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Volumn 29, Issue 5, 2000, Pages 464-479

Dediazoniation of p-hydroxybenzenediazonium ion in a neutral aqueous medium

Author keywords

Free radicals; Homolytic dediazoniation; Hydroquinone; Oxygen influence; p hydroxybenzenediazonium ion; P hydroxyphenyl radical; Quinone

Indexed keywords

1,4 BENZOQUINONE; ALCOHOL; DIAZONIUM COMPOUND; DIMETHYL SULFOXIDE; HYDROQUINONE; OXYGEN; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REDUCING AGENT; SEMIQUINONE;

EID: 0034281973     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0891-5849(00)00321-X     Document Type: Article
Times cited : (17)

References (55)
  • 2
    • 0021362253 scopus 로고
    • Tyramine is a major mutagen precursor in soy sauce, being convertible to a mutagen by nitrite
    • Ochiai M., Wakabayashi K., Nagao M., Sugimura T. Tyramine is a major mutagen precursor in soy sauce, being convertible to a mutagen by nitrite. Gann. 75:1984;1-3.
    • (1984) Gann. , vol.75 , pp. 1-3
    • Ochiai, M.1    Wakabayashi, K.2    Nagao, M.3    Sugimura, T.4
  • 3
    • 0023136827 scopus 로고
    • Formation of a highly mutagenic diazo compound from the bamethan-nitrite reaction
    • Kikugawa K., Kato T., Takeda Y. Formation of a highly mutagenic diazo compound from the bamethan-nitrite reaction. Mutat. Res. 172:1987;35-43.
    • (1987) Mutat. Res. , vol.172 , pp. 35-43
    • Kikugawa, K.1    Kato, T.2    Takeda, Y.3
  • 4
    • 0024336847 scopus 로고
    • Formation of a direct mutagen, diazo-N-nitrosoetilefrin, by interaction of etilefrin with nitrite
    • Kikugawa K., Kato T., Takeda Y. Formation of a direct mutagen, diazo-N-nitrosoetilefrin, by interaction of etilefrin with nitrite. Chem. Pharm. Bull. 37:1989;1600-1603.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 1600-1603
    • Kikugawa, K.1    Kato, T.2    Takeda, Y.3
  • 5
    • 37049067268 scopus 로고
    • Quintero, B.; Thomas, J. Alvarez, J. M. Simultaneous C- and N-nitrosation of synephrine. A kinetic study
    • Fernández-Liencres M.P., Carazo F., Cabeza M.C. Quintero, B.; Thomas, J. Alvarez, J. M. Simultaneous C- and N-nitrosation of synephrine. A kinetic study. J. Chem. Soc. Perkin Trans. 2:1993;2265-2273.
    • (1993) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 2265-2273
    • Fernández-Liencres, M.P.1    Carazo, F.2    Cabeza, M.C.3
  • 6
    • 0027701779 scopus 로고
    • Agaricus bisporus: An assessment of its carcinogenic potency
    • Toth B., Gannett P. Agaricus bisporus an assessment of its carcinogenic potency . Mycopathologia. 124:1993;73-77.
    • (1993) Mycopathologia , vol.124 , pp. 73-77
    • Toth, B.1    Gannett, P.2
  • 7
    • 0023328602 scopus 로고
    • Ranking possible carcinogenic hazards
    • Ames B.N., Magaw R., Gold L.S. Ranking possible carcinogenic hazards. Science. 236:1987;271-280.
    • (1987) Science , vol.236 , pp. 271-280
    • Ames, B.N.1    Magaw, R.2    Gold, L.S.3
  • 8
    • 0024556431 scopus 로고
    • Tumor induction by 4-(methyl)benzenediazonium sulfate in mice
    • Toth, B.; Taylor, J.; Mattson, B.; Gannett, P.; Tumor induction by 4-(methyl)benzenediazonium sulfate in mice. In Vivo 3:17-22; 1989.
