메뉴 건너뛰기




Volumn 117, Issue 20, 2013, Pages 6106-6115

Excited-state structure and dynamics of keto-amino cytosine: The 1ππ* state is nonplanar and its radiationless decay is not ultrafast

Author keywords

[No Author keywords available]

Indexed keywords

QUANTUM CHEMISTRY;

EID: 84878048420     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp401881b     Document Type: Article
Times cited : (42)

References (50)
  • 1
    • 0033869563 scopus 로고    scopus 로고
    • Flucytosine: A Review of its Pharmacology, Clinical Indications, Pharmacokinetics, Toxicity and Drug Interactions
    • Vermes, A.; Guchelaar, H.-J.; Dankert, J. Flucytosine: A Review of its Pharmacology, Clinical Indications, Pharmacokinetics, Toxicity and Drug Interactions J. Antimicrob. Chemother. 2000, 46, 171-179
    • (2000) J. Antimicrob. Chemother. , vol.46 , pp. 171-179
    • Vermes, A.1    Guchelaar, H.-J.2    Dankert, J.3
  • 2
    • 0035878715 scopus 로고    scopus 로고
    • Multimodality Therapy with a Replication-Conditional Herpes Simplex Virus 1 Mutant that Expresses Yeast Cytosine Deaminase for Intratumoral Conversion of 5-Fluorocytosine to 5-Fluorouracil
    • Nakamura, H.; Mullen, J. T.; Chandrasekhar, S.; Pawlik, T. M.; Yoon, S. S.; Tanabe, K. K. Multimodality Therapy with a Replication-Conditional Herpes Simplex Virus 1 Mutant that Expresses Yeast Cytosine Deaminase for Intratumoral Conversion of 5-Fluorocytosine to 5-Fluorouracil Cancer Res. 2001, 61, 5447-5452
    • (2001) Cancer Res. , vol.61 , pp. 5447-5452
    • Nakamura, H.1    Mullen, J.T.2    Chandrasekhar, S.3    Pawlik, T.M.4    Yoon, S.S.5    Tanabe, K.K.6
  • 3
    • 33645509483 scopus 로고    scopus 로고
    • A Novel Mechanism of Synergistic Cytotoxicity with 5-Fluorocytosine and Ganciclovir in Double Suicide Gene Therapy
    • Boucher, P. D.; Im, M. M.; Freytag, S. O.; Shewach, D. S. A Novel Mechanism of Synergistic Cytotoxicity with 5-Fluorocytosine and Ganciclovir in Double Suicide Gene Therapy Cancer Res. 2006, 66, 3230-3237
    • (2006) Cancer Res. , vol.66 , pp. 3230-3237
    • Boucher, P.D.1    Im, M.M.2    Freytag, S.O.3    Shewach, D.S.4
  • 4
    • 77951739934 scopus 로고    scopus 로고
    • Highly Efficient Gene Transfer to Solid Tumors in Vivo by Tumor Selective Replicating Retrovirus Vectors
    • Lu, Y.-C.; Luo, Y.-P.; Wang, Y.-W.; Tai, C.-K. Highly Efficient Gene Transfer to Solid Tumors in Vivo by Tumor Selective Replicating Retrovirus Vectors Int. J. Mol. Med. 2010, 25, 769-775
    • (2010) Int. J. Mol. Med. , vol.25 , pp. 769-775
    • Lu, Y.-C.1    Luo, Y.-P.2    Wang, Y.-W.3    Tai, C.-K.4
  • 5
    • 79952763586 scopus 로고    scopus 로고
    • Reprogramming of the Paternal Genome upon Fertilization Involves Genome-Wide Oxidation of 5-Methylcytosine
    • Iqbal, K.; Jin, S.-G.; Pfeifer, G. P.; Szabó, P. E. Reprogramming of the Paternal Genome upon Fertilization Involves Genome-Wide Oxidation of 5-Methylcytosine Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 3642-3648
    • (2011) Proc. Natl. Acad. Sci. U.S.A. , vol.108 , pp. 3642-3648
    • Iqbal, K.1    Jin, S.-G.2    Pfeifer, G.P.3    Szabó, P.E.4
  • 6
