메뉴 건너뛰기




Volumn 17, Issue 11, 2004, Pages 1510-1519

Spiroiminodihydantoin and guanidinohydantoin are the dominant products of 8-oxoguanosine oxidation at low fluxes of peroxynitrite: Mechanistic studies with 18O

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRIOXO[1,3,5]TRIAZINANE 1 CARBOXAMIDINE; 4 HYDROXYDIOXOIMIDAZOLIDINE 4 CARBOXYLIC ACID; 8 OXOGUANOSINE; ANION; DEHYDROGUANIDINOHYDANTOIN; GUANIDINE DERIVATIVE; GUANIDINOHYDANTOIN; GUANOSINE DERIVATIVE; HYDANTOIN DERIVATIVE; IMINE; N NITRO DEHYDROGUANIDINOHYDANTOIN; OXIDIZING AGENT; OXYGEN 18; PEROXYNITRITE; SPIRO COMPOUND; SPIROIMINODIHYDANTOIN; TRIAZINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

EID: 8844267545     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0400048     Document Type: Article
Times cited : (74)

References (69)
  • 1
  • 2
    • 0029037495 scopus 로고
    • The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide
    • Pryor, W. A., and Squadrito, G. L. (1995) The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide. Am. J. Physiol. 268, L699-L722.
    • (1995) Am. J. Physiol. , vol.268
    • Pryor, W.A.1    Squadrito, G.L.2
  • 4
    • 0032578174 scopus 로고    scopus 로고
    • The complex chemistry of peroxynitrite decomposition: New insights
    • Richeson, C. E., Mulder, P., Bowry, V. W., and Ingold, C. K. (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, C.K.4
  • 5
    • 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, 8867-8868.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8867-8868
    • Coddington, J.W.1    Hurst, J.K.2    Lymar, S.V.3
  • 6
    • 11944262823 scopus 로고
    • Rapid reaction between peroxonitrite ion and carbon dioxide: Implications for biological activity
    • Lymar, S. V., and Hurst, J. K. (1995) Rapid reaction between peroxonitrite 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
  • 7
    • 0030249458 scopus 로고    scopus 로고
    • Peroxynitrite reaction with carbon dioxide/carbonate: Kinetics and influence on peroxynitrite-mediated oxidations
    • Denicola, A., Freeman, B. A., Trujillo, M., and Radi, R. (1996) Peroxynitrite reaction with carbon dioxide/carbonate: Kinetics and influence on peroxynitrite-mediated oxidations. Arch. Biochem. Biophys. 333, 49-58.
    • (1996) Arch. Biochem. Biophys. , vol.333 , pp. 49-58
    • Denicola, A.1    Freeman, B.A.2    Trujillo, M.3    Radi, R.4
  • 8
    • 0029867717 scopus 로고    scopus 로고
    • Acceleration of peroxynitrite oxidations by carbon dioxide
    • Uppu, R. M., Squadrito, G. L., and Pryor, W. A. (1996) Acceleration of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys. 327, 335-343.
    • (1996) Arch. Biochem. Biophys. , vol.327 , pp. 335-343
    • Uppu, R.M.1    Squadrito, G.L.2    Pryor, W.A.3
  • 9
    • 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
  • 10
    • 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
  • 12
    • 0031750066 scopus 로고    scopus 로고
    • Manganese porphyrins as redox-coupled peroxynitrite reductases
    • Lee, J., Hunt, J. A., and Groves, J. T. (1998) Manganese porphyrins as redox-coupled peroxynitrite reductases. J. Am. Chem. Soc. 120, 6053-6061.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6053-6061
    • Lee, J.1    Hunt, J.A.2    Groves, J.T.3
  • 13
    • 0029117519 scopus 로고
    • Stopped-flow kinetic study of the reaction of ascorbic acid with peroxynitrite
    • Squadrito, G. L., Jin, X., and Pryor, W. A. (1995) Stopped-flow kinetic study of the reaction of ascorbic acid with peroxynitrite. Arch. Biochem. Biophys. 322, 53-59.
