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Research Article

Secondary radical attack on DNA nucleotides: reaction by addition to DNA bases and abstraction from sugars

Pages 387-399 | Published online: 03 Jul 2009

References

  • BARNES, J. P. and BERNHARD, W. A., 1993, The protonation state of one-electron reduced cytosine and adenine. 1. Initial protonation sites at low temperatures in glassy solids. Journal of Physical Chemistry, 97, 3401 —3408.
  • BARNES, J., BERNHARD, W. A. and MERCER, K., 1991, Distribution of electron trapping in DNA: protonation of one-electron reduced cytosine. Radiation Research, 126, 104–'07.
  • BARNES, J. P. and BERNHARD, W. A., 1994, One-electron reduced cytosine in acidic glasses: conformational states before and after proton transfer. Journal of Physical Chemistry, 98, 887–893.
  • BECKER, D., RAZSKAZOVSKII, Yu., CALLAGHAN, M. and SEVILLA, M. D., 1996, Electron spin resonance of DNA irradiated with a heavy-ion bean (1608+): evidence for damage to the deoxyribose phophate backbone. Radiation Research, 146, 361–368.
  • BECKER, D. and SEVILLA, M. D., 1993, The chemical con-sequences of radiation damage to DNA. Advances in Radiation Biology, edited by J. T. Lett and H. Adler. (New York: Academic Press), pp. 121–180.
  • BEHRENS, G., KOLTSENBUR GG. and SCHULTE-FROHLINDE, D., 1982, Model reactions for the degradation of DNA-4' radicals in aqueous solution. Fast hydrolysis of a-alkoxyal-kyl radicals with a leaving group in the /3-position followed by radical rearrangement and elemination reactions. Zeitschrift fur Naturforschung, 37c, 1205–1227.
  • BERNHARD, W. A., CLOSE, D. M., MERCER, K. R. and CORELLI, J. C., 1976, ESR of X-irradiated single crystals of 3'-cytidylic acid: hydrogen abstraction from C5' of the sugar moiety. Radiation Research, 66, 19–32.
  • BOTHE, E., QURESHI, E. A. and SCHULTE-FROHLINDE, D., 1984, Rate of OH radical induced strand break formation in single stranded DNA under anoxic conditions. An investi-gation of aqueous solutions using conductivity methods. Zeitschrift fur Naturforschung, 38c, 1030–1042.
  • Box, H. C., BUDZINSKI, E. E., DAWIDZIK, J. D., WALLACE, J. C., EVANS, M. S. and GOBEY, J. S., 1996, Radiation-induced formation of a crosslink between base moieties of deoxyg-uanosine and thymidine in deoxygenated solutions of d(CpGpTpA). Radiation Research, 145, 641 —643.
  • CATTERALL, H., DAVIES, M. J. and GILBERT, B. C., 1992, An EPR study of the transfer of radical-induced damage from the base to sugar in nucleic acid components: relevance to the occurrence of strand breakage. Journal of the Chemical Society Perkin Transactions 27 1379–1385.
  • CLOSE, D. M., FOUSE, G. W. and BERNHARD, W. A., 1977, ENDOR study of the 3aH radical in deoxycytidine 5'-phosphate*H20. Journal of Chemical Physics, 66, 4689–4693.
  • CLOSE, D. M., NELSON, W. H., SAGSTUEN, E. and HOL EE. 0., 1994, ESR and ENDOR study of single crystals of deoxyadenosine monohydrate X-irradiated at 10K. Radiation Research, 137, 300–309.
  • COLSON, A. 0. and SE VILLA, M. D., 1995, Structure and relative stability of deoxyribose radicals in a model DNA back-bone: Ab initio molecular orbital calculations. Journal of Physical Chemistry, 99, 3867–3874.
  • CULLIS, P. M., LANGMAN, S., PODMORE, I. D. and SYMONS, M. C. R., 1990, Effects of ionising radiation on deoxyribo-nucleic acid. Part VI. Effects of hydroxy radical scavengers on radiation damage to DNA. Journal of the Chemical Society Faraday Transactions, 86, 3267–3271.
