메뉴 건너뛰기




Volumn 12, Issue 10, 1999, Pages 1010-1018

Oxidation of acetaldehyde by peroxynitrite and hydrogen peroxide/iron(II). Production of acetate, formate, and methyl radicals

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; ACETALDEHYDE; ACETIC ACID; BENZENESULFONIC ACID DERIVATIVE; CARBON MONOXIDE; FORMIC ACID; FREE RADICAL; HYDROGEN PEROXIDE; IRON; NITRATE; NITRITE; OXIDIZING AGENT; PEROXYNITRITE;

EID: 0032725892     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990055i     Document Type: Article
Times cited : (54)

References (58)
  • 2
    • 0023838697 scopus 로고
    • A mutagenicity assessment of acetaldehyde
    • Dellarco, V. L. (1988) A mutagenicity assessment of acetaldehyde. Mutat. Res. 195, 1-20.
    • (1988) Mutat. Res. , vol.195 , pp. 1-20
    • Dellarco, V.L.1
  • 4
    • 0023860256 scopus 로고
    • Detection of a protein-acetaldehyde adduct in the liver of rats fed alcohol chronically
    • Lin, R. C., Smith, R. S., and Lumeng, L. (1988) Detection of a protein-acetaldehyde adduct in the liver of rats fed alcohol chronically. J. Clin. Invest. 81, 615-619.
    • (1988) J. Clin. Invest. , vol.81 , pp. 615-619
    • Lin, R.C.1    Smith, R.S.2    Lumeng, L.3
  • 5
    • 0023543188 scopus 로고
    • Antibodies against acetaldehyde-modified proteins epitopes in human alcoholics
    • Niemela, O., Klajner, F., Orrego, H., Vidnis, E., Blendis, L., and Israel, Y. (1987) Antibodies against acetaldehyde-modified proteins epitopes in human alcoholics. Hepatology 7, 1210-1214.
    • (1987) Hepatology , vol.7 , pp. 1210-1214
    • Niemela, O.1    Klajner, F.2    Orrego, H.3    Vidnis, E.4    Blendis, L.5    Israel, Y.6
  • 6
    • 0031416803 scopus 로고    scopus 로고
    • Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers
    • Fang, J.-L., and Vaca, C. E. (1997) Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis 18, 627-632.
    • (1997) Carcinogenesis , vol.18 , pp. 627-632
    • Fang, J.-L.1    Vaca, C.E.2
  • 7
    • 0023911853 scopus 로고
    • Spin-trapping of free radical species produced during microsomal metabolism of ethanol
    • Albano, E., Tomasi, A, Goria-Gatti, L., and Dianzani, M. U. (1988) Spin-trapping of free radical species produced during microsomal metabolism of ethanol. Chem.-Biol. Interact. 65, 223-234.
    • (1988) Chem.-Biol. Interact. , vol.65 , pp. 223-234
    • Albano, E.1    Tomasi, A.2    Goria-Gatti, L.3    Dianzani, M.U.4
  • 8
    • 0025372160 scopus 로고
    • In vivo formation of a free radical metabolite of ethanol
    • Knecht, K T., Bradford, B. U., and Mason, R. P. (1990) In vivo formation of a free radical metabolite of ethanol. Mol. Pharmacol. 38, 26-30.
    • (1990) Mol. Pharmacol. , vol.38 , pp. 26-30
    • Knecht, K.T.1    Bradford, B.U.2    Mason, R.P.3
  • 9
    • 0029962091 scopus 로고    scopus 로고
    • 1-Hydroxyethyl radical formation during NADPH- and NADH-dependent oxidation of ethanol by human liver microsomes
    • Rao, D. N. R., Yang, M.-X., Lasker, J. M., and Cederbaum, A I. (1996) 1-Hydroxyethyl radical formation during NADPH- and NADH-dependent oxidation of ethanol by human liver microsomes. Mol. Pharmacol. 49, 814-821.
    • (1996) Mol. Pharmacol. , vol.49 , pp. 814-821
    • Rao, D.N.R.1    Yang, M.-X.2    Lasker, J.M.3    Cederbaum, A.I.4
  • 10
    • 0027986438 scopus 로고
    • Ethanol-derived immunoreactive species formed by free radical mechanisms
    • Moncada, C., Torres, V., Varghese, G., Albano, E., and Israel, Y. (1994) Ethanol-derived immunoreactive species formed by free radical mechanisms. Mol. Pharmacol. 46, 786-791.
    • (1994) Mol. Pharmacol. , vol.46 , pp. 786-791
    • Moncada, C.1    Torres, V.2    Varghese, G.3    Albano, E.4    Israel, Y.5
  • 11
    • 0028812377 scopus 로고
    • Detection of antibodies against protein modified by hydroxyethyl free radicals in patients with alcoholic cirrhosis
    • Clot, P., Bellomo, G., Tabone, M., Aricó, S., and Albano, E. (1995) Detection of antibodies against protein modified by hydroxyethyl free radicals in patients with alcoholic cirrhosis. Gastroenterology 108, 201-207.
    • (1995) Gastroenterology , vol.108 , pp. 201-207
    • Clot, P.1    Bellomo, G.2    Tabone, M.3    Aricó, S.4    Albano, E.5
  • 12
    • 0025189864 scopus 로고
    • Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide
    • Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., and Freeman, B, A. (1990) Apparent hydroxyl radical production by peroxynitrite: implications for endothelial injury from nitric oxide and superoxide. Proc. Natl. Acad. Sci. U.S.A. 87, 1620-1625.
    • (1990) Proc. Natl. Acad. Sci. U.S.A. , vol.87 , pp. 1620-1625
    • Beckman, J.S.1    Beckman, T.W.2    Chen, J.3    Marshall, P.A.4    Freeman, B.5
  • 14
    • 0030781227 scopus 로고    scopus 로고
    • Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis
    • Kissner, R., Nauser, T., Bugnon, P., Lye, P. G., and Koppenol, W. H. (1997) Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis. Chem. Res. Toxicol. 10, 1285-1292.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1285-1292
    • Kissner, R.1    Nauser, T.2    Bugnon, P.3    Lye, P.G.4    Koppenol, W.H.5
  • 16
    • 0031819230 scopus 로고    scopus 로고
    • Nucleic acid alkylation by free radical metabolites of ethanol. Formation of 8-(1-hydroxyethy)guanine and 8-(2-hydroxyethyl)guanine adducts
    • Nakao, L. S., and Augusto, O. (1998) Nucleic acid alkylation by free radical metabolites of ethanol. Formation of 8-(1-hydroxyethy)guanine and 8-(2-hydroxyethyl)guanine adducts.Chem. Res. Toxicol. 11, 888-894.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 888-894
    • Nakao, L.S.1    Augusto, O.2
  • 17
    • 0031444007 scopus 로고    scopus 로고
    • Reactions of peroxynitrite with aldehydes as probes for the reactive intermediates responsible for biological nitration
    • Uppu, R. M., Winston, G. W., and Pryor, W. A. (1997) Reactions of peroxynitrite with aldehydes as probes for the reactive intermediates responsible for biological nitration. Chem. Res. Toxicol. 10, 1331-1337.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 1331-1337
    • Uppu, R.M.1    Winston, G.W.2    Pryor, W.A.3
  • 18
    • 0033601102 scopus 로고    scopus 로고
    • Cage-escape of geminate radical pairs can produce peroxynitrate from peroxynitrite under a variety of experimental conditions
    • in press
    • Hodges, G. R., and Ingold, K. U. (1999) Cage-escape of geminate radical pairs can produce peroxynitrate from peroxynitrite under a variety of experimental conditions. J. Am. Chem. Soc. (in press).
    • (1999) J. Am. Chem. Soc.
    • Hodges, G.R.1    Ingold, K.U.2
  • 19
    • 0029792288 scopus 로고    scopus 로고
    • Detection of secondary radicals from peroxynitrite-mediated oxidations by electron spin resonance
    • Augusto, O., Radi, R., Gatti, R. M., and Vasquez-Vivar, J. (1996) Detection of secondary radicals from peroxynitrite-mediated oxidations by electron spin resonance. Methods Enzymol. 269, 346-354.
