8-Nitroxanthine, an adduct derived from 2′-deoxyguanosine or DNA reaction with nitryl chloride

Chemical Research in Toxicology

Volumn 14, Issue 5, 2001, Pages 536-546

  Chen, Hauh Jyun Candy ^a   Chen, Yuan Mao ^a   Wang, Tze Fan ^a   Wang, Kuang Sian ^a   Shiea, Jentaie ^b  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^b NATIONAL SUN YAT SEN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

8 AMINOXANTHINE; 8 NITROGUANINE; 8 NITROXANTHINE; BORIC ACID; CHLORIDE; DEOXYGUANOSINE; DNA; GUANINE; HYPOCHLOROUS ACID; NITRIC ACID; NITRITE; NITROGEN DERIVATIVE; NITRONIUM TETRAFLUOROBORATE; NITROUS ACID; NITRYL CHLORIDE; PEROXYNITRITE; REACTIVE NITROGEN SPECIES; UNCLASSIFIED DRUG; XANTHINE DERIVATIVE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CARCINOGENESIS; CONTROLLED STUDY; DISEASE ASSOCIATION; DNA DAMAGE; HALF LIFE TIME; HOST RESISTANCE; INFECTION; INFLAMMATION; MASS SPECTROMETRY; NITRATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PHAGOCYTE; REDUCTION; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; TEMPERATURE DEPENDENCE; THYMUS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DNA DAMAGE; HALF-LIFE; HYDROGEN-ION CONCENTRATION; HYPOCHLOROUS ACID; MAGNETIC RESONANCE SPECTROSCOPY; NITRITES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; XANTHINES;

ANIMALIA;

EID: 0034997674     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0002334     Document Type: Article

References (56)