    • (1995) Arch. Biochem. Biophys. , vol.322 , pp. 53-59
    • Squadrito, G.L.1    Jin, X.2    Pryor, W.A.3
  • 15
    • 0025730414 scopus 로고
    • Peroxynitrite oxidation of sulfhydryls: The cytotoxic potential of superoxide and nitric oxide
    • Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite oxidation of sulfhydryls: The cytotoxic potential of superoxide and nitric oxide. J. Biol. Chem. 266, 4244-4259.
    • (1991) J. Biol. Chem. , vol.266 , pp. 4244-4259
    • Radi, R.1    Beckman, J.S.2    Bush, K.M.3    Freeman, B.A.4
  • 16
    • 0026782383 scopus 로고
    • Inactivation of α-1-proteinase inhibitor by peroxynitrite
    • Moreno, J. J., and Pryor, W. A. (1992) Inactivation of α-1-proteinase inhibitor by peroxynitrite. Chem. Res. Toxicol. 5, 425-431.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 425-431
    • Moreno, J.J.1    Pryor, W.A.2
  • 17
    • 0028335587 scopus 로고
    • Peroxynitrite-mediated oxidation of albumin to the protein-thiyl free radical
    • Gatti, R. M., Radi, R., and Augusto, O. (1994) Peroxynitrite-mediated oxidation of albumin to the protein-thiyl free radical. FEBS Lett. 348, 287-290.
    • (1994) FEBS Lett. , vol.348 , pp. 287-290
    • Gatti, R.M.1    Radi, R.2    Augusto, O.3
  • 18
    • 0028175539 scopus 로고
    • Mechanism of covalent modification of glyceraldehyde-3-phosphate dehydrogenase at its active site thiol by nitric oxide, peroxynitrite and related nitrosating agents
    • Mohr, S., Stamler, J. S., and Brune, B. (1994) Mechanism of covalent modification of glyceraldehyde-3-phosphate dehydrogenase at its active site thiol by nitric oxide, peroxynitrite and related nitrosating agents. FEBS Lett. 348, 223-227.
    • (1994) FEBS Lett. , vol.348 , pp. 223-227
    • Mohr, S.1    Stamler, J.S.2    Brune, B.3
  • 19
    • 0028937652 scopus 로고
    • Sensitivity of the essential zinc-thiolate moiety of yeast alcohol dehydrogenase to hypochlorite and peroxynitrite
    • Crow, J. P., Beckman, J. S., and McCord, J. M. (1995) Sensitivity of the essential zinc-thiolate moiety of yeast alcohol dehydrogenase to hypochlorite and peroxynitrite. Biochemistry 34, 3544-3552.
    • (1995) Biochemistry , vol.34 , pp. 3544-3552
    • Crow, J.P.1    Beckman, J.S.2    McCord, J.M.3
  • 20
    • 0025874048 scopus 로고
    • Peroxynitrite-induced membrane lipid peroxidation: The cytotoxic potential of superoxide and nitric oxide
    • Radi, R., Beckman, J. S., Bush, K. M., and Freeman, B. A. (1991) Peroxynitrite-induced membrane lipid peroxidation: The cytotoxic potential of superoxide and nitric oxide. Arch. Biochem. Biophys. 288 (2), 481-487.
    • (1991) Arch. Biochem. Biophys. , vol.288 , Issue.2 , pp. 481-487
    • Radi, R.1    Beckman, J.S.2    Bush, K.M.3    Freeman, B.A.4
  • 22
    • 0030577390 scopus 로고    scopus 로고
    • Effects of carbon dioxide/bicarbonate on induction of single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine, and base propenal mediated by peroxynitrite
    • Yermilov, V., Yoshie, Y., Rubio, J., and Ohshima, H. (1996) Effects of carbon dioxide/bicarbonate on induction of single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine, and base propenal mediated by peroxynitrite. FEBS Lett. 399, 67-70.