    • (1989) In Vivo , vol.3 , pp. 17-22
    • Toth, B.1    Taylor, J.2    Mattson, B.3    Gannett, P.4
  • 9
    • 0026715804 scopus 로고
    • Substitution of p- and o-hydroxyphenyl radicals at the 8 position of purine nucleosides by reaction with mutagenic p- and o-diazoquinones
    • Kikugawa K., Kato T., Kojima K. Substitution of p- and o-hydroxyphenyl radicals at the 8 position of purine nucleosides by reaction with mutagenic p- and o-diazoquinones. Mutat. Res. 268:1992;65-75.
    • (1992) Mutat. Res. , vol.268 , pp. 65-75
    • Kikugawa, K.1    Kato, T.2    Kojima, K.3
  • 10
    • 0026762289 scopus 로고
    • DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds
    • Kato T., Kojima K., Hiramoto K., Kikugawa K. DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds. Mutat. Res. 268:1992;105-114.
    • (1992) Mutat. Res. , vol.268 , pp. 105-114
    • Kato, T.1    Kojima, K.2    Hiramoto, K.3    Kikugawa, K.4
  • 11
    • 0028959058 scopus 로고
    • DNA strand breaking by carbon-centered radical generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus
    • Hiramoto K., Kaku M., Kato T., Kikugawa K. DNA strand breaking by carbon-centered radical generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus. Chem. Biol. Interact. 94:1995;21-36.
    • (1995) Chem. Biol. Interact. , vol.94 , pp. 21-36
    • Hiramoto, K.1    Kaku, M.2    Kato, T.3    Kikugawa, K.4
  • 12
    • 37049076778 scopus 로고
    • Electron paramagnetic resonance studies of the reaction of aryl radicals with nucleic acids and their components
    • Hazlewood C., Davies M.J., Gilbert B.C., Packer J.E. Electron paramagnetic resonance studies of the reaction of aryl radicals with nucleic acids and their components. J. Chem. Soc., Perkin Trans. 2:1995;2167-2174.
    • (1995) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 2167-2174
    • Hazlewood, C.1    Davies, M.J.2    Gilbert, B.C.3    Packer, J.E.4
  • 13
    • 0020078748 scopus 로고
    • Mutagenic and alkylating activities of 3-methyl-1-phenyltriazenes and their possible role as carcinogenic metabolites of the parent dimethyl compounds
    • Malaveille C., Brun G., Kolar G., Bartsch H. Mutagenic and alkylating activities of 3-methyl-1-phenyltriazenes and their possible role as carcinogenic metabolites of the parent dimethyl compounds. Cancer Res. 42:1982;1446-1453.
    • (1982) Cancer Res. , vol.42 , pp. 1446-1453
    • Malaveille, C.1    Brun, G.2    Kolar, G.3    Bartsch, H.4
  • 14
    • 33947292961 scopus 로고
    • Monosubstituted diazenes (diimides): Surprising intermediates
    • Kosower E.M. Monosubstituted diazenes (diimides) surprising intermediates . Acc. Chem. Res. 4:1971;193-198.
    • (1971) Acc. Chem. Res. , vol.4 , pp. 193-198
    • Kosower, E.M.1
  • 15
    • 0001590574 scopus 로고
    • Reactions of benzenediazonium ions with adenine and its derivatives
    • Chin A., Hung M.H., Stock L.M. Reactions of benzenediazonium ions with adenine and its derivatives. J. Org. Chem. 46:1981;2203-2207.
    • (1981) J. Org. Chem. , vol.46 , pp. 2203-2207
    • Chin, A.1    Hung, M.H.2    Stock, L.M.3
  • 16
    • 0001051085 scopus 로고
    • Reactions of benzenediazonium ions with guanine and its derivatives
    • Hung M.-H., Stock L.M. Reactions of benzenediazonium ions with guanine and its derivatives. J. Org. Chem. 47:1982;448-453.
