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Volumn 5, Issue 8, 1998, Pages 413-425

DNA-mediated electron transfer from a modified base to ethidium: π-stacking as a modulator of reactivity

Author keywords

Base stacking; Charge transport; DNA electron transfer; Ethidium; Intercalation

Indexed keywords


EID: 0032146044     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90158-2     Document Type: Article
Times cited : (149)

References (52)
  • 1
    • 0029833916 scopus 로고    scopus 로고
    • Oxidative DNA damage through long-range electron transfer
    • Hall, D.B., Holmlin, R.E. & Barton, J.K. (1996). Oxidative DNA damage through long-range electron transfer. Nature 382, 731-735.
    • (1996) Nature , vol.382 , pp. 731-735
    • Hall, D.B.1    Holmlin, R.E.2    Barton, J.K.3
  • 2
    • 0031005140 scopus 로고    scopus 로고
    • Sensitivity of DNA-mediated electron transfer to the intervening π-stack: A probe for the integrity of the DNA base stack
    • Hall, D.B. & Barton, J.K. (1997). Sensitivity of DNA-mediated electron transfer to the intervening π-stack: a probe for the integrity of the DNA base stack. J. Am. Chem, Soc. 119, 5045-5046.
    • (1997) J. Am. Chem, Soc. , vol.119 , pp. 5045-5046
    • Hall, D.B.1    Barton, J.K.2
  • 4
    • 0031149127 scopus 로고    scopus 로고
    • Long-range oxidation of guanine by Ru(III) in duplex DNA
    • Arkin, M.R. Stemp, E.D.A. & Barton, J.K., (1997). Long-range oxidation of guanine by Ru(III) in duplex DNA. Chem. Biol. 4, 389-400.
    • (1997) Chem. Biol. , vol.4 , pp. 389-400
    • Arkin, M.R.1    Stemp, E.D.A.2    Barton, J.K.3
  • 5
    • 84877627020 scopus 로고
    • Photosensitized formation of 7,8-dihydro-8-oxo-2'-deoxyguanosine (8-hydroxy-2'-deoxyguanosine) in DNA by riboflavin - A nonsinglet oxygen mediated reaction
    • Kasai, H., Yamaizumi, Z., Berger, M., & Cadet, J. (1992). Photosensitized formation of 7,8-dihydro-8-oxo-2'-deoxyguanosine (8-hydroxy-2'-deoxyguanosine) in DNA by riboflavin - a nonsinglet oxygen mediated reaction. J. Am. Chem. Soc. 114, 9692-9694.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9692-9694
    • Kasai, H.1    Yamaizumi, Z.2    Berger, M.3    Cadet, J.4
  • 6
    • 29544444893 scopus 로고
    • Photoinduced DNA cleavage via electron transfer: Demonstration that guanine residues located 5' to guanine are the most electron-donating sites
    • Saito, I., Takayama, M., Sugiyama, H., Nakatani, K., Tsuchida, A. & Yamamoto, M. (1995). Photoinduced DNA cleavage via electron transfer: demonstration that guanine residues located 5' to guanine are the most electron-donating sites. J. Am. Chem. Soc. 117, 6406-6407.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6406-6407
    • Saito, I.1    Takayama, M.2    Sugiyama, H.3    Nakatani, K.4    Tsuchida, A.5    Yamamoto, M.6
  • 7
    • 0030914362 scopus 로고    scopus 로고
    • Anthraquinone photonuclease structure determines its mode of binding to DNA and the cleavage chemistry observed
    • Breslin, DT. & Schuster, G.B. (1997). Anthraquinone photonuclease structure determines its mode of binding to DNA and the cleavage chemistry observed. J. Am. Chem. Soc. 119, 5043-5044.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5043-5044
    • Breslin, D.T.1    Schuster, G.B.2
  • 8
    • 33748366270 scopus 로고
    • Purine bases, nucleosides, and nucleotides - Aqueous-solution redox chemistry and transformation reactions of their radical cations and e' and OH Adducts
    • Steenken, S. (1987). Purine bases, nucleosides, and nucleotides - aqueous-solution redox chemistry and transformation reactions of their radical cations and e' and OH Adducts. Chem. Rev. 89, 503-520.
