Radical mechanisms of the decomposition of peroxynitrite and the peroxynitrite-CO2 adduct and of reactions with L-tyrosine and related compounds as studied by 15N chemically induced dynamic nuclear polarization

Archives of Biochemistry and Biophysics

Volumn 368, Issue 2, 1999, Pages 303-318

  Lehnig, Manfred ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

Cage reaction; Carbonate radical; CIDNP; Hydroxyl radical; N itrotyrosine; Nitration; Nitrophenol; Nitrosoperoxycarbonate; Peroxynitrite; Phenoxyl radical; Radical; Tyrosine

Indexed keywords

2 NITROPHENOL; 3 NITROTYROSINE; 4 NITROPHENOL; NITROGEN DIOXIDE; PEROXYNITRITE; PHENOL DERIVATIVE; PHENYLACETIC ACID DERIVATIVE; TYROSINE; TYROSINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; DECOMPOSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0033567373     PISSN: 00039861     EISSN: None     Source Type: Journal    
DOI: 10.1006/abbi.1999.1268     Document Type: Article

References (73)

1. Beckman J. S., Beckman T. W., Chen J., Marshall P. A., Freeman B. A. Proc. Natl. Acad. Sci. USA. 87:1990;1620-1624.
2. Ischiropoulos H., Zhu L., Chen J., Tsai M., Martin J. C., Smith C. D., Beckman J. S. Arch. Biochem. Biophys. 298:1992;431-437.
3. Haddad I. Y., Ischiropoulos H., Holm B. A., Beckman J. S., Baker J. R., Matalon S. Am. J. Physiol. 265:1993;L555-L564.
4. Berlett B. S., Friguet B., Yim M. B., Chock P. B., Stadtman E. R. Proc. Natl. Acad. Sci. USA. 93:1996;1776-1780.
5. Crow J. P., Ye Y. Z., Strong M., Kirk M., Barnes S., Beckman J. S. J. Neurochem. 69:1997;1945-1953.
6. Yamakura F., Taka H., Fujimura T., Murayama K. J. Biol. Chem. 273:1998;14085-14089.
7. Zou M., Martin Ch., Ullrich V. Biol. Chem. 378:1997;707-713.
8. Roberts E. S., Lin H.-l., Crowley J. R., Vuletich J. L., Osawa Y., Hollenberg P. F. Chem. Res. Toxicol. 11:1998;1067-1074.
9. Thomson L., Gadelha F. R., Peluffo G., Vercesi A. E., Radi R. Mol. Biochem. Parasitol. 98:1999;81-91.
10. Koppenol W. H. Chem. Res. Toxicol. 11:1998;716-717.
11. Beckman J. S. Chem. Res. Toxicol. 9:1996;836-844.
12. Coombes R. G., Golding J. G., Hadjigeorgiou P. J. Chem. Soc. Perkin Trans. 2. 1979;1451-1459.
13. Halfpenny E., Robinson P. L. J. Chem. Soc. 1952;928-938.
14. Richeson C. E., Mulder P., Bowry V. W., Ingold K. U. J. Am. Chem. Soc. 120:1998;7211-7219.
15. Prütz W. A., Mönig H., Butler J., Land E. J. Arch. Biochem. Biophys. 243:1985;125-134.
16. van der Vliet A., Eiserich J. P., O'Neill C. A., Halliwell B., Cross C. E. Arch. Biochem. Biophys. 319:1995;341-349.
17. Gow A., Duran D., Thom S. R., Ischiropoulos H. Arch. Biochem. Biophys. 333:1996;42-48.
18. Uppu R. M., Squadrito G. L., Pryor W. A. Arch. Biochem. Biophys. 327:1996;335-343.
19. Denicola A., Freeman B. A., Trujillo M., Radi R. Arch. Biochem. Biophys. 333:1996;49-58.
20. Lymar S. V., Jiang Q., Hurst J. K. Biochemistry. 35:1996;7855-7861.
21. Lymar S. V., Hurst J. K. J. Am. Chem. Soc. 117:1995;8867-8868.
22. Zhang H., Squadrito G. L., Pryor W. A. Nitric Oxide Biol. Chem. 1:1997;301-307.
23. Lymar S. V., Hurst J. K. Inorg. Chem. 37:1998;294-301.
24. Clemens A. H., Ridd J. H., Sandall J. P. B. J. Chem. Soc. Perkin Trans. 2:1984;1667-1672.
25. Ridd J. H., Trevellick S., Sandall J. P. B. J. Chem. Soc. Perkin Trans. 2:1992;573-577.
26. Beake B. D., Moodie R. B. J. Chem. Soc. Perkin Trans. 2:1998;1-5.
27. Uppu R. M., Lemercier J.-N., Squadrito G. L., Zhang H., Bolzan R. M., Pryor W. A. Arch. Biochem. Biophys. 358:1998;1-16.
28. Goodwin D. C., Gunther M. R., Hsi L. C., Crews B. C., Eling T. E., Mason R. P., Marnett L. J. J. Biol. Chem. 273:1998;8903-8909.