    • (1996) FEBS Lett. , vol.399 , pp. 67-70
    • Yermilov, V.1    Yoshie, Y.2    Rubio, J.3    Ohshima, H.4
  • 24
    • 0032806606 scopus 로고    scopus 로고
    • Peroxynitrite-induced reactions of synthetic oligonucleotides containing 8-oxoguanine
    • Tretyakova, N. Y., Niles, J. C., Burney, S., Wishnok, J. S., and Tannenbaum, S. R. (1999) Peroxynitrite-induced reactions of synthetic oligonucleotides containing 8-oxoguanine. Chem. Res. Toxicol. 12, 459-466.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 459-466
    • Tretyakova, N.Y.1    Niles, J.C.2    Burney, S.3    Wishnok, J.S.4    Tannenbaum, S.R.5
  • 26
    • 0030010723 scopus 로고    scopus 로고
    • Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA
    • Douki, T., and Cadet, J. (1996) Peroxynitrite mediated oxidation of purine bases of nucleosides and isolated DNA. Free Radical Res. Commun. 24, 369-380.
    • (1996) Free Radical Res. Commun. , vol.24 , pp. 369-380
    • Douki, T.1    Cadet, J.2
  • 27
    • 0033024623 scopus 로고    scopus 로고
    • DNA damage in deoxynucleosides and oligonucleotides treated with peroxynitrite
    • Burney, S., Niles, J. C., Dedon, P. C., and Tannenbaum, S. R. (1999) DNA damage in deoxynucleosides and oligonucleotides treated with peroxynitrite. Chem. Res. Toxicol. 12, 513-520.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 513-520
    • Burney, S.1    Niles, J.C.2    Dedon, P.C.3    Tannenbaum, S.R.4
  • 28
    • 0029135397 scopus 로고
    • Formation of 8-nitroguanine by the reaction of guanine with peroxynitrite in vitro
    • Yermilov, V., Rubio, J., Becchi, M., Friesen, M. D., Pignatelli, B., and Ohshima, H. (1995) Formation of 8-nitroguanine by the reaction of guanine with peroxynitrite in vitro. Carcinogenesis 16, 2045-2050.
    • (1995) Carcinogenesis , vol.16 , pp. 2045-2050
    • Yermilov, V.1    Rubio, J.2    Becchi, M.3    Friesen, M.D.4    Pignatelli, B.5    Ohshima, H.6
  • 29
    • 0035852024 scopus 로고    scopus 로고
    • A novel nitroimidazole compound formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-guanosine
    • Niles, J. C., Wishnok, J. S., and Tannenbaum, S. R. (2001) A novel nitroimidazole compound formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-guanosine. J. Am. Chem Soc. 123, 12147-12151.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12147-12151
    • Niles, J.C.1    Wishnok, J.S.2    Tannenbaum, S.R.3
  • 30
    • 0035810395 scopus 로고    scopus 로고
    • Spiroiminodihydantoin is the major product of the 8-oxo-7,8- dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue
    • Niles, J. C., Wishnok, J. S., and Tannenbaum, S. R. (2001) Spiroiminodihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue. Org. Lett. 3,963-966.
    • (2001) Org. Lett. , vol.3 , pp. 963-966
    • Niles, J.C.1    Wishnok, J.S.2    Tannenbaum, S.R.3
  • 31
    • 0032742691 scopus 로고    scopus 로고
    • Peroxynitrite reaction products of 3′,5′-di-O-acetyl-8-oxo-7, 8-dihydro-2′-deoxyguanosine
    • Niles, J. C., Burney, S., Singh, S., Wishnok, J. S., and Tannenbaum, S. R. (1999) Peroxynitrite reaction products of 3′,5′-di-O-acetyl-8- oxo-7,8-dihydro-2′-deoxyguanosine. Proc. Natl. Acad. Sci. U.S.A. 96, 11729-11734.