1. Ohshima, H., and Bartsch, H. (1994) Chronic infections and inflammatory processed as cancer risk factors: possible role of nitric oxide in carcinogenesis. Mutat. Res. 305, 253-264.
2. Gordon, L. I., and Weitzman, S. A. (1993) Inflammation and Cancer. Cancer J. 6, 257-261.
3. Koppenol, W. H., Moreno, J. J., Pryor, W. A., Ischiropoulos, H., and Beckman, J. S. (1992) Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide. Chem. Res. Toxicol. 5, 834-842.
4. Ischiropoulos, H., Zhu, L., and Beckman, J. S. (1992) Peroxynitrite formation from macrophage-derived nitric oxide. Arch. Biochem. Biophys. 298, 446-451.
5. 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.
6. Lymar, S. V., and Hurst, J. K. (1996) Carbon Dioxide: Physiological Catalyst for Peroxynitrite-Mediated Cellular Damage or Cellular Protectant? Chem. Res. Toxicol. 9, 845-850.
7. Lymar, S. V., Jiang, Q., and Hurst, J. K. (1996) Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35, 7855-7861.
8. Lemercier, J. N., Squadrito, G. L., and Pryor, W. A. (1995) Spin trap studies on the decomposition of peroxynitrite. Arch. Biochem. Biophys. 321, 31-39.
9. Beckman, J. S., Beckman, T. W., Chen, J., Marshall, P. A., and Freeman, B. (1990) Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide. Prop. Natl. Acad. Sci. U.S.A. 87, 1620-1624.
10. Maria, S. S., Lee, J., and Groves, J. T. (1997) Peroxynitrite rapidly permeates phospholipid membranes. Proc. Natl. Acad. Sci. U.S.A. 94, 14243-14248.
11. Denicola, A., Souza, J. M., and Radi, R. (1998) Diffusion of peroxynitrite across erythrocyte membranes. Proc. Natl. Acad. Sci. U.S.A. 95, 3566-3571.
12. Spencer, J. P. E., Wong, J., Jenner, A., Aruoma, O. I., Cross, C. E., and Halliwell, B. (1996) Base modification and strand breakage in isolated calf thymus DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3-morpholinosydnonimine. Chem. Res. Toxicol. 9, 1152-1158.
13. Douki, T., Cadet, J., and Ames, B. N. (1996) An adduct between peroxynitrite and 2′-deoxyguanosine: 4,5-dihydro-5-hydroxy-4-(nitrosooxy)-2′-deoxyguanosine. Chem. Res. Toxicol. 9, 3-7.
14. Arteel, G. E., Kadiiska, M. B., Rusyn, I., Bradford, B. U., Mason, R. P., Raleigh, J. A., and Thurman, R. G. (1999) Oxidative stress occurs in perfused rat liver at low oxygen tension by mechanisms involving peroxynitrite. Mol. Pharmacol. 55, 708-715.
15. Wu, G. S., Zhang, J., and Rao, N. A. (1997) Peroxynitrite and oxidative damage in experimental autoimmune uveitis. Invest. Ophthalmol. Visual Sci. 38, 1333-1339.
16. Koppal, T., Drake, J., Yatin, S., Jordan, B., Varadarajan, S., Bettenhausen, L., and Butterfield, D. A. (1999) Peroxynitrite-induced alterations in synaptosomal membrane proteins: insight into oxidative stress in Alzheimer's disease. J. Neurochem. 72, 310-317.
17. Pennathur, S., Jackson-Lewis, V., Przedborski, S., and Heinecke, J. W. (1999) Mass spectrometric quantification of 3-nitrotyrosine, ortho-tyrosine, and o,o′-dityrosine in brain tissue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated mice, a model of oxidative stress in Parkinson's disease. J. Biol. Chem. 274, 34621-34628.
18. Aoyama, K., Matsubara, K., Fujikawa, Y., Nagahiro, Y., Shimizu, K., Umegae, N., Hayase, N., Shiono, H., and Kobayashi, S. (2000) Nitration of manganese superoxide dismutase in cerebrospinal fluids is a marker for peroxynitrite-mediated oxidative stress in neurodegenerative diseases, Ann. Neurol. 47, 524-527.
19. Juedes, M. J., and Wogan, G. N. (1996) Peroxynitrite-induced mutation spectra of pSP189 following replication in bacteria and in human cells. Mutat. Res. 349, 51-61.
20. Yermilov, V., Yoshie, Y., Rubio, J., and Ohshima, H. (1996) Effects of carbon dioxide/bicarbonate on induction of DNA single-strand breaks and formation of 8-nitroguanine, 8-oxoguanine and base-propenal mediated by peroxynitrite. FEBS Lett. 399, 67-70.
21. Yermilov, V., Rubio, J., and Ohshima, H. (1995) Formation of 8-nitroguanine in DNA treated with peroxynitrite in vitro and its rapid removal from DNA by depurination. FEBS Lett. 376, 207-210.
22. 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.
23. 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.
24. Muller, T., Haussmann, H. J., and Schepers, G. (1997) Evidence for peroxynitrite as an oxidative stress-inducing compound of aqueous cigarette smoke fractions. Carcinogenesis 18, 295-301.
25. Pryor, W. A., and Stone, K. (1993) Oxidants in cigarette smoke. Radicals, hydrogen peroxide, peroxynitrate, and peroxynitrite. Ann. N. Y. Acad. Sci. 686, 12-27.
26. Byun, J., Henderson, J. P. Mueller, D. M., and Heinecke, J. W. (1999) 8-Nitro-2′-deoxyguanosine, a specific marker of oxidation by reactive nitrogen species, is generated by the myeloperoxidase-hydrogen peroxide-nitrite system of activated human phagocytes. Biochemistry 38, 2590-2600.
27. Eiserich, J. P., Cross, C. E., Jones, A. D., Halliwell, B., and van der Vliet, A. (1996) Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric oxide-mediated protein modification. J. Biol. Chem. 271, 19199-19208.
