메뉴 건너뛰기




Volumn 159, Issue 3, 2003, Pages 411-419

Electron and hole transfer from DNA base radicals to oxidized products of guanine in DNA

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; BROMINE; DNA; GUANINE;

EID: 0037337251     PISSN: 00337587     EISSN: None     Source Type: Journal    
DOI: 10.1667/0033-7587(2003)159[0411:EAHTFD]2.0.CO;2     Document Type: Article
Times cited : (30)

References (39)
  • 1
    • 0031027125 scopus 로고    scopus 로고
    • How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution
    • S. Steenken and S. V. Jovanovic, How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J. Am. Chem. Soc. 119, 617-618 (1997).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 617-618
    • Steenken, S.1    Jovanovic, S.V.2
  • 2
    • 0035200329 scopus 로고    scopus 로고
    • Redox equilibrium between guanyl radicals and thiocyanate influences base damage yields in gamma irradiated plasmid DNA. Estimation of the reduction potential of guanyl radicals in plasmid DNA in aqueous solution at physiological ionic strength
    • J. R. Milligan, J. A. Aguilera and J. F. Ward, Redox equilibrium between guanyl radicals and thiocyanate influences base damage yields in gamma irradiated plasmid DNA. Estimation of the reduction potential of guanyl radicals in plasmid DNA in aqueous solution at physiological ionic strength. Int. J. Radiat. Biol. 77, 1195-1205 (2001).
    • (2001) Int. J. Radiat. Biol. , vol.77 , pp. 1195-1205
    • Milligan, J.R.1    Aguilera, J.A.2    Ward, J.F.3
  • 3
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • C. J. Burrows and J. G. Muller, Oxidative nucleobase modifications leading to strand scission. Chem. Rev. 98, 1109-1152 (1998).
    • (1998) Chem. Rev. , vol.98 , pp. 1109-1152
    • Burrows, C.J.1    Muller, J.G.2
  • 4
    • 0030066087 scopus 로고    scopus 로고
    • Guanine radical cations are precursors of 7,8-dihydro-8-oxo-2′-deoxyguanosine but are not precursors of immediate strand breaks in DNA
    • P. M. Cullis, M. E. Malone and L. A. Merson-Davies, Guanine radical cations are precursors of 7,8-dihydro-8-oxo-2′-deoxyguanosine but are not precursors of immediate strand breaks in DNA. J. Am. Chem. Soc. 118, 2775-2781 (1996).
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2775-2781
    • Cullis, P.M.1    Malone, M.E.2    Merson-Davies, L.A.3
  • 5
    • 0034653650 scopus 로고    scopus 로고
    • The trap depth (in DNA) of 8-oxo-7,8-dihydro-2′-deoxyguanosine as derived from electrontransfer equilibria in aqueous solution
    • S. Steenken, S. Jovanovic and K. Bernhard, The trap depth (in DNA) of 8-oxo-7,8-dihydro-2′-deoxyguanosine as derived from electrontransfer equilibria in aqueous solution. J. Am. Chem. Soc., 122, 2373-2374 (2000).
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2373-2374
    • Steenken, S.1    Jovanovic, S.2    Bernhard, K.3
  • 6
    • 0033552260 scopus 로고    scopus 로고
    • Sequence and stacking dependence of 8-oxoguanine oxidation: Comparison of one-electron vs singlet oxygen mechanisms
    • R. P. Hickerson, F. Prat, J. G. Muller, C. S. Foote and C. J. Burrows, Sequence and stacking dependence of 8-oxoguanine oxidation: Comparison of one-electron vs singlet oxygen mechanisms. J. Am. Chem. Soc. 121, 9423-9428 (1999).
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9423-9428
    • Hickerson, R.P.1    Prat, F.2    Muller, J.G.3    Foote, C.S.4    Burrows, C.J.5
  • 7
    • 0033552244 scopus 로고    scopus 로고
    • Mechanism of charge transport in DNA: Internally-linked anthraquinone conjugates support phononassisted polaron hopping
    • D. Ly, L. Sanii and G. B. Schuster, Mechanism of charge transport in DNA: Internally-linked anthraquinone conjugates support phononassisted polaron hopping. J. Am. Chem. Soc. 121, 9400-9410 (1999).
