Influence of Oxygen on the Repair of Direct Radiation Damage to DNA by Thiols in Model Systems

References

• Adams G.E., McNaughton G.S., Michael B.D. Pulse radiolysis of sulfur compounds. Transactions of the Faraday Society 1968; 54: 902–910
   Google Scholar
• Aguilera J.A., Newton G.L., Fahey R.C., Ward J.F. Thiol uptake by Chinese hamster V79 cells and aerobic radioprotection as a function of the net charge on the thiol. Radiation Research 1992; 130: 194–204
   PubMed Web of Science ®Google Scholar
• Akhlaq S., Schuchmann M., von Sonntag C. The reverse of the ‘repair’ reaction of thiols: H-abstraction at carbon by thiyl radicals. International Journal of Radiation Biology 1987; 51: 91–102
   Web of Science ®Google Scholar
• Akhlaq M.S., von Sonntag C. Intermolecular hydrogen abstraction of thiyl radicals from thiols and the intermolecular complexing of the thiyl radical with the thiol group in 1,4-dithiothreitol. A pulse radiolysis study. Zeitschrift für Naturforschung C: Bioscience 1987; 42c: 134–140
   Google Scholar
• Alper T. Cellular Radiobiology. Cambridge University Press, Cambridge 1979
   Google Scholar
• Becker D., Sevilla M.D. The chemical consequences of radiation damage to DNA. Advances in Radiation Biology, J.T. Lett, H. Adler. Academic, New York 1993; 121–180, In
   Google Scholar
• Becker D., Swarts S., Champagne M., Sevilla M.D. An ESR investigation of the reactions of glutathione, cysteine and thiyl radicals: competitive formation of RSO*, R*, RSSR- * and RSS*. International Journal of Radiation Biology 1988; 53: 767–786
   Web of Science ®Google Scholar
• Bernhard W.A. Site of electron trapping in DNA as determined by ESR of one-electron-reduced oligonucleotides. Journal of Physical Chemistry 1989; 93: 2187–2189
   Web of Science ®Google Scholar
• Boon P.J., Cullis P.M., Symons M.C.R., Wren B.W. Effects of ionizing radiation on deoxyribonucleic acid and related systems. Part I. The role of oxygen. Journal of the Chemical Society Perkin Transactions 1984; 2: 1393–1399
   Google Scholar
• Boyle J. Microcirculatory hematocrit and blood flow. Journal of Theoretical Biology 1988; 131: 223–229
   PubMedGoogle Scholar
• Cadet J., Berger M., Demonchaux P., Lhomme J. Modifying effects of cysteine and aromatic sulfhydryl and disulfide agents on the radiation-induced decomposition of thymidine. Radiation Physics and Chemistry 1988; 32: 197–202
   Web of Science ®Google Scholar
• Candeias L.P., Steenken S. Structure and acidbase properties of one-electron-oxidized deoxyguanosine, guanosine and 1-methylguanosine. Journal of the American Chemical Society 1989; 111: 1094–1099
   Web of Science ®Google Scholar
• Colson A.O., Besler B.M., Close D.M., Sevilla M.D. Ab Initio molecular orbital calculations of DNA bases and their radical ions in various protonation states: evidence for proton transfer in G-C base pair anions. Journal of Physical Chemistry 1992; 96: 661–667
   Web of Science ®Google Scholar
• Cullis P.M., Jones G.D.D., Lea J., Symons M.C.R., Sweeney M. The effects of ionizing radiation on deoxyribonucleic acid. Part 5. The role of thiols in chemical repair. Journal of the Chemical Society, Perkin Transactions 1987; 2: 1907–1987
   Google Scholar
• d'Aquino M., Dunster C., Willson R.L. Vitamin A and gluthione-mediated free radical damage: competing reactions with polyunsaturated fatty acids and vitamin C. Biochemical Biophysical Research Communications 1989; 161: 1199–1203
   PubMed Web of Science ®Google Scholar
• Deeble D.J., Das S., von Sonntag C. Uracil derivatives: sites and kinetics of protonation of the radical anion and the UV spectra of the C95) and C(6) H-atom adducts. Journal of Physical Chemistry 1985; 89: 5784–5788
   Web of Science ®Google Scholar
• Edgren M., Larsson A., Nilsson K., Revesz L., Scott O.C.A. Lack of oxygen effect in glutathione defficient human cells in culture. International Journal of Radiation Biology 1980; 37: 299–306
   Web of Science ®Google Scholar