    • 80052476744 scopus 로고    scopus 로고
    • Demystifying DNA Demethylation
    • Nabel, C. S.; Kohli, R. M. Demystifying DNA Demethylation Science 2011, 333, 1229-1230
    • (2011) Science , vol.333 , pp. 1229-1230
    • Nabel, C.S.1    Kohli, R.M.2
  • 7
    • 82855176833 scopus 로고    scopus 로고
    • Epigenetic Reprogramming in Mouse Pre-Implementation Development and Primordial Germ Cells
    • Saitou, M.; Kagiwada, S.; Kurimoto, K. Epigenetic Reprogramming in Mouse Pre-Implementation Development and Primordial Germ Cells Development 2012, 139, 15-31
    • (2012) Development , vol.139 , pp. 15-31
    • Saitou, M.1    Kagiwada, S.2    Kurimoto, K.3
  • 8
    • 77149174143 scopus 로고    scopus 로고
    • Clinical Pharmacokinetics of Oral Controlled-Release 5-Fluorocytosine
    • Pai, M. P.; Bruce, H.; Felton, L. A. Clinical Pharmacokinetics of Oral Controlled-Release 5-Fluorocytosine Antimicrob. Agents Chemother. 2010, 54, 1237-1241
    • (2010) Antimicrob. Agents Chemother. , vol.54 , pp. 1237-1241
    • Pai, M.P.1    Bruce, H.2    Felton, L.A.3
  • 9
    • 79960563757 scopus 로고    scopus 로고
    • Comparative Analysis of Enzyme and Pathway Engineering Strategies for 5FC-Mediated Suicide Gene Therapy Applications
    • Johnson, A. J.; Ardiani, A.; Sanchez-Bonilla, M.; Black, M. E. Comparative Analysis of Enzyme and Pathway Engineering Strategies for 5FC-Mediated Suicide Gene Therapy Applications Cancer Gene Ther. 2011, 18, 533-542
    • (2011) Cancer Gene Ther. , vol.18 , pp. 533-542
    • Johnson, A.J.1    Ardiani, A.2    Sanchez-Bonilla, M.3    Black, M.E.4
  • 11
    • 0037032198 scopus 로고    scopus 로고
    • Intrinsic Lifetimes of the Excited State of DNA and RNA Bases
    • Kang, H.; Lee, K. T.; Jung, B.; Ko, Y. J.; Kim, S. K. Intrinsic Lifetimes of the Excited State of DNA and RNA Bases J. Am. Chem. Soc. 2002, 124, 12958-12959
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 12958-12959
    • Kang, H.1    Lee, K.T.2    Jung, B.3    Ko, Y.J.4    Kim, S.K.5
  • 12
    • 3042658494 scopus 로고    scopus 로고
    • Electronic Relaxation Dynamics in DNA and RNA Bases Studied by Time-Resolved Photoelectron Spectroscopy
    • Ullrich, S.; Schultz, T.; Zgierski, M. Z.; Stolow, A. Electronic Relaxation Dynamics in DNA and RNA Bases Studied by Time-Resolved Photoelectron Spectroscopy Phys. Chem. Chem. Phys. 2004, 6, 2796-2801
    • (2004) Phys. Chem. Chem. Phys. , vol.6 , pp. 2796-2801
    • Ullrich, S.1    Schultz, T.2    Zgierski, M.Z.3    Stolow, A.4
  • 13
    • 22944478333 scopus 로고    scopus 로고
    • Excited States Dynamics of DNA and RNA Bases: Characterization of a Stepwise Deactivation Pathway in the Gas Phase
    • Canuel, C.; Mons, M.; Piuzzi, F.; Tardivel, B.; Dimicoli, I.; Elhanine, M. Excited States Dynamics of DNA and RNA Bases: Characterization of a Stepwise Deactivation Pathway in the Gas Phase J. Chem. Phys. 2005, 122, 074316-74321
    • (2005) J. Chem. Phys. , vol.122 , pp. 074316-74321
    • Canuel, C.1    Mons, M.2    Piuzzi, F.3    Tardivel, B.4    Dimicoli, I.5    Elhanine, M.6
  • 16
    • 0038155145 scopus 로고    scopus 로고
