Nitrogen dioxide-dependent oxidation of uric acid in the human oral cavity under acidic conditions: Implications for its occurrence in acidic dental plaque

Chemical Research in Toxicology

Volumn 23, Issue 6, 2010, Pages 1067-1075

  Takahama, Umeo ^a   Hirota, Sachiko ^b  

^a KYUSHU DENTAL COLLEGE   (Japan)

^b KYUSHU WOMEN'S UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE OXIDASE; NITRITE; NITROGEN DIOXIDE; NITROGEN OXIDE; PEROXIDASE; URIC ACID; ACID; HYDROGEN PEROXIDE;

ACIDITY; ARTICLE; ENZYME INHIBITION; GINGIVA; HUMAN; MOUTH CAVITY; OXIDATION; PH; SALIVA; SIMULATION; TOOTH PLAQUE; ENZYMOLOGY; METABOLISM; MOUTH; OXIDATION REDUCTION REACTION;

ACIDS; DENTAL PLAQUE; GLUCOSE OXIDASE; HUMANS; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; MOUTH; NITROGEN DIOXIDE; OXIDATION-REDUCTION; PEROXIDASE; SALIVA; URIC ACID;

EID: 77953737021     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx1000464     Document Type: Article

References (50)

1. Zetterquist, W., Pedroletti, C., Lundberg, J. O., and Alving, K. (1999) Salivary contribution to exhaled nitric oxide Eur. Respir. J. 13, 327-333
2. Pannala, A. S., Mani, A. R., Spencer, J. P. E., Skinner, Y., Bruckdorfer, K. R., Moore, K. P., and Rice-Evans, C. A. (2003) The effect of dietary nitrate on salivary, plasma and urinary nitrate metabolism in humans Free Radical Biol. Med. 34, 576-584
3. Doel, J. J., Hector, M. P., Amirtham, C. V., Al-Anzan, L. A., Benjamin, N., and Allaker, R. P. (2004) Protective effect of salivary nitrate and microbial nitrate reductase activity against caries Eur. J. Oral Sci. 112, 424-428
4. Doel, J. J., Benjamin, N., Hector, M. P., Rogers, M., and Allaker, R. P. (2005) Evaluation of bacterial nitrate reduction in the human oral cavity Eur. J. Oral Sci. 113, 14-19
5. Palmerini, C. A., Palombari, R., Perito, S., and Arienti, G. (2003) NO synthesis in human saliva Free Radical Res. 37, 29-31
6. Takahama, U., Hirota, S., and Oniki, T. (2005) Production of nitric oxide-derived reactive nitrogen species in human oral cavity and their scavenging by salivary redox components Free Radical Res. 39, 737-745
7. Marsh, P. and Martin, M. V. (1999) Oral Microbiology, 4 th ed., Wright, Oxford, United Kingdom.
8. Edger, M. and Higham, S. (2004) Saliva and the control of plaque pH. In Saliva and Oral Health, 3 rd ed (Edger, M., Dawes, C., and O'Mullane, D., Eds.) pp 72 - 86, British Dental Association, London.
9. McNeill, K. and Hamilton, I. R. (2003) Acid tolerance response of biofilm cells Streptococcus mutans FEMS Microbiol. Lett. 221, 25-30
10. Takahama, U., Imamura, H., and Hirota, S. (2009) Nitration of the salivary component 4-hydroxyphenylacetic acid in the human oral cavity: Enhancement of nitration under acidic conditions Eur. J. Oral Sci. 117, 555-562
11. Carossa, S., Pera, P., Doglio, P., Lombardo, S., Colagrande, P., Brussino, L., Rolle, G., and Bucca, C. (2001) Oral nitric oxide during plaque deposition Eur. J. Clin. Invest. 31, 876-879
12. Bayindir, Y. Z., Polat, M. F., and Seven, N. (2005) Nitirc oxide concentrations in saliva and dental plaque in relation to caries experience and oral hygiene Caries Res. 39, 130-133
13. Zhang, H., Squadrito, G. L., and Pryor, W. A. (1997) The mechanism of the proxynitrite-carbon dioxide reaction probed using tyrosine Nitric Oxide 1, 301-307
14. Lancaster, J. R., Jr. (2006) Nitroxidative, nitrosative, and nitrative stress: Kinetic predictions of reactive nitrogen species chemistry under biological conditions Chem. Res. Toxicol. 19, 1160-1174
15. Halliwell, B. and Gutteridge, J. M. C. (1999) Free Radicals in Biology and Medicine, Oxford University Press, New York.
16. Espey, M. G., Miranda, K. M., Pluta, R. M., and Wink, D. A. (2000) Nitrosative capacity of macrophages is dependent on nitric-oxide synthase induction signals J. Biol. Chem. 275, 11341-11347
17. Hitora, S., Takahama, U., Ly, T. N., and Yamauchi, R. (2005) Quercetin-dependent inhibition of nitration induced by peroxidase/H 2O2/nitrite systems in human saliva and characterization of an oxidation product of quercetin formed during the inhibition J. Agric. Food Chem. 53, 3265-3272
18. Tenovuo, J. O. (1989) Nonimmunoglobulin defense factors in human saliva. In Human Saliva: Clinical Chemistry and Microbiology (Tenovuo, J. O., Ed.) Vol. 2, pp 55 - 91, CRC Press, Boca Raton.
19. Marquis, R. E. (1995) Oxygen metabolism, oxidative stress and acid-base physiology of dental plaque biofilms J. Ind. Microbiol. 15, 198-207
20. Zappacosta, B., Persichilli, S., De Sole, P., Mordente, A., and Giardina, B. (1999) Effect of smoking one cigarette on antioxidant metabolites in the saliva of healthy smoker Arch. Oral Biol. 44, 485-488
21. Nagler, R. M., Klein, I., Zarzhevsky, N., Drigues, N., and Renznick, A. (2002) Characterization of the differentiated antioxidant profile of human saliva Free Radical Biol. Med. 32, 268-277
22. Diab-Ladki, R., Pellat, B., and Chahine, R. (2003) Decrease in the total antioxidant activity of saliva in patients with periodontal diseases Clin. Oral Invest. 7, 103-107
23. Fujii, S., Yoshimura, T., and Kamada, H. (1996) Nitric oxide trapping efficiencies of water-soluble iron (III) complexes with dithiocarbamate derivatives Chem. Lett. 785-786
24. Kalyanaraman, B. (1996) Detection of nitric oxide by electron spin resonance in chemical, photochemical, cellular, physiological, and pathophysiological systems Methods Enzymol. 268, 168-187
25. Skinner, K. A., White, C. R., Patel, R., Tan, S., Barnes, S., Kirk, M., Darley-Usmar, V., and Parks, D. A. (1996) Nirtrosation of uric acid by peroxynitrite. Formation of a vasoactive nitric oxide donor J. Biol. Chem. 272, 24491-24497
26. Maples, K. R. and Mason, R. P. (1988) Free Radical metabolite of uric acid J. Biol. Chem. 263, 1709-1712
27. Doherty, A. M. M., Garley, M. S., Haine, N., and Stedman, G. (1997) Formation of an adduct between thiocyanate ion and nitrosyl thiocyanate J. Chem. Soc., Dalton Trans. 2163-2166
28. Pietraforte, D., Castelli, M., Metere, A., Scorza, G., Samoggia, P., Menditto, A., and Minetti, M. (2006) Salivary uric acid at the acidic pH of the stomach is the principal defense against nitrite-derived reactive species: Sparing effects of chlorogenic acid and serum albumin Free Radical Biol. Med. 41, 175301763
29. Caulfield, J. L., Wishnok, J. S., and Tannenbaum, S. R. (1998) Nitric oxide-induced deamination of cytosine and guanine in deoxynucleosides and oligonucleosides J. Biol. Chem. 237, 12689-12695
30. Espey, M. G., Thomas, D. D., Miranda, K., and M., Wink, D. A. (2002) Focusing of nitric oxide mediated nitrosation and oxidative nitrosylation as a consequence of reaction with superoxide Proc. Natl. Acad. Sci. U.S.A. 99, 11127-11132
31. Lakshmi, V. M., Nauseef, W. M., and Zenser, T. V. (2005) Myeloperoxidase potentiates nitric oxide-mediated nitrosation J. Biol. Chem. 280, 1746-1753
32. Wink, D. A., Nims, R. W., Darbyshire, J. F., Christodoulou, D., Hanbauer, L., Cox, G. W., Laval, F., Laval, J., Cook, J. A., Krishna, M. C., DeGraff, W. G., and Mitchell, J. B. (1994) Reaction kinetics for nitrosation of cysteine and glutathione in aerobic nitric oxide solution at neutral pH. Insights into the fate and physiological effects of intermediates generated in the NO/O 2 reaction Chem. Res. Toxicol. 7, 519-525