• Ewing D. Application of radiation chemistry to studies in the radiation biology of microorganisms. Radiation Chemistry, Farhataziz, M.A.J. Rodgers. VCH, New York 1987; 501–526, In
   Google Scholar
• Fahey R.C. Protection of DNA by thiols. Pharmacology and Therapeutics 1988; 39: 101–108
   PubMed Web of Science ®Google Scholar
• Greenstock C.L. Oxy-Radicals and the radiobiological oxygen effect. Israel Journal of Chemistry 1984; 24: 1–10
   Google Scholar
• Gregoli S., Olast M., Bertinchamps A. Radiolytic pathways in γ-irradiated DNA: influence of chemical and conformational factors. Radiation Research 1982; 89: 238–254
   PubMed Web of Science ®Google Scholar
• Grierson L., Hildenbrand K., Bothe E. Intra-molecular transfer reaction of the glutathione thiyl radical into a non-sulphur-centered radical: a pulse radiolysis and EPR study. International Journal of Radiation Biology 1992; 62: 265–277
   PubMed Web of Science ®Google Scholar
• Held K.D., Harrop H.A., Michael B.D. Effects of oxygen and sulphydryl-containing compounds on irradiated transforming DNA. II. Glutathione, cysteine and cysteamine. International Journal of Radiation Biology 1984; 45: 615–626
   Web of Science ®Google Scholar
• Hoffman M.Z., Hayon E. One-electron reduction of the disulfide linkage in aqueous solution. Formation, protonation and decay kinetics of the RSSR-radical. Journal of the American Chemical Society 1972; 94: 7950–7957
   Google Scholar
• Hole E.O., Sagstuen E., Nelson W.H., Close D.M. Primary reduction and oxidation of thymine derivatives. ESR/ENDOR of thymine derivatives. ESR/ENDOR of thymidine and 1-methylthymine irradiated at 10K. Journal of Phyical Chemistry 1991; 95: 1494–1503
   Web of Science ®Google Scholar
• Holroyd R.A., Glass J.W. Radicals formed by electron transfer to pyrimidine derivatives. International Journal of Radiation Biology 1968; 14: 445–454
   Web of Science ®Google Scholar
• Horowitz A., Rajbenbach L.A. The free radical mechanism of the decomposition of alkylsulfonyl chlorides in liquid cyclohexane. Journal of the American Chemical Society 1975; 97: 10–13
   Google Scholar
• Howard-Flanders P. Effect of oxygen on the radiosensitivity of bacteriophage in the presence of sulphydryl compounds. Nature 1960; 186: 485–487
   PubMed Web of Science ®Google Scholar
• Hutchinson F. Sulfhydryl groups and the oxygen effect on irradiated dilute solutions of enzymes and nucleic acids. Radiation Research 1961; 14: 721–723
   PubMed Web of Science ®Google Scholar
• Klayman D.L., Copeland E.S. Radioprotective agents. Encyclopedia of Chemical Technology, R.E. Kirk, D.F. Othmer. Wiley, New York 1982; 801–832, In
   Google Scholar
• Lal M. Co-60 γ-radiolysis of reduced glutathione in aerated solutions at pH values between 1–7·0. Canadian Journal of Chemistry 1976; 54: 1092–1097
   Web of Science ®Google Scholar
• Michael B.D., Prise K.M., Fahey R.C., Folkard M. Radical multiplicity in radiation-induced DNA strand breaks: implications for chemical modifications. The Early Effects of Radiation on DNA, E.M. Fielden, P. O'Neill. Springer-Verlag, New York 1991; 333–346, In
   Google Scholar
• Micic P.I., Markovic V.M., Nenadovic M.T. Pulse radiolysis of amino acids containing sulfur. Bulletin de la Societe Chimique Beograd 1975; 40: 277–284
   Google Scholar
• Milvy P. Dose dependence of the transfer of radiation-induced free radicals from DNA to cysteamine. Radiation Research 1971; 47: 83–93
   PubMedGoogle Scholar
• Mönig J., Asmus K.-D., Forni L.G., Willson R. On the reaction of molecular oxygen with thiyl radicals: a re-examination. International Journal of Radiation Biology 1987; 52: 589–602
   Web of Science ®Google Scholar
• Morse M.L., Dahl R.H. Cellular glutathione is a key to the oxygen effect in radiation damage. Nature 1978; 271: 660–662
   PubMed Web of Science ®Google Scholar
• Newton G.L., Dwyer T.J., Kim T., Ward J.F., Fahey R.C. Determination of the acid dissociation constants for WR-1065 by proton NMR spectroscopy. Radiation Research 1992; 131: 143–151
   PubMed Web of Science ®Google Scholar