    • (1987) Chem. Rev. , vol.89 , pp. 503-520
    • Steenken, S.1
  • 9
    • 1842330888 scopus 로고    scopus 로고
    • Oxidative thymine dimer repair in the DNA helix
    • Dandliker, P.J., Holmlin, R.E. & Barton, J.K. (1997). Oxidative thymine dimer repair in the DNA helix. Science 275, 1465-1468.
    • (1997) Science , vol.275 , pp. 1465-1468
    • Dandliker, P.J.1    Holmlin, R.E.2    Barton, J.K.3
  • 11
    • 0027769742 scopus 로고
    • Long-range photoinduced electron transfer through a DNA helix
    • Murphy, C.J., et al., & Barton, J.K. (1993). Long-range photoinduced electron transfer through a DNA helix. Science 262, 1025-1029.
    • (1993) Science , vol.262 , pp. 1025-1029
    • Murphy, C.J.1    Barton, J.K.2
  • 13
    • 0030003850 scopus 로고    scopus 로고
    • Luminescence quenching in supramolecular systems - A comparison of DNA-mediated and SDS micelle-mediated photoinduced electron transfer between metal complexes
    • Arkin, M.R., Stemp, E.D.A., Turro, C., Turro, N.J. & Barton, J.K. (1996). Luminescence quenching in supramolecular systems - a comparison of DNA-mediated and SDS micelle-mediated photoinduced electron transfer between metal complexes. J. Am. Chem. Soc. 118, 2267-2274.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2267-2274
    • Arkin, M.R.1    Stemp, E.D.A.2    Turro, C.3    Turro, N.J.4    Barton, J.K.5
  • 14
    • 0029846245 scopus 로고    scopus 로고
    • Rates of DNA-mediated electron transfer between metallointercalators
    • Arkin, M.R., et al., & Barbara, P.F. (1996). Rates of DNA-mediated electron transfer between metallointercalators. Science 273, 475-480.
    • (1996) Science , vol.273 , pp. 475-480
    • Arkin, M.R.1    Barbara, P.F.2
  • 15
    • 0029688093 scopus 로고    scopus 로고
    • Electron transfer between metal complexes bound to DNA: Is DNA a molecular wire?
    • Stemp, E.D.A. & Barton, J.K. (1996). Electron transfer between metal complexes bound to DNA: is DNA a molecular wire? Met. Ions Biol. Sys. 33, 325.
    • (1996) Met. Ions Biol. Sys. , vol.33 , pp. 325
    • Stemp, E.D.A.1    Barton, J.K.2
  • 17
    • 0030665685 scopus 로고    scopus 로고
    • Photo-induced electron-transfer in ethidium-modified DNA duplexes: Dependence on distance and base stacking
    • Kelley, S.O., Holmlin, R.E., Stemp, E.D.A, & Barton, J.K. (1997). Photo-induced electron-transfer in ethidium-modified DNA duplexes: dependence on distance and base stacking J. Am. Chem. Soc. 119, 9861-9870.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 9861-9870
    • Kelley, S.O.1    Holmlin, R.E.2    Stemp, E.D.A.3    Barton, J.K.4
  • 18
    • 0031041964 scopus 로고    scopus 로고
    • Electrochemistry of methylene-blue bound to a DNA-modified electrode
    • Kelley, S.O., Jackson, N.M., Barton, J.K. & Hill, M.G. (1997). Electrochemistry of methylene-blue bound to a DNA-modified electrode . Bioconj. Chem. 8, 31-37.
    • (1997) Bioconj. Chem. , vol.8 , pp. 31-37
    • Kelley, S.O.1    Jackson, N.M.2    Barton, J.K.3    Hill, M.G.4
  • 19
    • 0021318863 scopus 로고
    • Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: A possible electron-transfer effect
    • Baguley, B.C. & LeBret, M. (1984). Quenching of DNA-ethidium fluorescence by amsacrine and other antitumor agents: a possible electron-transfer effect. Biochemistry. 23, 937-943.
    • (1984) Biochemistry , vol.23 , pp. 937-943
    • Baguley, B.C.1    LeBret, M.2
  • 20
    • 0025310110 scopus 로고
    • The possible role of electron-transfer complexes in the antitumor action of amsacrine analogues
    • Baguley, B.C. (1990). The possible role of electron-transfer complexes in the antitumor action of amsacrine analogues. Biophys. Chem. 35, 203-212.
