메뉴 건너뛰기




Volumn 32, Issue 21, 2004, Pages 6154-6163

Electron transfer in DNA duplexes containing 2-methyl-1,4-naphthoquinone

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; ALKALI; ANTHRAQUINONE; CATION; COMPLEMENTARY DNA; CYTOSINE; DNA BASE; DOUBLE STRANDED DNA; GUANINE; INTERCALATING AGENT; MENADIONE; METAL DERIVATIVE; OLIGONUCLEOTIDE; OXIDIZING AGENT; RADICAL; THYMINE;

EID: 13444256527     PISSN: 03051048     EISSN: None     Source Type: Journal    
DOI: 10.1093/nar/gkh950     Document Type: Article
Times cited : (23)

References (49)
  • 3
    • 0037871659 scopus 로고    scopus 로고
    • Rapid radical formation by DNA charge transport through sequences lacking intervening guanines
    • Yoo,J., Delaney,S., Stemp,E.D.A. and Barton,J.K. (2003) Rapid radical formation by DNA charge transport through sequences lacking intervening guanines. J. Am. Chem. Soc., 125, 6640-6641.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6640-6641
    • Yoo, J.1    Delaney, S.2    Stemp, E.D.A.3    Barton, J.K.4
  • 4
    • 3042734817 scopus 로고    scopus 로고
    • Effects of the photooxidant on DNA-mediated charge transport
    • Williams,T.T., Dohno,C., Stemp,E.D. and Barton,J.K. (2004) Effects of the photooxidant on DNA-mediated charge transport. J. Am. Chem. Soc., 126, 8148-8158.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 8148-8158
    • Williams, T.T.1    Dohno, C.2    Stemp, E.D.3    Barton, J.K.4
  • 5
    • 0035997345 scopus 로고    scopus 로고
    • Long-distance electron transfer through DNA
    • Giese,B. (2002) Long-distance electron transfer through DNA. Annu. Rev. Biochem., 71, 51-70.
    • (2002) Annu. Rev. Biochem. , vol.71 , pp. 51-70
    • Giese, B.1
  • 6
    • 0035110550 scopus 로고    scopus 로고
    • Dynamics of photoinduced charge transfer and hole transport in synthetic DNA hairpins
    • Lewis,F.D., Letsinger,R.L. and Wasielewski,M.R. (2001) Dynamics of photoinduced charge transfer and hole transport in synthetic DNA hairpins. Acc. Chem. Res., 34, 159-170.
    • (2001) Acc. Chem. Res. , vol.34 , pp. 159-170
    • Lewis, F.D.1    Letsinger, R.L.2    Wasielewski, M.R.3
  • 7
    • 0035915333 scopus 로고    scopus 로고
    • Charge transport in DNA via thermally induced hopping
    • Bixon,M. and Jortner,J. (2001) Charge transport in DNA via thermally induced hopping. J. Am. Chem. Soc., 123, 12556-12567.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12556-12567
    • Bixon, M.1    Jortner, J.2
  • 8
    • 0035913290 scopus 로고    scopus 로고
    • Direct observation of hole transfer through DNA by hopping between adenine bases and by tunnelling
    • Giese,B., Amaudrut,J., Kohler,A.K., Spormann,M. and Wessely,S. (2001) Direct observation of hole transfer through DNA by hopping between adenine bases and by tunnelling. Nature, 412, 318-320.
    • (2001) Nature , vol.412 , pp. 318-320
    • Giese, B.1    Amaudrut, J.2    Kohler, A.K.3    Spormann, M.4    Wessely, S.5
  • 10
    • 0034058321 scopus 로고    scopus 로고
    • Long-range charge transfer in DNA: Transient structural distortions control the distance dependence
    • Schuster,G.B. (2000) Long-range charge transfer in DNA: transient structural distortions control the distance dependence. Acc. Chem. Res., 33, 253-260.
