Skip to main content

The Development of Chemical Damage of DNA in Aqueous Solution

  • Conference paper

Part of the book series: NATO ASI Series ((ASIH,volume 54))

Abstract

A summary of results obtained in our laboratory is given concerning the formation of free radicals produced in DNA and components of DNA following ionization or reaction with OH radicals in aqueous solution and the rate of their conversion and decay. In the case of laser excitation biphotonic ionization of the nucleobases takes place and the radicalcations primarily formed are converted to neutral base radicals by deprotonation or by reaction with water. The neutral base radicals have their highest free spin densities at the nitrogens and oxygens of the nucleobases (N- and O-radicals). In contrast reaction with OH radicals leads primarily to carbon radicals by addition to the double bonds of the nucleobases and to sugar radicals by H abstraction. The reactions, the rate of the conversion and the decay of these radicals in DNA in aqueous solution is discussed with special regard to the radicals leading to strand break (sb) formation. In cells the decay is dominated by the reaction of the DNA radicals with endogenous thiols.

This is a preview of subscription content, log in via an institution.

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Adinarayana M, Bothe E, and Schulte-Frohlinde D (1988) Hydroxyl radical-induced strand break formation in single-stranded polynucleotides and single-stranded DNA in aqueous solution as measured by light scattering and by conductivity. Int J Radiat Biol 54:723–737

    Article  PubMed  CAS  Google Scholar 

  • Bernhard W A (1989) Sites of electron trapping in DNA as determined by ESR of one-electron-reduced oligonucleotides. J Phys Chem 93:2187–2189

    Article  CAS  Google Scholar 

  • Bothe E, Behrens G, Bohm E, Sethuram B, and Schulte-Frohlinde D (1986) Hydroxyl radical-induced strand break formation. of poly(U) in the presence of oxygen. Comparison of the rates as determined by conductivity, ESR and rapid-mix experiments with a thiol. Int J Radiat Biol 49:57–66

    Article  CAS  Google Scholar 

  • Bothe E, Hankiewicz E, and Schulte-Frohlinde D (1990) Pulsradiolysis of poly(U). In Preparation

    Google Scholar 

  • Bothe E, Qureshi G A, and Schulte-Frohlinde D (1983) Rate of OH radical induced strand break formation in single stranded DNA under anoxic conditions. An investigation in aqueous solutions using conductivity methods. Z Naturforsch 38c: 1030–1042

    CAS  Google Scholar 

  • Bothe E, Schulte-Frohlinde D (1982) Release of K+ and H+ from poly U in aqueous solution upon γ and electron irradiation. Rate of strand break formation in poly U. Z Naturforsch 37c:l191–1204

    CAS  Google Scholar 

  • Bresler S E, Sverdlov A G, Noskin L A, and Stepanova I M (1975) Influence of genotype of bacterial cells on radioprotective action of indolilealkylamines. Stud biophys 53:163–166

    Google Scholar 

  • Cullis P M, Symons M C R, Sweeney M C, Jones G D D, and McClymont J D (1986) The effect of ionizing radiation on deoxyribonucleic acid. Part 4. The role of hydrogen peroxide. J Chem Soc Perkin Trans II 1671–1676

    Google Scholar 

  • Deeble D J, Schuchmann M N, Steenken S, and von Sonntag C (1990) Direct evidence for the formation of thymine radical cations from the reaction of SO4 with thymine derivatives: a pulse radiolysis study with optical conductance detection. J Phys Chem submitted

    Google Scholar 

  • Fahey R C, Newton G L, Aguilera J A, and Ward J F (1990) Thiol uptake and radioprotection for V-79 cells as a function of the net charge of the thiol. Abstracts of papers, Ep-6. Thirty-eight Annual Meeting of the Radiation Research Society, New Orleans, Louisiana, April 7–12

    Google Scholar 

  • Fahey R C, Prise K, Davies S, Michael B, Stratford M, and Watfa R (1989) The effect of counterion condensation and coion depletion on the rates of repair of pBR322 DNA radicals by thiols. In: Gray Laboratory Annual Report (Michael B and Hance M eds), London: Cancer Research Campaign pp 127–129

    Google Scholar 

  • Gräslund A, Ehrenberg A, Rupprecht A, Ström G, and Crespi H (1975) Ionic base radicals in γ-irradiated oriented non-deuterate and fully deuterated DNA. Int J Radiat Biol 28:313–323

    Article  Google Scholar 

  • Hazra D K, Steenken S (1983) Pattern of OH radical addition to cytosine and 1–, 3–, 5– and 6-substituted cytosine. Electron transfer and dehydration reactions of the OH adducts. J Am Chem Soc 105:4380–4386

    Article  CAS  Google Scholar 

  • Held K D, Harrop H A, and Michael B D (1984) Effect of oxygen and sulphydryl-containing compounds on irradiated tranforming DNA. HI Reaction rates. Int J Radiat Biol 45:627–636

