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Volumn 12, Issue 8, 2013, Pages 1328-1340

Excited state proton-coupled electron transfer in 8-oxoG-C and 8-oxoG-A base pairs: A time dependent density functional theory (TD-DFT) study

Author keywords

[No Author keywords available]

Indexed keywords

8-HYDROXYGUANINE; ADENINE; CYTOSINE; DNA; GUANINE; PROTON; 8 HYDROXYGUANINE; DRUG DERIVATIVE;

EID: 84881107471     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c3pp25430e     Document Type: Article
Times cited : (15)

References (55)
  • 1
    • 0001347975 scopus 로고
    • Isolation and identification of the irradiation product of thymine
    • R. Beukers W. Berends Isolation and identification of the irradiation product of thymine Biochim. Biophys. Acta 1960 41 550 551
    • (1960) Biochim. Biophys. Acta , vol.41 , pp. 550-551
    • Beukers, R.1    Berends, W.2
  • 2
    • 0002622056 scopus 로고
    • Unraveling the molecular pathway from sunlight to skin cancer
    • J. S. Taylor Unraveling the molecular pathway from sunlight to skin cancer Acc. Chem. Res. 1994 27 76 82
    • (1994) Acc. Chem. Res. , vol.27 , pp. 76-82
    • Taylor, J.S.1
  • 4
    • 84866393093 scopus 로고    scopus 로고
    • Electronic excited states responsible for dimer formation upon UV absorption directly by thymine strands: Joint experimental and theoretical study
    • A. Banyasz T. Douki R. Improta T. Gustavsson D. Onidas I. Vayá M. Perron D. Markovitsi Electronic excited states responsible for dimer formation upon UV absorption directly by thymine strands: joint experimental and theoretical study J. Am. Chem. Soc. 2012 134 14834 14845
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 14834-14845
    • Banyasz, A.1    Douki, T.2    Improta, R.3    Gustavsson, T.4    Onidas, D.5    Vayá, I.6    Perron, M.7    Markovitsi, D.8
  • 5
    • 67749129320 scopus 로고    scopus 로고
    • Thymine dimerization in DNA model systems: Cyclobutane photolesion is predominantly formed via the singlet channel
    • W. J. Schreier J. Kubon N. Regner K. Haiser T. E. Schrader W. Zinth P. Clivio P. Gilch Thymine dimerization in DNA model systems: cyclobutane photolesion is predominantly formed via the singlet channel J. Am. Chem. Soc. 2009 131 5038 5039
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5038-5039
    • Schreier, W.J.1    Kubon, J.2    Regner, N.3    Haiser, K.4    Schrader, T.E.5    Zinth, W.6    Clivio, P.7    Gilch, P.8
  • 7
    • 84555187188 scopus 로고    scopus 로고
    • Electron donor acceptor interactions with flanking purines influence the efficiency of thymine photodimerization
    • Z. Pan M. Hariharan J. D. Arkin A. S. Jalilov M. McCullagh G. C. Schatz F. D. Lewis Electron donor acceptor interactions with flanking purines influence the efficiency of thymine photodimerization J. Am. Chem. Soc. 2011 133 20793 20798
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 20793-20798
    • Pan, Z.1    Hariharan, M.2    Arkin, J.D.3    Jalilov, A.S.4    McCullagh, M.5    Schatz, G.C.6    Lewis, F.D.7
  • 10
    • 79953710352 scopus 로고    scopus 로고
    • Chemical investigation of light induced DNA bipyrimidine damage and repair
    • K. Heil D. Pearson T. Carell Chemical investigation of light induced DNA bipyrimidine damage and repair Chem. Soc. Rev. 2011 40 4271 4278
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 4271-4278
    • Heil, K.1    Pearson, D.2    Carell, T.3
  • 12
    • 84862866174 scopus 로고    scopus 로고
    • Photorepair of cyclobutane pyrimidine dimers by 8-oxopurine nucleosides
    • K. V. Nguyen C. J. Burrows Photorepair of cyclobutane pyrimidine dimers by 8-oxopurine nucleosides J. Phys. Org. Chem. 2012 25 574 577