    • (1990) Biophys. Chem. , vol.35 , pp. 203-212
    • Baguley, B.C.1
  • 21
    • 0000715189 scopus 로고
    • Dynamics of electron transfer between intercalated polycyclic molecules: Effect of interspersed bases
    • Brun, A.M. & Harriman, A. (1992). Dynamics of electron transfer between intercalated polycyclic molecules: effect of interspersed bases. J. Am. Chem. Soc. 114, 3656-3660.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3656-3660
    • Brun, A.M.1    Harriman, A.2
  • 22
    • 0000731910 scopus 로고
    • Photoinduced electron-transfer in DNA matrix from intercalated ethidium to condensed methylviologen
    • Fromherz, P. & Rieger, B. (1986). Photoinduced electron-transfer in DNA matrix from intercalated ethidium to condensed methylviologen. J. Am, Chem. Soc. 108, 5361-5362.
    • (1986) J. Am, Chem. Soc. , vol.108 , pp. 5361-5362
    • Fromherz, P.1    Rieger, B.2
  • 23
    • 0029104810 scopus 로고
    • Electron transfer through DNA: Site-specific modification of duplex DNA with ruthenium donors and acceptors
    • Meade, T.J. & 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.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 352-354
    • Meade, T.J.1    Kayyem, J.F.2
  • 25
    • 0031920828 scopus 로고    scopus 로고
    • Distance-dependent photoinduced electron transfer in synthetic single strand and hairpin DNA
    • Lewis F.D. & Letsinger, R.L. (1998). Distance-dependent photoinduced electron transfer in synthetic single strand and hairpin DNA. J. Biol. Inorg. Chem. 3, 215-221.
    • (1998) J. Biol. Inorg. Chem. , vol.3 , pp. 215-221
    • Lewis, F.D.1    Letsinger, R.L.2
  • 26
    • 0031906759 scopus 로고    scopus 로고
    • Distance dependence of photoinduced electron transfer in DNA
    • Fukui, K & Tanaka, K. (1998). Distance dependence of photoinduced electron transfer in DNA. Angew. Chem. Int. Ed. 37, 158-161.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 158-161
    • Fukui, K.1    Tanaka, K.2
  • 27
    • 0014243279 scopus 로고
    • Photoelectric effects of deoxyribonucleic acid
    • Snart, R.S. (1968). Photoelectric effects of deoxyribonucleic acid. Biopolymers 6, 293-297.
    • (1968) Biopolymers , vol.6 , pp. 293-297
    • Snart, R.S.1
  • 28
    • 0010882932 scopus 로고
    • Electron migration in hydrated DNA and collagen at low-temperatures. 1. Effect of water concentration
    • Vanlith, D., Eden, J., Warman, J.M. & Hummel A. (1986). Electron migration in hydrated DNA and collagen at low-temperatures. 1. Effect of water concentration. J. Chem. Soc. Faraday Trans. 82, 2933-2943.
    • (1986) J. Chem. Soc. Faraday Trans. , vol.82 , pp. 2933-2943
    • Vanlith, D.1    Eden, J.2    Warman, J.M.3    Hummel, A.4
  • 30
    • 0001563761 scopus 로고
    • Electron conduction and trapping in DNA - An electron-spin-resonance study
    • Cullis, P.M., McClymont, J.D. & Symons, M.C.R. (1990). Electron conduction and trapping in DNA - an electron-spin-resonance study. J. Chem. Soc. Faraday Trans. 86, 591-592.
    • (1990) J. Chem. Soc. Faraday Trans. , vol.86 , pp. 591-592
    • Cullis, P.M.1    McClymont, J.D.2    Symons, M.C.R.3
  • 31
    • 37049077820 scopus 로고
    • Effects of ionizing-radiation on deoxyribonucleic-acid. 7. Electron-capture at cytosine and thymine
    • Cullis, P.M., McClymont, J.D. & Malone, M.E. (1992). Effects of ionizing-radiation on deoxyribonucleic-acid. 7. Electron-capture at cytosine and thymine. J. Chem. Soc. Perkins Trans. 2 10, 1695-1702.