    • (1982) J. Org. Chem. , vol.47 , pp. 448-453
    • Hung, M.-H.1    Stock, L.M.2
  • 17
    • 0001229312 scopus 로고
    • Different patterns of mutagenicity of arenediazonium ions in V79 cells and Salmonella typhimurium TA102: Evidence for different mechanisms of actions
    • Lawson T., Gannett P.M., Yau W.M., Dalal N.S., Toth B. Different patterns of mutagenicity of arenediazonium ions in V79 cells and Salmonella typhimurium TA102 evidence for different mechanisms of actions . J. Agric. Food Chem. 43:1995;2627-2635.
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 2627-2635
    • Lawson, T.1    Gannett, P.M.2    Yau, W.M.3    Dalal, N.S.4    Toth, B.5
  • 20
    • 0029031993 scopus 로고
    • One-electron reduction of arenediazonium compounds by physiological electron donors generates aryl radicals. An EPR and spin trapping investigation
    • Reszka K.J., Chignell C.F. One-electron reduction of arenediazonium compounds by physiological electron donors generates aryl radicals. An EPR and spin trapping investigation. Chem. Biol. Interact. 96:1995;223-234.
    • (1995) Chem. Biol. Interact. , vol.96 , pp. 223-234
    • Reszka, K.J.1    Chignell, C.F.2
  • 21
    • 0031474811 scopus 로고    scopus 로고
    • Aryl radical formation during the metabolism of arylhidrazines by microsomes
    • Gannett P.M., Shi X., Lawson T., Kolar C., Toth B. Aryl radical formation during the metabolism of arylhidrazines by microsomes. Chem. Res. Toxicol. 10:1997;1372-1377.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1372-1377
    • Gannett, P.M.1    Shi, X.2    Lawson, T.3    Kolar, C.4    Toth, B.5
  • 22
    • 0026040838 scopus 로고
    • Molecular mechanisms of quinone cytotoxicity
    • O'Brian P.J. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact. 80:1991;1-41.
    • (1991) Chem. Biol. Interact. , vol.80 , pp. 1-41
    • O'Brian, P.J.1
  • 23
    • 0003027545 scopus 로고
    • Redox cycling drugs and DNA damage
    • B. Haliwell, & O.I. Aruoma. Chicester, UK: Ellis Horwood Ltd
    • Butler J., Hoey B.M. Redox cycling drugs and DNA damage. Haliwell B., Aruoma O.I., DNA and free radicals. 1993;243-265 Ellis Horwood Ltd, Chicester, UK.
    • (1993) DNA and free radicals , pp. 243-265
    • Butler, J.1    Hoey, B.M.2
  • 24
    • 0000303016 scopus 로고    scopus 로고
    • The kinetics and thermodynamics of quinone-semiquinone-hydroquinone systems under physiological conditions
    • Roginsky V.A., Pisarenko L.M., Bors W., Michel C. The kinetics and thermodynamics of quinone-semiquinone-hydroquinone systems under physiological conditions. J. Chem. Soc., Perkin Trans. 2:1999;871-876.
    • (1999) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 871-876
    • Roginsky, V.A.1    Pisarenko, L.M.2    Bors, W.3    Michel, C.4
  • 28
    • 33751154708 scopus 로고
    • Benzenediazonium ion. Generality, consistency, and preferability of the electron density based dative bonding model
    • Glaser R., Horan J.C. Benzenediazonium ion. Generality, consistency, and preferability of the electron density based dative bonding model. J. Org. Chem. 60:1995;7518-7528.
    • (1995) J. Org. Chem. , vol.60 , pp. 7518-7528
    • Glaser, R.1    Horan, J.C.2
  • 29
    • 0030696787 scopus 로고    scopus 로고
    • Electron-density relaxation and oppositely signed reaction constants in dual substituent parameter relationships in dediazoniation reactions
    • Glaser R., Horan C.J., Zollinger H. Electron-density relaxation and oppositely signed reaction constants in dual substituent parameter relationships in dediazoniation reactions. Angew. Chem. Int. Ed. Engl. 36:1997;2210-2213.
