1770 Chem. Res. Toxicol., Vol. 23, No. 11, 2010
Massari et al.
(14) Thornalley, P., Yurek-George, A., and Argirov, O. K. (2000) Kinectics
and mechanism of the reaction of aminoguanidine with the R-oxoal-
dehydes glyoxal, methylglyoxal, and 3-deoxyglucosone under physi-
ological conditions. Biochem. Pharmacol. 60, 55–65.
(15) Massari, J., Fujiy, D. E., Dutra, F., Vaz, S. M., Costa, A. C. O., Micke,
G. A., Tavares, M. F. M., Tokikawa, R., Assunc¸a˜o, N. A., and Bechara,
E. J. H. (2008) Radical acetylation of 2′-deoxyguanosine and L-
histidine coupled to the reaction of diacetyl with peroxynitrite in
aerated medium. Chem. Res. Toxicol. 21, 879–887.
(34) Beers, R. F., and Sizer, W. I. (1952) A spectrophotometric method
for measuring the breakdown of hydrogen peroxide by catalase. J. Biol.
Chem. 195, 133–140.
(35) Hughes, M. N., and Nicklin, H. G. (1968) Chemistry of pernitrites. I.
Kinetics of decomposition of pernitrous acid. J. Chem. Soc. A, 450–
452.
(36) Gilbert, R. P., and Brandt, R. B. (1975) Spectrophotometric determi-
nation of methyl glyoxal with 2,4-dinitrophenylhydrazine. Anal. Chem.
47, 2418–2422.
(37) Betterton, E. A., and Hoffman, M. R. (1987) Kinetics, mechanism,
and thermodynamics of the reversible-reaction of methylglyoxal
(CH3COCHO) with S(IV). J. Phys. Chem. 91, 3011–3020.
(38) 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.
(39) Uppu, R. M., Squadrito, G. L., and Pryor, W. A. (1996) Acceleration
of peroxynitrite oxidations by carbon dioxide. Arch. Biochem. Biophys.
327, 335–343.
(40) Denicola, A., Freeman, B. A., Trujillo, M., and Radi, R. (1996)
Peroxynitrite reaction with carbon dioxide/bicarbonate: Kinetics and
influence on peroxynitrite-mediated oxidations. Arch. Biochem. Bio-
phys. 333, 49–58.
(41) Gupta, D., Harish, B., Kissner, R., and Koppenol, W. H. (2009)
Peroxynitrate is formed rapidly during decomposition of peroxynitrite
at neutral pH. Dalton Trans., 5730–5736.
(42) Miyamoto, S., Ronsein, G. E., Correˆa, T. C., Martinez, G. R., Medeiros,
M. H. G., and Di Mascio, P. (2009) Direct evidence of singlet
molecular oxygen generation from peroxynitrate, a decomposition
product of peroxynitrite. Dalton Trans., 5720–5729.
(43) Gunther, M. R., Peters, J. A., and Sivaneri, M. K. (2002) Histidinyl
radical formation in the self-peroxidation reaction of bovine copper-
zinc superoxide dismutase. J. Biol. Chem. 277, 9160–9166.
(44) Makino, K., Suzuki, N., Moriya, F., Rokushika, S., and Hatano, H.
(1981) A fundamental-study on aqueous-solutions of 2-methyl-2-
nitrosopropane as a spin trap. Radiat. Res. 86, 294–310.
(45) Nakayama, M., Saito, K., Sato, E., Nakayama, K., Terawaki, H., Ito,
S., and Kohno, M. (2007) Radical generation by the non-enzymatic
reaction of methylglyoxal and hydrogen peroxide. Redox Rep. 12, 125–
133.
(46) Gatti, R. M., Alvarez, B., Vasquez-Vivar, J., Radi, R., and Augusto,
O. (1998) Formation of spin trap adducts during the decomposition
of peroxynitrite. Arch. Biochem. Biophys. 349, 36–46.
(47) Royer, L. O., Knudsen, F. S., de Oliveira, M. A., Tavares, M. F. M.,
and Bechara, E. J. H. (2004) Peroxynitrite-initiated oxidation of
acetoacetate and 2-methylacetoacetate esters by oxygen: Potential
sources of reactive intermediates in keto acidoses. Chem. Res. Toxicol.
17, 1725–1732.
(48) Guo, R., Davies, C. A., Nielsen, B. R., Hamilton, L., Symons, M. C. R.,
and Winyard, P. G. (2002) Reaction of the spin trap 3,5-dibromo-4-
nitrosobenzene sulfonate with human biofluids. Biochim. Biophys. Acta
1572, 133–142.
(49) Trelle, M. B., and Jensen, O. N. (2008) Utility of immonium ions for
assignment of ε-N-acetyllysine-containing peptides by tandem mass
spectrometry. Anal. Chem. 80, 3422–3430.
(50) Va´squez-Vivar, J., Denicola, A., Radi, R., and Augusto, O. (1997)
Peroxynitrite-mediated decarboxylation of pyruvate to both carbon
dioxide and carbon dioxide radical anion. Chem. Res. Toxicol. 10,
786–794.