    • (1992) J. Chem. Soc. Perkins Trans. 2 , vol.10 , pp. 1695-1702
    • Cullis, P.M.1    McClymont, J.D.2    Malone, M.E.3
  • 32
    • 0025946762 scopus 로고
    • Intramolecular semiquinone disproportionation in DNA - Pulse-radiolysis study of the one-electron reduction of daunorubicin intercalated in DNA
    • Houee-Levin, C., Gardes-Albert, M., Rouscilles, A., Ferradini, C. & Hickel, B. (1991). Intramolecular semiquinone disproportionation in DNA - pulse-radiolysis study of the one-electron reduction of daunorubicin intercalated in DNA. Biochemistry 30, 8216-8222.
    • (1991) Biochemistry , vol.30 , pp. 8216-8222
    • Houee-Levin, C.1    Gardes-Albert, M.2    Rouscilles, A.3    Ferradini, C.4    Hickel, B.5
  • 33
    • 0001630799 scopus 로고
    • One-electron redox potentials of purines and pyrimidines
    • Jovanovic, S.V. & Simic, M.G. (1986). One-electron redox potentials of purines and pyrimidines. J. Phys. Chem. 90, 974-978.
    • (1986) J. Phys. Chem. , vol.90 , pp. 974-978
    • Jovanovic, S.V.1    Simic, M.G.2
  • 34
    • 0030781942 scopus 로고    scopus 로고
    • Quantitative modeling of DNA-mediated electron-transfer between metallointercalators
    • Olson, E.J.C., Hu, D., Hörmann, A. & Barbara, P.F. (1997). Quantitative modeling of DNA-mediated electron-transfer between metallointercalators. J. Phys. Chem. 101, 299-303.
    • (1997) J. Phys. Chem. , vol.101 , pp. 299-303
    • Olson, E.J.C.1    Hu, D.2    Hörmann, A.3    Barbara, P.F.4
  • 36
    • 0000927026 scopus 로고    scopus 로고
    • A reinvestigation by circular dichroism and NMR: Ru(II) and Rh(III) metallointercalators bind non-cooperatively to DNA
    • Franklin, S.J., Treadway, C.R. & Barton, J.K. (1998). A reinvestigation by circular dichroism and NMR: Ru(II) and Rh(III) metallointercalators bind non-cooperatively to DNA. Inorg. Chem., in press.
    • (1998) Inorg. Chem., in Press
    • Franklin, S.J.1    Treadway, C.R.2    Barton, J.K.3
  • 37
    • 0022004980 scopus 로고
    • Electron transfers in chemistry and biology
    • Marcus, R.A. & Sutin, N. (1985). Electron transfers in chemistry and biology. Biochim. Biophys. Acta. 811, 265-322.
    • (1985) Biochim. Biophys. Acta , vol.811 , pp. 265-322
    • Marcus, R.A.1    Sutin, N.2
  • 38
    • 0000977394 scopus 로고
    • Long-range electron-transfer in donor (spacer) acceptor molecules and proteins
    • Bowler, B.E., Raphael, A.L. & Gray, H.B. (1990). Long-range electron-transfer in donor (spacer) acceptor molecules and proteins. Prog, Inorg. Chem, 38, 259-322.
    • (1990) Prog, Inorg. Chem , vol.38 , pp. 259-322
    • Bowler, B.E.1    Raphael, A.L.2    Gray, H.B.3
  • 39
    • 0025861617 scopus 로고
    • Ethidium-bromide does not fluoresce when intercalated adjacent to 7-deazaguanine in duplex DNA
    • Latimer, L.J.P. & Lee, J.S. (1991). Ethidium-bromide does not fluoresce when intercalated adjacent to 7-deazaguanine in duplex DNA. J. Biol. Chem. 266, 13849.
    • (1991) J. Biol. Chem. , vol.266 , pp. 13849
    • Latimer, L.J.P.1    Lee, J.S.2
  • 40
    • 0013793175 scopus 로고
    • Complex formation between ethidium bromide and nucleic acids
    • Waring, MJ. (1965). Complex formation between ethidium bromide and nucleic acids. J. Mol. Biol. 13, 269-282.
    • (1965) J. Mol. Biol. , vol.13 , pp. 269-282
    • Waring, M.J.1
  • 41
    • 0014202608 scopus 로고
    • A fluorescent complex between ethidioum bromide and nucleic acids: Physical-chemical characterization
    • LePecq, J.B. & Paoletti, C. (1976). A fluorescent complex between ethidioum bromide and nucleic acids: physical-chemical characterization. J. Mol. Biol. 27, 87-106.