• O'Neill P. Pulse radiolytic study of the interaction of thiols and ascorbate with OH adducts of dGMP and dG: implications for DNA repair processes. Radiation Research 1983; 96: 198–210
   PubMed Web of Science ®Google Scholar
• Prütz W.A. ‘Chemical repair’ in irradiated DNA solutions containing thiols and/or disulphides. Further evidence for disulphide radical anions acting as electron donors. International Journal of Radiation Biology 1989; 56: 21–33
   PubMed Web of Science ®Google Scholar
• Prütz W.A., Mönig H. On the effect of oxygen or copper(II) in radiation-induced degradation of DNA in the presence of thiols. International Journal of Radiation Biology 1987; 52: 677–682
   Web of Science ®Google Scholar
• Quintiliani M. Cellular thiols and radiation response. Baxendale Memorial Symposium, V. Balzani. Centro Stampa Lo Scarabeo, Bologna 1983; 81–108, In
   Google Scholar
• Quintiliani M. The oxygen effect in radiation inactivation of DNA and enzymes. International Journal of Radiation Biology 1986; 50: 573–594
   Web of Science ®Google Scholar
• Revesz L. The role of endogenous thiols in intrinsic radioprotection. International Journal of Radiation Biology 1985; 47: 361–368
   Web of Science ®Google Scholar
• Sagstuen E., Hole E.O., Nelson W.H., Close D.M. Structure of the primary reduction product of thymidine after X-irradiation at 10 K. Journal of Physical Chemistry 1989; 93: 5974–5977
   Google Scholar
• Schöneich C., Asmus K.-D. Reaction of thiyl radicals with alcohols, ethers and polyunsaturated fatty acids: a possible role of thiyl free radicals in thiol mutagenesis?. Radiation and Environmental Biophysics 1990; 29: 263–271
   PubMed Web of Science ®Google Scholar
• Schöneich C., Asmus K.-D., Dillinger U., von Bruehhausen F.V. Thiyl radical attack on polyunsaturated fatty acids: a possible route to lipid peroxidation. Biochemical and Biophysical Research Communications 1989; 161: 113–120
   PubMed Web of Science ®Google Scholar
• Schöneich C., Dillinger U., von Bruehhausen F., Asmus K. Oxidation of polyunsaturated fatty acids and lipids through thiyl and sulfonyl radicals: Reaction kinetics, and influence of oxygen and structure of thiyl radicals. Archives of Biochemistry and Biophysics 1992; 292: 456–467
   PubMed Web of Science ®Google Scholar
• Schulte-Frohlinde D., Simic M.G., Görner H. Laser-induced strand break formation in DNA and. Photochemistry and Photobiology 1990; 52: 1137–1151
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Becker D., Yan M. The formation and structure of the sulfoxyl radicals RSO·, RSOO·, RSO·2, and RSO2OO· from the reaction of cysteine, glutathione and penicillamine thiyl radicals with molecular oxygen. International Journal of Radiation Biology 1990a; 57: 65–81
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Becker D., Yan M. Structure and reactivity of peroxyl and sulphoxyl radicals from measurement of oxygen-17 hyperfine couplings: relationship with Taft substituent parameters. Journal of The Chemical Society Faraday Transactions 1990b; 86: 3279–3286
   Google Scholar
• Sevilla M.D., Becker D., Yan M., Summerfield S.R. Relative abundance of primary ion radicals in γ-irradiated DNA: cytosine vs. thymine anion and guanine vs. adenine cation. Journal of Physical Chemistry 1991a; 95: 3409–3415
   Web of Science ®Google Scholar
• Sevilla M.D., Van Paemel C., Zorman G. Reactions of the cation and anion radicals of several DNA bases. Journal of Physical Chemistry 1972; 76: 3577–3582
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Yan M., Becker D. Thiol peroxyl radical formation from the reaction of cysteine thiyl radical with molecular oxygen: an ESR investigation. Biochemical and Biophysical Research Communications 1988; 155: 405–410
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Yan M., Becker D., Gillich S. ESR investigations of the reactions of radiation-produced thiyl and DNA peroxyl radicals: formation of sulfoxyl radicals. Free Radical Research Communications 1989; 6: 99–102
   PubMed Web of Science ®Google Scholar
