Modification of the reductive pathway in gamma-irradiated DNA by electron scavengers: Targeting the sugar-phosphate backbone

Radiation Research

Volumn 149, Issue 5, 1998, Pages 422-432

  Razskazovskii, Yurii ^a   Roginskaya, Marina ^a   Sevilla, Michael D ^a  

^a OAKLAND UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL TISSUE; ARTICLE; DNA DAMAGE; ELECTRON SPIN RESONANCE; GAMMA IRRADIATION; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; RADIOSENSITIVITY; REDUCTION; SALMON;

ACRYLAMIDE; ACRYLAMIDES; BIPHENYL COMPOUNDS; CYSTEAMINE; DNA; DNA ADDUCTS; DNA DAMAGE; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTRONS; GAMMA RAYS; IODOACETAMIDE; LITHIUM CHLORIDE; ONIUM COMPOUNDS; OXIDATION-REDUCTION; REFERENCE STANDARDS; SUGAR PHOSPHATES; SULFONIUM COMPOUNDS; TEMPERATURE; THYMIDINE MONOPHOSPHATE;

ANIMALIA; LETHRINIDAE;

EID: 0031923112     PISSN: 00337587     EISSN: None     Source Type: Journal    
DOI: 10.2307/3579781     Document Type: Article

References (65)

1. D. W. Whillans, G. E. Adams and P. Neta, Electron-affinic sensitization. VI. A pulse radiolysis and ESR comparison of some 2-and 5-nitroimidazoles. Radiat. Res. 62, 407-421 (1975).
2. G. E. Adams, I. R. Flockhart, C. E. Smithen, I. J. Stratford, P. Wardman and M. E. Watts, Electron-affinic sensitization. VII. A correlation between structures, one-electron reduction potentials, and efficiencies of nitroimidazoles as hypoxic cell radiosensitizers. Radiat. Res. 67, 9-20 (1976).
3. G. E. Adams, Hypoxic cell sensitizers for radiotherapy. Int. J. Radiat. Oncol. Biol. Phys. 4, 135-141 (1978).
4. G. E. Adams, I. Ahmed, E. M. Fielden, P. O'Neill and I. J. Stratford, The development of some nitroimidazoles as hypoxic cell sensitizers. Cancer Clin. Trials 3, 37-42 (1980).
5. G. E. Adams, I. Ahmed, E. D. Clarke, P. O'Neill, J. Parrick, I. J. Stratford, R. G. Wallace, P. Wardman and M. E. Watts, Structure-activity relationships in the development of hypoxic cell radiosensitizers. III. Effects of basic substituents in nitroimidazole sidechains. Int. J. Radiat. Biol. 38, 613-626 (1980).
6. G. E. Adams, E. M. Fielden, C. Hardy, B. C. Millar, I. J. Stratford and C. Williamson, Radiosensitization of hypoxic mammalian cells in vitro by some 5-substituted-4-nitroimidazoles. Int. J. Radiat. Biol. 40, 153-161 (1981).
7. G. E. Adams, I. Ahmed, P. W. Sheldon and I. J. Stratford, Radiation sensitization and chemopotentiation: RSU 1069, a compound more efficient than misonidazole in vitro and in vivo. Br. J. Cancer 49, 571-577 (1984).
8. P. O'Neill, T. C. Jenkins, I. J. Stratford, A. R. J. Silver, I. Ahmed, S. S. McNeil, E. M. Fielden and G. E. Adams, Mechanism of action of some bioreducible 2-nitroimidazoles: Comparison of in vitro cytotoxicity and ability to induce DNA strand breakage. Anti-Cancer Drug Design 1, 271-280 (1987).
9. G. E. Adams, Failla Memorial Lecture: Redox, radiation, and reductive bioactivation. Radiat. Res. 132, 129-139 (1992).
10. J. D. Zimbrick, J. F. Ward and L. S. Myers, Jr., Studies on the chemical basis of cellular radiosensitization by 5-bromouracil substitution in DNA. I. Pulse-and steady-state radiolysis of 5-bromouracil and thymine. Int. J. Radiat. Biol. 16, 505-523 (1969).
11. J. D. Zimbrick, J. F. Ward and L. S. Myers, Jr., Studies on the chemical basis of cellular radiosensitization by 5-bromouracil substitution in DNA. II. Pulse-and steady-state radiolysis of bromo-uracil-substituted and unsubstituted DNA. Int. J. Radiat. Biol. 16, 525-534 (1969).
12. G. E. Adams and R. L. Willson, On the mechanism of BUdR sensitization: A pulse radiolysis study on the electron transfer in nucleic acid derivatives. Int. J. Radiat. Biol. 22, 589-597 (1972).
13. K. Bansal, L. K. Patterson and R. H. Schuler, The production of halide ion in the radiolysis of aqueous solutions of 5-halouracils. J. Phys. Chem. 76, 2386-2392 (1972).
14. K. Bhatia and R. H. Schuler, Uracilyl radical production in the radiolysis of aqueous solutions of 5-halouracils. J. Phys. Chem. 77, 1888-1896 (1973).
15. -. J. Phys. Chem. 87, 3966-3971 (1983).
16. G. W. Buchko and M. Weinfeld, Influence of nitrogen, oxygen, and nitroimidazole radiosensitizers on DNA damage induced by ionizing irradiation. Biochemistry 32, 2186-2193 (1993).
17. C. von Sonntag, The Chemical Basis of Radiation Biology. Taylor & Francis, London and New York, 1987.
18. Y. Razskazovskii, S. G. Swarts, J. M. Falcone, C. Taylor and M. D. Sevilla, Competitive electron scavenging by chemically modified pyrimidine bases in bromine-doped DNA: Relative efficiencies and relevance to intrastrand electron migration distances. J. Phys. Chem. 101, 1460-1467 (1997).
19. A. F. Fuciarelli, E. C. Sisk and J. D. Zimbrick, Electron migration in oligonucleotides upon γ-irradiation in solution. Int. J. Radiat. Biol. 65, 409-418 (1994).
20. P. M. Cullis, M. C. R. Symons, B. W. Wren and S. Gregoli, Effects of ionizing radiation on deoxyribonucleic acid. Part 3. The effect of iodoacetamide. J. Chem. Soc. Perkin Trans. 2, 1819-1825 (1985).
21. W. Wang, Y. Razskazovskii and M. D. Sevilla, Secondary radical attack on DNA nucleotides: Reaction by addition to DNA bases and abstraction from sugar. Int. J. Radiat. Biol. 71, 387-399 (1997).
22. P. M. Cullis, J. D. McClymont and M. C. R. Symons, Electron conduction and trapping in DNA. An electron spin resonance study. J. Chem. Soc. Faraday Trans. 86, 591-592 (1990).
23. A. Pezeshk, M. C. R. Symons and J. D. McClymont, Electron movement along DNA strands: Use of intercalators and electron paramagnetic resonance spectroscopy. J. Phys. Chem. 100, 18562-18566 (1996).
24. B. S. Wildi, S. W. Taylor and H. A. Potratz, The preparation of triarylsulfonium halides by the action of aryl Grignard reagents on diphenyl sulfoxide. J. Am. Chem. Soc. 73, 1965-1967 (1952).
25. J. Collette, D. McGreer, R. Crawford, F. Chubb and R. B. Sandin, Synthesis of some cyclic iodonium salts. J. Am. Chem. Soc. 78, 3819-3820 (1954).
26. A. N. Nesmeyanov, I. N. Lisichkina, A. N. Vanchikov and T. P. Tolstaya, New cyclic diarylbromonium salts. Doklady Akademii Nauk SSSR 228, 99-101 (1976).
27. Y. Razskazovskii and M. D. Sevilla, Reactions of sulfonyl peroxyl radicals with DNA and its components: Hydrogen abstraction from the sugar backbone versus addition to pyrimidine double bonds. Int. J. Radiat. Biol. 69, 75-87 (1996).
28. S. Gregoli, M. Olast and A. Bertinchamps, Radiolytic pathways in γ-irradiated DNA: Influence of chemical and conformational factors. Radiat. Res. 89, 238-254 (1982).
29. M. L. van Lith, J. M. Warman, M. P. de Haas and A. Hummel, Electron migration in hydrated DNA and collagen at low temperatures. J. Chem. Soc. Faraday Trans. 82, 2933-2943 (1986).
30. N. J. Tao and S. M. Lindsay, Structure of DNA hydration shells studied by Raman spectroscopy. Biopolymers 28, 1019-1030 (1989).
31. • formation. Radiat. Res. 145, 673-680 (1996).
32. R. A. Holroyd and J. W. Glass, Radicals formed by electron transfer to pyrimidine derivatives. Int. J. Radiat. Biol. 14, 445-454 (1968).
33. -) in aqueous solution. J. Phys. Chem. Ref. Data 17, 513-886 (1988).
34. C. Van Paemel, H. Frumin, V. L. Brooks, R. Failor and M. D. Sevilla, Protonation reactions at carbon sites in the anion radicals of certain unsaturated compounds and aromatic amino acids. J. Phys. Chem. 79, 839-845 (1975).
35. J. Barnes, W. A. Bernhard and K. R. Mercer, Distribution of electron trapping in DNA: Protonation of one-electron reduced cytosine. Radiat. Res. 126, 104-107 (1991).
36. M. D. Sevilla, D. Becker, M. Yan and S. R. Summerfield, Relative abundance of primary ion radicals in γ-irradiated DNA: Cytosine vs. thymine anion and guanine vs. adenine cation. J. Phys. Chem. 95, 3409-3415 (1991).
37. P. M. Cullis, J. D. McClymont, M. E. Malone, A. N. Mather, I. D. Podmore, M. C. Sweeney and M. C. R. Symons, Effects of ionizing radiation on deoxyribonucleic acid. Part 7. Electron capture at cytosine and thymine. J. Chem. Soc. Perkin Trans. 2, 1695-1702 (1992).
38. J. Barnes and W. A. Bernhard, The protonation state of one-electron reduced cytosine and adenine. 1. Initial protonation sites at low temperatures in glassy solids. J. Phys. Chem. 97, 3401-3408 (1993).
39. J. P. Barnes and W. A. Bernhard, One-electron reduced cytosine in acidic glasses: Conformational states before and after proton transfer. J. Phys. Chem. 98, 887-893 (1994).
40. M. Yan, D. Becker, S. Summerfield, P. Renke and M. D. Sevilla, Relative abundance and reactivity of primary ion radicals in γ-irradiated DNA at low temperatures. 2. Single vs. double-stranded DNA. J. Phys. Chem. 96, 1983-1989 (1992).
41. W. Wang and M. D. Sevilla, Protonation of nucleobase anions in gamma-irradiated DNA and model systems. Which DNA base is the ultimate sink for the electron? Radiat. Res. 138, 9-17 (1994).
42. J. Huttermann, Electron spin resonance of radiation-induced free radicals in irradiated single crystals of thymine monohydrate. Int. J. Radiat. Biol. 17, 249-259 (1970).
43. M. D. Sevilla, An electron spin resonance study of the photoionization of thymine. The thymine cation and anion radicals. J. Phys. Chem. 75, 626-631 (1971).
44. M. D. Sevilla, C. Van Paemel and G. Zorman, Reactions of the cation and anion radicals of several DNA bases. J. Phvs. Chem. 76, 3577-3582 (1972).
45. M. C. R. Symons, Identification of the products resulting from the direct effects of γ-irradiation on thymidine. J. Chem. Soc. Perkin Trans. 2, 1303-1307 (1988).
46. J. Hüttermann, M. Röhrig and W. Köhnlein, Free radicals from irradiated lyophilized DNA: Influence of water of hydration. Int. J. Radiat. Biol. 61, 299-313 (1992).
47. J. Hüttermann, M. Lange and J. Ohlmann, Mechanistic aspects of radiation-induced free radical formation in frozen aqueous solutions of DNA constituents: Consequences for DNA? Radiat. Res. 131, 18-23 (1992).
48. M. Lange, B. Weiland and J. Hüttermann, Influence of electron scavengers on the radical formation in thymidine-5′-monophosphate and DNA in frozen aqueous solutions and glasses. Int. J. Radiat. Biol. 68, 475-486 (1995).
49. K. K. Iu, J. Kuczynski, S. J. Fuerniss and J. K. Thomas, Laser flash-photolysis of arylsulfonium salts - studies of photoproduced proton kinetics and mechanism in polar solvents by a pH-jump method. J. Am. Chem. Soc. 114, 4871-4878 (1992).
50. K. M. Welsh, J. L. Dektar, M. A. Garciagaribaya, N. P. Hacker and N. J. Turro, Photo-CIDNP and nanosecond laser flash photolysis studies on the photodecomposition of triarylsulfonium salts. J. Org. Chem. 57, 4179-4184 (1992).
51. P. F. A. Buijsen and N. P. Hacker, Photochemical reaction of onium salts with N,N-dimethylaniline - evidence for photoinduced electron transfer. Tetrahedron Lett. 34, 1557-1560 (1993).
52. Y. Bi and D. C. Neckers, Photochemical reaction of halogenated xanthene dye with diaryliodonium salts. J. Photochem. Photobiol. Ser. A 74, 221-230 (1993).
53. W. Wang and M. D. Sevilla, Reactions of cysteamine with individual DNA base radicals in γ-irradiated nucleotides at low temperature. Int. J. Radiat. Biol. 66, 1-13 (1994).
54. M. E. Malone, P. M. Cullis, M. C. R. Symons and A. W. Parker, Biphotonic photoionization of cytosine and its derivatives with UV radiation at 248 nm: An EPR study in low-temperature perchlorate glasses. J. Phys. Chem. 99, 9299-9308 (1995).
55. D. Becker, S. Summerfield, S. Gillich and M. D. Sevilla, Influence of oxygen on the repair of direct radiation damage to DNA by thiols in model systems. Int. J. Radiat. Biol. 65, 537-548 (1994).
56. D. M. Close, Where are the sugar radicals in irradiated DNA? Radiat. Res. 147, 663-673 (1997).
57. D. M. Close, Sugar radical conformations in A-DNA. Radiat. Res. 148, 512-513 (1997). [extended abstract]
58. M. D. Sevilla and M. L. Engelhardt, Mechanisms for radiation damage in DNA constituents and DNA. Faraday Discuss. Chem. Soc. 63, 255-263 (1978).
59. M. E. Malone, M. C. R. Symons and A. W. Parker, An EPR study of photoionized thymine and its derivatives at 77 K. J. Chem. Soc. Perkin Trans. 2, 2067-2075 (1993).
60. V. B. Odonnell, D. G. Tew, O. T. G. Jones and P. J. England, Studies on the inhibitory mechanism of iodonium compounds with special reference to neutrophil NADPH oxidase. Biochem. J. 290. 41-49 (1993).
61. D. G. Tew, Inhibition of Cytochrome-P(450) reductase by the diphenyliodonium cation - Kinetic analysis and covalent modifications. Biochemistry 32, 10209-10215 (1993).
62. A. Majander, M. Finel and M. Wikstrom, Diphenyleneiodonium inhibits reduction of iron-sulfur clusters in the mitochondrial NADH-ubiquinone oxidoreductase. J. Biochem. 269, 21037-21042 (1994).
63. V. B. Odonnell, G. C. M. Smith and O. T. G. Jones, Involvement of phenyl radicals in iodonium compound inhibition of flavoenzymes. Mol. Pharmacol. 46, 778-785 (1994).
64. W. Wang and M. D. Sevilla, Reactions of cysteamine with individual DNA base radicals in γ-irradiated nucleotides at low temperature. Int. J. Radiat. Biol. 66, 1-13 (1994).
65. • addition to the DNA bases: Electron affinities and ionization potentials. J. Phys. Chem. 99, 13033-13037 (1995).