    • (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2210-2213
    • Glaser, R.1    Horan, C.J.2    Zollinger, H.3
  • 30
    • 0033524889 scopus 로고    scopus 로고
    • Sigma-dative and π-backdative phenylcation-dinitrogen interactions and opposing sign reaction constants in dual substituent parameter relations
    • Glaser R., Horan C.J., Lewis M., Zollinger H. Sigma-dative and π-backdative phenylcation-dinitrogen interactions and opposing sign reaction constants in dual substituent parameter relations. J. Org. Chem. 64:1999;902-913.
    • (1999) J. Org. Chem. , vol.64 , pp. 902-913
    • Glaser, R.1    Horan, C.J.2    Lewis, M.3    Zollinger, H.4
  • 31
    • 0000024970 scopus 로고
    • EPR and spin trapping investigation of free radicals from the reaction of 4-methoxybenzenediazonium tetrafluoroborate with melanin and melanin precursors
    • Reszka K.J., Chignell C.F. EPR and spin trapping investigation of free radicals from the reaction of 4-methoxybenzenediazonium tetrafluoroborate with melanin and melanin precursors. J. Am. Chem. Soc. 115:1993;7752-7760.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 7752-7760
    • Reszka, K.J.1    Chignell, C.F.2
  • 32
    • 0001855543 scopus 로고
    • 13C-polarization observed during reduction of diazonium salts, using the pulse Fourier Transform technique
    • 13C-polarization observed during reduction of diazonium salts, using the pulse Fourier Transform technique. Tetrahedron Lett. 1972;2581-2584.
    • (1972) Tetrahedron Lett. , pp. 2581-2584
    • Berger, S.1    Hauff, S.2    Niederer, P.3    Rieker, A.4
  • 34
    • 0007728370 scopus 로고
    • Acylarylnitrosamines. Part 1. Electron spin resonance studies relevant to the mechanism of decomposition of acylarylnitrosamines in various solvents
    • Cadogan, J. I. G.; Paton, R. M.; Thomson, C. Acylarylnitrosamines. Part 1. Electron spin resonance studies relevant to the mechanism of decomposition of acylarylnitrosamines in various solvents. J. Chem. Soc. (B) 583-595; 1971.
    • (1971) J. Chem. Soc. (B) , pp. 583-595
    • Cadogan, J.I.G.1    Paton, R.M.2    Thomson, C.3
  • 35
    • 2942545129 scopus 로고
    • Radical reactions of arenediazonium ions: An easy entry into the chemistry of the aryl radical
    • Galli C. Radical reactions of arenediazonium ions an easy entry into the chemistry of the aryl radical . Chem. Rev. 88:1988;765-792.
    • (1988) Chem. Rev. , vol.88 , pp. 765-792
    • Galli, C.1
  • 36
    • 0001333703 scopus 로고
    • Direct observation of the cyclopropene vinylcarbene rearrangement: Matrix-isolation of bicyclo(3.1.0)hexa-3,5-dien-2-ones
    • Bucher G., Sander W. Direct observation of the cyclopropene vinylcarbene rearrangement matrix-isolation of bicyclo(3.1.0)hexa-3,5-dien-2-ones . J. Org. Chem. 57:1992;1346-1351.
    • (1992) J. Org. Chem. , vol.57 , pp. 1346-1351
    • Bucher, G.1    Sander, W.2
  • 37
    • 0031597120 scopus 로고    scopus 로고
    • A new method for monitoring dediazoniation reactions: Simultaneous monitoring of concentration and rates of product formation and loss of starting material for the dediazoniation of p-methylbenzenediazonium tetrafluoroborate
    • García Meijide M.C., Bravo Diaz C., Romsted L.S. A new method for monitoring dediazoniation reactions simultaneous monitoring of concentration and rates of product formation and loss of starting material for the dediazoniation of p-methylbenzenediazonium tetrafluoroborate . Int. J. Chem. Kinet. 30:1998;31-39.