29. Challis B. C., Higgins R. J. J. Chem. Soc. Perkin Trans. 2. 1972;2365-2368.
30. Wink D. A., Darbyshire J. F., Nims R. W., Saavedra J. E., Ford P. C. Chem. Res. Toxicol. 6:1993;23-27.
31. Pires M., Rossi M. J., Ross D. S. Int. J. Chem. Kinet. 26:1994;1207-1227.
32. Eiserich J. P., Butler J., van der Vliet A., Cross C. E., Halliwell B. Biochem. J. 310:1995;745-749.
33. Bargon J., Fischer H., Johnsen U. Z. Naturforsch. 22a:1967;1551-1555.
34. Ward H. R., Lawler R. G. J. Am. Chem. Soc. 89:1967;5518-5519.
35. Kaptein R., Oosterhoff J. L. Chem. Phys. Lett. 4:1969;195-197.
36. Closs G. L. J. Am. Chem. Soc. 91:1969;4552-4554.
37. Kaptein R. Chem. Commun. 1971;732-733.
38. Clemens A. H., Ridd J. H., Sandall J. P. B. J. Chem. Soc. Perkin Trans. 2:1984;1659-1665.
39. Butler A. R., Rutherford T. J., Short D. M., Ridd J. H. Chem. Commun. 1997;669-670.
40. Lehnig M. J. Chem. Soc. Perkin Trans. 2:1996;1943-1948.
41. Lehnig M. Acta. Chem. Scand. 51:1997;211-213.
42. Lehnig M., Schürmann K. Eur. J. Org. Chem. 1998;913-918.
43. Lehnig M. Tetrahedron Lett. 40:1999;2299-2302.
44. Benton D. J., Moore P. J. Chem. Soc. (A). 1970;3179-3182.
45. Saha A., Goldstein S., Cabelli D., Czapski G. Free Radical Biol. Med. 24:1998;653-659.
46. Morton J. R., Preston K. F., Strach S. J. J. Phys. Chem. 83:1979;533-535.
47. Morton J. R., Preston K. F. Fischer H. Landolt-Börnstein, New Series, Group II, Magnetic Properties of Free Radicals. 1987;54-57 Springer-Verlag, Berlin.
48. Logager T., Sehested K. J. Phys. Chem. 97:1993;6664-6669.
49. Thomas J. K. Adv. Rad. Chem. 1:1969;103-198.
50. Kissner R., Nauser Th., Bugnon P., Lye P. G., Koppenol W. H. Chem. Res. Toxicol. 10:1997;1285-1292.
51. Stanbury D. M., deMaine M. M., Goodloe G. J. Am. Chem. Soc. 111:1989;5496-5498.
52. Grätzel M., Henglein A., Lilie J., Beck G. Ber. Bunsenges. Phys. Chem. 73:1969;646-653.
53. Schwartz S. E., White W. H. Adv. Environ. Sci. Technol. 12:1983;1-116.
54. Houk K. N., Condroski K. R., Pryor W. A. J. Am. Chem. Soc. 118:1996;13002-13006.
55. Pfeiffer S., Gorren A. C. F., Schmidt K., Werner E. R., Hansert B., Bohle D. S., Mayer B. J. Biol. Chem. 272:1997;3465-3470.
56. Mahoney L. R. J. Am. Chem. Soc. 92:1970;5262-5263.
57. Alvarez B., Denicola A., Radi R. Chem. Res. Toxicol. 8:1995;859-864.
58. Huie R. E. Toxicology. 89:1994;193-216.
59. Fairhurst S. A., Morton J. R., Preston K. F. Chem. Phys. Lett. 95:1983;30-32.
60. Behar D., Czapski G., Duchovny I. J. Phys. Chem. 74:1970;2206-2210.
61. Lilie J., Hanrahan R. J., Henglein A. Radiat. Phys. Chem. 11:1978;225-227.
62. Merenyi G., Lind J. Chem. Res. Toxicol. 10:1987;1216-1220.
63. Chen S.-N., Hoffman M. Z. Rad. Res. 56:1973;40-47.
64. Hitchcock D. I. Chem. Zentralbl. 1924;2249.
65. Kirsch M., Lomonosova E. E., Korth H.-G., Sustmann R., de Groot H. J. Biol. Chem. 273:1998;12716-12724.
66. van der Vliet A., O'Neill C. A., Halliwell B., Cross C. E., Kaur H. FEBS Lett. 339:1994;89-92.
67. Hoggett J. G., Moodie R. B., Penton J. R., Schofield K. Nitration and Aromatic Reactivity. 1971;Cambridge Univ. Press, Cambridge.
68. Ramezanian M. S., Padmaja S., Koppenol W. H. Chem. Res. Toxicol. 9:1996;232-240.
69. Lemercier J.-N., Padmaja S., Cueto R., Squadrito G. L., Uppu R. M., Pryor W. A. Arch. Biochem. Biophys. 345:1997;160-170.
70. Radner F., Wall A., Loncar M. Acta. Chem. Scand. 44:1990;152-157.
71. Al-Obaidi U., Moodie R. B. J. Chem. Soc. Perkin Trans. 2. 1985;467-472.
72. Halliwell B. FEBS Lett. 411:1997;157-160.
73. Pfeiffer S., Mayer B. J. Biol. Chem. 273:1998;27280-27285.