28. Schmitt, D., Shen, Z., Zhang, R., Colles, S. M., Wu, W., Salomon, R. G., Chen, Y., Chisolm, G. M., Hazen, S. L. (1999) Leukocytes utilize myeloperoxidase-generated nitrating intermediates as physiological catalysts for the generation of biologically active oxidized lipids and sterols in serum. Biochemistry 38, 16904-16915.
29. 2 system. Nucleic Acids Symp. Ser. 42, 155-156.
30. Shapiro, R., and Pohl, S. H. (1968) The reaction of ribonucleosides with nitrous acid. Side products and kinetics. Biochemistry 7, 448-455.
31. Nelson, D. P., and Kiesow, L. A. (1972) Enthalpy of decomposition of hydrogen peroxide by catalase at 25 degrees C. Anal. Biochem. 49, 474-478.
32. Uppu, R. M., and Pryor, W. A. (1996) Biphasic synthesis of high concentrations of peroxynitrite using water-insoluble alkyl nitrite and hydrogen peroxide. Method Enzymol. 269, 322-329.
33. Beckman, J. S., Chen, J., Ischiropoulos, H., and Crow, J. P. (1994) Oxidative chemistry of peroxynitrite. Methods Enzymol. 233, 229-240.
34. Morris, J. C. (1966) The acid ionization constant of HOC1 from 5 to 35 degrees. J. Phys. Chem. 70, 3798-3805.
35. Sodum, R. S., Nie, G., and Fiala, E. S. (1993) 8-Aminoguanine: a base modification produced in rat liver nucleic acids by the hepatocarcinogen 2-nitropropane. Chem. Res. Toxicol. 6, 269-276.
36. Yermilov, V., Rubio, 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.
37. Redemann, C. T., and Redemann, C. E. (1955) 5-Amino-2,3-dihydro-1,4-phthalazinedione. Org. Synth. Coll. 3, 69-70.
38. Wu, K. Y., Scheller, N., Ranasinghe, A., Yen, T. Y., Sangaiah, R., Giese, R, and Swenberg, J. A. (1999) A gas chromatography/ electron capture/negative chemical ionization high-resolution mass spectrometry method for analysis of endogenous and exogenous N7-(2-hydroxyethyl)guanine in rodents and its potential for human biological monitoring. Chem. Res. Toxicol. 12, 722-729.
39. Olah, G. A., Malhotra, and Narang, S. C. (1989) Nitration. Methods and Mechanisms, p 92-132, VCH Publishers, New York.
40. 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.
41. Lewis, R. S., Tannenbaum, S. R., and Deen, W. M. (1995) Kinetics of N-nitrosation in oxygenated nitric oxide solutions at physiological pH: Role of nitrous anhydride and effects of phosphate and chloride. J. Am. Chem. Soc. 117, 3933-3939.
42. 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.
43. Ohshima, H., Celan, I., Chazotte, L., Pignatelli, B., and Mower, H. F. (1999) Analysis of 3-nitrotyrosine in biological fluids and protein hydrolyzates by high-performance liquid chromatography using a postseparation, on-line reduction column and electrochemical detection: Results with various nitrating agents. Nitric Oxide 3, 132-141.
44. Lakshmi, V. M., Hsu, F. F., Davis, B. B., and Zenser, T. V. (2000) Nitrating reactive nitric oxygen species transform acetaminophen to 3-nitroacetaminophen. Chem. Res. Toxicol. 13, 891-899.
45. van Dalen, C. J., Winterbourn, C. C., Senthilmohan, R., and Kettle, A. J. (2000) Nitrite as a substrate and inhibitor of myeloperoxidase. Implications for nitration and hypochlorous acid production at sites of inflammation. J. Biol. Chem. 275, 11638-11644.
46. Klebanoff, S. J. (1993) Reactive nitrogen intermediates and antimicrobial activity: Role of nitrite. Free Radical Biol. Med. 14, 351-360.
47. Tannenbaum, S. R., Weisman, M., and Fett, D. (1976) The effect of nitrate intake on nitrite formation in human saliva. Food Cosmet. Toxicol. 14, 549-552.
48. Leone, A. M., Francis, P. L., Rhodes, P., and Moncada, S. (1994) A rapid and simple method for the measurement of nitrite and nitrate in plasma by high performance capillary electrophoresis. Biochem. Biophys. Res. Commun. 200, 951-957.
49. 15N]nitrate in biological fluids. Anal. Biochem. 126, 131-138.
50. Kharitonov, S. A., Chung, K. F., Evans, D., O'Connor, B. J., and Barnes, P. J. (1996) Increased exhaled nitric oxide in asthma is mainly derived from the lower respiratory tract. Am. J. Respir. Crit. Care Med. 153, 1773-1780.
51. Weiss, S. J., Klein, R., Slivka, A., and Wei, M. (1982) Chlorination of taurine by human neutrophils. Evidence for hypochlorous acid generation. J. Clin. Invest. 70, 598-607.
52. Foote, C. S., Goyne, T. E., and Lehrer, R. I. (1983) Assessment of chlorination by human neutrophils. Nature 301, 715-716.
53. Whiteman, M., Spencer, J. P., Jenner, A., and Halliwell, B. (1999) Hypochlorous acid-induced DNA base modification: potentiation by nitrite: Biomarkers of DNA damage by reactive oxygen species. Biochem. Biophys. Res. Commun. 257, 572-576.
54. Hazen, S. L., Hsu, F. F., Mueller, D. M., Crowley, J. R., and Heinecke, J. W. (1996) Human neutrophils employ chlorine gas as an oxidant during phagocytosis. J. Clin. Invest. 98, 1283-1289.
55. Evans, T. J., Buttery, L. D., Carpenter, A., Springall, D. R., Polak, J. M., and Cohen, J. (1996) Cytokine-treated human neutrophils contain inducible nitric oxide synthase that produces nitration of ingested bacteria. Proc. Natl. Acad. Sci. U.S.A. 93, 9553-9558.
56. Eiserich, J. P., Hristova, M., Cross, C. E., Jones, A. D., Freeman, B. A., Halliwell, B., and van der Vliet, A. (1999) Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils. Nature 391, 393-397.