Enhancement of iron(II)-dependent reduction of nitrite to nitric oxide by thiocyanate and accumulation of iron(II)/thiocyanate/nitric oxide complex under conditions simulating the mixture of saliva and gastric juice

Chemical Research in Toxicology

Volumn 25, Issue 1, 2012, Pages 207-215

  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

ASCORBIC ACID; FERRIC ION; FERROUS ION; NITRIC OXIDE; NITRITE; OXYGEN; REACTIVE NITROGEN OXIDE SPECIES; REACTIVE NITROGEN SPECIES; THIOCYANATE; UNCLASSIFIED DRUG;

ACIDITY; AEROBIC METABOLISM; ANAEROBIC METABOLISM; ARTICLE; AUTOOXIDATION; ELECTROCHEMICAL ANALYSIS; HUMAN; NORMAL HUMAN; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; REACTION ANALYSIS; REDUCTION; SALIVA; SIMULATION; STOMACH JUICE; TIME;

ASCORBIC ACID; FERROUS COMPOUNDS; GASTRIC JUICE; HUMANS; IRON; NITRIC OXIDE; NITRITES; OXIDATION-REDUCTION; OXYGEN CONSUMPTION; SALIVA; THIOCYANATES;

EID: 84855857642     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200438q     Document Type: Article

References (55)

