schreiber, J.2    Fisher, V.3    Mason, R.P.4
  • 30
    • 0024253422 scopus 로고
    • Characterization of a glutathione conjugate of the 1,4-benzosemiquinone-free radical formed in rat hepatocytes
    • Ramakrishna Rao D.N., Takahashi N., Mason R.P. Characterization of a glutathione conjugate of the 1,4-benzosemiquinone-free radical formed in rat hepatocytes. J. Biol. Chem. 263:1988;17081-17086.
    • (1988) J. Biol. Chem. , vol.263 , pp. 17081-17086
    • Ramakrishna Rao, D.N.1    Takahashi, N.2    Mason, R.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.