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9400-9410
    • Ly, D.1    Sanii, L.2    Schuster, G.B.3
  • 8
    • 0031593021 scopus 로고    scopus 로고
    • Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: The effect of gaps and traps on long-range radical cation migration
    • S. M. Gasper and G. B. Schuster, Intramolecular photoinduced electron transfer to anthraquinones linked to duplex DNA: The effect of gaps and traps on long-range radical cation migration. J. Am. Chem. Soc. 119, 12762-12771 (1997).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12762-12771
    • Gasper, S.M.1    Schuster, G.B.2
  • 9
    • 0035131362 scopus 로고    scopus 로고
    • Direct spectroscopic observation of 8-oxo-7,8-dihydro-2′-deoxyguanosine radicals in double-stranded DNA generated by one-electron oxidation at a distance by 2-aminopurine radicals
    • V. Shafirovich, J. Cadet, D. Gasparutto, A. Dourandin, W. Huang and N. E. Geacintov, Direct spectroscopic observation of 8-oxo-7,8-dihydro-2′-deoxyguanosine radicals in double-stranded DNA generated by one-electron oxidation at a distance by 2-aminopurine radicals. J. Phys. Chem. B 105, 586-592 (2001).
    • (2001) J. Phys. Chem. B , vol.105 , pp. 586-592
    • Shafirovich, V.1    Cadet, J.2    Gasparutto, D.3    Dourandin, A.4    Huang, W.5    Geacintov, N.E.6
  • 10
    • 0032576130 scopus 로고    scopus 로고
    • 7,8-Dihydro-8-oxo-2′-deoxyguanosine residues in DNA are radiation damage "hot" spots in the direct radiation damage pathway
    • Z. A. Doddridge, P. M. Cullis, G. D. D. Jones and M. E. Malone, 7,8-Dihydro-8-oxo-2′-deoxyguanosine residues in DNA are radiation damage "hot" spots in the direct radiation damage pathway. J. Am. Chem. Soc. 120, 10998-10999 (1998).
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10998-10999
    • Doddridge, Z.A.1    Cullis, P.M.2    Jones, G.D.D.3    Malone, M.E.4
  • 12
    • 0033024623 scopus 로고    scopus 로고
    • DNA damage in dexoynucleoside and oliguncleotides treated with peroxynitrite
    • S. Burney, J. C. Niles, P. C. Dedon and S. R. Tannenbaum, DNA damage in dexoynucleoside and oliguncleotides treated with peroxynitrite. Chem. Res. Toxicol. 12, 513-520 (1999).
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 513-520
    • Burney, S.1    Niles, J.C.2    Dedon, P.C.3    Tannenbaum, S.R.4
  • 14
    • 0033555373 scopus 로고    scopus 로고
    • Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine
    • V. Duarte, J. G. Muller and C. J. Burrows, Insertion of dGMP and dAMP during in vitro DNA synthesis opposite an oxidized form of 7,8-dihydro-8-oxoguanine. Nucleic Acids Res. 27, 496-502 (1999).
    • (1999) Nucleic Acids Res. , vol.27 , pp. 496-502
    • Duarte, V.1    Muller, J.G.2    Burrows, C.J.3
  • 15
    • 0034932109 scopus 로고    scopus 로고
    • Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model
    • W. Luo, J. M. Muller, E. M. Rachlin and C. J. Burrows, Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model. Chem. Res. Toxicol. 14, 927-938 (2001).
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 927-938
    • Luo, W.1    Muller, J.M.2    Rachlin, E.M.3    Burrows, C.J.4
  • 16
    • 0032742691 scopus 로고    scopus 로고
    • Peroxynitrite reaction products of 3′,5′-di-O-acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine
    • J. C. Niles, S. Burney, S. P. Singh, J. S. Wishnok and S. R. Tannenbaum, Peroxynitrite reaction products of 3′,5′-di-O-acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine. Proc. Natl. Acad. Sci. USA 96, 11729-11734 (1999).
    • (1999) Proc. Natl. Acad. Sci. USA , vol.96 , pp. 11729-11734
    • Niles, J.C.1    Burney, S.2    Singh, S.P.3    Wishnok, J.S.4    Tannenbaum, S.R.5
  • 17
    • 0034079273 scopus 로고    scopus 로고
    • A novel nitration product formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-7,8-dihydro-8-oxoguanosine
    • J. C. Niles, J. S. Wishnok and S. R. Tannenbaum, A novel nitration product formed during the reaction of peroxynitrite with 2′,3′,5′-tri-O-acetyl-7,8-dihydro-8-oxoguanosine. Chem. Res. Toxicol. 13, 390-396 (2000).
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 390-396
    • Niles, J.C.1    Wishnok, J.S.2    Tannenbaum, S.R.3
  • 18
    • 0028812702 scopus 로고
    • Photosensitized reaction of 8-oxo-7,8-di-hydro-2′-dexoyguanosine: Derivative. Formation of dioxetane and hydroperoxide intermediates
    • C. Sheu and C. S. Foote, Photosensitized reaction of 8-oxo-7,8-di-hydro-2′-dexoyguanosine: derivative. Formation of dioxetane and hydroperoxide intermediates. J. Am. Chem. Soc. 117, 474-477 (1995).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 474-477
    • Sheu, C.1    Foote, C.S.2
  • 19
    • 0028788870 scopus 로고
    • Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxoguanosine formed by photooxidation of a guanosine derivative
    • C. Sheu and C. S. Foote, Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxoguanosine formed by photooxidation of a guanosine derivative. J. Am. Chem. Soc. 117, 6439-6442 (1995).