    • (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 11729-11734
    • Niles, J.C.1    Burney, S.2    Singh, S.3    Wishnok, J.S.4    Tannenbaum, S.R.5
  • 32
    • 0034079273 scopus 로고    scopus 로고
    • A novel nitration product formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-Nitro-N'-[2,3,5-tri-O-acetyl-β-D-erythro-pentofuranosyl)-2, 4-dixoimidazolidin-5-ylidinelguanidine
    • Niles, J. C., Wishnok, J. S., and Tannenbaum, S. R. (2000) A novel nitration product formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-7,8-dihydro-8-oxoguanosine: N-Nitro-N'-[2,3,5-tri-O-acetyl-β-D-erythro-pentofuranosyl)-2, 4-dixoimidazolidin-5-ylidinelguanidine. Chem. Res. Toxicol. 13, 390-396.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 390-396
    • Niles, J.C.1    Wishnok, J.S.2    Tannenbaum, S.R.3
  • 33
    • 0028007172 scopus 로고
    • Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury
    • Haddad, I. Y., Pataki, G., Hu, P., Galliani, C., Beckman, J. S., and Matalon, S. (1994) Quantitation of nitrotyrosine levels in lung sections of patients and animals with acute lung injury. J. Clin. Invest. 94, 2407-2413.
    • (1994) J. Clin. Invest. , vol.94 , pp. 2407-2413
    • Haddad, I.Y.1    Pataki, G.2    Hu, P.3    Galliani, C.4    Beckman, J.S.5    Matalon, S.6
  • 35
    • 0027930057 scopus 로고
    • Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitrotyrosine in serum synovial fluid from rheumatoid patients
    • Kaur, H., and Halliwell, B. (1994) Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. Nitrotyrosine in serum synovial fluid from rheumatoid patients. FEBS Lett. 350, 9-12.
    • (1994) FEBS Lett. , vol.350 , pp. 9-12
    • Kaur, H.1    Halliwell, B.2
  • 37
    • 0034487279 scopus 로고    scopus 로고
    • A novel procedure for generating both nitric oxide and superoxide in situ from chemical sources at any chosen mole ratio. First application: Tyrosine oxidation and a comparison with preformed peroxynitrite
    • Hodges, G. R., Marwaha, J., Paul, T., and Ingold, K. U. (2000) A novel procedure for generating both nitric oxide and superoxide in situ from chemical sources at any chosen mole ratio. First application: Tyrosine oxidation and a comparison with preformed peroxynitrite. Chem. Res. Toxicol. 13, 1287-1293.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 1287-1293
    • Hodges, G.R.1    Marwaha, J.2    Paul, T.3    Ingold, K.U.4
  • 38
    • 0032538450 scopus 로고    scopus 로고
    • Lack of tyrosine nitration by peroxynitrite generated at physiological pH
    • Pfeiffer, S., and Mayer, B. (1998) Lack of tyrosine nitration by peroxynitrite generated at physiological pH. J. Biol. Chem. 273, 27280-27285.
    • (1998) J. Biol. Chem. , vol.273 , pp. 27280-27285
    • Pfeiffer, S.1    Mayer, B.2
  • 39
    • 0034092778 scopus 로고    scopus 로고
    • Dityrosine formation outcompetes tyrosine nitration at low steady-state concentrations of peroxynitrite. Implications for tyrrosine modification by nitric oxide/superoxide in vivo
    • Pfeiffer, S., Schmidt, K., and Mayer, B. (2000) Dityrosine formation outcompetes tyrosine nitration at low steady-state concentrations of peroxynitrite. Implications for tyrrosine modification by nitric oxide/superoxide in vivo. J. Biol. Chem. 275, 6346-6352.