    • Ultrafast Internal Conversion of Excited Cytosine via the Lowest ππ* Electronic Singlet States
    • Merchan, M.; Serrano-Andrés, L. Ultrafast Internal Conversion of Excited Cytosine via the Lowest ππ* Electronic Singlet States J. Am. Chem. Soc. 2003, 125, 8108-8109
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 8108-8109
    • Merchan, M.1    Serrano-Andrés, L.2
  • 17
    • 23844533009 scopus 로고    scopus 로고
    • Vibrational Spectroscopy of the Guanine-Cytosine Base Pair: Experiment, Harmonic and Anharmonic Calculations and the Nature of the Anharmonic Couplings
    • Brauer, B.; Gerber, R. B.; Kabelac, M.; Hobza, P.; Bakker, J. M.; Riziq, A. G. A.; de Vries, M. S. Vibrational Spectroscopy of the Guanine-Cytosine Base Pair: Experiment, Harmonic and Anharmonic Calculations and the Nature of the Anharmonic Couplings J. Phys. Chem. A 2005, 109, 6974-6984
    • (2005) J. Phys. Chem. A , vol.109 , pp. 6974-6984
    • Brauer, B.1    Gerber, R.B.2    Kabelac, M.3    Hobza, P.4    Bakker, J.M.5    Riziq, A.G.A.6    De Vries, M.S.7
  • 19
    • 62849101535 scopus 로고    scopus 로고
    • Are the Five Natural DNA/RNA Base Monomers a Good Choice from Natural Selection?
    • Serrano-Andrés, L.; Merchan, M. Are the Five Natural DNA/RNA Base Monomers a Good Choice from Natural Selection? J. Photochem. Photobiol., C 2009, 10, 21-32
    • (2009) J. Photochem. Photobiol., C , vol.10 , pp. 21-32
    • Serrano-Andrés, L.1    Merchan, M.2
  • 20
    • 0036206634 scopus 로고    scopus 로고
    • Pairing of the Nucleobases Guanine and Cytosine in the Gas Phase Studied by IR-UV Double-Resonance Spectroscopy and Ab Initio Calculations
    • Nir, E.; Janzen, C.; Imhof, P.; Kleinermanns, K.; de Vries, M. S. Pairing of the Nucleobases Guanine and Cytosine in the Gas Phase Studied by IR-UV Double-Resonance Spectroscopy and Ab Initio Calculations Phys. Chem. Chem. Phys. 2002, 4, 732-739
    • (2002) Phys. Chem. Chem. Phys. , vol.4 , pp. 732-739
    • Nir, E.1    Janzen, C.2    Imhof, P.3    Kleinermanns, K.4    De Vries, M.S.5
  • 22
    • 0242659985 scopus 로고    scopus 로고
    • The Nucleobase Cytosine and the Cytosine Dimer Investigated by Double-Resonance Laser Spectroscopy and Ab initio Calculations
    • Nir, E.; Hünig, I.; Kleinermanns, K.; de Vries, M. S. The Nucleobase Cytosine and the Cytosine Dimer Investigated by Double-Resonance Laser Spectroscopy and Ab initio Calculations Phys. Chem. Chem. Phys. 2003, 5, 4780-4785
    • (2003) Phys. Chem. Chem. Phys. , vol.5 , pp. 4780-4785
    • Nir, E.1    Hünig, I.2    Kleinermanns, K.3    De Vries, M.S.4
  • 24
    • 0030731143 scopus 로고    scopus 로고
    • High-Level Electron Correlation Calculations on some Tautomers of Cytosine
    • Fogarasi, G. High-Level Electron Correlation Calculations on some Tautomers of Cytosine J. Mol. Struct. 1997, 413, 271-278
    • (1997) J. Mol. Struct. , vol.413 , pp. 271-278
    • Fogarasi, G.1
  • 25
    • 84961979214 scopus 로고    scopus 로고
    • CCSD(T) Study of the Relative Stabilities of Cytosine Tautomers
    • Kobayashi, R. A CCSD(T) Study of the Relative Stabilities of Cytosine Tautomers J. Phys. Chem. A 1998, 102, 10813-10817
    • (1998) J. Phys. Chem. A , vol.102 , pp. 10813-10817
    • Kobayashi, R.A.1
  • 26
    • 0037149133 scopus 로고    scopus 로고
    • Relative Stabilities of Three Low-Energy Tautomers of Cytosine: A Coupled Cluster Electron Correlation Study
    • Fogarasi, G. Relative Stabilities of Three Low-Energy Tautomers of Cytosine: A Coupled Cluster Electron Correlation Study J. Phys. Chem. A 2002, 106, 1381-1390
    • (2002) J. Phys. Chem. A , vol.106 , pp. 1381-1390
    • Fogarasi, G.1
  • 27
    • 84962432615 scopus 로고    scopus 로고
    • Correlated Ab Initio Study of Cytosine and Its Tautomers in the Gas Phase, in a Microhydrated Environment and in Aqueous Solution
    • Trygubenko, S. A.; Bogdan, T. V.; Rueda, M.; Orozco, M.; Luque, F. J.; Sponer, J.; Slavicek, P.; Hobza, P. Correlated Ab Initio Study of Cytosine and Its Tautomers in the Gas Phase, in a Microhydrated Environment and in Aqueous Solution Phys. Chem. Chem. Phys. 2002, 4, 4192-4203
    • (2002) Phys. Chem. Chem. Phys. , vol.4 , pp. 4192-4203
    • Trygubenko, S.A.1    Bogdan, T.V.2    Rueda, M.3    Orozco, M.4    Luque, F.J.5    Sponer, J.6    Slavicek, P.7    Hobza, P.8
  • 28
    • 0345763760 scopus 로고    scopus 로고
    • Systematic Quantum Chemical Study of DNA-Base Tautomers
    • Piacenza, M.; Grimme, S. Systematic Quantum Chemical Study of DNA-Base Tautomers J. Comput. Chem. 2004, 25, 83-98
    • (2004) J. Comput. Chem. , vol.25 , pp. 83-98
    • Piacenza, M.1    Grimme, S.2
  • 29
    • 3042568990 scopus 로고    scopus 로고
    • Theoretical Studies of the Unimolecular and Bimolecular Tautomerization of Cytosine
    • Yang, Z.; Rodgers, M. T. Theoretical Studies of the Unimolecular and Bimolecular Tautomerization of Cytosine Phys. Chem. Chem. Phys. 2004, 6, 2749-2757
    • (2004) Phys. Chem. Chem. Phys. , vol.6 , pp. 2749-2757
    • Yang, Z.1    Rodgers, M.T.2
  • 30
    • 34648833631 scopus 로고    scopus 로고
    • Cytosine Neutral Molecules and Cation-Radicals in the Gas-Phase - Structures, Energetics, Ion Chemistry, and Neutralization-Reionization Mass Spectrometry
    • Wolken, J. K.; Yao, C.; Turecek, F.; Polce, M. J.; Wesdemiotis, C. Cytosine Neutral Molecules and Cation-Radicals in the Gas-Phase-Structures, Energetics, Ion Chemistry, and Neutralization-Reionization Mass Spectrometry Int. J. Mass Spectrom. 2007, 267, 30-42
    • (2007) Int. J. Mass Spectrom. , vol.267 , pp. 30-42
    • Wolken, J.K.1    Yao, C.2    Turecek, F.3    Polce, M.J.4    Wesdemiotis, C.5
  • 31
    • 25844448817 scopus 로고    scopus 로고
    • Quantum Chemical Investigation of the Electronic Spectra of the Keto, Enol and Keto-Imine Tautomers of Cytosine
    • Tomic, K.; Tatchen, J.; Marian, C. M. Quantum Chemical Investigation of the Electronic Spectra of the Keto, Enol and Keto-Imine Tautomers of Cytosine J. Phys. Chem. A 2005, 109, 8410-8418
    • (2005) J. Phys. Chem. A , vol.109 , pp. 8410-8418
    • Tomic, K.1    Tatchen, J.2    Marian, C.M.3
  • 33
    • 27744607055 scopus 로고    scopus 로고
    • On the Origin of the Ultrafast Internal Conversion of Electronically Excited Pyrimidine Bases