    • (2012) J. Phys. Org. Chem. , vol.25 , pp. 574-577
    • Nguyen, K.V.1    Burrows, C.J.2
  • 13
    • 80052794513 scopus 로고    scopus 로고
    • A prebiotic role for 8-oxoguanosine as a flavin mimic in pyrimidine dimer photorepair
    • K. V. Nguyen C. J. Burrows A prebiotic role for 8-oxoguanosine as a flavin mimic in pyrimidine dimer photorepair J. Am. Chem. Soc. 2011 133 14586 14589
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 14586-14589
    • Nguyen, K.V.1    Burrows, C.J.2
  • 14
    • 84871273149 scopus 로고    scopus 로고
    • Whence flavins? Redox-active ribonucleotides link metabolism and genome repair to the RNA world
    • K. V. Nguyen C. J. Burrows Whence flavins? Redox-active ribonucleotides link metabolism and genome repair to the RNA world Acc. Chem. Res. 2012 45 2151 2159
    • (2012) Acc. Chem. Res. , vol.45 , pp. 2151-2159
    • Nguyen, K.V.1    Burrows, C.J.2
  • 15
    • 84962439884 scopus 로고    scopus 로고
    • Mechanism for repair of thymine dimers by photoexcitation of proximal 8-oxo-7,8-dihydroguanine
    • I. Anusiewicz I. Świerszcz P. Skurski J. Simons Mechanism for repair of thymine dimers by photoexcitation of proximal 8-oxo-7,8-dihydroguanine J. Phys. Chem. A 2013 117 1240 1253
    • (2013) J. Phys. Chem. A , vol.117 , pp. 1240-1253
    • Anusiewicz, I.1    Świerszcz, I.2    Skurski, P.3    Simons, J.4
  • 18
    • 84865989291 scopus 로고    scopus 로고
    • Photoinduced damage to cellular DNA: Direct and photosensitized reactions
    • J. Cadet S. Mouret J.-L. Ravanat T. Douki Photoinduced damage to cellular DNA: direct and photosensitized reactions Photochem. Photobiol. 2012 88 1048 1065
    • (2012) Photochem. Photobiol. , vol.88 , pp. 1048-1065
    • Cadet, J.1    Mouret, S.2    Ravanat, J.-L.3    Douki, T.4
  • 19
    • 77957929396 scopus 로고    scopus 로고
    • Proton-coupled electron transfer in DNA on formation of radiation-produced ion radicals
    • A. Kumar M. D. Sevilla Proton-coupled electron transfer in DNA on formation of radiation-produced ion radicals Chem. Rev. 2010 110 7002 7023
    • (2010) Chem. Rev. , vol.110 , pp. 7002-7023
    • Kumar, A.1    Sevilla, M.D.2
  • 21
    • 33746915664 scopus 로고    scopus 로고
    • Role of electron-driven proton-transfer processes in the excited-state deactivation of the adenine-thymine base pair
    • S. Perun A. L. Sobolewski W. Domcke Role of electron-driven proton-transfer processes in the excited-state deactivation of the adenine-thymine base pair J. Phys. Chem. A 2006 110 9031 9038
    • (2006) J. Phys. Chem. A , vol.110 , pp. 9031-9038
    • Perun, S.1    Sobolewski, A.L.2    Domcke, W.3
  • 23
    • 29144451968 scopus 로고    scopus 로고
    • Tautomeric selectivity of the excited-state lifetime of guanine cytosine base pairs: The role of electron-driven proton-transfer processes
    • A. L. Sobolewski W. Domcke C. Hättig Tautomeric selectivity of the excited-state lifetime of guanine cytosine base pairs: the role of electron-driven proton-transfer processes Proc. Natl. Acad. Sci. U. S. A. 2005 102 17903 17906
    • (2005) Proc. Natl. Acad. Sci. U. S. A. , vol.102 , pp. 17903-17906
    • Sobolewski, A.L.1    Domcke, W.2    Hättig, C.3
  • 24
    • 34547681413 scopus 로고    scopus 로고
    • Ultrafast electronic relaxation in guanosine is promoted by hydrogen bonding with cytidine
    • N. K. Schwalb F. Temps Ultrafast electronic relaxation in guanosine is promoted by hydrogen bonding with cytidine J. Am. Chem. Soc. 2007 129 9272 9273
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 9272-9273
    • Schwalb, N.K.1    Temps, F.2