  • CULLIS, P. M., MALONE, M. E., PODMORE, I. D. and SYMONS, M. C. R., 1995, The site of protonation of one-electron reduced cytosine and its derivatives in aqueous-methanol glass. Journal of Physical Chemistry, 99, 9293–9298.
  • CULLIS, P. M., MCCLYMONT, J. D., MALONE, M. E., MATHER, A. N., PODMORE, I. D., SWEENEY, M. C. and SYMONS, M. C. R., 1992, Effects of ionizing radiation on deoxyribo-nucleic acid. Part 7. Electron capture at cytosine and thymine. Journal of the Chemical Society, Perkin Transactions 2, 1695–1702.
  • CULLIS, P. M., PODMORE, I., LAWSON, M., SYMONS, M. C. R., DALGARNO, B. and MCCLYMONT, J., 1989, The site of electron capture in irradiated dexoyribonucleic acid: cyto-sine vs. thymine. Journal of the Chemical Society Chemical Communications, 1003–1005.
  • Cumis, P. M., SYMONS, M. C. R., WREN, B. W. and GREGOLI, S., 1985, Effects of ionizing radiation on deoxyribonucleic acid. Part 3. The effect of iodoacetamide. Journal of the Chemical Society Perkin Transactions 27 1819–1825.
  • DEEBLE, D. J. DAS, S. AND VON SONNTAG, C., 1985, Uracil derivatives: sites and kinetics of protonation of the radical anion and the UV spectra of the C(5) and C(6) H-atom adducts. Journal of Physical Chemistry, 89, 5784–5788.
  • DEEBLE, D. J., SCHUCHMANN, M. N., SCHUCHMANN, H.-P., STEENKEN, S. AND VON SONNTAG, C., 1990, Direct evid-ence for the formation of thymine radical cations from the reaction of SOr with thymine derivatives: a pulse radiolysis study with optical and conductance detection. Journal of Physical Chemistry, 94, 8186-8192.
  • DEEBLE, D. J., SCHULZ, D. AND VON SONNTAG, C., 1986, Reactions of OH radicals with poly(U) in deoxygenated solutions. Site of OH radical attack and the kinetics of base release. International Journal of Radiation Biology, 49, 915–916.
  • DEEBLE, D. J. AND VON SONNTAG, C., 1984, y-radiolysis of poly(U) in aqueous solution. The role of primary sugar and base radicals in the release of undamaged uracil. International J ournal of Radiation Biology, 46, 247–260.
  • DIZDAROGLU, M., VON SONNTAG, C. and SCHULTE-FROHLINDE, D., 1975, Strand breaks and sugar release by y-Irradiation of DNA in aqueous solution. Journal of American Chemical Society, 97, 2277–2278.
  • DIZDAROUGLU, M. and Susmc, M. G., 1984, Radiation-induced formation of thymine-thymine crosslinks. International Journal of Radiation Biology, 46, 241–246.
  • GAJEWSKI, E., FUCIARELLI, F. and DIZDAROGLU, M 1988, Structure of hydroxyl radical-induced DNA-protein crosslinks in calf thymus nucleohistone in vitro. International Journal of Radiation Biology, 54, 445–459.
  • GREGOLI, S., OLAST, M. and BERTINCHAMPS, A" 1974, Free radicalsiny-irradiatedfrozensolutionsofdeoxyadenosine-5'-monophosphate. A computer analysis of temperature-dependent E SR spectra. Radiation Research, 60, 388–404.
  • GREGOLI, S., OLAST, M. and BERTINCHAMPS, A" 1976, Free-radical formation in deoxythymidine-5'-monophosphate y-irradiated in frozen solution. A computer assisted ana-lysis of temperature dependent ESR spectra. Radiation Research, 65, 202–219.
  • GREGOLI, S., OLAST, M. and BERTINCHAMPS, A" 1977, Free radical formation in deoxyguanosine-5'-monophosphate y-irradiated in frozen solution. A computer-assisted anal-ysis of temperature dependent ESR spectra. Radiation Research, 72, 201–217.
  • GREGOLI, S., OLAST, M. and BERTINCHAMPS, A" 1979, Charge-migration phenomena in y-irradiated costacking com-plexes of DNA nucleotides II. An ESR study of various complexes in frozen solution. Radiation Research, 77, 417–431.