    • (1998) Int. J. Chem. Kinet. , vol.30 , pp. 31-39
    • García Meijide, M.C.1    Bravo Diaz, C.2    Romsted, L.S.3
  • 39
    • 0007728786 scopus 로고    scopus 로고
    • 2 complex in a linoleic acid-DNA system
    • 2 complex in a linoleic acid-DNA system. Redox Rep. 2:1996;63-68.
    • (1996) Redox Rep. , vol.2 , pp. 63-68
    • Cao, E.1    Liu, X.2    Xu, N.3
  • 41
    • 4243426582 scopus 로고
    • (5th ed.). Argentina: Addison-Wesley Iberoamericana
    • Morrison, R. T.; Boyd, R. N. Química orgá;1qnica (5th ed.). Argentina: Addison-Wesley Iberoamericana; 1990:981.
    • (1990) Química orgá;1qnica , pp. 981
    • Morrison, R.T.1    Boyd, R.N.2
  • 42
    • 0023505008 scopus 로고
    • Spin trapping: ESR parameters of spin adducts
    • Buettner G.R. Spin trapping ESR parameters of spin adducts . Free Radic. Biol. Med. 3:1987;259-303.
    • (1987) Free Radic. Biol. Med. , vol.3 , pp. 259-303
    • Buettner, G.R.1
  • 43
    • 0027355428 scopus 로고
    • ESR spin trapping studies into the nature of the oxidizing species formed in the fenton reaction: Pitfalls associated with the use of 5,5-dimethyl-1-pyrroline-N-oxide in the detection of the hydroxyl radical
    • Burkitt M.J. ESR spin trapping studies into the nature of the oxidizing species formed in the fenton reaction pitfalls associated with the use of 5,5-dimethyl-1-pyrroline-N-oxide in the detection of the hydroxyl radical . Free Radic. Res. Commun. 18:1993;43-57.
    • (1993) Free Radic. Res. Commun. , vol.18 , pp. 43-57
    • Burkitt, M.J.1
  • 44
    • 0027957717 scopus 로고
    • A kinetic approach to the selection of a sensitive spin trapping system for the detection of hydroxyl radical
    • Pou S., Ramos C.L., Gladwell T., Renks E., Centra M., Young D., Cohen M.S., Rosen G.M. A kinetic approach to the selection of a sensitive spin trapping system for the detection of hydroxyl radical. Anal. Biochem. 217:1994;76-83.
    • (1994) Anal. Biochem. , vol.217 , pp. 76-83
    • Pou, S.1    Ramos, C.L.2    Gladwell, T.3    Renks, E.4    Centra, M.5    Young, D.6    Cohen, M.S.7    Rosen, G.M.8
  • 45
    • 0020664909 scopus 로고
    • The effect of spin traps on phenylhydrazine-induced hemolysis
    • Hill H.A.O., Thornally P.J. The effect of spin traps on phenylhydrazine-induced hemolysis. Biochim. Biophys. Acta. 762:1983;44-51.
    • (1983) Biochim. Biophys. Acta , vol.762 , pp. 44-51
    • Hill, H.A.O.1    Thornally, P.J.2
  • 46
    • 0000031386 scopus 로고
    • Electron spin resonance study of the hyperfine splitting constants of naturally abundant carbon-13 and nitrogen-15 in diphenylmethyl tert-butyl aminoxyl (nitroxide). Solvent and temperature effects
    • Janzen E.G. Electron spin resonance study of the hyperfine splitting constants of naturally abundant carbon-13 and nitrogen-15 in diphenylmethyl tert-butyl aminoxyl (nitroxide). Solvent and temperature effects. Can. J. Chem. 62:1984;1653-1657.
    • (1984) Can. J. Chem. , vol.62 , pp. 1653-1657
    • Janzen, E.G.1
  • 47
    • 0000045352 scopus 로고
    • Substituent effects in the polarography of aromatic diazonium salts
    • Elofson R.M., Gadallah F.F. Substituent effects in the polarography of aromatic diazonium salts. J. Org. Chem. 34:1969;854-857.