33. Dojindo Catalogue, 25 th ed., (2007) Dojindo Laboratories: Kumamoto, Japan, pp 154-156.
34. Hiramoto, K., Tomiyama, S., and Kikugawa, K. (1997) Appearance of electron spin resonance signals in the interaction of dithoicarbamate-Fe(II) with nitrogen dioxide and nitrite Free Radical Res. 27, 505-509
35. Vanin, A. F., Liu, X., Samouilov, A., Stukan, R. A., and Zwier, J. L. (2000) Redox properties of iron-dithiocarbamates and their nitrosyl derivatives: Implications for their use as traps of nitric oxide in biological systems Biochim. Biophys. Acta 1474, 365-377
36. Mansson-Rahemtulla, B., Rahemtulla, F., Baldone, D. C., Pruitt, K. M., and Hjerpe, A. (1988) Purification and characterization of salivary peroxidase Biochemistry 27, 233-239
37. Pruitt, K. M., Mansson-Rahemtulla, B., Baldone, D. C., and Rahemtulla, F. (1988) Steady-state kinetics of thiocyanate oxidation catalyzed by human salivary peroxidase Biochemistry 27, 240-245
38. Ford, E., Hughes, M. N., and Wardman, P. (2002) Kinetics of the reaction of nitrogen dioxide with glutathione, cystein, and uric acid at physiological pH Free Radical Biol. Med. 32, 1314-1323
39. Vasquez-Vivar, J., Santos, A. M., Junqueira, V. B. C., and Augusto, O. (1996) Peroxynitrite-mediated formation of free radicals in human plasma: EPR detection of ascrobyl, albumin-thiyl and uric acid-derived free radicals Biochem. J. 314, 869-876
40. Galbraith, J. M. and Schaefer, H. F., III (1996) The nitrosyl azide potential energy hypersurface: A high-energy-density boom or burst? J. Am. Chem. Soc. 118, 4860-4870
41. Doherty, A. M. M., Dadcliffe, M. D., and Stedman, G. (1999) Kinetics of oxidation of nitrogen compounds by cerium (IV) J. Chem. Soc., Dalton Trans. 3311-3316
42. Takahama, U., Ryu, K., Oniki, T., and Hirota, S. (2007) Dual-function of thiocyanate on nitrite-induced formation of reactive nitrogen oxide species in human oral cavity: Inhibition under neutral and enhancement under acidic conditions Free Radical Res. 41, 1289-1300
43. Takahama, U., Hirota, S., and Kawagishi, S. (2009) Effects of pH on nitrite-induced formation of reactive nitrogen oxide species and their scavenging by phenolic antioxidants in human oral cavity Free Radical Res. 43, 250-261
44. Goldstein, S., Lind, J., and Merenyi, G. (2005) Chemistry of peroxynitrites as compared to peroxinitrates Chem. Rev. 105, 2457-2470
45. van der Vliet, A., Eiserich, J. P., Halliwell, B., and Cross, C. E. (1997) Formation of reactive nitrogen species during peroxidase-catalyzed oxidation of nitrite. A potential additional mechanism of nitric oxide-dependent toxicity J. Biol. Chem. 272, 7617-7625
46. Burner, U., Furtmuller, P. G., Kettle, A. J., Koppenol, W. H., and Obinger, C. (2000) Mechanism of reaction myeloperoxidase with nitrite J. Biol. Chem. 275, 20597-20601
47. Bian, K., Gao, Z., Weisbrodt, N., and Murad, F. (2003) The nature of heme/iron-induced protein tyrosin nitration Proc. Natl. Acad. Sci. U.S.A. 100, 5712-5717
48. Nishioka, T., Kimura, M., and Takahama, U. (1996) Effects of pH and thiocyanate on hydrogen peroxide-induced evolution of molecular oxygen in human saliva Arch. Oral Biol. 41, 911-917
49. Takahama, U., Hirota, S., and Oniki, T. (2006) Thiocyanate cannot inhibit the formation of reactive nitrogen species in the human oral cavity in the presence of high concentration of nitrite: Detection of reactive nitrogen species with 4,5-diaminofluorescein Chem. Res. Toxicol. 19, 1066-1073
50. Tenovuo, J. and Anttonen, T. (1980) Peroxidase-catalyzed hypothiocyanite production in human salivary sediment in relation to oral health Caries Res. 14, 269-275