    • Zgierski, M. Z.; Patchkovskii, S.; Fujiwara, T.; Lim, E. C. On the Origin of the Ultrafast Internal Conversion of Electronically Excited Pyrimidine Bases J. Phys. Chem. A 2005, 109, 9384-9387
    • (2005) J. Phys. Chem. A , vol.109 , pp. 9384-9387
    • Zgierski, M.Z.1    Patchkovskii, S.2    Fujiwara, T.3    Lim, E.C.4
  • 34
    • 27744506847 scopus 로고    scopus 로고
    • Ab Initio Study of a Biradical Radiationless Decay Channel of the Lowest Excited Electronic State of Cytosine and its Derivatives
    • Zgierski, M. Z.; Patchkovskii, S.; Fujiwara, T.; Lim, E. C. Ab Initio Study of a Biradical Radiationless Decay Channel of the Lowest Excited Electronic State of Cytosine and its Derivatives J. Chem. Phys. 2005, 123, 081101-081105
    • (2005) J. Chem. Phys. , vol.123 , pp. 081101-081105
    • Zgierski, M.Z.1    Patchkovskii, S.2    Fujiwara, T.3    Lim, E.C.4
  • 35
    • 20344381582 scopus 로고    scopus 로고
    • Singlet Excited-State Dynamics of 5-Fluorocytosine and Cytosine: An Experimental and Computational Study
    • Blancafort, L.; Cohen, B.; Hare, P. M.; Kohler, B.; Robb, M. A. Singlet Excited-State Dynamics of 5-Fluorocytosine and Cytosine: An Experimental and Computational Study J. Phys. Chem. A 2005, 109, 4431-4436
    • (2005) J. Phys. Chem. A , vol.109 , pp. 4431-4436
    • Blancafort, L.1    Cohen, B.2    Hare, P.M.3    Kohler, B.4    Robb, M.A.5
  • 37
    • 34248149537 scopus 로고    scopus 로고
    • Radiationless Decay Mechanism of Cytosine: An Ab Initio Study with Comparisons to the Fluorescent Analogue 5-Methyl-2-pyrimidinone
    • Kistler, K. A.; Matsika, S. Radiationless Decay Mechanism of Cytosine: An Ab Initio Study with Comparisons to the Fluorescent Analogue 5-Methyl-2-pyrimidinone J. Phys. Chem. A 2007, 111, 2650-2661
    • (2007) J. Phys. Chem. A , vol.111 , pp. 2650-2661
    • Kistler, K.A.1    Matsika, S.2
  • 38
    • 44849141095 scopus 로고    scopus 로고
    • Three-State Conical Intersections in Cytosine and Pyrimidinone Bases
    • Kistler, K. A.; Matsika, S. Three-State Conical Intersections in Cytosine and Pyrimidinone Bases J. Chem. Phys. 2008, 128, 215102-215116
    • (2008) J. Chem. Phys. , vol.128 , pp. 215102-215116
    • Kistler, K.A.1    Matsika, S.2
  • 39
    • 57349136711 scopus 로고    scopus 로고
    • Excited-State Dynamics of Cytosine Reveal Multiple Intrinsic Subpicosecond Pathways
    • Hudock, H. R.; Martínez, T. J. Excited-State Dynamics of Cytosine Reveal Multiple Intrinsic Subpicosecond Pathways ChemPhysChem 2008, 9, 2486-2490
    • (2008) ChemPhysChem , vol.9 , pp. 2486-2490
    • Hudock, H.R.1    Martínez, T.J.2
  • 40
    • 79952720281 scopus 로고    scopus 로고
    • Photodynamical Simulations of Cytosine: Characterization of the Ultrafast Bi-Exponential UV Deactivation
    • Barbatti, M.; Aquino, A. J. A.; Szymczak, J. J.; Nachtigallova, D.; Lischka, H. Photodynamical Simulations of Cytosine: Characterization of the Ultrafast Bi-Exponential UV Deactivation Phys. Chem. Chem. Phys. 2011, 13, 6145-6155
    • (2011) Phys. Chem. Chem. Phys. , vol.13 , pp. 6145-6155
    • Barbatti, M.1    Aquino, A.J.A.2    Szymczak, J.J.3    Nachtigallova, D.4    Lischka, H.5
  • 41
    • 80052331128 scopus 로고    scopus 로고