(51) Miyamoto, S., Ronsein, G. E., Prado, F. M., Uemi, M., Correˆa, T. C.,
Toma, I. N., Bertolucci, A., Oliveira, M. C., Motta, F. D., Medeiros,
M. H. G., and Di Mascio, P. (2007) Biological hydroperoxides and
singlet molecular oxygen generation. IUBMB Life 59, 322–331.
(52) Kitamura, Y., Kawase, M., and Ohmori, S. (2008) Formate excretion
in urine of rats fed dimethylaminoazobenzene-rich diets: The possibility
of formate formation from D-lactate. Acta Med. Okayama 62, 193–203.
(16) Yang, D., Tang, T., Chen, J., Wang, X., Bartberger, M. D., Houk,
K. N., and Olson, L. (1999) Ketone-catalyzed decomposition of
peroxynitrite via dioxirane intermediates. J. Am. Chem. Soc. 121,
11976–11983.
(17) Uppu, R. M., Winston, G. W., and Pryor, W. A. (1997) Reactions of
peroxynitrite with aldehydes as probes for reactive intermediates
responsible for biological nitration. Chem. Res. Toxicol. 10, 1331–
1337.
(18) Nakao, L. S., Ouchi, D., and Augusto, O. (1999) Oxidation of
acetaldehyde by peroxynitrite hydrogen peroxide-iron(II). Production
of acetate and methyl radicals. Chem. Res. Toxicol. 12, 1010–1018.
(19) Augusto, O., Bonini, M. G., Amanso, A. M., Linares, E., Santos, C. C.,
and Menezes, S. L. (2002) Nitrogen dioxe and carbonate radical anion:
Two emerging radicals in biology. Free Radical Biol. Med. 32, 841–
859.
(20) Lobachev, V. L., and Rudakov, E. S. (2006) The chemistry of
peroxynitrite: Reaction mechanisms and kinetics. Russ. Chem. ReV.
75, 375–396.
(21) Medinas, D. B., Cerchiaro, G., Trindade, D. F., and Augusto, O. (2007)
The carbonate radical and related oxidants derived from bicarbonate
buffer. IUBMB Life 59, 255–262.
(22) Ferrer-Sueta, G., and Radi, R. (2009) Chemical biology of peroxyni-
trite: Kinetics, diffusion, and radicals. ACS Chem. Biol. 4, 161–177.
(23) Pacher, P., Beckman, J. S., and Liaudet, L. (2007) Nitric oxide and
peroxynitrite in health and disease. Physiol. ReV. 87, 315–424.
(24) Szabo´, C., Ischiropoulos, H., and Radi, R. (2007) Peroxynitrite:
Biochemistry, pathophysiology and development of therapeutics. Nat.
ReV. Drug DiscoVery 6, 662–680.
(25) Radi, R. (2004) Nitric oxide, oxidants, and protein tyrosine nitration.
Proc. Natl. Acad. Sci. U.S.A. 101, 4003–4008.
(26) Ferrer-Sueta, G., Vitturi, D., Batinic-Haberle, I., Fridovich, I., Gold-
stein, S., Czapski, G., and Radi, R. (2003) Reactions of manganese
porphyrins with peroxynitrite and carbonate radical anion. J. Biol.
Chem. 278, 27432–27438.
(27) Goldstein, S., and Mere´nyi, G. (2008) The chemistry of peroxynitrite:
Implications for biological activity. Methods Enzymol. 436, 49–61.
(28) Rebrin, I., Bregere, C., Gallaher, T. K., and Sohal, R. S. (2008)
Detection and characterization of peroxynitrite-induced modifications
of tyrosine, tryptophan, and methionine residues by tandem mass
spectrometry. Methods Enzymol. 441, 283–294.
(29) Ahmed, N., Babaei-Jadidi, R., Howell, S. K., Beisswenger, P. J., and
Thornalley, P. J. (2005) Degradation products of proteins damaged
by glycation, oxidation and nitration in clinical type 1 diabetes.
Diabetologia 48, 1590–1603.
(30) Ahmed, N., Dobler, D., Dean, M., and Thornalley, P. J. (2005) Peptide
mapping identifies hotspot site of modification in human serum
albumin by methylglyoxal involved in ligand binding and esterase
activity. J. Biol. Chem. 290, 5724–5732.
(31) Kouzarides, T. (2000) Acetylation: A regulatory modification to rival
phosphorylation? EMBO J. 19, 1176–1179.
(32) Kaur, H., Leung, K. H. W., and Perkins, M. J. (1981) A water-soluble,
nitroso-aromatic spin-trap. J. Chem. Soc., Chem. Commun. 3, 142–
143.
(33) Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., and
Freeman, B. A. (1990) Apparent hydroxyl radical production of
peroxynitrite. Implications for endothelial injury from nitric oxide and
superoxide. Proc. Natl. Acad. Sci. U.S.A. 87, 1620–1624.
TX1002244