    • (1996) Methods Enzymol. , vol.269 , pp. 346-354
    • Augusto, O.1    Radi, R.2    Gatti, R.M.3    Vasquez-Vivar, J.4
  • 20
    • 0343580474 scopus 로고    scopus 로고
    • Peroxynitrite-mediated decarboxylation of pyruvate to both carbon dioxide and carbon dioxide anion radical
    • Vasquez-Vivar, J., Denicola, A., Radi, R., and Augusto, O. (1997) Peroxynitrite-mediated decarboxylation of pyruvate to both carbon dioxide and carbon dioxide anion radical. Chem. Res. Toxicol. 10, 786-794.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 786-794
    • Vasquez-Vivar, J.1    Denicola, A.2    Radi, R.3    Augusto, O.4
  • 22
    • 0032578174 scopus 로고    scopus 로고
    • The complex chemistry of peroxynitrite decomposition: New insights
    • Richeson, C. E., Mulder, P., Bowry, V. W., and Ingold, K. U. (1998) The complex chemistry of peroxynitrite decomposition: new insights. J. Am. Chem. Soc. 120, 7211-7219.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7211-7219
    • Richeson, C.E.1    Mulder, P.2    Bowry, V.W.3    Ingold, K.U.4
  • 23
    • 0040122091 scopus 로고    scopus 로고
    • Peroxynitrous acid homolyzes into •OH and •N02 radicals
    • Merényi, G., Lind, J., Goldestein, S., and Czapski, G. (1998) Peroxynitrous acid homolyzes into •OH and •N02 radicals. Chem. Res. Toxicol. 11, 712-713.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 712-713
    • Merényi, G.1    Lind, J.2    Goldestein, S.3    Czapski, G.4
  • 24
    • 0001163528 scopus 로고    scopus 로고
    • 2-catalyzed one-electron oxidations by peroxynitrite: Properties of the reactive intermediate
    • 2-catalyzed one-electron oxidations by peroxynitrite: properties of the reactive intermediate, Inorg. Chem. 37, 294-301.
    • (1998) Inorg. Chem. , vol.37 , pp. 294-301
    • Lymar, S.V.1    Hurst, J.K.2
  • 25
    • 0032522210 scopus 로고    scopus 로고
    • 2: Evidence for carbonate radical production
    • 2: evidence for carbonate radical production. J. Am. Chem. Soc. 120, 3458-3463.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3458-3463
    • Goldstein, S.1    Czapski, G.2
  • 26
    • 0033574624 scopus 로고    scopus 로고
    • Direct detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide
    • Bonini, M. G., Radi, R., Ferrer-Sueta, G., da-Costa Ferreira, A. M., and Augusto, O. (1999) Direct detection of the carbonate radical anion produced from peroxynitrite and carbon dioxide. J. Biol. Chem. 274, 10802-10806.
    • (1999) J. Biol. Chem. , vol.274 , pp. 10802-10806
    • Bonini, M.G.1    Radi, R.2    Ferrer-Sueta, G.3    Da-Costa Ferreira, A.M.4    Augusto, O.5
  • 27
    • 0033599558 scopus 로고    scopus 로고
    • Hydroxyl radical formation during peroxynitrous acid decomposition
    • Coddington, J. W., Hurst, J. K., and Lymar, S. V. (1999) Hydroxyl radical formation during peroxynitrous acid decomposition. J. Am. Chem. Soc. 121, 2438-2443.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2438-2443
    • Coddington, J.W.1    Hurst, J.K.2    Lymar, S.V.3
  • 29
    • 0000980609 scopus 로고
    • Diabetes mellitus
    • (Braunwald, E., Isselbacher, K. J., Petersorf, R. G., Wilson, J. D., Martin, J. B., and Fauci, A. S., Eds.) McGraw-Hill, New York
    • Foster, D. W. (1987) Diabetes mellitus. In Harrison's Principles of Internal Medicine (Braunwald, E., Isselbacher, K. J., Petersorf, R. G., Wilson, J. D., Martin, J. B., and Fauci, A. S., Eds.) pp 1778-1796, McGraw-Hill, New York.
    • (1987) Harrison's Principles of Internal Medicine , pp. 1778-1796
    • Foster, D.W.1
  • 31
    • 0032032567 scopus 로고    scopus 로고
    • Determination of optimal conditions for synthesis of peroxynitrite by mixing acidified hydrogen peroxide with nitrite
    • Saha, A., Goldstein, S., Cabelli, D., and Czaspki, G. (1998) Determination of optimal conditions for synthesis of peroxynitrite by mixing acidified hydrogen peroxide with nitrite. Free Radical Biol. Med. 24, 653-659.
    • (1998) Free Radical Biol. Med. , vol.24 , pp. 653-659
    • Saha, A.1    Goldstein, S.2    Cabelli, D.3    Czaspki, G.4
  • 32
    • 0029661922 scopus 로고    scopus 로고
    • 3+, and oxygen react with DNA-derived radicals formed during iron-mediated Fenton reactions
    • 3+, and oxygen react with DNA-derived radicals formed during iron-mediated Fenton reactions. Biochemistry 35, 12212-12219.
    • (1996) Biochemistry , vol.35 , pp. 12212-12219
    • Henle, E.S.1    Luo, Y.2    Linn, S.3
  • 33
    • 0026768075 scopus 로고
    • Detection of lipid radicals by electron paramagnetic resonance spin trapping using intact cells enriched with polyunsaturated acids
    • North, J. A., Spectro, A. A., and Buettner, G. (1992) Detection of lipid radicals by electron paramagnetic resonance spin trapping using intact cells enriched with polyunsaturated acids. J. Biol. Chem. 267, 5743-5746.