    • Distinguishing between Relaxation Pathways by Combining Dissociative Ionization Pump Probe Spectroscopy and Ab Initio Calculations: A Case Study of Cytosine
    • Kotur, M.; Weilnach, T. C.; Zhou, C.; Kistler, K. A.; Matsika, S. Distinguishing between Relaxation Pathways by Combining Dissociative Ionization Pump Probe Spectroscopy and Ab Initio Calculations: A Case Study of Cytosine J. Chem. Phys. 2011, 134, 184309-184318
    • (2011) J. Chem. Phys. , vol.134 , pp. 184309-184318
    • Kotur, M.1    Weilnach, T.C.2    Zhou, C.3    Kistler, K.A.4    Matsika, S.5
  • 42
    • 10044252181 scopus 로고    scopus 로고
    • Key Role of a Threefold State Crossing in the Ultrafast Decay of Electronically Excited Cytosine
    • Blancafort, L.; Robb, M. A. Key Role of a Threefold State Crossing in the Ultrafast Decay of Electronically Excited Cytosine J. Phys. Chem. A 2004, 108, 10609-10614
    • (2004) J. Phys. Chem. A , vol.108 , pp. 10609-10614
    • Blancafort, L.1    Robb, M.A.2
  • 43
    • 84862841174 scopus 로고    scopus 로고
    • Benchmark Studies on the Building Blocks of DNA. 1. Superiority of Coupled Cluster Methods in Describing the Excited States of Nucleobases in the Franck-Condon Region
    • Szalay, P. G.; Watson, T. J.; Perera, A.; Lotrich, V. F.; Bartlett, R. J. Benchmark Studies on the Building Blocks of DNA. 1. Superiority of Coupled Cluster Methods in Describing the Excited States of Nucleobases in the Franck-Condon Region J. Phys. Chem. A 2012, 116, 6702-6710
    • (2012) J. Phys. Chem. A , vol.116 , pp. 6702-6710
    • Szalay, P.G.1    Watson, T.J.2    Perera, A.3    Lotrich, V.F.4    Bartlett, R.J.5
  • 45
    • 81555209820 scopus 로고    scopus 로고
    • 1 State Structure, Methyl Torsional Barrier Heights, and Fast Intersystem Crossing Dynamics of 5-Methyl-2-hydroxypyrimidine
    • 1 State Structure, Methyl Torsional Barrier Heights, and Fast Intersystem Crossing Dynamics of 5-Methyl-2-hydroxypyrimidine J. Phys. Chem. A 2011, 115, 13281-13290
    • (2011) J. Phys. Chem. A , vol.115 , pp. 13281-13290
    • Lobsiger, S.1    Frey, H.M.2    Leutwyler, S.3    Morgan, P.4    Pratt, D.5
  • 46
    • 79953169879 scopus 로고    scopus 로고
    • Low-Lying Excited-States and Nonradiative Processes of the Adenine Analogues 7H- and 9H-2-Aminopurine
    • Lobsiger, S.; Sinha, R. K.; Trachsel, M.; Leutwyler, S. Low-Lying Excited-States and Nonradiative Processes of the Adenine Analogues 7H- and 9H-2-Aminopurine J. Chem. Phys. 2011, 134, 114307-114320
    • (2011) J. Chem. Phys. , vol.134 , pp. 114307-114320
    • Lobsiger, S.1    Sinha, R.K.2    Trachsel, M.3    Leutwyler, S.4
  • 50
    • 77951950048 scopus 로고    scopus 로고
    • Supersonic Jet UV Spectrum and Nonradiative Processes of the Thymine Analogue 5-Methyl-2-hydroxypyrimidine
    • Lobsiger, S.; Frey, H. M.; Leutwyler, S. Supersonic Jet UV Spectrum and Nonradiative Processes of the Thymine Analogue 5-Methyl-2-hydroxypyrimidine Phys. Chem. Chem. Phys. 2010, 12, 5032-5040
    • (2010) Phys. Chem. Chem. Phys. , vol.12 , pp. 5032-5040
    • Lobsiger, S.1    Frey, H.M.2    Leutwyler, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.