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6439-6442
    • Sheu, C.1    Foote, C.S.2
  • 20
    • 0035817980 scopus 로고    scopus 로고
    • The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine
    • W. Luo, J. G. Muller and C. J. Burrows, The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Org. Lett. 3, 2801-2804 (2001).
    • (2001) Org. Lett. , vol.3 , pp. 2801-2804
    • Luo, W.1    Muller, J.G.2    Burrows, C.J.3
  • 21
    • 0034624588 scopus 로고    scopus 로고
    • Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine
    • W. Luo, J. G. Muller, E. M. Rachlin and C. J. Burrows, Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine. Org. Lett. 2, 613-616 (2000).
    • (2000) Org. Lett. , vol.2 , pp. 613-616
    • Luo, W.1    Muller, J.G.2    Rachlin, E.M.3    Burrows, C.J.4
  • 22
    • 0035105114 scopus 로고    scopus 로고
    • Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro-2′-deoxyguanosine but not of 2′-deoxyguanosine
    • V. Shafirovich, J. Cadet, D. Gasparutoo, A. Dourandin and N.E. Geacintov, Nitrogen dioxide as an oxidizing agent of 8-oxo-7,8-dihydro-2′-deoxyguanosine but not of 2′-deoxyguanosine. Chem. Res. Toxicol. 14, 233-241 (2001)
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 233-241
    • Shafirovich, V.1    Cadet, J.2    Gasparutoo, D.3    Dourandin, A.4    Geacintov, N.E.5
  • 23
    • 33750980336 scopus 로고
    • Equilibrium between hydroxyl radicals and thallium(II) and the oxidation potential of OH(aq)
    • H.A. Schwarz and R. W. Dodson, Equilibrium between hydroxyl radicals and thallium(II) and the oxidation potential of OH(aq). J. Phys. Chem. 88, 3643-3647 (1984).
    • (1984) J. Phys. Chem. , vol.88 , pp. 3643-3647
    • Schwarz, H.A.1    Dodson, R.W.2
  • 24
    • 0033761611 scopus 로고    scopus 로고
    • DNA strand-break yields after post-irradiation incubation with base excision repair endonucleases implicate hydroxyl radical pairs in doublestrand break formation
    • J. R. Milligan, J. A. Aguilera, R. A. Paglinawan and J. F. Ward, DNA strand-break yields after post-irradiation incubation with base excision repair endonucleases implicate hydroxyl radical pairs in doublestrand break formation. Int. J. Radiat. Biol. 76, 1305-1314 (2000).
    • (2000) Int. J. Radiat. Biol. , vol.76 , pp. 1305-1314
    • Milligan, J.R.1    Aguilera, J.A.2    Paglinawan, R.A.3    Ward, J.F.4
  • 27
    • 0001713872 scopus 로고
    • Electron spin resonance evidence for intra- and intermolecular σσ* bonding in methionine radicals: Relative stabilities of S-Cl, S-Br, S-N, and S-S three-electron bonds
    • M. H. Champagne, M. W. Mullins, A. O. Colson and M. D. Sevilla, Electron spin resonance evidence for intra- and intermolecular σσ* bonding in methionine radicals: Relative stabilities of S-Cl, S-Br, S-N, and S-S three-electron bonds. J. Phys. Chem. 95, 6487 (1991).
    • (1991) J. Phys. Chem. , vol.95 , pp. 6487
    • Champagne, M.H.1    Mullins, M.W.2    Colson, A.O.3    Sevilla, M.D.4
  • 28
    • 0001036231 scopus 로고    scopus 로고
    • Electron spin resonance study of electron transfer rates in DNA: Determination of the tunneling constant for single-step excess electron transfer
    • A. Messer, K. Carpenter, K. Forzley, J. Buchanan, S. Yang, Y. Razskazovkii, Z. Cai and M. D. Sevilla, Electron spin resonance study of electron transfer rates in DNA: Determination of the tunneling constant for single-step excess electron transfer. J. Phys. Chem. B 104, 1128-1136 (2000).
    • (2000) J. Phys. Chem. B , vol.104 , pp. 1128-1136
    • Messer, A.1    Carpenter, K.2    Forzley, K.3    Buchanan, J.4    Yang, S.5    Razskazovkii, Y.6    Cai, Z.7    Sevilla, M.D.8
  • 29
    • 0001392072 scopus 로고
    • 1-substituted thymine π-cation radicals
    • 1-substituted thymine π-cation radicals. J. Phys. Chem. 80, 1898-1901 (1976).