    • (1992) J. Biol. Chem. , vol.267 , pp. 5743-5746
    • North, J.A.1    Spectro, A.A.2    Buettner, G.3
  • 34
    • 0028455102 scopus 로고
    • Simulation of multiple isotropic spin-trap EPR spectra
    • Duling, D. R. (1994) Simulation of multiple isotropic spin-trap EPR spectra. J. Magn. Reson. 104, 105-110.
    • (1994) J. Magn. Reson. , vol.104 , pp. 105-110
    • Duling, D.R.1
  • 37
    • 0002668281 scopus 로고
    • Chemistry of iron and copper in radical reactions
    • (Rice-Evans, C. A., and Burdon, R. H., Eds.) Elsevier Science B. V., Amsterdam
    • Koppenol, W. H. (1994) Chemistry of iron and copper in radical reactions. In Free Radical Damage and its Control (Rice-Evans, C. A., and Burdon, R. H., Eds.) pp 3-24, Elsevier Science B. V., Amsterdam.
    • (1994) Free Radical Damage and Its Control , pp. 3-24
    • Koppenol, W.H.1
  • 39
    • 0030724502 scopus 로고    scopus 로고
    • Detection of free radicals produced from the reaction of cytochrome P-450 with linoleic acid hydroperoxide
    • Rota, C., Barr, D. P., Martin, M. V., Guengerich, F. P., Tomasi, A., and Mason, R. P. (1997) Detection of free radicals produced from the reaction of cytochrome P-450 with linoleic acid hydroperoxide. Biochem. J. 328, 565-571.
    • (1997) Biochem. J. , vol.328 , pp. 565-571
    • Rota, C.1    Barr, D.P.2    Martin, M.V.3    Guengerich, F.P.4    Tomasi, A.5    Mason, R.P.6
  • 41
    • 11944262823 scopus 로고
    • Rapid reaction between peroxynitrite ion and carbon dioxide: Implications for biological activity
    • Lymar, S. V., and Hurst, J. K. (1995) Rapid reaction between peroxynitrite ion and carbon dioxide: implications for biological activity. J. Am. Chem. Soc. 117, 8867-8868.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 8867-8868
    • Lymar, S.V.1    Hurst, J.K.2
  • 42
    • 0032928174 scopus 로고    scopus 로고
    • Direct observation of intermediates in the reaction of peroxynitrite with carbon dioxide
    • Meli, R., Nauser, T., and Koppenol, W. H. (1999) Direct observation of intermediates in the reaction of peroxynitrite with carbon dioxide. Helv. Chim. Acta 82, 722-725.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 722-725
    • Meli, R.1    Nauser, T.2    Koppenol, W.H.3
  • 43
    • 0344660458 scopus 로고
    • Reaction of aldehyde and hydrogen peroxide in aqueous solution. Kinetics of the initial reaction
    • Satterfield, C. N., and Case, L. C. (1954) Reaction of aldehyde and hydrogen peroxide in aqueous solution. Kinetics of the initial reaction. Ind. Eng. Chem. 46, 998-1001.
    • (1954) Ind. Eng. Chem. , vol.46 , pp. 998-1001
    • Satterfield, C.N.1    Case, L.C.2
  • 44
    • 0031023654 scopus 로고    scopus 로고
    • Metabolic fate of peroxynitrite in aqueous solution. Reaction with nitric oxide and pH-dependent decompositon to nitrite and oxygen in a 2:1 stoichiometry
    • Pfeiffer, S., Gorren, A. C. F., Schmidt, K., Werner, E. R., Hansert, B., Bohle, D. S., and Mayer, B. (1997) Metabolic fate of peroxynitrite in aqueous solution. Reaction with nitric oxide and pH-dependent decompositon to nitrite and oxygen in a 2:1 stoichiometry. J. Biol. Chem. 272, 3465-3470.
    • (1997) J. Biol. Chem. , vol.272 , pp. 3465-3470
    • Pfeiffer, S.1    Gorren, A.C.F.2    Schmidt, K.3    Werner, E.R.4    Hansert, B.5    Bohle, D.S.6    Mayer, B.7
  • 45
    • 0024586569 scopus 로고
    • Chemiluminescence from acetaldehyde oxidation by xanthine oxidase involves generation of and interactions with hydroxyl radicals
    • Puntarulo, S., and Cederbaum, A. I. (1989) Chemiluminescence from acetaldehyde oxidation by xanthine oxidase involves generation of and interactions with hydroxyl radicals. Alcohol.: Clin. Exp. Res. 13, 84-90.