    • (1976) J. Mol. Biol. , vol.27 , pp. 87-106
    • LePecq, J.B.1    Paoletti, C.2
  • 42
    • 0014572779 scopus 로고
    • Fluorescence decay time characteristics of the complex between ethidium bromide and nucleic acids
    • Burns, V.W.F. (1969). Fluorescence decay time characteristics of the complex between ethidium bromide and nucleic acids. Arch. Biochem. Biophys. 133, 420-424.
    • (1969) Arch. Biochem. Biophys. , vol.133 , pp. 420-424
    • Burns, V.W.F.1
  • 43
    • 0017372923 scopus 로고
    • Mechanism of ethidium bromide fluorescence enhancement on binding to nucleic acids
    • Olmstead, J. & Kearns, D.R. (1977). Mechanism of ethidium bromide fluorescence enhancement on binding to nucleic acids. Biochemistry 16, 3647-3654.
    • (1977) Biochemistry , vol.16 , pp. 3647-3654
    • Olmstead, J.1    Kearns, D.R.2
  • 44
    • 0020674698 scopus 로고
    • Base-stacking and base-pairing contributions to helix stability - Thermodynamics of double-helix formation with CCGG, CCGGP, CCGGAP, ACCGGP, CCGGUP, and ACCGGUP
    • Petersheim, M. & Turner, D.H. (1983). Base-stacking and base-pairing contributions to helix stability - thermodynamics of double-helix formation with CCGG, CCGGP, CCGGAP, ACCGGP, CCGGUP, and ACCGGUP. Biochemistry 22, 256-263.
    • (1983) Biochemistry , vol.22 , pp. 256-263
    • Petersheim, M.1    Turner, D.H.2
  • 45
    • 0029773892 scopus 로고    scopus 로고
    • Theoretical studies of GC-specific photocleavage of DNA via electron-transfer: Significant lowering of ionization-potential and 5'-localization of HOMO of stacked GG bases in B-form DNA
    • Sugiyama, H. & Saito, I. (1996). Theoretical studies of GC-specific photocleavage of DNA via electron-transfer: significant lowering of ionization-potential and 5'-localization of HOMO of stacked GG bases in B-form DNA. J. Am. Chem. Soc. 118, 7063-7068.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7063-7068
    • Sugiyama, H.1    Saito, I.2
  • 47
    • 0022011006 scopus 로고
    • Electrically conductive metallomacrocyclic assemblies
    • Marks, T.J. (1985) Electrically conductive metallomacrocyclic assemblies. Science 227, 881-889.
    • (1985) Science , vol.227 , pp. 881-889
    • Marks, T.J.1
  • 50
    • 0031898071 scopus 로고    scopus 로고
    • Present status and future directions of research in electron transfer mediated by DNA
    • Netzel, T.L. (1998). Present status and future directions of research in electron transfer mediated by DNA. J. Biol. Inorg. Chem. 3, 210-214.
    • (1998) J. Biol. Inorg. Chem. , vol.3 , pp. 210-214
    • Netzel, T.L.1
  • 51
    • 0029808706 scopus 로고    scopus 로고
    • The acridine ring selectively intercalated into a DNA helix at various types of abasic sites-double-strand formation and photophysical properties
    • Fukui, K. & Tanaka, K. (1996). The acridine ring selectively intercalated into a DNA helix at various types of abasic sites-double-strand formation and photophysical properties. Nucleic Acids. Res. 24, 3926-3967.
    • (1996) Nucleic Acids. Res. , vol.24 , pp. 3926-3967
    • Fukui, K.1    Tanaka, K.2
  • 52
    • 49149135789 scopus 로고
    • Deoxynucleoside phosphoramidites - A new class of key intermediates for deoxypolynucleotide synthesis
    • Beaucage, S.L. & Caruthers, M.H. (1981). Deoxynucleoside phosphoramidites - a new class of key intermediates for deoxypolynucleotide synthesis. Tetrahedron Lett. 22, 1859-1802.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 1859-11802
    • Beaucage, S.L.1    Caruthers, M.H.2


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