Electron transfer in DNA? Competition by ultra-fast proton transfer?

Biological Chemistry

Volumn 378, Issue 11, 1997, Pages 1293-1297

  Steenken, Steen ^a  

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

Author keywords

Charge transfer; Photochemistry; Radiation chemistry

Indexed keywords

BASE PAIRING; DNA HELIX; DNA STRAND; ELECTRON TRANSPORT; PHOTOCHEMISTRY; PRIORITY JOURNAL; PROTON TRANSPORT; REVIEW;

BASE COMPOSITION; DNA; ELECTRON TRANSPORT; PROTONS;

EID: 0030694463     PISSN: 14316730     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (39)

1. Barnes, J.P., Bernhard, W.A. (1995). The electron scavenging ability of the DNA bases in glassy matrices X irradiated at 4 K. J. Phys. Chem. 99, 11248-11254.
2. Becker, D., and Sevilla, M.D. (1993). The chemical consequences of radiation damage to DNA. Adv. Radiat. Biol. 17, 121-180.
3. Beratan, D.N., Priyadarshy, S., and Risser, S.M. (1997). DNA: Insulator or wire? Chem. Biol. 4, 3-8.
4. Bernhard, W.A. (1981). Solid-state radiation chemistry of DNA: The bases. Adv. Radiat. Biol. 9, 199-280.
5. Bernhard, W.A. (1991). Initial sites of one electron attachment in DNA. NATO ASI, Ser. H54, 141-154.
6. Brun, A.M., Harriman, A. (1994). Energy-and electron-transfer processes involving palladium porphyrins bound to DNA. J. Am. Chem. Soc. 116, 10383-10393.
7. Candeias, L.P., and Steenken, S. (1989). Structure and acid-base properties of one-electron-oxidized deoxyguanosine, guanosine, and 1-methylguanosine. J. Am. Chem. Soc. 111, 1094-1099.
8. Close, D.M. (1991). ESR and ENDOR of irradiated solids of biological interest. Magn. Reson. Rev. 15, 241-284.
9. Colson, A.O., Besler, B., and Sevilla, M.D. (1992). Ab initio molecular orbital calculations on DNA base pair radical ions: Effect of base pairing on proton-transfer energies, electron affinities and ionization potentials. J. Phys. Chem. 96, 9787-9794.
10. Dandliker, P.J., Holmlin, R.E., and Barton, J.K. (1997). Oxidative thymine dimer repair in the DNA helix. Science 275, 1465-1468.
11. Dee, D., and Baur, M.E. (1974). Charge and excitation migration in DNA chains. J. Chem. Phys. 60, 541-560.
12. Douhal, A., Kim, S.K., and Zewail, A.H. (1995). Femtosecond molecular dynamics of tautomerization in model base pairs. Nature 378, 260-263.
13. Gregoli, S., Olast, M., and Bertinchamps, A. (1979). Charge-migration phenomena in γ-irradiated costacking complexes of DNA-nucleotides. II. An ESR study of various complexes in frozen solution. Radiat. Res. 77, 417-431.
14. Gregoli, S., Olast, M., and Bertinchamps, A. (1982). Radiolytic pathways in γ-irradiated DNA: Influence of chemical and conformational factors. Radiat. Res. 89, 238-254.
15. Hall, D.B., Holmlin, R.E., and Barton, J.K. (1996). Oxidative DNA damage through long-range electron transfer. Nature 382, 731 -735.
16. Hüttermann, J. (1991). Radical ions and their reactions in DNA and its constituents. Contribution of electron spin resonance spectroscopy. In: Radical Ionic Systems: Properties in Condensed Phases, Lund, A. and Shiotani, M., eds., (Dordrecht, The Netherlands: Kluwer), pp. 435-462.
17. Hush, N.S., and Cheung, S.A. (1975). Ionization potentials and donor properties of nucleic acid bases and related compounds. Chem. Phys. Lett. 24, 11-13.
18. 3+ to DNA. J. Am. Chem. Soc. 119, 1454-1455.
19. Meade, T.J., and Kayyem, J.F. (1995). Electron transfer through DNA: Site-specific modification of duplex DNA with ruthenium donors and acceptors. Angew. Chem. Int. Ed. Engl. 34, 352-354.
