Reaction of HO· with Guanine derivatives in aqueous solution: Formation of two different redox-active OH-adduct radicals and their unimolecular transformation reactions. Properties of G(-H)·

Chemistry - A European Journal

Volumn 6, Issue 3, 2000, Pages 475-484

  Candeias, Luis P ^a   Steenken, Steen ^a,b  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

DNA oxidation; Electron transfer; Kinetics; Radicals

Indexed keywords

8 HYDROXYGUANINE; DEOXYGUANOSINE; DNA BASE; GUANINE DERIVATIVE; HYDROXYL RADICAL;

AQUEOUS SOLUTION; ARTICLE; DERIVATIZATION; ELECTRON TRANSPORT; MOLECULAR RECOGNITION; OXIDATION REDUCTION REACTION; PROTON TRANSPORT; REACTION ANALYSIS;

EID: 0034603173     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000204)6:3<475::AID-CHEM475>3.0.CO;2-E     Document Type: Article

References (63)

1. J. Cadet, M. Berger, A. Shaw, in Mechanisms of DNA Damage and Repair (Eds.: M. G. Simic, L. Grossman, A. C. Upton), Plenum, New York, London, 1986, pp. 69-74.
2. K. C. Curdy, R. Kohen, B. N. Ames, in Oxygen Radicals in Biology and Medicine, Vol. 49 (Eds.: M. G. Simic, K. A. Taylor, J. F. Ward, C. von Sonntag), Plenum, New York, London, 1988, pp. 479-482.
3. Oxygen Radicals in Biology and Medicine, Vol. 49 (Eds.: M. G. Simic, K. A. Taylor, J. F. Ward, C. von Sonntag), Plenum, New York, London, 1988, pp. 483-489.
4. H. Kasai, S. Nishimura, in Oxidative Stress (Ed.: H. Sics), Academic Press, London 1991, pp. 99-116.
5. G. V. Buxton, C. L. Greenstock, W. P. Helman, A. B. Ross, J. Phys. Chem. Ref. Data 1988, 17, 513.
6. R. Cathcart, E. Schwiers, R. L. Saul, B. N. Ames, Proc. Natl. Acad. Sci. USA 1984, 81, 5633.
7. F. Hutchinson, Progr. Nucleic Acid Res. Molec. Biol. 1985, 32, 115.
8. O. I. Aruoma, B. Halliwell, E. Gajewski, M. Dizdaroglu, J. Biol. Chem. 1989, 264, 20509.
9. In addition, other derivatives such as 5,6-dihydroxycytosine or thymine (and thymidine) glycol have been used to assess oxidative damage inflicted upon DNA in vivo (see ref. [6]).
10. M. Berger, M. de Hazen, A. Neijari, J. Fournier, J. Guignard, H. Pezerat, J. Cadet, Carcinogenesis 1993, 14, 41.
11. W. F. Blakely, A. F. Fuciarelli, B. J. Wegher, M. Dizdaroglu, Radiat. Res. 1990, 121, 338.
12. W. A. Bernhard. Adv. Radiat. Biol. Med. 1981, 9, 199.
13. S. Steenken. Chem. Rev. 1989, 89, 503.
14. D. M. Close, Magn. Reson. Rev. 1991, 15, 241.
15. J. Hüttermann, in Radical Ionic Systems: Properties in Condensed Phases (Eds.: A. Lund, M. Shiotani), Kluwer, Dordrecht, 1991, pp. 435-462.
16. D. Becker, M. D. Sevilla, Adv. Radiat. Biol. Med. 1993, 17, 121.
17. P. O'Neill, E. M. Fielden, Adv. Radiat. Biol. Med. 1993, 17, 53.
18. S. Steenken, Biol. Chem. 1997, 378, 1293.
19. S. Steenken, S. V. Jovanovic, J. Am. Chem. Soc. 1997, 119, 617.
20. J. Cadet, M. Berger, Int. J. Radiat. Biol. 1985, 47, 127.
21. P. O'Neill, Radiat. Res. 1983, 96, 198.
22. S. V. Jovanovic, M. G. Simic, Biochim. Biophys. Acta 1989, 1008, 39.
23. S. Fujita, S. Steenken, J. Am. Chem. Soc. 1981, 103, 2540.
24. D. K. Hazra, S. Steenken, J. Am. Chem. Soc. 1983, 105, 4380.
25. A. J. S. C. Vieira, S. Steenken, J. Phys. Chem. 1987, 91, 4138.
26. For a review, see ref. [13].
27. S. Steenken, P. Neta, J. Phys. Chem. 1982, 86, 3661.
28. This is consistent with results reported previously (see ref. [21]).
29. .4-OH (see Scheme 2 or 3).
30. + followed by protonation of the adduct to give the hydroperoxide and its subsequent decomposition by the "Cadet-mechanism" (see above).
31. + followed by protonation of the adduct to give the hydroperoxide and its subsequent decomposition by the "Cadet-mechanism" (see above).
32. S. Steenken, P. Neta, J. Am. Chem. Soc. 1982, 104, 1244.
33. L. P. Candeias, S. Steenken, J. Am. Chem. Soc. 1989, 111, 1094.
34. K.-D. Asmus, D. J. Deeble, A. Garner, K. M. Idriss Ali, G. Scholes, Br. J. Cancer Suppl. 1978, 37, 46.
35. a for this compound (see ref. [32]).
36. A. J. S. C. Vieira, S. Steenken, J. Am. Chem. Soc. 1987, 109, 7441.
37. A. J. S. C. Vieira, S. Steenken, J. Am. Chem. Soc. 1990, 112, 6986.
38. S. Steenken, in Free Radicals in Synthesis and Biology, Vol. C260 (Ed.: F. Minisci), Kluwer, Dordrecht, 1989, pp. 213-231.
39. R. P. Bell, The Proton in Chemistry, Cornell University Press, Ithaca, NY, 1973.
40. J. Jordan, G. J. Ewing, Inorg. Chem. 1962, 1, 587.
41. The 8-hydroxy form coexists in aqueous solution with the 8-oxo form. In the case of dGuo, the 8-oxo form is dominant, see S. J. Culp, B. P. Cho, F. F. Kadlubar, F. E. Evans, Chem. Res. Toxicol. 1989, 2, 416.
42. M. G. Simic, S. V. Jovanovic, Mechanisms of DNA Damage and Repair (Eds.: M. G. Simic, L. Grossman, A. C. Upton), Plenum, New York, London, 1986, pp. 39-49.
43. It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M. Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA ( K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
44. It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M. Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA ( K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
45. It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M. Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA ( K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
46. It is interesting that 8-hydroxy-derivatives of dGuo were also not formed on photochemical production (by sensitization by riboflavin) of the radical cation of dGuo in dilute aqueous solution of dGuo, in contrast to when the dGuo radical cation was generated in ds DNA, in which 8-HOdGuo was produced in high yield (see H. Kasai, Z. Yamaizumi, M. Berger, J. Cadet, J. Am. Chem. Soc. 1992, 114, 9692). This can be explained by assuming a much longer lifetime of the radical cation in DNA ( K. Hildenbrand, D. Schulte-Frohlinde, Free Radical Res. Commun. 1990, 11, 195, have measured the lifetime of the deprotonated dGuo radical cation in ds DNA in aqueous solution to be 5 s, while in ss DNA its lifetime was too short to be measured) compared with the monomeric dGuo, such that only in ds DNA the very slow hydration reaction has a chance to proceed (an alternative is that the hydration reaction is much faster in ds DNA than in the case of the "monomeric" radical cation). For further discussion, see A. Spassky, D. Angelov, Biochemistry 1997, 36, 6571 and D. Angelov, A. Spassky, M. Berger, J. Cadet, J. Am. Chem. Soc. 1997, 119, 11373.
47. Addition of water at a position other than C8 is conceivable.
48. L. P. Candeias, S. Steenken, J. Am. Chem. Soc. 1992, 114, 699.
49. T. Melvin, S. W. Botchway, A. W. Parker, P. O'Neill, J. Am. Chem. Soc. 1996, 118, 10031.
50. P. M. Cullis, M. E. Malone, L. A. Merson-Davies, J. Am. Chem. Soc. 1996, 118, 2775.
51. E. Meggers, M. E. Michel-Beyerle, B. Giese, J. Am. Chem. Soc. 1998, 120, 12950.
52. J. Jortner, M. Bixon, T. Langenbacher, M. E. Michel-Beyerle, Proc. Natl. Acad. Sci. USA 1998, 95, 12759.
53. M. E. Nunez, D. B. Hall, J. K. Barton, Chem. Biol. 1999, 6, 85.
54. T. Melvin, M. A. Plumb, S. W. Botchway, P. O'Neill, A. W. Parker, Photochem. Photobiol. 1995, 61, 584.
55. I. Saito, M. Takayama, H. Sugiyama, K. Nakatani, J. Am. Chem. Soc. 1995, 117, 6406.
56. H. Sies, W. A. Schulz, S. Steenken, J. Photochem. Photobiol. 1996, 32, 97.
57. H. Sugiyama, I. Saito, J. Am. Chem. Soc. 1996, 118, 7063.
58. S. M. Gasper, G. B. Schuster, J. Am. Chem. Soc. 1997, 117 12762.
59. For a review on oxidative strand scission of nucleic acids, see W. K Pogozelski, T. D. Tullius, Chem. Rev. 1998, 98, 1089.
60. + my be due to an impurity in the ribose used.
61. M. Dizdaroglu, C. von Sonntag, D. Schulte-Frohlinde, J. Am. Chem. Soc. 1975, 97, 2277.
62. D. Schulte-Frohlinde, Radioprotectors and Anticarcinogens, Vol. 8 (Eds.: O. F. Nygaard, M. G. Simic), Academic Press, New York, 1983, pp. 53-71.
63. The remaining 13-18% are due to radicals formed by H-abstraction from the deoxyribose moiety.