Release of superoxide from nucleoside peroxyl radicals, a double-edged sword?

Journal of the American Chemical Society

Volumn 120, Issue 20, 1998, Pages 4903-4909

  Tallman, Keri A ^a   Tronche, Christopher ^a   Yoo, Dong Jin ^a   Greenberg, Marc M ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; RADICAL; SUPEROXIDE;

AEROBIC METABOLISM; ARTICLE; BIODEGRADATION; DETOXIFICATION; DNA DAMAGE; DNA DEGRADATION; ULTRAVIOLET RADIATION;

EID: 0032572092     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973200s     Document Type: Article

References (44)

1. (a) Porter, N. A. In Organic Peroxides; Ando, W., Ed.; John Wiley & Son, Ltd.: Chichester, England, 1992.
2. (b) Porter, N. A.; Mills, K. A.; Carter, R. L. J. Am. Chem. Soc. 1994, 116, 6690.
3. (c) Porter, N. A.; Mills, K. A.; Caldwell, S. E.; Dubay, G. R. J. Am. Chem. Soc. 1994, 116, 6697.
4. (a) von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor and Francis: London, 1987.
5. (b) Breen, A. P.; Murphy, J. A. Free Radical Biol. Med. 1995, 18, 1033.
6. (a) Deeble, D. J.; von Sonntag, C. Int. J. Radiat. Biol. 1986, 49, 927.
7. (b) Schulte-Frohlinde, D.; Bothe, E. Z. Naturforsch. 1984, 39c, 315.
8. Greenberg, M. M.; Barvian, M. R.; Cook, G. P.; Goodman, B. K.; Matray, T. J.; Tronche, C.; Venkatesan, H. J. Am. Chem. Soc. 1997, 119, 1828.
9. Neta, P.; Grodkowski, J.; Ross, A. B. J. Phys. Chem. Ref. Data 1996, 25, 709.
10. Tronche, C.; Goodman, B. K.; Greenberg, M. M. Chem. Biol., in press.
11. (a) Lesiak, K. B.; Wheeler, K. T. Radiat. Res. 1990, 121, 328.
12. (b) Ide, H.; Yamaoka, T.; Kimura, Y. Biochemistry 1994, 33, 7127.
13. von Sonntag, C.; Schuchmann, H.-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229.
14. Schuchmann, M. N.; Schuchmann, H.-P.; von Sonntag, C. J. Am. Chem. Soc. 1990, 112, 403.
15. (a) Deeble, D. J.; von Sonntag, C. Int. J. Radiat. Biol. 1987, 51, 791.
16. (b) Al-Sheikhly, M. I.; Hissung, A.; Schuchmann, H.-P.; Schuchmann, M. N.; von Sonntag, C.; Garner, A.; Scholes, G. J. Chem. Soc., Perkin Trans. 2 1984, 601.
17. (a) Meijler, M. M.; Zelenko, O.; Sigman, D. S. J. Am. Chem. Soc. 1997, 119, 1135.
18. (b) Meschwitz, S. M.; Schultz, R. G.; Ashley, G. W.; Goldberg, I. H. Biochemistry 1992, 31, 9117.
19. (a) Walling, C. Acc. Chem. Res. 1975, 8, 125.
20. (b) Haber, F.; Weiss, J. Proc. R. Chem. Soc. London, Sect. A 1934, 147, 332.
21. (c) Fenton, H. J. H. J. Chem. Soc. 1894, 65, 899.
22. Tamir, S.; Burney, S.; Tannenbaum, S. R. Chem. Res. Toxicol. 1996, 9, 821.
23. Goodman, B. K.; Greenberg, M. M. J. Org. Chem. 1996, 61, 2.
24. Experiments carried out using a water soluble tin hydride reagent (tris[3-(2-methoxyethoxy)propyl]stannane) complicated the product analysis, and will be reported on at a later date. For the synthesis of this water soluble tin hydride reagent see: Light, J.; Breslow, R. In Organic Syntheses; Coffen, D. L., Ed.; Wiley: New York, 1994; Vol. 72, p 199.
25. Barvian, M. R.; Greenberg, M. M. J. Org. Chem. 1993, 58, 6151.
26. Mayer, S.; Prandi, J. Tetrahedron Lett. 1996, 37, 3117.
27. (a) Armitage, B.; Yu, C.; Devadoss, C.; Schuster, G. B. J. Am. Chem. Soc. 1994, 116, 9847.
28. (b) McCord, J. M.; Fridovich, I. J. Biol. Chem. 1969, 244, 6049.
29. Misra, H. P.; Fridovich, I. J. Biol. Chem. 1972, 247, 3170.
30. See the Supporting Information.
31. Tronche, C.; Martinez, F. N.; Horner, J. H.; Newcomb, M.; Senn, M.; Giese, B. Tetrahedron Lett. 1996, 37, 5845.
32. (a) Schulte-Frohlinde, D.; Behrens, G.; Önal, A. Int. J. Radiat. Biol. 1986, 50, 103.
33. (b) Chenier, J. H. B.; Furimsky, E.; Howard, J. A. Can. J. Chem. 1974, 52, 3682.
34. Newcomb, M. Tetrahedron 1993, 49, 1151.
35. Rong, X. X.; Pan, H.-Q.; Dolbier, W. R. Jr.; Smart, B. E. J. Am. Chem. Soc. 1994, 116, 4521.
36. EPR spin trapping experiments using 5,5-dimethylpyrroline N-oxide were also unfruitful. Multiple trapping products were observed. Furthermore, the superoxide adduct is unstable under the photolysis conditions.
37. It was independently demonstrated that the deoxyribonolactone (1) does not undergo deuterium or oxygen exchange under the reaction conditions.
38. Robins, M. J.; Trip, E. M. Tetrahedron Lett. 1974, 3369.
39. The yield of 6 was >90% of the amount of 10 consumed during photolysis. Consumption of 10 was established by reversed-phase HPLC. The yield of 6 was determined by GC/MS analysis following persilylation. Both compounds were quantitated using internal standards.
40. (a) Bennett, J. E. J. Chem. Soc., Faraday Trans. 1990, 86, 3247.
41. (b) During the photolysis (2 h), ∼25% of a solution of 10 (50 μM) is converted in the RPR-100 photoreactor (equipped with one lamp). On the basis of this level of conversion, we estimate that the steady-state concentration of 4 during photolysis is at the nanomolar level. Consequently, the rate of reaction of two molecules of 4 (using the rate constant in ref 29a) is significantly slower than trapping of 4 by thiol.
42. Hildenbrand, K.; Schulte-Frohlinde, D. Int. J. Radiat. Biol. 1997, 71, 377.
43. Howard, J. A. In Free Radical Chain Reactions, Part II; Kochi, J. K., Ed.; John Wiley & Son, Inc.: New York, 973.
44. Greenberg, M. M.; Yoo, D. J.; Goodman, B. K. Nucleosides Nucleotides 1997, 16, 33.