  • 25
    • 34248171118 scopus 로고    scopus 로고
    • Ultrafast repair of irradiated DNA: Nonadiabatic ab initio simulations of the guanine-cytosine photocycle
    • P. R. L. Marwick N. L. Doltsinis Ultrafast repair of irradiated DNA: nonadiabatic ab initio simulations of the guanine-cytosine photocycle J. Chem. Phys. 2007 126 175102 175106
    • (2007) J. Chem. Phys. , vol.126 , pp. 175102-175106
    • Marwick, P.R.L.1    Doltsinis, N.L.2
  • 26
    • 13544277677 scopus 로고    scopus 로고
    • Formation of 8-oxo-7,8-dihydroguanine-radicals in γ-irradiated DNA by multiple one-electron oxidations
    • L. I. Shukla A. Adhikary R. Pazdro D. Becker M. D. Sevilla Formation of 8-oxo-7,8-dihydroguanine-radicals in γ-irradiated DNA by multiple one-electron oxidations Nucleic Acids Res. 2004 32 6565 6574
    • (2004) Nucleic Acids Res. , vol.32 , pp. 6565-6574
    • Shukla, L.I.1    Adhikary, A.2    Pazdro, R.3    Becker, D.4    Sevilla, M.D.5
  • 27
    • 0034653650 scopus 로고    scopus 로고
    • The trap depth (in DNA) of 8-oxo-7,8-dihydro-2′deoxyguanosine as derived from electron-transfer equilibria in aqueous solution
    • S. Steenken S. V. Jovanovic M. Bietti K. Bernhard The trap depth (in DNA) of 8-oxo-7,8-dihydro-2′deoxyguanosine as derived from electron-transfer equilibria in aqueous solution J. Am. Chem. Soc. 2000 122 2373 2374
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 2373-2374
    • Steenken, S.1    Jovanovic, S.V.2    Bietti, M.3    Bernhard, K.4
  • 28
    • 84877627020 scopus 로고
    • Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin: A non singlet oxygen mediated reaction
    • H. Kasai Z. Yamaizumi M. Berger J. Cadet Photosensitized formation of 7,8-dihydro-8-oxo-2′-deoxyguanosine (8-hydroxy-2′-deoxyguanosine) in DNA by riboflavin: a non singlet oxygen mediated reaction J. Am. Chem. Soc. 1992 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
  • 29
    • 51649086880 scopus 로고    scopus 로고
    • Oxidatively generated damage to the guanine moiety of DNA: Mechanistic aspects and formation in cells
    • J. Cadet T. Douki J.-L. Ravanat Oxidatively generated damage to the guanine moiety of DNA: mechanistic aspects and formation in cells Acc. Chem. Res. 2008 41 1075 1083
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1075-1083
    • Cadet, J.1    Douki, T.2    Ravanat, J.-L.3
  • 33
    • 0037337251 scopus 로고    scopus 로고
    • Electron and hole transfer from DNA base radicals to oxidized product of guanine in DNA
    • Z. Cai M. D. Sevilla Electron and hole transfer from DNA base radicals to oxidized product of guanine in DNA Radiat. Res. 2003 159 411 419
    • (2003) Radiat. Res. , vol.159 , pp. 411-419
    • Cai, Z.1    Sevilla, M.D.2
  • 35
    • 55849117399 scopus 로고    scopus 로고
    • Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections
    • J.-D. Chai M. Head-Gordon Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections Phys. Chem. Chem. Phys. 2008 10 6615 6620
    • (2008) Phys. Chem. Chem. Phys. , vol.10 , pp. 6615-6620
    • Chai, J.-D.1    Head-Gordon, M.2
  • 36
    • 40149109196 scopus 로고    scopus 로고
    • Systematic optimization of long-range corrected hybrid density functionals
    • J.-D. Chai M. Head-Gordon Systematic optimization of long-range corrected hybrid density functionals J. Chem. Phys. 2008 128 084106
    • (2008) J. Chem. Phys. , vol.128 , pp. 084106
    • Chai, J.-D.1    Head-Gordon, M.2
  • 38
    • 84881086929 scopus 로고    scopus 로고
    • JMOL, An Open-Source Java Viewer for Chemical Structures in 3D,; see
    • JMOL, An Open-Source Java Viewer for Chemical Structures in 3D, 2004; see http://jmol.sourceforge.net