• Sevilla M.D., Yan M., Becker D., Gillich S. Reaction of DNA peroxyl radicals with cysteamine and glutathione: the formation of sulfoxyl radicals. Eicosanoids and Other Bioactive Lipids in Cancer and Radiation Injury, K.V. Honn, L.J. Marnett, S. Nigam, T.L. Walden, Jr. Kluwer, Boston 1991b; 87–91, In
   Google Scholar
• Simic M.G., Hunter E.P.L. Interaction of free radicals and antioxidants. Radioprotectors and Anticarcinogens, O.F. Nygaard, M.G. Simic. Academic, New York 1983; 449–460, In
   Google Scholar
• Simic M.G., Hunter E.P.L. Antioxidants. Chemical Changes in Food During Processing, T. Richardson, J.W. Finley. AVI, Westport, CT 1985; 107–119, In
   Google Scholar
• Simone G., Tamba M., Quintiliani M. Role of glutathione in affecting the radiosensitivity of molecular and cellular systems. Radiation and Environmental Biophysics 1983; 22: 215–223
   PubMed Web of Science ®Google Scholar
• Smoluk G.D., Fahey R.C., Ward J.F. Interaction of glutathione and other low-molecular-weight thiols with DNA: evidence for counterion condensation and coion depletion near DNA. Radiation Research 1988; 114: 3–10
   PubMed Web of Science ®Google Scholar
• Steenken S. Electron transfer induced acidity/basicity and reactivity changes of purine and pyrimidine bases. Consequences of redox processes for DNA base pairs. Free Radical Research Communications 1992; 16: 349–379
   PubMed Web of Science ®Google Scholar
• Steenken S., Telo J.P., Novais H.M., Candeias L.P. One-electron-reduction potentials of pyrimidine bases, nucleosides, and nucleotides in aqueous solution. Consequences for DNA redox chemistry. Journal of the American Chemical Society 1992; 114: 4701–4709
   Web of Science ®Google Scholar
• Swarts S.G., Becker D., DeBolt S., Sevilla M.D. An electron spin resonance investigation of the structure and formation of sulfinyl radicals: reaction of peroxyl radicals with thiols. Journal of Physical Chemistry 1989; 93: 155–161
   Google Scholar
• Tamba M., O'Neill P. Redox properties of thiol free radicals with antioxidants ascorbate and chlorpromazine: role in radioprotection. Journal of the Chemical Society Perkin Transactions 1991; 2: 1681–1685
   Google Scholar
• Tamba M., Simone G., Quintiliani M. Interactions of thiyl free radicals with oxygen: a pulse radiolysis study. International Journal of Radiation Biology 1986; 50: 595–600
   Web of Science ®Google Scholar
• von Sonntag C., Zhang X., Schuchmann H.P. Nouveaux aspects de la chimie des thiols et des disulfides sous rayonnement en solution aqueuse. Journal de Chimie Physique 1991; 88: 987–992
   Google Scholar
• Vos O., Roos-Verhey S.D. Radioprotection by glutathione esters and cysteamine in normal and glutathione-depleted mammalian cells. International Journal of Radiation Biology 1988; 53: 273–281
   Web of Science ®Google Scholar
• Wardman P. Conjugation and oxidation of glutathione via thiyl free radicals. Glutathione Conjugation: Mechanisms and Biological Significance, H. Sies, B. Ketterer. Academic, London 1988; 43–72, In
   Google Scholar
• Willson R.L., Wardman P., Asmus K.-D. Interaction of dGMP radical with cysteamine and promethazine as possible model of DNA repair. Nature 1974; 252: 323–324
   PubMed Web of Science ®Google Scholar
• Yan M., Becker D., Summerfield S., Renke P., Sevilla M.D. Relative abundance and reactivity of primary ion radicals in γ-irradiated DNA at low temperatures. 2. Single vs. double-stranded DNA. Journal of Physical Chemistry 1992; 96: 1983–1989
   Web of Science ®Google Scholar
• Zheng S., Newton G.L., Gonick G., Fahey R.C., Ward J.F. Radioprotection of DNA by thiols: relationship between the net charge on a thiol and its ability to protect DNA. Radiation Research 1988; 114: 11–27
   PubMed Web of Science ®Google Scholar
• Zheng S., Newton G.L., Ward J.F., Fahey R.C. Aerobic radioprotection of pBR322 by thiols: effect of thiol net charge upon scavenging of hydroxyl radicals and repair of DNA radicals. Radiation Research 1992; 130: 183–193
   PubMed Web of Science ®Google Scholar