1. Fisher, A. E. O. and Naughton, D. P. (2004) Iron supplements: the quick fix with long consequences Nutr. J. 3, 2
2. Hiraishi, H., Terano, A., Ota, S., Mutoh, H., Razandi, M., Sugimoto, T., and Ivey, K. J. (1991) Role for iron in reactive oxygen species-mediated cytotoxicity to cultured rate gastric mucosal cells Am. J. Physiol. 260, G556-G563
3. Kadiiska, M. B., Burkitt, M. J., Xiang, Q. H., and Mason, R. P. (1995) Iron supplementation generates hydroxyl radical in vivo. An ESR spin-trapping investigation J. Clin. Invest. 96, 1653-1657
4. 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 (Pubitemid 39456958)
5. 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 (Pubitemid 40313834)
6. Palmerini, C. A., Palombari, R., Perito, S., and Arienti., G. (2003) NO synthesis in human saliva Free Radical Res. 37, 29-31 (Pubitemid 36124327)
7. 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 (Pubitemid 36254831)
8. Zetterquist, W., Pedroletti, C., Lundberg, J. O., and Alving, K. (1999) Salivary contribution to exhaled nitric oxide Eur. Respir. J. 13, 327-333 (Pubitemid 29086828)
9. Bodis, S. and Haregewoin, A. (1994) Significantly reduced salivary nitric oxide levels in smakers Anal. Oncol. 5, 371-372 (Pubitemid 24142376)
10. Xia, D., Deng, D., and Wang, S. (2003) Alterations of nitrate and nitrite content in saliva, serum, and urine in patients with salivary dysfunction J. Oral. Pathol. Med. 32, 95-99 (Pubitemid 36604035)
11. 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
12. Webb, H. W. (1923). Absorption of Nitrous Gases, Edward Arnold & Co., London.
13. Oldreive, C. and C. Rice-Evans, C. (2001) The mechanisms for nitration and nitrotyrosine formation in vitro and in vivo: Impact of diet Free Radical Res. 35 (2001) 215-231 (Pubitemid 32734224)
14. Licht, W. R., Tannenbaum, S. R., and Deen, W. M. (1988) Effects of ascorbic acid and thiocyanate on nitrosation of proline in the dog stomach Carcinogenesis 9, 365-372
15. Sobala, G., Schorah, C. J., Pignatelli, B., Crabtree, J. E., Martin, I. G., Scott, N., and Quirke, P. (1993) High gastric juice ascorbic acid concentrations in members of a gastric cancer family Carcinogenesis 14, 291-292 (Pubitemid 23143409)
16. Dobrowska-Ufniarz, E., Dzieniszwski, J., Jarosz, M., and Wartanowicz, M. (2002) Vitamin C concentration in gastric juice in patients with precancerous lesion of the stomach and gastric cancer Med. Sci. Monit. 8, CR96-CR103
17. O'Conner, H. J., Achorah, C. J., Habibzedah, N., Axon, A. T. R., and Cockel, R. (1989) Vitamin C in the human stomach: relation to gastric pH, gastrodoudenal disease and possible sources Gut 30, 436-442
18. Rathbone, B. J., Johnson, A. W., Wyatt, J. I., Kelleher, J., Heatley, R. V., and Losowsky, M. S. (1989) Ascorbic acid: a factor concentrated in human gastric juice Clin. Sci. 76, 237-241 (Pubitemid 19078476)
19. Waring, A. J., Drake, I. M., Schorah, C. J., White, K. L., Lynch, D. A., Axon, A. T., and Dixon, M. F. (1996) Ascorbic acid and total vitamin C concentrations in plasma, gastric juice, and gastrointestinal mucosa: effects of gastritis and oral supplementation Gut 38, 171-176 (Pubitemid 26048696)
20. 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 (Pubitemid 127780686)
21. Takahama, U., Hirota, S., Yamamoto, A., and Oniki, T. (2003) Oxygen uptake during the mixing of saliva with ascorbic acid under acidic conditions: possibility of its occurrence in the stomach FEBS Lett. 550, 64-68 (Pubitemid 37281358)
22. Takahama, U. and Hirota., S. (2008) Reduction of nitrous acid to nitric oxide by coffee melanoidins and enhancement of the reduction by thiocyanate: possibility of its occurrence in the stomach J. Agric. Food Chem. 56, 4736-4744 (Pubitemid 351999405)
23. Lewis, R. S. and Deen, W. M. (1994) Kinetics of the reaction of nitric oxide with oxygen in aqueous solutions Chem. Res. Toxicol. 7, 568-574 (Pubitemid 24232355)
24. Kharitonov, V. G., Sundquist, A. R., and Sharma, V. S. (1994) Kinetics of nitric oxide autoxidation in aqueous solution J. Biol. Chem. 269, 5881-5883 (Pubitemid 24242965)
25. 2 within the hydrophobic interior of biological membranes Proc. Natl. Acad. Sci. U.S.A. 95, 2175-2179 (Pubitemid 28145914)
26. Bonner, F. T. and Pearsall, K. A. (1982) Aqueous nitrosyliron(II) chemistry. 1. Reduction of nitrite and nitric oxide by iron(II) and (trioxodinitrato)iron(II) in acetate buffer. Intermediacy of nitrosyl hydride Inorg. Chem. 21, 1973-1978
27. Pearsall, K. A. and Bonner, F. T. (1982) Aqueous nitrosyliron(II) chemistry. 2. Kinetics and mechanism of nitric oxide reduction. The dinitrosyl complex Inorg. Chem. 21, 1978-1985
28. Summers, D. P. and Chang, S. (1993) Prebiotic ammonia from reduction of nitrite by iron(II) on the early earth Nature 365, 630-633 (Pubitemid 24420444)
29. Tai, Y. L. and Dempsey, B. A. (2009) Nitrite reduction with hydrous ferric oxide and Fe(II): stoichiometry, rate, and mechanism Water Res. 43, 546-55
