Formation of S-nitrosothiols via direct nucleophilic nitrosation of thiols by peroxynitrite with elimination of hydrogen peroxide

Journal of Biological Chemistry

Volumn 273, Issue 46, 1998, Pages 30255-30262

  Van Der Vliet, Albert ^a   Chr 't Hoen, Peter A ^a,b   Wong, Patrick S Y ^a   Bast, Aalt ^b,c   Cross, Carroll E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c MAASTRICHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN PEROXIDE; PEROXYNITRITE; THIOL DERIVATIVE;

ARTICLE; BLOOD VESSEL TONE; LEUKOCYTE ADHERENCE; NEUROTRANSMISSION; NITROSATION; PRIORITY JOURNAL; THROMBOCYTE AGGREGATION; VASODILATATION;

ASCORBIC ACID; CELLS, CULTURED; CHEMILUMINESCENT MEASUREMENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTRON SPIN RESONANCE SPECTROSCOPY; GLUTATHIONE; HUMANS; HYDROGEN PEROXIDE; HYDROGEN-ION CONCENTRATION; KINETICS; NITRATES; NITRIC OXIDE;

EID: 15144349362     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.273.46.30255     Document Type: Article

References (67)

1. Moncada, S., and Higgs, A. (1993) N. Engl. J. Med. 329, 2002-2012
2. Stamler, J. S., Singel, D. J., and Loscalzo, J. (1992) Science 258, 1898-1902
3. Beckman, J. S., and Koppenol, W. H. (1996) Am. J. Physiol. 271, C1424-C1437
4. Stamler, J. S., Simon, D. I., Osborne, J. A., Mullins, M. E., Jaraki, O., Michel, T., Singel, D. J., and Loscalzo, J. (1992) Proc. Natl. Acad. Sci. U. S. A. 89, 444-448
5. Gaston, B., Reilly, J., Drazen, J. M., Fackler, J., Ramdey, P., Arnelle, D., Mullins, M. E., Sugarbaker, D. J., Chee, C., Singel, D. J., Loscalzo, J., and Stamler, J. S. (1993) Proc. Natl. Acad. Sci. U. S. A. 90, 10957-10961
6. Jia, L., Bonaventura, C., Bonaventura, J., and Stamler, J. S. (1996) Nature 380, 221-226
7. Butler, A. R., and Rhodes, P. (1987) Anal. Biochem. 249, 1-9
8. Singh, R. J., Hogg, N., Joseph, J., and Kalyanaraman, B. (1996) J. Biol. Chem. 271, 18596-18603
9. Nikitovic, D., and Holmgren, A. (1996) J. Biol. Chem. 271, 19180-19185
10. Aleryani, S., Milo, E., Rose, Y., and Kostka, P. (1998) J. Biol. Chem. 273, 6041-6045
11. Stamler, J. S. (1994) Cell 78, 931-936
12. De Groote, M. A., Granger, D., Xu, Y., Campbell, G., Prince, R., and Fang, F. C. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 6399-6403
13. Liu, Z., Rudd, M. A., Freedman, J. E., and Loscalzo, J. (1998) J. Pharmacol. Exp. Ther. 284, 526-534
14. Wink, D. A., Nims, R. W., Darbyshire, J. F., Christodoulou, D., Hanbauer, I., Cox, G. W., Laval, F., Laval, J., Cook, J. A., Krishna, M. C., DeGraff, W. G., and Mitchell, J. B. (1994) Chem. Res. Toxicol. 7, 519-525
15. Kharitonov, V. G., Sundquist, A. R. and Sharma, V. S. (1995) J. Biol. Chem. 270, 28158-28164
16. Hogg, N., Singh, R. J., and Kalyanaraman, B. (1996) FEBS Lett. 382, 223-228
17. Goldstein, S., and Czapski, G. (1996) J. Am. Chem. Soc. 118, 3419-3425
18. Wade, R. S., and Castro, C. E. (1990) Chem. Res. Toxicol. 3, 289-291
19. Boese, M., Mordvintcev, P. I., Vanin, A. F., Busse, R., and Mülsch, A. (1995) J. Biol. Chem. 270, 29244-29249
20. Radi, R., Beckman, J. S., Bush, K. M. and Freeman, B. A. (1991) J. Biol. Chem. 266, 4244-4250
21. Pryor, W. A., and Squadrito, G. L. (1995) Am. J. Physiol 268, L699-L722
22. Moro, M. A., Darley-Usmar, V. M., Goodwin, D. A., Read, N. G., Zamora-Pino, R., Feelisch, M., Radomski, M. W., and Moncada, S. (1994) Proc. Natl. Acad. Sci. U. S. A. 91, 6702-6706
23. Mayer, B., Schrammel, A., Klatt, P., Koesling, D., and Schmidt, K. (1995) J. Biol. Chem. 270, 17355-17360
24. Tarpey, M. M., Beckman, J. S., Ischiropoulos, H., Gore, J. Z., and Brock, T. A. (1995) FEBS Lett. 364, 314-318
25. Mayer, B., Pfeiffer, S., Schrammel, A., Koesling, D., Schmidt, K., and Brunner, F. (1998) J. Biol. Chem. 273, 3264-3270
26. Liu, S., Beckman, J. S., and Ku, D. D. (1994) J. Pharmacol. Exp. Ther. 268, 1114-1121
27. Villa, L. M., Salas, E., Darley-Usmar, V. M., Radomski, M. W., and Moncada, S. (1994) Proc. Natl. Acad. Sci. U. S.A. 91, 12383-12387
28. Wu, M., Pritchard, K. A., Kaminski, P. M., Fayngersh, R. P., Hintze, T. H., and Wolin, M. S. (1994) Am. J. Physiol. 266, H2108-H2113
29. Lefer, D. J., Scalia, R., Campbell, B., Nossuli, T., Hayward, R., Salamon, M., Grayson, J., and Lefer, A. M. (1997) J. Clin. Invest. 99, 684-691
30. Pou, S., Pou, W. S., Bredt, D. S., Snyder, S. H. and Rosen, G. M. (1992) J. Biol. Chem. 267, 24173-24176
31. Xia, Y., Dawson, V. L., Dawson, T. M., Snyder, S. H., and Zweier, J. L. (1996) Proc. Natl. Acad. Sci. U. S. A. 93, 6770-6774
32. Lymar, S. V., and Hurst, J. K. (1996) Chem. Res. Toxicol. 9, 845-850
33. Radi, R. (1996) Methods Enzymol. 269, 354-366
34. Karoui, H., Hogg, N., Fréjaville, C., Tordo, P., and Kalyanaraman, B. (1996) J. Biol. Chem. 271, 6000-6009
35. Quijano, C., Alvarez, B., Gatti, R. M., Auguste, O., and Radi, R. (1997) Biochem. J. 322, 167-173
36. Hughes, M. N., Nicklin, H. G., and Sackrule, W. A. C. (1971) J. Chem. Soc. A, 3722-3725
37. Davidson, C. A., Kaminski, P. M., Wu, M., and Wolin, M. S. (1996) Am. J. Physiol. 270, H1038-H1043
38. Zhang, H., Squadrito, G. L., Uppu, R. M., Lemercier, J.-N., Cueto, R., and Pryor, W. A. (1997) Arch. Biochem. Biophys. 339, 183-189
39. Feelisch, M. (1991) J. Cardiovasc. Pharmacol. 17, Suppl. 3, 25-33
40. Cameron, D. R., Borrajo, A. M. P., Bennett, B. M., and Thatcher, G. R. J. (1995) Can. J. Chem. 73, 1627-1638
41. Artz, J. D., Yang, K., Lock, J., Sanchez, C., Bennett, B. M., and Thatcher, G. R. J. (1996) Chem. Commun., 927-928
42. Wink, D. A., Darbyshire, J. F., Nims, R. W., Saavedra, J. E., and Ford, P. C. (1993) Chem. Res. Toxicol. 6, 23-27
43. Beckman, J. S., Chen, J., Ischiropoulos, H., and Crow, J. P. (1994) Methods Enzymol. 233, 229-240
44. Oae, S., Shinhama, K., Fujimori, K., and Kim, Y. H. (1980) Bull. Chem. Soc. Jpn. 53, 775-784
45. van der Vliet, A., Eiserich, J. P., Halliwell, B., and Cross, C. E. (1997) J. Biol. Chem. 272, 7617-7625
46. Maragos, C. M., Morley, D., Wink, D. A., Dunams, T. M., Saavedra, J. E., Hoffman, A., Bove, A. A., Isaac, L., Hrabie, J. A., and Reefer, L. K. (1991) J. Med. Chem. 34, 3242-3247
47. McCord, J. M., and Fridovich, I. (1969) J. Biol. Chem. 244, 6049-6055
48. Beckman, J. S., and Conger, K. A. (1995) Methods Companion Methods Enzymol. 7, 35-39
49. Braman, R. S., and Hendrix, S. A. (1989) Anal. Chem. 61, 2715-2718
50. Newton, G. L., Dorian, R., and Fahey, R. C. (1981) Anal. Biochem. 114, 383-387
51. Yamamoto, Y., Brodsky, M. H., Baker, J. C., and Ames, B. N. (1987) Anal. Biochem. 160, 7-13
52. Mathews, W. R., and Kerr, S. W. (1993) J. Pharmacol. Exp. Ther. 267, 1529-1537
53. Bartlett, D., Church, D. F., Bounds, P. L., and Koppenol, W. H. (1995) Free Radical Biol. Med. 18, 85-92
54. Pfeiffer, S., Leopold, E., Hemmens, B., Schmidt, K., Werner, E., and Mayer, B. (1997) Free Radical Biol. Med. 22, 787-794
55. Sokolovsky, M., Harell, D., and Riordan, J. F. (1969) Biochemistry 8, 4740-4745
56. Pryor, W. A., Church, D. F., Govindan, C. K., and Crank, G. (1982) J. Org. Chem. 47, 156-159
57. Lemercier, J.-N., Squadrito, G. L., and Pryor, W. A. (1995) Arch. Biochem. Biophys. 321, 31-39
58. Lymar, S. V., Jiang, Q., and Hurst, J. K. (1996) Biochemistry 35, 7855-7861
59. Moro, M. A., Darley-Usmar, V. M., Lizasoain, I., Su, Y., Knowles, R. G., Radomski, M. W., and Moncada, S. (1995) Br. J. Pharmacol. 116, 1999-2004
60. White, C. R., Moellering, D., Patel, R. P., Kirk, M., Barnes, S., and Darley-Usmar, V. M. (1997) Biochem. J. 328, 517-524
61. Williams, D. L. H. (1997) Nitric Oxide Biol. Chem. 1, 522-527
62. Koppenol, W. H., Moreno, J. J., Pryor, W. A., Ischiropoulos, H., and Beckman, J. S. (1992) Chem. Res. Toxicol. 5, 834-842
63. Gow, A. J., Buerk, D. G., and Ischiropoulos, H. (1997) J. Biol. Chem. 272, 2841-2845
64. Mallozzi, C., Di Stasi, A. M. M., and Minetti, M. (1997) FASEB J. 11, 1281-1290
65. Phelps, D. T., Ferro, T. J., Higgins, P. J., Shankar, R., Parker, D. M., and Johnson, A. (1995) Am. J. Physiol. 269, L551-L559
66. Foresti, R., Clark, J. E., Green, C. J., and Motterlini, R. (1997) J. Biol. Chem. 272, 18411-18417
67. Eich, R. F., Li, T., Lemon, D. D., Doherty, D. H., Curry, S. R., Aitken, J. F., Mathews, A. J., Johnson, K. A., Smith, R. D., Phillips, G. N., and Olson, J. S. (1996) Biochemistry 35, 6976-6983