    • (2004)
  • 39
    • 84861921942 scopus 로고    scopus 로고
    • Gaussian, Inc., Pittsburgh, PA
    • GaussView, Gaussian, Inc., Pittsburgh, PA, 2003
    • (2003) GaussView
  • 40
    • 84862287054 scopus 로고    scopus 로고
    • Photoreaction channels of the guanine-cytosine base pair explored by long-range corrected TDDFT calculations
    • S. Yamazaki T. Taketsugu Photoreaction channels of the guanine-cytosine base pair explored by long-range corrected TDDFT calculations Phys. Chem. Chem. Phys. 2012 14 8866 8877
    • (2012) Phys. Chem. Chem. Phys. , vol.14 , pp. 8866-8877
    • Yamazaki, S.1    Taketsugu, T.2
  • 42
    • 0034301458 scopus 로고    scopus 로고
    • CC2 excitation energy calculations on large molecules using the resolution of the identity approximation
    • C. Hättig F. Weigend CC2 excitation energy calculations on large molecules using the resolution of the identity approximation J. Chem. Phys. 2000 113 5154 5161
    • (2000) J. Chem. Phys. , vol.113 , pp. 5154-5161
    • Hättig, C.1    Weigend, F.2
  • 43
    • 10844225583 scopus 로고
    • The second-order approximate coupled cluster singles and doubles model CC2
    • O. Christiansen H. Koch P. Jorgensen The second-order approximate coupled cluster singles and doubles model CC2 Chem. Phys. Lett. 1995 243 409 418
    • (1995) Chem. Phys. Lett. , vol.243 , pp. 409-418
    • Christiansen, O.1    Koch, H.2    Jorgensen, P.3
  • 44
    • 84962367328 scopus 로고    scopus 로고
    • A gas phase ab initio excited state geometry optimization study of thymine, cytosine and uracil
    • M. K. Shukla P. C. Mishra A gas phase ab initio excited state geometry optimization study of thymine, cytosine and uracil Chem. Phys. 1999 240 319 329
    • (1999) Chem. Phys. , vol.240 , pp. 319-329
    • Shukla, M.K.1    Mishra, P.C.2
  • 45
    • 84962360726 scopus 로고    scopus 로고
    • An ab initio study of excited states of guanine in the gas phase and aqueous media: Electronic transitions and mechanism of spectral oscillations
    • M. K. Shukla S. K. Mishra A. Kumar P. C. Mishra An ab initio study of excited states of guanine in the gas phase and aqueous media: electronic transitions and mechanism of spectral oscillations J. Comput. Chem. 2000 21 826 846
    • (2000) J. Comput. Chem. , vol.21 , pp. 826-846
    • Shukla, M.K.1    Mishra, S.K.2    Kumar, A.3    Mishra, P.C.4
  • 46
    • 34547213343 scopus 로고    scopus 로고
    • Electronic spectra, excited state structures and interactions of nucleic acid bases and base assemblies: A review
    • M. K. Shukla J. Leszczynski Electronic spectra, excited state structures and interactions of nucleic acid bases and base assemblies: a review J. Biomol. Struct. Dyn. 2007 25 93 118
    • (2007) J. Biomol. Struct. Dyn. , vol.25 , pp. 93-118
    • Shukla, M.K.1    Leszczynski, J.2
  • 47
    • 33645774356 scopus 로고    scopus 로고
    • Conical intersections and double excitations in time-dependent density functional theory
    • B. G. Levine C. Ko J. Quenneville T. J. Martínez Conical intersections and double excitations in time-dependent density functional theory Mol. Phys. 2006 104 1039 1051
    • (2006) Mol. Phys. , vol.104 , pp. 1039-1051
    • Levine, B.G.1    Ko, C.2    Quenneville, J.3    Martínez, T.J.4
  • 48
    • 52949099100 scopus 로고    scopus 로고
    • Mixed time-dependent density-functional theory/classical trajectory surface hopping study of oxirane photochemistry
    • E. Tapavicza I. Tavernelli U. Rothlisberger C. Filippi M. E. Casida Mixed time-dependent density-functional theory/classical trajectory surface hopping study of oxirane photochemistry J. Chem. Phys. 2008 129 124108