    • (2000) Acc. Chem. Res. , vol.33 , pp. 253-260
    • Schuster, G.B.1
  • 11
    • 1542377678 scopus 로고    scopus 로고
    • Mechanism for radical cation transport in duplex DNA oligonucleotides
    • Liu,C.S., Hemandez,R. and Schuster,G.B. (2004) Mechanism for radical cation transport in duplex DNA oligonucleotides. J. Am. Chem. Soc., 126, 2877-2884.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 2877-2884
    • Liu, C.S.1    Hemandez, R.2    Schuster, G.B.3
  • 13
    • 0037951371 scopus 로고    scopus 로고
    • Base sequence effects in radical cation migration in duplex DNA: Support for the polaron-like hopping model
    • Liu,C.S. and Schuster,G.B. (2003) Base sequence effects in radical cation migration in duplex DNA: support for the polaron-like hopping model. J. Am. Chem. Soc., 125, 6098-6102.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 6098-6102
    • Liu, C.S.1    Schuster, G.B.2
  • 14
    • 0032211030 scopus 로고    scopus 로고
    • Guanine is the target for direct ionisation damage in DNA, as detected using excision enzymes
    • Melvin,T., Cunniffe,S.M.T., O'Neill,P., Parker,A.W. and Roldan-Arjona,T. (1998) Guanine is the target for direct ionisation damage in DNA, as detected using excision enzymes. Nucleic Acids Res. 26, 4935-4942.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 4935-4942
    • Melvin, T.1    Cunniffe, S.M.T.2    O'Neill, P.3    Parker, A.W.4    Roldan-Arjona, T.5
  • 15
    • 0036464514 scopus 로고    scopus 로고
    • Long-range oxidative damage in duplex DNA: The effect of bulged G in a G-C tract and tandem G/A mispairs
    • Boone,E. and Schuster,G.B. (2002) Long-range oxidative damage in duplex DNA: the effect of bulged G in a G-C tract and tandem G/A mispairs. Nucleic Acids Res., 30, 830-837.
    • (2002) Nucleic Acids Res. , vol.30 , pp. 830-837
    • Boone, E.1    Schuster, G.B.2
  • 16
    • 0033485712 scopus 로고    scopus 로고
    • Long-range guanine damage in single-stranded DNA: Charge transport through a duplex bridge and in a single-stranded overhang
    • Kan,Y.Z. and Schuster,G.B. (1999) Long-range guanine damage in single-stranded DNA: charge transport through a duplex bridge and in a single-stranded overhang. J. Am. Chem. Soc., 121, 10857-10864.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10857-10864
    • Kan, Y.Z.1    Schuster, G.B.2
  • 17
    • 0036397870 scopus 로고    scopus 로고
    • Temperature-dependence of UV laser one-electron oxidative guanine modifications as a probe of local stacking fluctuations and conformational transitions
    • Spassky,A. and Angelov,D. (2002) Temperature-dependence of UV laser one-electron oxidative guanine modifications as a probe of local stacking fluctuations and conformational transitions. J. Mol. Biol. 323, 9-15.
    • (2002) J. Mol. Biol. , vol.323 , pp. 9-15
    • Spassky, A.1    Angelov, D.2
  • 18
    • 0020649713 scopus 로고
    • Photosensitization of pyrimidines by 2-methylnaphthoquinone in water: A laser flash photolysis study
    • Fisher,G.J. and Land,E.J. (1983) Photosensitization of pyrimidines by 2-methylnaphthoquinone in water: a laser flash photolysis study. Photochem. Photobiol., 37, 27-32.
    • (1983) Photochem. Photobiol. , vol.37 , pp. 27-32
    • Fisher, G.J.1    Land, E.J.2
  • 19
    • 0022872749 scopus 로고
    • Sensitized photo-oxidation of thymidine by 2-methyl-1,4-naphthoquinone. Characterization of the stable photoproducts
    • Decarroz,C., Wagner,J.R., van Lier,J.E., Krishna,C.M., Riesz,P. and Cadet,J. (1986) Sensitized photo-oxidation of thymidine by 2-methyl-1,4-naphthoquinone. Characterization of the stable photoproducts. Int. J. Radiat. Biol., 50, 491-505.
    • (1986) Int. J. Radiat. Biol. , vol.50 , pp. 491-505
    • Decarroz, C.1    Wagner, J.R.2    van Lier, J.E.3    Krishna, C.M.4    Riesz, P.5    Cadet, J.6
  • 20
    • 0023555882 scopus 로고
    • Specific deprotonation reactions of the pyrimidine radical cation resulting from the menadione mediated photosensitization of 2′-deoxycytidine
    • Decarroz,C., Wagner,J.R. and Cadet,J. (1987) Specific deprotonation reactions of the pyrimidine radical cation resulting from the menadione mediated photosensitization of 2′-deoxycytidine. Free Radic. Res. Commun., 2, 295-301.
    • (1987) Free Radic. Res. Commun. , vol.2 , pp. 295-301
    • Decarroz, C.1    Wagner, J.R.2    Cadet, J.3
  • 21
    • 0023387690 scopus 로고
    • Menadione sensitized photooxidation of nucleic acid and protein constituents. An ESR and spin-trapping study
    • Krishna,C.M., Decarroz,C., Wagner,J.R., Cadet,J. and Riesz,P. (1987) Menadione sensitized photooxidation of nucleic acid and protein constituents. An ESR and spin-trapping study. Photochem. Photobiol. 46, 175-182.
    • (1987) Photochem. Photobiol. , vol.46 , pp. 175-182
    • Krishna, C.M.1    Decarroz, C.2    Wagner, J.R.3    Cadet, J.4    Riesz, P.5
  • 22
    • 0025470591 scopus 로고
    • Quinone sensitized electron transfer photooxidation of nucleic acids: Chemistry of thymine and thymidine radical cations in aqueous solution
    • Wagner,J.R., van Lier,J.E. and Johnston,L.J. (1990) Quinone sensitized electron transfer photooxidation of nucleic acids: chemistry of thymine and thymidine radical cations in aqueous solution. Photochem. Photobiol., 52, 333-343.
    • (1990) Photochem. Photobiol. , vol.52 , pp. 333-343
    • Wagner, J.R.1    van Lier, J.E.2    Johnston, L.J.3
  • 24
    • 0026591033 scopus 로고
    • Endogenous oxidative damage of deoxycytidine in DNA
    • Wagner,J.R., Hu,C.C. and Ames,B.N. (1992) Endogenous oxidative damage of deoxycytidine in DNA. Proc. Natl Acad. Sci. USA 89, 3380-3384.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 3380-3384
    • Wagner, J.R.1    Hu, C.C.2    Ames, B.N.3
  • 25
    • 0028315896 scopus 로고
    • Thymidine hydroperoxides - Structural assignment, conformational features, and thermal decomposition in water
    • Wagner,J.R., van Lier,J.E., Berger,M. and Cadet,J. (1994) Thymidine hydroperoxides - structural assignment, conformational features, and thermal decomposition in water. J. Am. Chem. Soc., 116, 2235-2242.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 2235-2242
    • Wagner, J.R.1    van Lier, J.E.2    Berger, M.3    Cadet, J.4
  • 26
    • 0029860415 scopus 로고    scopus 로고
    • Photosensitized oxidation of 5-methyl-2′-deoxycytidine by 2-methyl-1,4-naphthoquinone: Characterization of 5-(hydroperoxymethyl)-2′-deoxycytidine and stable methyl group oxidation products
    • Bienvenu,C., Wagner,J.R. and Cadet,J. (1996) Photosensitized oxidation of 5-methyl-2′-deoxycytidine by 2-methyl-1,4-naphthoquinone: characterization of 5-(hydroperoxymethyl -2′-deoxycytidine and stable methyl group oxidation products. J. Am. Chem. Soc., 118, 11406-11411.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11406-11411
    • Bienvenu, C.1    Wagner, J.R.2    Cadet, J.3
  • 27
    • 0033526304 scopus 로고    scopus 로고
    • Hydroxyl-radical-induced decomposition of 2′-deoxycytidine in aerated aqueous solutions
    • Wagner,J.R., Decarroz,C., Berger,M. and Cadet,J. (1999) Hydroxyl-radical-induced decomposition of 2′-deoxycytidine in aerated aqueous solutions. J. Am. Chem. Soc., 121, 4101-4110.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 4101-4110
    • Wagner, J.R.1    Decarroz, C.2    Berger, M.3    Cadet, J.4
  • 28
    • 0000697633 scopus 로고
    • Photobromination of side-chain methyl groups on arenes with N-bromosuccinimide. Convient and selective synthesis of bis(bromomethyl)-and (bromomethyl) methylarenes
    • Futamura,S. and Zong,Z.M. (1992) Photobromination of side-chain methyl groups on arenes with N-bromosuccinimide. Convient and selective synthesis of bis(bromomethyl)-and (bromomethyl) methylarenes. Bull. Chem. Soc. Jpn., 65, 345-348.
    • (1992) Bull. Chem. Soc. Jpn. , vol.65 , pp. 345-348
    • Futamura, S.1    Zong, Z.M.2
  • 29
    • 0021236667 scopus 로고
    • 2,3-Dimethyl-1,4-naphthoquinone derivatives as bioreductive alkylating agents with cross-linking potential
    • Lin,T.S., Antonini,I., Cosby,L.A. and Sartorelli,A.C. (1984) 2,3-Dimethyl-1,4-naphthoquinone derivatives as bioreductive alkylating agents with cross-linking potential. J. Med. Chem., 27, 813-815.
    • (1984) J. Med. Chem. , vol.27 , pp. 813-815
    • Lin, T.S.1    Antonini, I.2    Cosby, L.A.3    Sartorelli, A.C.4
  • 30
    • 0033230545 scopus 로고    scopus 로고
    • Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels
    • Oswald,B., Patsenker,L., Duschl,J., Szmacinski,H., Wolfbeis,O.S. and Terpetschnig,E. (1999) Synthesis, spectral properties, and detection limits of reactive squaraine dyes, a new class of diode laser compatible fluorescent protein labels. Bioconjug. Chem., 10, 925-931.
    • (1999) Bioconjug. Chem. , vol.10 , pp. 925-931
    • Oswald, B.1    Patsenker, L.2    Duschl, J.3    Szmacinski, H.4    Wolfbeis, O.S.5    Terpetschnig, E.6
  • 31
    • 0028078938 scopus 로고
    • Functionalization of oligonucleotides with amino groups and attachment of amino specific reporter groups
    • Agrawal,S. (1994) Functionalization of oligonucleotides with amino groups and attachment of amino specific reporter groups. Methods Mol. Biol., 26, 93-120.
    • (1994) Methods Mol. Biol. , vol.26 , pp. 93-120
    • Agrawal, S.1
  • 32
    • 0033552244 scopus 로고    scopus 로고
    • Mechanism of charge transport in DNA: Internally-linked anthraquinone conjugates support phonon-assisted polaron hopping
    • Ly,D., Sanii,L. and Schuster,G.B. (1999) Mechanism of charge transport in DNA: internally-linked anthraquinone conjugates support phonon-assisted polaron hopping. J. Am. Chem. Soc., 121, 9400-9410.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9400-9410
    • Ly, D.1    Sanii, L.2    Schuster, G.B.3
  • 33
    • 0344443359 scopus 로고    scopus 로고
    • Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone
    • Liu,Z.J., Gao,Y. and Wang,Y.S. (2003) Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone. Nucleic Acids Res., 31, 5413-5424.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 5413-5424
    • Liu, Z.J.1    Gao, Y.2    Wang, Y.S.3
  • 34
    • 0036229483 scopus 로고    scopus 로고
    • Cross-linked thymine-purine base tandem lesions: Synthesis, characterization, and measurement in gamma-irradiated isolated DNA
    • Bellon,S., Ravanat,J.L., Gasparutto,D. and Cadet,J. (2002) Cross-linked thymine-purine base tandem lesions: synthesis, characterization, and measurement in gamma-irradiated isolated DNA. Chem. Res. Toxicol., 15, 598-606.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 598-606
    • Bellon, S.1    Ravanat, J.L.2    Gasparutto, D.3    Cadet, J.4
  • 35
    • 0037414324 scopus 로고    scopus 로고
    • Model studies of DNA C5′ radicals. Selective generation and reactivity of 2′-deoxyadenosin-5′-yl radical
    • Chatgilialoglu,C., Guerra,M. and Mulazzani,Q.G. (2003) Model studies of DNA C5′ radicals. Selective generation and reactivity of 2′-deoxyadenosin-5′-yl radical. J. Am. Chem. Soc., 125, 3839-3848.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 3839-3848
    • Chatgilialoglu, C.1    Guerra, M.2    Mulazzani, Q.G.3
  • 37
    • 0030294883 scopus 로고    scopus 로고
    • The reaction of triplet 2-methyl-1,4-naphthoquinone (menadione) with DNA and polynucleotides
    • Melvin,T., Bothe,E. and Schultefrohlinde,D. (1996) The reaction of triplet 2-methyl-1,4-naphthoquinone (menadione) with DNA and polynucleotides. Photochem. Photobiol., 64, 769-776.
    • (1996) Photochem. Photobiol. , vol.64 , pp. 769-776
    • Melvin, T.1    Bothe, E.2    Schultefrohlinde, D.3
  • 38
    • 0029833916 scopus 로고    scopus 로고
    • Oxidative DNA damage through long-range electron transfer
    • Hall,D.B., Holmlin,R.E. and 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
  • 39
    • 0033168214 scopus 로고    scopus 로고
    • The effect of secondary structure and O2 on the formation of direct strand breaks upon UV irradiation of 5-bromodeoxyuridine-containing oligonucleotides
    • Cook,G.P., Chen,T., Koppisch,A.T. and Greenberg,M.M. (1999) The effect of secondary structure and O2 on the formation of direct strand breaks upon UV irradiation of 5-bromodeoxyuridine-containing oligonucleotides. Chem. Biol., 6, 451-459.
    • (1999) Chem. Biol. , vol.6 , pp. 451-459
    • Cook, G.P.1    Chen, T.2    Koppisch, A.T.3    Greenberg, M.M.4
  • 41
    • 0033555454 scopus 로고    scopus 로고
    • Electron transfer between bases in double helical DNA
    • Kelley,S.O. and Barton,J.K. (1999) Electron transfer between bases in double helical DNA. Science, 283, 375-381.
    • (1999) Science , vol.283 , pp. 375-381
    • Kelley, S.O.1    Barton, J.K.2
  • 42
    • 0034703740 scopus 로고    scopus 로고
    • Long-distance charge transport in DNA: Sequence-dependent radical cation injection efficiency
    • Sanii,L. and Schuster,G.B. (2000) Long-distance charge transport in DNA: sequence-dependent radical cation injection efficiency. J. Am. Chem. Soc., 122, 11545-11546.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11545-11546
    • Sanii, L.1    Schuster, G.B.2
  • 43
    • 0025924082 scopus 로고
    • 32P-Postlabeling detection of radiation-induced DNA damage: Identification and estimation of thymine glycols and phosphoglycolate termini
    • Weinfeld,M. and Soderlind,K.J. (1991) 32P-Postlabeling detection of radiation-induced DNA damage: identification and estimation of thymine glycols and phosphoglycolate termini. Biochemistry, 30, 1091-1097.
    • (1991) Biochemistry , vol.30 , pp. 1091-1097
    • Weinfeld, M.1    Soderlind, K.J.2
  • 44
    • 0036096226 scopus 로고    scopus 로고
    • HPLC isolation and mass spectrometric characterization of two isomers of thymine glycols in oligodeoxynucleotides
    • Wang,Y.S. (2002) HPLC isolation and mass spectrometric characterization of two isomers of thymine glycols in oligodeoxynucleotides. Chem. Res. Toxicol., 15, 671-676.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 671-676
    • Wang, Y.S.1
  • 45
    • 0032517343 scopus 로고    scopus 로고
    • Characterization and chemical stability of photooxidized oligonucleotides that contain
    • Gasparutto,D., Ravanat,J.L., Gerot,O. and Cadet,J. (1998) Characterization and chemical stability of photooxidized oligonucleotides that contain 2,2-diamino-4-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]-5(2H -oxazolone. J. Am. Chem. Soc., 120, 10283-10286.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 10283-10286
    • Gasparutto, D.1    Ravanat, J.L.2    Gerot, O.3    Cadet, J.4
  • 46
    • 0344443359 scopus 로고    scopus 로고
    • Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone
    • Liu,Z., Gao,Y. and Wang,Y. (2003) Identification and characterization of a novel cross-link lesion in d(CpC) upon 365-nm irradiation in the presence of 2-methyl-1,4-naphthoquinone. Nucleic Acids Res., 31, 5413-5424.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 5413-5424
    • Liu, Z.1    Gao, Y.2    Wang, Y.3
  • 47
    • 0035822186 scopus 로고    scopus 로고
    • Guanine modifications following ionization of DNA occurs predominantly via intra- and not interstrand charge migration: An experimental and theoretical study
    • O'Neill,P., Parker,A.W., Plumb,M.A. and Siebbeles,L.D.A. (2001) Guanine modifications following ionization of DNA occurs predominantly via intra- and not interstrand charge migration: an experimental and theoretical study. J. Phys. Chem. B, 105, 5283-5290.
    • (2001) J. Phys. Chem. B , vol.105 , pp. 5283-5290
    • O'Neill, P.1    Parker, A.W.2    Plumb, M.A.3    Siebbeles, L.D.A.4
  • 48
    • 0035930027 scopus 로고    scopus 로고
    • UV laser photolysis of DNA: Effect of duplex stability on charge-transfer efficiency
    • Douki,T., Angelov,D. and Cadet,J. (2001) UV laser photolysis of DNA: effect of duplex stability on charge-transfer efficiency. J. Am. Chem. Soc., 123, 11360-11366.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11360-11366
    • Douki, T.1    Angelov, D.2    Cadet, J.3
  • 49
    • 0032980386 scopus 로고    scopus 로고
    • Modification of DNA bases by photosensitized one-electron oxidation
    • Douki,T. and Cadet,J. (1999) Modification of DNA bases by photosensitized one-electron oxidation. Int. J. Radiat. Biol., 75, 571-581.
    • (1999) Int. J. Radiat. Biol. , vol.75 , pp. 571-581
    • Douki, T.1    Cadet, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.