  • HILDENBRAND, K., BEHRENS, G. and SCHULTE-FROHLINDE, D 1989, Comparison of the reaction of *OH and of SO radicalswith pyrimidine nycleosides. An electron spin resonance study in aqueous solution. J ournal of the Chemical Society Perkin Transactions, 2, 283–289.
  • HOL EE. 0., NELSON, W. H., SAGSTUEN, E. and CLOSE, D. NI" 1992a, Free radical formation in single crystals of 2'-deoxyguanosine 5'-monophosphate tetrahydrate di-sodium salt: an EPR/ENDOR study. Radiation Research, 129, 119–138.
  • HOL EE. 0., NELSON, W. H., SAGSTUEN, E. and CLOSE, D. NI" 1992b, Free radical formation in X-irradiated anhydrous crystals of inosine studied by EPR and ENDOR spectro-scopy. Radiation Research, 130, 148–159.
  • HOL EE. 0. and SAGSTUEN, E., 1987, Free radical formation in crystals of 2.-deoxyguanosine 5.-monophosphate irradi-ated at 15K: an ESR study. Radiation Research, 109, 190–205.
  • HOL EE. 0., SAGSTUEN, E., NELSON, W. H. and CLOSE, D. NI" 1991, Primary reduction and oxidation of thymine deriv-atives. ESR/ENDOR of thymine derivatives. ESR/END OR of thymidine and 1 methylthymine irradi-ated at 10K. Journal of Physical Chemistry, 95, 1494–1503.
  • HOLROYD, R. A. and GLASS, J. W., 1968, Radicals formed by electron transfer to pyrimidine derivatives. International Journal of Radiation Biology, 14, 445–454.
  • HUTCHINSON, F., 1973, The lesions produced by ultraviolet light in DNA containing 5-bromouracil. Quarterly Reviews of Biophysics, 6, 201–246.
  • HUTTERIVIANN, J., 1970, Electron spin resonance of radiation-induced free radicals in irradiated single crystals of thym- meInternational Journal of Radiation Biology,17, 249–259.
  • LANGE, M., WEILAND, B. and HUTTERMANN, J., 1995, Influence of electron scavengers on the radical formation in thymidine-5'-monophosphate and DNA in frozen aque-ous solutions and glasses. International Journal of Radiation Biology, 68, 475–486.
  • LA VERE, T., BECKER, D. and SEVILLA, M. D., 1996, Yields of OH in gamma-irradiated DNA as a function of DNA hydration: hole transfer in competition with OH forma-tion. Radiation Research, 145, 361–368.
  • MALONE, M. E., CULLIS, P. M., SYMONS, M. C. R. and PARKER, A. W., 1995, Biphotonic photoionization of cytosine and its derivatives with UV radiation at 248 nm: an EPR study in low-temperature perchlorate glasses. Journal of Physical Chemistry, 99, 9299–9308.
  • MALONE, M. E., SYMONS, M. C. R. and PARKER, A. W., 1993, An EPR study of photoionized thymine and its derivatives at 77K. Journal of the Chemical Society, Perkin Transactions 27 2067–2075.
  • SAGSTUEN, E., HOL EE. 0., NELSON, W. H. and CLOSE, D. M., 1989, Structure of the primary reduction product of thymidine after X irradiation at 10K. Journal of Physical Chemistry, 93, 5974–5977.
  • SAMSKOG, P.-0., KISPERT, L. D. and KALYANARAMAN, B.,1984, Structure of the aa* radical anion in irradiated iodoac eta - mide. An electron paramagnetic resonance and INDO study. Journal of the Chemical Society of Faraday Transactions 2, 80, 267–274.
  • SCHULTE-FROHLINDE, D., 1989, The effect of oxygen and thiols on the radiation damage of DNA. Free Radical Research Communications, 6, 181–182.
  • SCHULTE-FROHLINDE, D. and BOTH EE., 1984, Identification of a major pathway of strand break formation in poly U induced by hydrogen radicals in presence of oxygen. Zeitschrift fur Naturforschung, 39c, 315–319.
  • SCHULTE-FROHLINDE, D. AND VON SONNTAG, C., 1990, Sugar lesions in cell radiobiology. UCLA symposia colloquium: ionizing radiation damage to DNA: molecular aspects, edited by S. W. Wallace and R. B. Painter (New York: Wiley-Liss), pp. 31–42.
  • SEVILLA, M. D., 1971, An electron spin resonance study of the photoionization of thymine. The thymine cation and anion radicals. Journal of Physical Chemistry, 75, 626–631.
  • SEVILLA, M. D. and BECKER, D., 1994, Radiation damage in DNA. Electron Spin Resonance (A Specialist Periodical Report), 14, 130–165.
  • SEVILLA, M. D., BECKER, D., YAN, M. and SUMMERFIELD, S. R., 1991, Relative abundance of primary ion radicals in y-irradiated DNA: cytosine vs. thymine anion and guanine vs. adenine cation. Journal of Physical Chemistry, 95, 3409-3415.
  • SEVILLA, M. D. and ENGELHARDT, M. L., 1978, Mechanisms for radiation damage in DNA consituents and DNA. Faraday Discussions of The Chemical Society, 63, 255–263.
  • SEVILLA, M. D., FAILoR, R., CLARK, C., HOLROYD, R. A. and PETTEI, M., 1976, Electron transfer in dinucleoside phos-phate anions. Journal of Physical Chemistry, 80, 353–358.
  • SEVILLA, M. D., SURYANARAYANA, D. and MOREHOUSE, K. M., 1981, ESR study of DNA base cation radicals produced by attack of oxidizing radicals. journal of Physical Chemistry, 85, 1027–1031.
  • SEVILLA, M. D., VAN PAEMEL, C. and ZORMAN, G., 1972, Reactions of the cation and anion radicals of several DNA bases. Journal of Physical Chemistry, 76, 3577–3582.
  • SHAW, A. A., VOITURIEZ, L., CADET, J., GREGOLI, S. and SYMONS, M. M. C. R., 1988, Identification of the products resulting from the direct effect of y-radiation on thymid- Journal of the Chemical Society, Perkin Transactions 2, 1303–1307.
  • SWARTS, S. G., BECKER, D., SEVILLA, M. D. and WHEELER, K. T., 1996, Radiation-induced DNA damage as a function of hydration. II. Base damage from electron-loss centers. Radiation Research, 145, 304–314.
  • SYMONS, M. C. R., 1987, Application of electron spin resonance spectroscopy to the study of the effects of ionising radi-ation on DNA and DNA complexes. journal of the Chemical Society, Faraday Transactions I, 83, 1–11.
  • SYMONS, M. C. R., 1988, Identification of the products resulting from the direct effects of y-irradiation on thymidine. Journal of the Chemistry Society, Perkin Transactions 2, 1303–1307.
  • VON SONNTAG, C., 1987a, The Chemical Basis of Radiation Biology. (London: Taylor & Francis), pp. 232–253.
  • VON SONNTAG, C., 1987b, The Chemical Basis of Radiation Biology. (London: Taylor & Francis), p. 181.
  • WANG, W. and SEVILLA, M. D., 1994a, Protonation of nucleobase anions in gamma-irradiated DNA and model systems. Which DNA base is the ultimate sink for the electron? Radiation Research, 138, 9–17.
  • WANG, W. and SEVILLA, M. D., 1994b, Reactions of cysteamine with individual DNA base radicals in y-irradiated nucleot-ides at low temperature. International Journal of Radiation Biology, 66, 1–13.
  • YAN, M., BECKER, D., SUMMERFIELD, S., RENKE, P. and SEVILLA, M. D., 1992, Relative abundance and reactivity of prim-ary ion radicals in y-irradiated DNA at low temperatures. 2. Single vs. double-stranded DNA. Journal of Physical Chemistry, 96, 1983–1989.
  • ZIMBRICK, J. D., WARD, J. F. and MYERS, L. S., JR., 1969, Studies on the chemical basis of cellular radiosensitization by 5-bromouracil substitution in DNA. II. Pulse- and steady state radiolysis of bromouracil-substituted and unsubstituted DNA. International J ournal of Radiation Biology, 16, 525–534.

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