    • (2000) J. Biol. Chem. , vol.275 , pp. 6346-6352
    • Pfeiffer, S.1    Schmidt, K.2    Mayer, B.3
  • 40
    • 0034603053 scopus 로고    scopus 로고
    • Tyrosine nitration by simultaneous generation of (.)NO and O-(2) under physiological conditions. How the radicals do the job
    • Goldstein, S., Czapski, G., Lind, J., and Merenyi, G. (2000) Tyrosine nitration by simultaneous generation of (.)NO and O-(2) under physiological conditions. How the radicals do the job. J. Biol. Chem. 275, 3031-3036.
    • (2000) J. Biol. Chem. , vol.275 , pp. 3031-3036
    • Goldstein, S.1    Czapski, G.2    Lind, J.3    Merenyi, G.4
  • 42
    • 0029991419 scopus 로고    scopus 로고
    • Synthesis of peroxynitrite in a two-phase system using isoamyl nitrite and hydrogen peroxide
    • Uppu, R. M., and Pryor, W. A. (1996) Synthesis of peroxynitrite in a two-phase system using isoamyl nitrite and hydrogen peroxide. Anal. Biochem. 236, 242-249.
    • (1996) Anal. Biochem. , vol.236 , pp. 242-249
    • Uppu, R.M.1    Pryor, W.A.2
  • 43
    • 37049135943 scopus 로고
    • The chemistry of pernitrites. Part I. Kinetics of decomposition of pernitrous acid
    • Hughes, M. N., and Nicklin, H. G. (1968) The chemistry of pernitrites. Part I. Kinetics of decomposition of pernitrous acid. J. Chem. Soc. 450-452.
    • (1968) J. Chem. Soc. , pp. 450-452
    • Hughes, M.N.1    Nicklin, H.G.2
  • 45
    • 0001453407 scopus 로고
    • O-transfer reactions of carbonate radical-anion
    • Lilie, J., Hanrahan, R., and Henglein, A. (1978) O-transfer reactions of carbonate radical-anion. Radiat. Phys. Chem. 11, 225-227.
    • (1978) Radiat. Phys. Chem. , vol.11 , pp. 225-227
    • Lilie, J.1    Hanrahan, R.2    Henglein, A.3
  • 46
    • 0034624588 scopus 로고    scopus 로고
    • Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine
    • Luo, W., Muller, J. G., Rachlin, E. M., and Burrows, C. J. (2000) Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine. Org. Lett. 2, 613-616.
    • (2000) Org. Lett. , vol.2 , pp. 613-616
    • Luo, W.1    Muller, J.G.2    Rachlin, E.M.3    Burrows, C.J.4
  • 47
    • 0026772501 scopus 로고
    • Redox ribonucleosides. Isolation and characterization of 5-hydroxyuridine, 8 hydroxy guanosine, and 8-hydroxyadenosine from Torula yeast RNA
    • Yanagawa, H., Ogawa, Y., and Ueno, M. (1992) Redox ribonucleosides. Isolation and characterization of 5-hydroxyuridine, 8 hydroxy guanosine, and 8-hydroxyadenosine from Torula yeast RNA. J. Biol. Chem. 267, 13320-13326.
    • (1992) J. Biol. Chem. , vol.267 , pp. 13320-13326
    • Yanagawa, H.1    Ogawa, Y.2    Ueno, M.3
  • 49
    • 0034653650 scopus 로고    scopus 로고
    • The trap depth (in DNA) of 8-Oxo-7,8-dihydro-2′-deoxyguanosine as derived from electron-transfer equilibria in aqueous solution
    • Steenken, S., Jovanovic, S. V., Bietti, M., and Bernhard, K. (2000) The trap depth (in DNA) of 8-Oxo-7,8-dihydro-2′-deoxyguanosine as derived from electron-transfer equilibria in aqueous solution. J. Am. Chem. Soc. 122, 2373-2374.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2373-2374
    • Steenken, S.1    Jovanovic, S.V.2    Bietti, M.3    Bernhard, K.4
  • 50
    • 0001874683 scopus 로고
    • Reduction potentials involving inorganic free radicals in aqueous solution
    • Stanbury, D. M. (1989) Reduction potentials involving inorganic free radicals in aqueous solution. Adv. Inorg. Chem. 33, 69-138.