30. Epstein, I. R., Kustin, K., and Simoyi, R. H. (1982) Systematic design of chemical oscillators. 6. Nitrous acid decomposition catalyzed by an iron(II) complex: tris(3,4,7,8-tetramethyl-1,10-phenanthroline)iron(II) J. Am. Chem. Soc. 104, 712-717 (Pubitemid 12476998)
31. Volk, J., Gorelik, S., Granit, R., Kohen, R., and Kanner, J. (2009) The dual function of nitrite under stomach conditions is modulated by reducing compounds Free Radical Biol. Med. 47, 496-502
32. Lister, M. W. and Rivington, D. E. (1955) Some measurements on the iron(III) -thiocyanate system in aqueous solution Can. J. Chem. 33, 1572-1590
33. Nasu, A., Takagi, H., Phmiya, Y., and Sekine, T. (1999) Solvent extraction of iron(II) and iron(III) as anionic thiocyanate complexes with tetrabutyamminium ions into chloroform Anal. Sci. 15, 177-180
34. Duncan, C., Dougall, H., Johnston, P., Green, S., Brogan, R., Leifert, C., Smith, L., Golden, M., and Benjamin, N. (1995) Chemical generation of nitric oxide in the mouth from the enterosalivary circulation of dietary nitrate Nat. Med. 1, 546-551
35. Ferguson, D. B. (1989) Salivary electolytes. In Human Saliva. Clinical Chemistry and Microbiology (Ternovuo, J., Ed.) Vol. 1, pp 75-99, CRC Press, Boca Raton, FL.
36. Tsuge, K., Kataoka, M., and Seto, Y. (2000) Cyanide and thiocyanate levels in blood and saliva of healthy adult volunteers J. Health Sci. 46, 343-350
37. Fujii, S., Yoshimura, T., and Kamada, H. (1996) Nitric oxide trapping efficiencies of water-soluble iron(III) complexes with dithiocarbamate derivatives Chem. Lett. 25, 785-786
38. Zimmer, W., Danneberg, G., and Bothe, H. (1985) Amperometric method for determining nitrous oxide in denitrification and in nitrogenase-catalyzed nitrous oxide reduction Curr. Microbiol. 12, 341-346 (Pubitemid 16170568)
39. Rayson, M. S., Mackie, J. C., Kennedy, E. M., and Dlugogroski, B. Z. (2011) Experimental study of decomposition of aqueous nitrosyl thiocyanate Inrog. Chem. 50, 7440-7452
40. Dojindo Laboratories, Co. (2007) Dojindo Catalogue, 25 th ed., p. 157, Dojindo Laboratories, Co., Kumamoto, Japan.
41. Andrade, R., Viana, C. O., Guadagnin, S. G., Reyes, F. G. R., and Rath, S. (2003) A flow-injection spectrophotometric method for nitrate and nitrite determination through nitric oxide generation Food Chem. 80, 597-602 (Pubitemid 36144002)
42. Zhao, Z. and Cai, X. (1988) Determination of trace nitrite by catalytic polarography in ferrous ion thiocyanate medium J. Electroanal. Chem. Interface Electrochem. 252, 361-370
43. Halliwell, B. and Gutteridge, J. M. C. (1999) Free Radical in Biology and Medicine, Oxford University Press, Oxford, U.K.
44. DeFelippis, M. R., Faraggi, M., and Klapper, M. H. (1990) Redox potentials of azide and dithiocyanate radicals J. Phys. Chem. 94, 2420-2424
45. Day, C. L., Stowell, K. M., Baker, E. N., and Tweedie, J. W. (1992) Studies of the N-terminal half of human lactoferrin produced from the cloned cDNA demonstrate that interlobe interactions modulate iron release J. Biol. Chem. 267, 13857-13862
46. Conrad, M. E., Umbreit, J. N., and Moore, E. G. (1991) A role for mucin in the absorbance of inorganic iron and other metal cations. A study in rates Gastroenterology 100, 129-136
47. Cohen, R. E. and Levine, M. J. (1989) Salivary Glycoproteins, in Human Saliva. Clinical Chemistry and Microbiology (Ternovuo, J., Ed.) Vol. 1, pp 101-130, CRC Press, Boca Raton, FL.
48. Budavari, S., Ed. (1989) The Merck Index, 11nth ed., Merck Co., Inc., Rahway, NJ.
49. Takahama, U. and Oniki, T. (2004) Salivary thiocyanate/nitrite inhibits hydroxylation of 2-hydroxybenzoic acid induced by hydrogen peroxide/Fe(II) systems under acidic conditions: possibility of thiocyanate/nitrite-dependent scavenging of hydroxyl radical in the stomach Biochim. Biophys. Acta 1675, 130-138 (Pubitemid 39463262)
50. Takahama, U., Tanaka, M., Oniki, T., and Hirota, S. (2007) Reactions of thiocyanate in the mixture of nitrite and hydrogen peroxide under acidic conditions: investigation of the reactions simulating the mixture of saliva and gastric juice Free Radical Res. 41, 627-637 (Pubitemid 46845582)
51. Takahama, U., Oniki, T., and Murata, H. (2002) The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach FEBS Lett. 518, 116-118 (Pubitemid 34454975)
52. Pannala, A. S., Mani, A. R., Rice-Evans, C. A., and Moore, K. P. (2006) pH-dependent nitration of para-hydroxyphenylactic acid in the stomach Free Radical Biol. Med. 41, 896-901 (Pubitemid 44247542)
53. Toblli, J. E. and Brignoli, R. (2007) Iron(III)-hydroxide polymaltose complex in iron deficiency anemia/review and meta-analysis Arzneim. Forsch. 57, 431-438 (Pubitemid 47055994)
54. Geisser, P. (2007) Safety and efficacy of iron(III)-hydroxide polymaltose complex/a review of over 25 years experience Arzneim. Forsch. 57, 439-452 (Pubitemid 47055995)
55. Saha, L., Pandhi, P., Gopalan, S., Malhotra, S., and Saha, P. K. (2007) Comparison of efficacy, tolerability, and cost of iron polymaltose complex with ferrous sulphate in the treatment of iron deficeicy anemia in pregnant women Med. Gen. Med. 9, 1-7