20. Novais, H.M., and Steenken, S. (1986). ESR studies of electron and hydrogen adducts of thymine and uracil and their derivatives and of 4,6-dihydroxypyrimidines in aqueous solution. Comparison with data from solid state. The protonation at carbon of the electron adducts. J. Am. Chem. Soc. 108, 1-6.
21. Olson, E.J.C., Hu, D., Hörmann, A., and Barbara, P.F. (1997). Quantitative modeling of DNA-mediated electron transfer between metallointercalators. J. Phys. Chem. B 101, 299-303.
22. Orlov, V.M., Smirnov, A.N., and Varshavsky, Y.M., (1976). Ionization potentials and electron-donor ability of nucleic acid bases and their analogues. Tetrahedr. Lett., 4377-4378.
23. Priyadarshy, S., Risser, S.M., and Beratan, D.N. (1996). DNA is not a molecular wire: Protein-like electron-transfer predicted for an extended π-electron system. J. Phys. Chem. 100, 17678-17682.
24. Rein, R., and Harris, F.E. (1964). Proton tunneling in radiation-induced mutation. Science 146, 649-650.
25. Rein, R., and Harris, F.E. (1965). Studies of hydrogen-bonded systems. II Tunneling and tautomeric equilibria in the N-H ... N hydrogen bond of the guanine-cytosine base pair. J. Chem. Phys. 42, 2177-2180.
26. Sevilla, M.D., Failor, R., Clark, C., Holroyd, R.A., and Pettei, M. (1976). Electron transfer in dinucleoside phosphate anions. J. Phys. Chem. 80, 353-358.
27. - and OH adducts. Chem. Rev. 89, 503-520.
28. Steenken, S. (1992). Electron-transfer-induced acidity/basicity and reactivity changes of purine and pyrimidine bases. Consequences of redox processes for DNA base pairs. Free Rad. Res. Commun. 16, 349-379.
29. Steenken, S., Telo, J.P., Novais, H.M., and Candeias, L.P. (1992). One-electron-reduction potentials of pyrimidine bases, nucleosides, and nucleotides in aqueous solution. Consequences for DNA redox chemistry. J. Am. Chem. Soc. 114, 4701-4709.
30. Steenken, S., and Jovanovic, S.V. (1997). How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J. Am. Chem. Soc. 119, 617-618.
31. Stemp, E.D.A., and Barton, J.K. (1996). Electron transfer between metal complexes bound to DNA: Is DNA a wire? Metal Ions in Biol. Systems 33, 325-365.
32. van Lith, D., Warman, J.M., de Haas, M.P., and Hummel, A. (1986a). Electron migration in hydrated DNA and collagen at low temperatures. Part 1. Effect of water concentration. J. Chem. Soc. Faraday Trans. 1 82, 2933-2944.
33. van Lith, D., Eden, J., Warman, J.M., and Hummel, A. (1986b). Electron migration in hydrated DNA and collagen at low temperatures. Part 2. The effect of additives. J. Chem. Soc. Faraday Trans. 1 82, 2945-2950.
34. Warman, J.M., de Haas, M.P., and Rupprecht, A. (1996). DNA: a molecular wire? Chem. Phys. Lett. 249, 319-322.
35. Whillans, D.W. (1975). Studies of electron migration in DNA in aqueous solution using intercalating dyes. Biochim. Biophys. Acta 414, 193-205.
36. Wilson, E.K. (1996). Charge transfer in DNA. Oxidative damage occurs at a distance. Chem. Eng. News. ?, 9-10.
37. Wilson, E.K. (1997). DNA: Insulator or wire? Chem. Eng. News 75, 33-39.
38. Yan, M., Becker, D., Summerfield, S., Renke, P., and Sevilla, M.D. (1992). 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.
39. Zewail, A.H. (1996). Femtochemistry: Recent progress in studies of dynamics and control of reactions and their transition states. J. Phys. Chem. 100, 12701-12724.