    • (1976) J. Phys. Chem. , vol.80 , pp. 1898-1901
    • Sevilla, M.D.1
  • 30
    • 0034229275 scopus 로고    scopus 로고
    • Electron spin resonance study of electron transfer in DNA: Inter-double strand tunneling processes
    • Z. Cai and M. D. Sevilla, Electron spin resonance study of electron transfer in DNA: Inter-double strand tunneling processes. J. Phys. Chem. B 104, 6942-6949 (2000).
    • (2000) J. Phys. Chem. B , vol.104 , pp. 6942-6949
    • Cai, Z.1    Sevilla, M.D.2
  • 31
    • 0034321087 scopus 로고    scopus 로고
    • Electron spin resonance study of the temperature dependence of electron transfer in DNA: Competitive processes of tunneling, protonation at carbon, and hopping
    • Z. Cai, Z. Gu and M. D. Sevilla, Electron spin resonance study of the temperature dependence of electron transfer in DNA: Competitive processes of tunneling, protonation at carbon, and hopping. J. Phys. Chem. B 104, 10406-10411 (2000).
    • (2000) J. Phys. Chem. B , vol.104 , pp. 10406-10411
    • Cai, Z.1    Gu, Z.2    Sevilla, M.D.3
  • 32
    • 0035963790 scopus 로고    scopus 로고
    • Electron spin resonance study of electron and hole transfer in DNA: Effects of hydration, aliphatic amine cations, and histone proteins
    • Z. Cai, Z. Gu and M. D. Sevilla, Electron spin resonance study of electron and hole transfer in DNA: Effects of hydration, aliphatic amine cations, and histone proteins. J. Phys. Chem. B 105, 6031-6041 (2001).
    • (2001) J. Phys. Chem. B , vol.105 , pp. 6031-6041
    • Cai, Z.1    Gu, Z.2    Sevilla, M.D.3
  • 33
    • 0037076061 scopus 로고    scopus 로고
    • Excess electron transfer in DNA: Studies on the effect of base sequence and proton transfer
    • Z. Cai, X. Li and M. D. Sevilla, Excess electron transfer in DNA: Studies on the effect of base sequence and proton transfer. J. Phys. Chem. B 106, 2755-2762 (2002).
    • (2002) J. Phys. Chem. B , vol.106 , pp. 2755-2762
    • Cai, Z.1    Li, X.2    Sevilla, M.D.3
  • 34
    • 84912968631 scopus 로고
    • Long-range tunnelling electron transfer in chemical reactions
    • R. F. Khairutdinov and K. I. Zamaraev, Long-range tunnelling electron transfer in chemical reactions. Russ. Chem. Rev. 47, 518-530 (1978).
    • (1978) Russ. Chem. Rev. , vol.47 , pp. 518-530
    • Khairutdinov, R.F.1    Zamaraev, K.I.2
  • 35
    • 0033569373 scopus 로고    scopus 로고
    • Energetics and rate of electron transfer in DNA from base radical anions to electron-affinic intercalators in aqueous solution
    • R. F. Anderson and G. A. Wright, Energetics and rate of electron transfer in DNA from base radical anions to electron-affinic intercalators in aqueous solution. Phys. Chem. Chem. Phys. 1, 4827-4831 (1999).
    • (1999) Phys. Chem. Chem. Phys. , vol.1 , pp. 4827-4831
    • Anderson, R.F.1    Wright, G.A.2
  • 36
  • 37
    • 84995069472 scopus 로고
    • An ESR study of π-cation radicals in dinucleoside phosphates and DNA produced by photoionization
    • M. D. Sevilla, J. B. D'Arcy, K. M. Morehouse and M. L. Engelhardt, An ESR study of π-cation radicals in dinucleoside phosphates and DNA produced by photoionization. Photochem. Photobiol. 29, 37-42 (1979).
    • (1979) Photochem. Photobiol. , vol.29 , pp. 37-42
    • Sevilla, M.D.1    D'Arcy, J.B.2    Morehouse, K.M.3    Engelhardt, M.L.4
  • 38
    • 0030008802 scopus 로고    scopus 로고
    • Yields of OH· in gamma-irradiated DNA as a function of DNA hydration: Hole transfer in competition with OH· formation
    • T. La Vere, D. Becker and M. D. Sevilla, Yields of OH· in gamma-irradiated DNA as a function of DNA hydration: Hole transfer in competition with OH· formation. Radiat. Res. 145, 673-680 (1996).
    • (1996) Radiat. Res. , vol.145 , pp. 673-680
    • La Vere, T.1    Becker, D.2    Sevilla, M.D.3
  • 39
    • 0024501624 scopus 로고
    • Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA
    • L. P. Candeias and S. Steenken, Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA. J. Am. Chem. Soc. 111, 1094-1099 (1989).
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1094-1099
    • Candeias, L.P.1    Steenken, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.