    • (1989) Alcohol.: Clin. Exp. Res. , vol.13 , pp. 84-90
    • Puntarulo, S.1    Cederbaum, A.I.2
  • 46
    • 0028260824 scopus 로고
    • Free radical activation of acetaldehyde and its role in protein alkylation
    • Albano, E., Clot, P., Comoglio, A., Dianzani, M. U., and Tomasi, A. (1994) Free radical activation of acetaldehyde and its role in protein alkylation. FEBS Lett. 348, 65-69.
    • (1994) FEBS Lett. , vol.348 , pp. 65-69
    • Albano, E.1    Clot, P.2    Comoglio, A.3    Dianzani, M.U.4    Tomasi, A.5
  • 47
    • 0025168419 scopus 로고
    • DNA cleavage during ethanol metabolism: Role of superoxide radicals and catalytic iron
    • Rajasinghe, H., Jayatilleke, E., and Raw, S. (1990) DNA cleavage during ethanol metabolism: role of superoxide radicals and catalytic iron. Life Sci. 47, 807-814.
    • (1990) Life Sci. , vol.47 , pp. 807-814
    • Rajasinghe, H.1    Jayatilleke, E.2    Raw, S.3
  • 49
    • 0026000505 scopus 로고
    • Electron spin resonance study of free radicals produced from ethanol and acetaldehyde after exposure to a Fenton system or to brain and liver microsomes
    • Gonthier, B., Jeunet, A., and Barret, L. (1991) Electron spin resonance study of free radicals produced from ethanol and acetaldehyde after exposure to a Fenton system or to brain and liver microsomes. Alcohol 8, 369-375.
    • (1991) Alcohol , vol.8 , pp. 369-375
    • Gonthier, B.1    Jeunet, A.2    Barret, L.3
  • 50
    • 0000123597 scopus 로고
    • The rapid hydration of the acetyl radical. A pulse radiolysis study of acetaldehyde in aqueous solution
    • Schuchmann, M. N., and von Sonntag, C. (1988) The rapid hydration of the acetyl radical. A pulse radiolysis study of acetaldehyde in aqueous solution. J. Am. Chem, Soc. 110, 5698-5701.
    • (1988) J. Am. Chem, Soc. , vol.110 , pp. 5698-5701
    • Schuchmann, M.N.1    Von Sonntag, C.2
  • 51
    • 0040292083 scopus 로고
    • Thiol catalysis of the homolytic decomposition of aldehydes
    • Harris, E. F. P., and Waters, W. A. (1952) Thiol catalysis of the homolytic decomposition of aldehydes. Nature 170, 212-213.
    • (1952) Nature , vol.170 , pp. 212-213
    • Harris, E.F.P.1    Waters, W.A.2
  • 52
    • 37049094912 scopus 로고
    • Electron spin resonance studies. Part L. Reactions of alkoxyl radicals generated from alkyl hydroperoxides and titanium(III) ion in aqueous solution
    • Gilbert, B., Holmes, R. G. G., Laue, H. A. H., and Norman, R. O. C. (1976) Electron spin resonance studies. Part L. Reactions of alkoxyl radicals generated from alkyl hydroperoxides and titanium(III) ion in aqueous solution. J. Chem. Soc., Perkin Trans. 2, 1047-1052.
    • (1976) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1047-1052
    • Gilbert, B.1    Holmes, R.G.G.2    Laue, H.A.H.3    Norman, R.O.C.4
  • 54
    • 0000181094 scopus 로고
    • Formation and decay of peroxynitric acid: A pulse radiolysis study
    • Logagen, T., and Sehested, K. (1993). Formation and decay of peroxynitric acid: A pulse radiolysis study. J. Phys. Chem. 97, 10047-10052.
    • (1993) J. Phys. Chem. , vol.97 , pp. 10047-10052
    • Logagen, T.1    Sehested, K.2
  • 57
    • 0019436209 scopus 로고
    • Determinants of plasma free acetaldehyde levels during the oxidation of ethanol. Effects of chronic ethanol feeding
    • Pikkarainen, P. H., Gordon, E. R., Lebsack, M. E., and Lieber, C. S. (1981) Determinants of plasma free acetaldehyde levels during the oxidation of ethanol. Effects of chronic ethanol feeding. Biochem. Pharmacol. 30, 799-802.
    • (1981) Biochem. Pharmacol. , vol.30 , pp. 799-802
    • Pikkarainen, P.H.1    Gordon, E.R.2    Lebsack, M.E.3    Lieber, C.S.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.