    Article  CAS  Google Scholar 

  • Hildenbrand K, Behrens G, Herak J N, and Schulte-Frohlinde D (1989) Comparison of the reaction OH and SO4 radicals with pyrimidine nucleosides. An electron spin resonance study in aqueous solution J Chem Soc Perkin Trans 2 283–289

    Google Scholar 

  • Hildenbrand K, Schulte-Frohlinde D (1989) ESR studies on the mechanism of hydroxyl radical-induced strand breakage of polyuridylic acid. Int J Radiat Biol 55:725–738

    Article  PubMed  CAS  Google Scholar 

  • Hildenbrand K, Schulte-Frohlinde D (1990) ESR spectra of radicals of single-stranded and double-stranded DNA in aqueous solution. Implication for OH-induced strand breakage. Free Rad Res Commun, accepted

    Google Scholar 

  • Lafleur M V M, Woldhuis J, and Loman H (1980) Effects of sulphydryl compounds on radiation damage in biologically active DNA. Int J Radiat Biol 37:493–498

    Article  CAS  Google Scholar 

  • Lemaire D G E, Bothe E, and Schulte-Frohlinde D (1984) Yields of radiation-induced main chain scission of poly U in aqueous solution: strand break formation via base radicals. Int J Radiat Biol 45:351–358

    Article  CAS  Google Scholar 

  • Liphard M, Bothe E, and Schulte-Frohlinde D (1990) The influence of glutathione and single-strand breakage in DNA irradiated in aqueous solution in the absence and presence of oxygen. Int J Radiat Biol, in press

    Google Scholar 

  • Ludwig C, Rettberg P, and Schulte-Frohlinde D (1990) The influence of thiol-repaired damaged sites on the survival of M13-DNA. In preparation

    Google Scholar 

  • Michael B D, Harrop H A, and Held K D (1981) Timescale and mechanisms of the oxygen effect in irradiated bacteria. In: Oxygen and Oxy-Radicals in Chemistry and Biology. (Rodgers M A J and Powers E L eds.) New York: Academic Press

    Google Scholar 

  • Michael B D, Prise K, Fahey R, and Davies S (1990) Chemical repair of DNA single and double strand break precursor radicals: implactions for models of chemical modification. Abstract of papers, ARR Biennal Meeting, Clarendon Laboratory and St. Johns College, Oxford, April 4–6

    Google Scholar 

  • Michaels H B, Hunt J W (1977) Radiolysis of the double-stranded polynucleotides poly(A+U) and DNA in the presence of oxygen. Radiat Res 72:32–47

    Article  PubMed  CAS  Google Scholar 

  • Müller M (1983) Untersuchungen zum OH-induzierten Strangbruch von Poly(C) in wässriger Lösung. Dissertation, Universitat Bochum

    Google Scholar 

  • O’Neill P, Davies S E (1986) A pulse radiolytic study of the interaction of nitroxyls with free-radical adducts of purines: consequences for radiosensitization. Int J Radiat Biol 49:937–950

    Article  Google Scholar 

  • O’Neill P, Davies S E (1987) Pulse radiolytic study of the interaction of SO/ with deoxynucleotides. Possible implication for direct energy deposition. Int J4 Radiat Biol 52:577–587

    Article  Google Scholar 

  • Nikogosyan D N (1990) Two-quantum UV photochemistry of nucleic acids: comparison with conventional low-intensity UV photochemistry and radiation chemistry. Int J Radiat Biol 57:233–299

    Article  PubMed  CAS  Google Scholar 

  • Prakash Rao P J, Bothe E, and Schulte-Frohlinde D (1990) Reaction of dithiothreitol with radical precursors of strand breakage in single-stranded DNA in anoxic aqueous solution: A study by pulse radiolysis and by light scattering. In preparation

    Google Scholar 

  • Prise K, Davies S, Michael B, and Conlan J (1989) Fast chemical repair of DNA strand break precursors: the role of protein sulphydryls. In: Gray Laboratory Annual Report. London: Cancer Research Campaign

    Google Scholar 

  • Roots R, Okada S (1975) Estimation of life times and diffusion distances of radicals involved in X-ray-induced DNA strand breaks or killing of mammalian cells. Radiat Res 64:306–320

    Article  PubMed  CAS  Google Scholar 

  • Rustgi S N, Riesz P (1978) An esr and spin-trapping study of the reaction of the SO4 radical with protein and nucleic acid constituents. Int J Radiat Biol 34:301–316

    Article  CAS  Google Scholar 

  • Sargentini N J, Smith K C (1986) Quantitation of the involvement of the recA, recB, recC, recF, red, recN, lex A, radA, radB, uvrD, and umuC genes in the repair of X-ray-induced DNA double-strand breaks in Escherichia coli. Radiat Res 107:58–72