    • (2008) J. Chem. Phys. , vol.129 , pp. 124108
    • Tapavicza, E.1    Tavernelli, I.2    Rothlisberger, U.3    Filippi, C.4    Casida, M.E.5
  • 49
    • 83055197004 scopus 로고    scopus 로고
    • Excited state proton transfer is not involved in the ultrafast deactivation of guanine cytosine pair in solution
    • L. Biemann S. A. Kovalenko K. Kleinermanns R. Mahrwald M. Markert R. Improta Excited state proton transfer is not involved in the ultrafast deactivation of guanine cytosine pair in solution J. Am. Chem. Soc. 2011 133 19664 19667
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 19664-19667
    • Biemann, L.1    Kovalenko, S.A.2    Kleinermanns, K.3    Mahrwald, R.4    Markert, M.5    Improta, R.6
  • 50
    • 84862292644 scopus 로고    scopus 로고
    • Solvent effects on electron-driven proton-transfer processes: Adenine-thymine base pairs
    • M. Dargiewicz M. Biczysko R. Improta V. Barone Solvent effects on electron-driven proton-transfer processes: adenine-thymine base pairs Phys. Chem. Chem. Phys. 2012 14 8981 8989
    • (2012) Phys. Chem. Chem. Phys. , vol.14 , pp. 8981-8989
    • Dargiewicz, M.1    Biczysko, M.2    Improta, R.3    Barone, V.4
  • 51
    • 36749084541 scopus 로고    scopus 로고
    • Ultrafast excited-state deactivation and energy transfer in guanine-cytosine DNA double helices
    • F.-A. Miannay A. Bányász T. Gustavsson D. Markovitsi Ultrafast excited-state deactivation and energy transfer in guanine-cytosine DNA double helices J. Am. Chem. Soc. 2007 129 14574 14575
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 14574-14575
    • Miannay, F.-A.1    Bányász, A.2    Gustavsson, T.3    Markovitsi, D.4
  • 52
    • 50249116705 scopus 로고    scopus 로고
    • Ground-state recovery following UV excitation is much slower in G·C-DNA duplexes and hairpins than in mononucleotides
    • C. E. Crespo-Hernández K. de La Harpe B. Kohler Ground-state recovery following UV excitation is much slower in G·C-DNA duplexes and hairpins than in mononucleotides J. Am. Chem. Soc. 2008 130 10844 10845
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 10844-10845
    • Crespo-Hernández, C.E.1    De La Harpe, K.2    Kohler, B.3
  • 53
    • 72249119730 scopus 로고    scopus 로고
    • Deuterium isotope effect on excited-state dynamics in an alternating GC oligonucleotide
    • K. de La Harpe C. E. Crespo-Hernández B. Kohler Deuterium isotope effect on excited-state dynamics in an alternating GC oligonucleotide J. Am. Chem. Soc. 2009 131 17557 17559
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 17557-17559
    • De La Harpe, K.1    Crespo-Hernández, C.E.2    Kohler, B.3
  • 54
    • 67650536677 scopus 로고    scopus 로고
    • Direct observation of the hole protonation state and hole localization site in DNA-oligomers
    • A. Adhikary D. Khanduri M. D. Sevilla Direct observation of the hole protonation state and hole localization site in DNA-oligomers J. Am. Chem. Soc. 2009 131 8614 8619
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 8614-8619
    • Adhikary, A.1    Khanduri, D.2    Sevilla, M.D.3
  • 55
    • 70349246461 scopus 로고    scopus 로고
    • Influence of hydration on proton transfer in the guanine-cytosine radical cation (G+-C) base pair: A density functional theory study
    • A. Kumar M. D. Sevilla Influence of hydration on proton transfer in the guanine-cytosine radical cation (G+-C) base pair: a density functional theory study J. Phys. Chem. B 2009 113 11359 11361
    • (2009) J. Phys. Chem. B , vol.113 , pp. 11359-11361
    • Kumar, A.1    Sevilla, M.D.2


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