    • (1989) Adv. Inorg. Chem. , vol.33 , pp. 69-138
    • Stanbury, D.M.1
  • 51
    • 0025812909 scopus 로고
    • Electron-transfer reaction rates and equilibria of the carbonate and sulfate radical anions
    • Huie, R. E., Clifton, C. L., and Neta, P. (1991) Electron-transfer reaction rates and equilibria of the carbonate and sulfate radical anions. Radiat. Phys. Chem. 38, 477-481.
    • (1991) Radiat. Phys. Chem. , vol.38 , pp. 477-481
    • Huie, R.E.1    Clifton, C.L.2    Neta, P.3
  • 52
    • 84889557831 scopus 로고
    • Rate constants for reactions of inorganic radicals in aqueous solution
    • Neta, P., Huie, R. E., and Ross, A. B. (1988) Rate constants for reactions of inorganic radicals in aqueous solution. J. Phys. Chem. Ref. Data 17, 1027-1284.
    • (1988) J. Phys. Chem. Ref. Data , vol.17 , pp. 1027-1284
    • Neta, P.1    Huie, R.E.2    Ross, A.B.3
  • 53
    • 0035816604 scopus 로고    scopus 로고
    • The carbonate radical is a site-selective oxidizing agent of guanine in double-stranded oligonucleotides
    • Shafirovich, V., Dourandin, A., Huang, W., and Geacintov, N. E. (2001) The carbonate radical is a site-selective oxidizing agent of guanine in double-stranded oligonucleotides. J. Biol. Chem. 276, 24621-24626.
    • (2001) J. Biol. Chem. , vol.276 , pp. 24621-24626
    • Shafirovich, V.1    Dourandin, A.2    Huang, W.3    Geacintov, N.E.4
  • 54
    • 0035105114 scopus 로고    scopus 로고
    • Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro-2′- deoxyguanosine but not of 2′-deoxyguanosine
    • Shafirovich, V., Cadet, J., Gasparutto, D., Dourandin, A., and Geacintov, N. E. (2001) Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro- 2′-deoxyguanosine but not of 2′-deoxyguanosine. Chem. Res. Toxicol. 14, 233-241.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 233-241
    • Shafirovich, V.1    Cadet, J.2    Gasparutto, D.3    Dourandin, A.4    Geacintov, N.E.5
  • 55
    • 84918833988 scopus 로고
    • Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms, and hydroxy lradicals
    • Buxton, G. V., Greenstock, C. L., Helman, W. P., and Ross, A. B. (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms, and hydroxy lradicals. J. Phys. Chem. Ref Data 17, 513-886.
    • (1988) J. Phys. Chem. Ref. Data , vol.17 , pp. 513-886
    • Buxton, G.V.1    Greenstock, C.L.2    Helman, W.P.3    Ross, A.B.4
  • 56
  • 58
    • 0036917332 scopus 로고    scopus 로고
    • Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide
    • Chworos, A., Seguy, C., Pratviel, G., and Meunier, B. (2002) Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide. Chem. Res. Toxicol. 15, 1643-1651.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 1643-1651
    • Chworos, A.1    Seguy, C.2    Pratviel, G.3    Meunier, B.4
  • 59
    • 0035817980 scopus 로고    scopus 로고
    • The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine
    • Luo, W., Muller, J. G., and Burrows, C. J. (2001) The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8- dihydroguanosine. Org. Lett. 3, 2801-2804.