    Article  PubMed  CAS  Google Scholar 

  • Scholes G, Willson R L, and Ebert M (1969) Pulse radiolysis of aqueous solutions of deoxyribonucleotides and of DNA: Reaction with hydroxyl-radicals. Chem Commun 17–18

    Google Scholar 

  • Schulte-Frohlinde D (1986) Comparison of mechanisms for DNA strand break formation by the direct and indirect effect of radiation. In: Mechanisms of DNA Damage and Repair. (Simic M G, Grossman L, and Upton A D eds.) Basic Life Science Vol. 38 New York: Plenum Press pp 19–27

    Google Scholar 

  • Schulte-Frohlinde D (1989) Studies of radiation effects on DNA in aqueous solution. ICRU News 4–15

    Google Scholar 

  • Schulte-Frohlinde D, Behrens G, and Oenal A (1986) Lifetime of peroxyl radicals of poly(U), poly(A) and single- and double-stranded DNA and the rate of their reaction with thiols. Int J Radiat Biol 50:103–110

    Article  CAS  Google Scholar 

  • Schulte-Frohlinde D, Bothe E (1990) Determination of the constants of the Alper formula for single- strand breaks from kinetic measurements on DNA in aqueous solution and comparison with data from cells. Int J Radiat Biol accepted

    Google Scholar 

  • Schulte-Frohlinde D, Hildenbrand K (1989) Electron spin resonance studies of the reaction of OH and SO4 radicals with DNA. In: Free radicals in synthesis and biology. (Minicsi F ed.) NATO ASI series C, Vol. 260, Bardolino, Italy 1988. Dordrecht: Kluwer pp 335–359

    Google Scholar 

  • Schulte-Frohlinde D, Opitz J, Gorner H, and Bothe E (1985) Model studies for the direct effect of high-energy irradiation on DNA. Mechanism of strand breakformation induced by photoionization of poly U in aqueous solution. Int J Radiat Biol 48:397–408

    Article  CAS  Google Scholar 

  • Schulte-Frohlinde D, Rettberg P, Hartke A, and Jeremic L (1990) Relationship between thiol induced repair and repair by enzymes. Contribution to: 3rd International Conference on Anticarcinogenesis and Radiation Protection, held at Dubrovnik, Yugoslavia, October 15–21, 1989

    Google Scholar 

  • Steenken S (1989) Purine bases, nucleosides and nucleotides: Aqueous solution redox chemistry and transformation reactions of their radical cations, e– and OH adducts. Chem Rev 89:503–520

    Article  CAS  Google Scholar 

  • Vieira A J S C, Steenken S (1987) Pattern of OH radical reaction with N6,N6–dimethyladenosine. Production of three isomeric OH adducts and their dehydration and ring opening reactions. J Am Chem Soc 109:7441–7448

    Article  CAS  Google Scholar 

  • von Sonntag, The Chemical Basis of Radiation Biology (1987) London: Taylor and Francis

    Google Scholar 

  • Wala M, Bothe E, Gorner H, and Schulte–Frohlinde D (1990) Quantum yields for generation of hydrated electrons and single–strand breaks in poly(A), poly(C) and single stranded DNA in aqueous solution upon 20–ns laser excitation at 248 nm. Photochem Photobiol, to be published

    Google Scholar 

  • Ward J F (1981) Some biochemical consequences of the spatial distribution of ionizing radiation produced free radicals. Radiat Res 86:185–195

    Article  PubMed  CAS  Google Scholar 

  • Ward J F, Kuo I (1978) Radiation damage to DNA in aqueous solution: a comparison of the response of the single–standed form with that of the double stranded form. Radiat Res 75:278–285

    Article  PubMed  CAS  Google Scholar 

  • Washino K, Schnabel W (1982) OH Radical-induced main chain scission of poly(ribo–adenylic acid). Macromol Chem Rapid Commund 3:427–430

    Article  CAS  Google Scholar 

  • Willson R L, Wardman P, and Asmus K–D (1974) Interaction of dGMP radical with cysteamine and promethazine as possibel model of DNA repair. Nature 252:323–324

    Article  PubMed  CAS  Google Scholar 

  • Ye M, Nelson J M, and Miller J H (1990) Superhelicity increases the sensitivity of plasmid DNA to strand break induction by X-rays. Abstract of papers, Ei–22. Thirty–eight Annual Meeting of the Radiaton Research Society, New Orleans, Louisiana, April 712

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Springer-Verlag Berlin Heidelberg

About this paper

Cite this paper

Schulte-Frohlinde, D., Bothe, E. (1991). The Development of Chemical Damage of DNA in Aqueous Solution. In: Fielden, E.M., O’Neill, P. (eds) The Early Effects of Radiation on DNA. NATO ASI Series, vol 54. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-75148-6_34

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-75148-6_34

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-75150-9

  • Online ISBN: 978-3-642-75148-6

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics