Formation of Nitroxyl and Hydroxyl Radical in Solutions of Sodium Trioxodinitrate: Effects of pH and cytotoxicity

Journal of Biological Chemistry

Volumn 278, Issue 44, 2003, Pages 42761-42768

  Ivanova, Juliana ^a   Salama, Guy ^b   Clancy, Robert M ^c   Schor, Nina F ^d   Nylander, Karen D ^d   Stoyanovsky, Detcho A ^a  

^a UNIVERSITY OF PITTSBURGH MEDICAL CENTER   (United States)

^b UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

^c NEW YORK UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d CHILDREN S HOSPITAL OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; DIMERIZATION; HYDROLYSIS; IONS; OXIDATION; PH EFFECTS; PHENOLS; REDOX REACTIONS; SODIUM COMPOUNDS; TOXICITY;

METAL IONS; REDOX POTENTIAL;

BIOCHEMISTRY;

ALCOHOL; BENZENE 1,2 DIOL; BENZENE 1,4 DIOL; BENZENE DERIVATIVE; HYDROXYL RADICAL; NITRIC ACID DERIVATIVE; NITROXYL RADICAL; PEROXYNITRITE; PHENOL; RADICAL; SODIUM TRIOXODINITRATE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ACIDOSIS; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DIMERIZATION; FENTON REACTION; FIBROBLAST; HUMAN; HUMAN CELL; HYDROLYSIS; HYDROXYLATION; NEUROBLASTOMA CELL; OXIDATION; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

ANTIOXIDANTS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DISINFECTANTS; ELECTRON SPIN RESONANCE SPECTROSCOPY; FIBROBLASTS; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; HYDROXYL RADICAL; KINETICS; MODELS, CHEMICAL; NITRITES; NITROGEN OXIDES; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; PHENOL; TEMPERATURE; TIME FACTORS;

LETHRINIDAE;

EID: 0242384943     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M305544200     Document Type: Article

References (68)

1. Murphy, M. E., and Sies, H. (1991) Proc. Natl. Acad. Sci. U. S. A. 88, 10860-10864
2. Sharpe, M. A., and Cooper, C. E. (1998) Biochem. J. 332, 9-19
3. Jensen, D. E., Belka, G. K., and Du Bois, G. C. (1998) Biochem. J. 331, 659-668
4. Wong, P. S., Hyun, J., Fukuto, J. M., Shirota, F. N., DeMaster, E. G., Shoeman, D. W., and Nagasawa, H. T. (1998) Biochemistry 37, 5362-5371
5. Hogg, N., Singh, R. J., and Kalyanaraman, B. (1996) FEBS Lett. 382, 223-228
6. Chazotte-Aubert, L., Oikawa, S., Gilibert, I., Bianchini, F., Kawanishi, S., and Ohshima, H. (1999) J. Biol. Chem. 274, 20909-20915
7. Vaananen, A. J., Moed, M., Tuominen, R. K., Helkamaa, T. H., Wiksten, M., Liesi, P., Chiueh, C. C., and Rauhala, P. (2003) Free Radical Res. 37, 381-389
8. Naughton, P., Foresti, R., Bains, S. K., Hoque, M., Green, C. J., and Motterlini, R. (2002) J. Biol. Chem. 277, 40666-40674
9. Ellis, A., Li, C. G., and Rand, M. J. (2000) Br. J. Pharmacol. 129, 315-322
10. Conway, T. T., DeMaster, E. G., Lee, M. J., and Nagasawa, H. T. (1998) J. Med. Chem. 41, 2903-2909
11. DeMaster, E. G., Redfern, B., Quast, B. J., Dahlseid, T., and Nagasawa, H. T. (1997) Alcohol 14, 181-189
12. Kim, W. K., Choi, Y. B., Rayudu, P. V., Das, P., Asaad, W., Arnelle, D. R., Stamler, J. S., and Lipton, S. A. (1999) Neuron 24, 461-469
13. Choi, Y. B., Tenneti, L., Le, D. A., Ortiz, J., Bai, G., Chen, H. S., and Lipton, S. A. (2000) Nat. Neurosci. 3, 15-21
14. Paolocci, N., Katori, T., Champion, H. C., St. John, M. E., Miranda, K. M., Fukuto, J. M., Wink, D. A., and Kass, D. A. (2003) Proc. Natl. Acad. Sci. U. S. A. 100, 5537-5542
15. Ohshima, H., Gilibert, I., and Bianchini, F. (1999) Free Radical Biol. Med. 26, 1305-1313
16. Bai, P., Bakondi, E., Szabo, E., Gergely, P., Szabo, C., and Virag, L. (2001) Free Radical Biol. Med. 31, 1616-1623
17. Doyle, M. P., Mahapatro, S. N., Broene, R. D., and Guy, J. K. (1988) J. Am. Chem. Soc. 110, 593-599
18. Xia, Y., Cardounel, A. J., Vanin, A. F., and Zweier, J. L. (2000) Free Radical Biol. Med. 29, 793-797
19. Miranda, K. M., Nims, R. W., Thomas, D. D., Espey, M. G., Citrin, D., Bartberger, M. D., Paolocci, N., Fukuto, J. M., Feelisch, M., and Wink, D. A. (2003) J. Inorg. Biochem. 93, 52-60
20. Stoyanovsky, D. A., Clancy, R. M., and Cederbaum, A. I. (1999) J. Am. Chem. Soc. 121, 5093-5094
21. Kirsch, M., and de Groot, H. (2002) J. Biol. Chem. 277, 13379-13388
22. Halliwell, B., and Gutteridge, J. M. (1990) Methods Enzymol. 186, 1-85
23. Gasbarrini, A., Borle, A. B., Farghali, H., Francavilla, A., and Van Thiel, D. (1992) J. Biol. Chem. 267, 7545-7552
24. Stubbs, M., McSheehy, P. M., Griffiths, J. R., and Bashford, C. L. (2000) Mol. Med. Today 6, 15-19
25. Waldmann, R. (2001) Adv. Exp. Med. Biol. 502, 293-304
26. Smith, P. A. S., and Hein, G. E. (1960) J. Am. Chem. Soc. 82, 5731-5740
27. Stoyanovsky, D. A., and Cederbaum, A. I. (1999) Chem. Res. Toxicol. 12, 730-736
28. Hughes, M. N., and Wimbledon, P. E. (1976) J. Chem. Soc. Dalton Trans. 703-704
29. Bonner, F. T., and Ravid, B. (1975) J. Inorg. Chem. 14, 558-563
30. Loechler, E. L., Schneider, A. M., Schwartz, D. B., and Hollocher, T. C. (1987) J. Am. Chem. Soc. 109, 3076-3087
31. Anderson, J. H. (1963) Analyst 88, 494-499
32. Stoyanovsky, D. A., Melnikov, Z., and Cederbaum, A. I. (1999) Anal. Chem. 71, 715-721
33. Buettner, G. R. (1987) Free Radical Biol. Med. 3, 259-303
34. Janzen, E. G., Kotake, Y., and Hinton, R. D. (1992) Free Radical Biol. Med. 12, 169-173
35. Towell, J., and Kalyanaraman, B. (1991) Anal. Biochem. 196, 111-119
36. Al-Ajlouni, A. M., and Gould, E. S. (1999) Inorg. Chem. 38, 1592-1595
37. Bartberger, M. D., Liu, W., Ford, E., Miranda, K. M., Switzer, C., Fukuto, J. M., Farmer, P. J., Wink, D. A., and Houk, K. N. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 10958-10963
38. Novakov, C. P., Feierman, D., Cederbaum, A. I., and Stoyanovsky, D. A. (2001) Chem. Res. Toxicol. 14, 1239-1246
39. Miranda, K. M., Espey, M. G., Yamada, K., Krishna, M., Ludwick, N., Kim, S., Jourd'heuil, D., Grisham, M. B., Feelisch, M., Fukuto, J. M., and Wink, D. A. (2001) J. Biol. Chem. 276, 1720-1727
40. Field, R. J., Raghavan, N. V., and Brummer, J. G. (1982) J. Am. Chem. Soc. 86, 2443-2449
41. Hage, J. P., Llobet, A., and Sawyer, D. T. (1995) Bioorg. Med. Chem. 3, 1383-1388
42. Raghavan, N. V., and Steenken, S. (1980) J. Am. Chem. Soc. 102, 3495-3499
43. Ito, S., Mitarai, A., Hikino, M., Hirama, M., and Sasaki, K. (1992) J. Org. Chem. 57, 6937-6941
44. Stoyanovsky, D. A., Osipov, A. N., Quinn, P. J., and Kagan, V. E. (1995) Arch. Biochem. Biophys. 323, 343-351
45. Veltwisch, D., Janata, E., Asmus, K. D., and Saito, Y. (1980) J. Chem. Soc. Perkin Trans. 2, 146-153
46. Motohashi, N., and Saito, Y. (1993) Chem. Pharm. Bull. 41, 1842-1845
47. Jacobi, J. (2002) Am. J. Health Syst. Pharm. 59, Suppl. 1, S3-S8
48. Andersson, S. E., Lexmuller, K., Johansson, A., and Ekstrom, G. M. (1999) J. Rheumatol. 26, 2018-2024
49. Hockenbery, D. M., Oltvai, Z. N., Yin, X. M., Milliman, C. L., and Korsmeyer, S. J. (1993) Cell 75, 241-251
50. Pierce, G. B., Parchment, R. E., and Lewellyn, A. L. (1991) Differentiation 46, 181-186
51. Shafirovich, V., and Lymar, S. V. (2002) Proc. Natl. Acad. Sci. U. S. A. 99, 7340-7345
52. Bartberger, M. D., Fukuto, J. M., and Houk, K. N. (2001) Proc. Natl. Acad. Sci. U. S. A. 98, 2194-2198
53. Vanuffelen, B. E., Van Der Zee, J., De Koster, B. M., Vansteveninck, J., and Elferink, J. G. (1998) Biochem. J. 330, 719-722
54. Hughes, M. N. (1999) Biochim. Biophys. Acta 1411, 263-272
55. Donald, C. E., Hughes, M. N., Thompson, J. M., and Bonner, F. T. (1986) Inorg. Chem. 25, 2676-2677
56. Uppu, R. M., Lemercier, J. N., Squadrito, G. L., Zhang, H., Bolzan, R. M., and Pryor, W. A. (1998) Arch. Biochem. Biophys. 358, 1-16
57. Daiber, A., Mehl, M., and Ullrich, V. (1998) Nitric Oxide 2, 259-269
58. Buchholz, J. R., and Powell, R. E. (1965) J. Am. Chem. Soc. 87, 2350-2353
59. Wink, D. A., Feelisch, M., Fukuto, J., Chistodoulou, D., Jourd'heuil, D., Grisham, M. B., Vodovotz, Y., Cook, J. A., Krishna, M., DeGraff, W. G., Kim, S., Gamson, J., and Mitchell, J. B. (1998) Arch. Biochem. Biophys. 351, 66-74
60. Ohshima, H., Yoshie, Y., Auriol, S., and Gilibert, I. (1998) Free Radical Biol. Med. 25, 1057-1065
61. Nelli, S., Hillen, M., Buyukafsar, K., and Martin, W. (2000) Br. J. Pharmacol. 131, 356-362
62. Kigoshi, M., Sato, K., and Niki, E. (1993) Bull. Chem. Soc. Japan 66, 2949-2954
63. Vaupel, P. W., Frinak, S., and Bicher, H. I. (1981) Cancer Res. 41, 2008-2013
64. Owens, L. M., Fralix, T. A., Murphy, E., Cascio, W. E., and Gettes, L. S. (1996) Circulation 94, 10-13
65. Ma, X. L., Gao, F., Liu, G. L., Lopez, B. L., Christopher, T. A., Fukuto, J. M., Wink, D. A., and Feelisch, M. (1999) Proc. Natl. Acad. Sci. U. S. A. 96, 14617-14622
66. Nagasawa, H. T., Kawle, S. P., Elberling, J. A., DeMaster, E. G., and Fukuto, J. M. (1995) J. Med. Chem. 38, 1865-1871
67. Lee, M. J., Nagasawa, H. T., Elberling, J. A., and DeMaster, E. G. (1992) J. Med. Chem. 35, 3648-3652
68. Lee, M. J., Shoeman, D. W., Goon, D. J., and Nagasawa, H. T. (2001) Nitric Oxide 5, 278-287