    • (2001) Org. Lett. , vol.3 , pp. 2801-2804
    • Luo, W.1    Muller, J.G.2    Burrows, C.J.3
  • 60
    • 0031171324 scopus 로고    scopus 로고
    • Electrochemical and enzymatic oxidation of guanosine and 8-hydroxyguanosine and the effects of oxidation products in mice
    • Goyal, R. N., Jain, M., and Garg, D. K. (1997) Electrochemical and enzymatic oxidation of guanosine and 8-hydroxyguanosine and the effects of oxidation products in mice. Bioelectrochem. Bioenerg. 43, 105-114.
    • (1997) Bioelectrochem. Bioenerg. , vol.43 , pp. 105-114
    • Goyal, R.N.1    Jain, M.2    Garg, D.K.3
  • 62
    • 0030757239 scopus 로고    scopus 로고
    • Identification of the true product of the urate oxidase reaction
    • Kahn, K., Serfozo, P., and Tipton, P. A. (1997) Identification of the true product of the urate oxidase reaction. J. Am. Chem. Soc. 119, 5435-5442.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5435-5442
    • Kahn, K.1    Serfozo, P.2    Tipton, P.A.3
  • 63
    • 1542509982 scopus 로고
    • The mechanism for the conversion of uric acid into uroxanate and allantoin. A new base-induced 1,2-carboxylate shift
    • Poje, M., and Sokolic-Maravic, L. (1988) The mechanism for the conversion of uric acid into uroxanate and allantoin. A new base-induced 1,2-carboxylate shift. Tetrahedron 44, 6723-6728.
    • (1988) Tetrahedron , vol.44 , pp. 6723-6728
    • Poje, M.1    Sokolic-Maravic, L.2
  • 64
    • 0003122318 scopus 로고
    • The free radical decomposition of peroxymonosulfate
    • Marsh, C., and Edwards, J. O. (1989) The free radical decomposition of peroxymonosulfate. Prog. React. Kinet. 15, 35-75.
    • (1989) Prog. React. Kinet. , vol.15 , pp. 35-75
    • Marsh, C.1    Edwards, J.O.2
  • 65
  • 66
    • 0033555373 scopus 로고    scopus 로고
    • Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine
    • Duarte, V., Muller, J. G., and Burrows, C. J. (1999) Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Res. 27, 496-502.
    • (1999) Nucleic Acids Res. , vol.27 , pp. 496-502
    • Duarte, V.1    Muller, J.G.2    Burrows, C.J.3
  • 67
    • 0030942577 scopus 로고    scopus 로고
    • The nitric oxide/superoxide assay. Insights into the biological chemistry of the NO/O-2. Interaction
    • Kelm, M., Dahmann, R., Wink, D., and Feelisch, M. (1997) The nitric oxide/superoxide assay. Insights into the biological chemistry of the NO/O-2. interaction. J. Biol. Chem. 272, 9922-9932.
    • (1997) J. Biol. Chem. , vol.272 , pp. 9922-9932
    • Kelm, M.1    Dahmann, R.2    Wink, D.3    Feelisch, M.4
  • 68
    • 0030566871 scopus 로고    scopus 로고
    • Kinetic study of the reaction of ebselen with peroxynitrite
    • Masumoto, H., Kissner, R., Koppenol, W. H., and Sies, H. (1996) Kinetic study of the reaction of ebselen with peroxynitrite. FEBS Lett. 398, 179-182.
    • (1996) FEBS Lett. , vol.398 , pp. 179-182
    • Masumoto, H.1    Kissner, R.2    Koppenol, W.H.3    Sies, H.4
  • 69
    • 0031460696 scopus 로고    scopus 로고
    • Peroxynitrite rapidly permeates phospholipid membranes
    • Marla, S. S., Lee, J., and Groves, J. T. (1997) Peroxynitrite rapidly permeates phospholipid membranes. Proc. Natl. Acad. Sci. U.S.A. 94, 14243-14248.
    • (1997) Proc. Natl. Acad. Sci. U.S.A. , vol.94 , pp. 14243-14248
    • Marla, S.S.1    Lee, J.2    Groves, J.T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.