    • (1969) J. Org. Chem. , vol.34 , pp. 854-857
    • Elofson, R.M.1    Gadallah, F.F.2
  • 49
    • 0028493343 scopus 로고
    • Formation and reactivity of phenylperoxyl radicals in aqueous solutions
    • Alfassi Z.B., Marguet S., Neta P. Formation and reactivity of phenylperoxyl radicals in aqueous solutions. J. Phys. Chem. 98:1994;8019-8023.
    • (1994) J. Phys. Chem. , vol.98 , pp. 8019-8023
    • Alfassi, Z.B.1    Marguet, S.2    Neta, P.3
  • 50
    • 0001211477 scopus 로고
    • Cyclopentylperoxyl and cyclohexylperoxyl radicals in aqueous solutions: A study by product analysis and pulse radiolysis
    • Zegota H., Schuchmann M.N., von Sonntag C. Cyclopentylperoxyl and cyclohexylperoxyl radicals in aqueous solutions a study by product analysis and pulse radiolysis . J. Phys. Chem. 88:1984;5589-5593.
    • (1984) J. Phys. Chem. , vol.88 , pp. 5589-5593
    • Zegota, H.1    Schuchmann, M.N.2    Von Sonntag, C.3
  • 51
    • 33845280973 scopus 로고
    • Reduction of arenediazonium salts by hydroquinone. Kinetics and mechanism for the electron-transfer step
    • Brown K.C., Doyle M.P. Reduction of arenediazonium salts by hydroquinone. Kinetics and mechanism for the electron-transfer step. J. Org. Chem. 53:1988;3255-3261.
    • (1988) J. Org. Chem. , vol.53 , pp. 3255-3261
    • Brown, K.C.1    Doyle, M.P.2
  • 52
    • 0031254204 scopus 로고    scopus 로고
    • Photochemistry of water-soluble quinones. Production of water derived spin adduct
    • Alegria A.E., Ferrer A., Sepúlveda E. Photochemistry of water-soluble quinones. Production of water derived spin adduct. Photochem. Photobiol. 66:1997;436-442.
    • (1997) Photochem. Photobiol. , vol.66 , pp. 436-442
    • Alegria, A.E.1    Ferrer, A.2    Sepúlveda, E.3
  • 53
    • 0026397675 scopus 로고
    • Elevated 8-hydroxydeoxyguanosine levels in DNA of diethylstilbestrol-treated Syrian hamsters: Covalent DNA damage by free radicals generated by redox cycling of diethylstilbestrol
    • Roy D., Floyd R.A., Liehr J.G. Elevated 8-hydroxydeoxyguanosine levels in DNA of diethylstilbestrol-treated Syrian hamsters covalent DNA damage by free radicals generated by redox cycling of diethylstilbestrol . Cancer Res. 51:1991;3882-3885.
    • (1991) Cancer Res. , vol.51 , pp. 3882-3885
    • Roy, D.1    Floyd, R.A.2    Liehr, J.G.3
  • 54
    • 0026625531 scopus 로고
    • Reactivity of hypervalent iron with biological compounds
    • Bielski B.H.J. Reactivity of hypervalent iron with biological compounds. Ann. Neurol. 32:1992;528-532.
    • (1992) Ann. Neurol. , vol.32 , pp. 528-532
    • Bielski, B.H.J.1
  • 55
    • 0031024633 scopus 로고    scopus 로고
    • A comparative study of the redox-cycling of a quinone (Rifamycin S) and a quinonimine (Rifabutin) antibiotic by rat liver microsomes
    • Rao D.N.R., Cederbaum A.I. A comparative study of the redox-cycling of a quinone (Rifamycin S) and a quinonimine (Rifabutin) antibiotic by rat liver microsomes. Free Radic. Biol. Med. 22:1997;439-446.
    • (1997) Free Radic. Biol. Med. , vol.22 , pp. 439-446
    • Rao, D.N.R.1    Cederbaum, A.I.2


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