Mapping the ultrafast dynamics of adenine onto its nucleotide and oligonucleotides by time-resolved photoelectron imaging

Journal of Physical Chemistry Letters

Volumn 5, Issue 5, 2014, Pages 843-848

  Chatterley, Adam S ^a,b,c   West, Christopher W ^a   Roberts, Gareth M ^b,d   Stavros, Vasilios G ^b   Verlet, Jan R R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

^c LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^d UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

anion photoelectron spectroscopy; conical intersections; DNA damage; excited state dynamics; nonradiative decay; photophysics

Indexed keywords

ANION PHOTOELECTRON SPECTROSCOPY; CONICAL INTERSECTION; DNA DAMAGES; EXCITED-STATE DYNAMICS; NONRADIATIVE DECAYS; PHOTOPHYSICS;

ISOMERS; PHOTOELECTRON SPECTROSCOPY;

OLIGONUCLEOTIDES;

EID: 84897786631     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz500264c     Document Type: Article

References (43)

1. Schreier, W. J.; Schrader, T. E.; Koller, F. O.; Gilch, P.; Crespo-Hernández, C. E.; Swaminathan, V. N.; Carell, T.; Zinth, W.; Kohler, B. Thymine Dimerization in DNA Is an Ultrafast Photoreaction Science 2007, 315, 625-629
2. Middleton, C. T.; de La Harpe, K.; Su, C.; Law, Y. K.; Crespo-Hernández, C. E.; Kohler, B. DNA Excited-State Dynamics: From Single Bases to the Double Helix Annu. Rev. Phys. Chem. 2009, 60, 217-239
3. Crespo-Hernández, C. E.; Cohen, B.; Hare, P. M.; Kohler, B. Ultrafast Excited-State Dynamics in Nucleic Acids Chem. Rev. 2004, 104, 1977-2020
4. Sagan, C. Ultraviolet Selection Pressure on the Earliest Organisms J. Theor. Biol. 1973, 39, 195-200
5. Ullrich, S.; Schultz, T.; Zgierski, M. Z.; Stolow, A. Direct Observation of Electronic Relaxation Dynamics in Adenine via Time-Resolved Photoelectron Spectroscopy J. Am. Chem. Soc. 2004, 126, 2262-2263
6. 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, 074316-074316
7. Satzger, H.; Townsend, D.; Zgierski, M. Z.; Patchkovskii, S.; Ullrich, S.; Stolow, A. Primary Processes Underlying the Photostability of Isolated DNA Bases: Adenine Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10196-10201
8. Bisgaard, C. Z.; Satzger, H.; Ullrich, S.; Stolow, A. Excited-State Dynamics of Isolated DNA Bases: A Case Study of Adenine ChemPhysChem 2009, 10, 101-110
9. Wells, K. L.; Hadden, D. J.; Nix, M. G. D.; Stavros, V. G. Competing πσ* States in the Photodissociation of Adenine J. Phys. Chem. Lett. 2010, 1, 993-996
10. 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
11. 1 πσ* State J. Chem. Phys. 2007, 126, 124312
12. Kleinermanns, K.; Nachtigallová, D.; de Vries, M. S. Excited State Dynamics of DNA Bases Int. Rev. Phys. Chem. 2013, 32, 308-342
13. Serrano-Andrés, L.; Merchán, M.; Borin, A. C. Adenine and 2-Aminopurine: Paradigms of Modern Theoretical Photochemistry Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 8691-8696
14. Barbatti, M.; Aquino, A. J. A.; Szymczak, J. J.; Nachtigallová, D.; Hobza, P.; Lischka, H. Relaxation Mechanisms of UV-Photoexcited DNA and RNA Nucleobases Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 21453-21458
15. Barbatti, M.; Lischka, H. Nonadiabatic Deactivation of 9H-Adenine: A Comprehensive Picture Based on Mixed Quantum-Classical Dynamics J. Am. Chem. Soc. 2008, 130, 6831-6839
16. Barbatti, M.; Lan, Z.; Crespo-Otero, R.; Szymczak, J. J.; Lischka, H.; Thiel, W. Critical Appraisal of Excited State Nonadiabatic Dynamics Simulations of 9H-Adenine J. Chem. Phys. 2012, 137, 22A503-514
17. Serrano-Andrés, L.; Merchán, M. Are the Five Natural DNA/RNA Base Monomers a Good Choice from Natural Selection?: A Photochemical Perspective J. Photochem. Photobiol. C 2009, 10, 21-32
18. Ludwig, V.; da Costa, Z. M.; do Amaral, M. S.; Borin, A. C.; Canuto, S.; Serrano-Andrés, L. Photophysics and Photostability of Adenine in Aqueous Solution: A Theoretical Study Chem. Phys. Lett. 2010, 492, 164-169
19. Yamazaki, S.; Kato, S. Solvent Effect on Conical Intersections in Excited-State 9H-Adenine: Radiationless Decay Mechanism in Polar Solvent J. Am. Chem. Soc. 2007, 129, 2901-2909
20. Conti, I.; Garavelli, M.; Orlandi, G. Deciphering Low Energy Deactivation Channels in Adenine J. Am. Chem. Soc. 2009, 131, 16108-16118
21. Chen, J.; Thazhathveetil, A. K.; Lewis, F. D.; Kohler, B. Ultrafast Excited-State Dynamics in Hexaethyleneglycol-Linked DNA Homoduplexes Made of A·T Base Pairs J. Am. Chem. Soc. 2013, 135, 10290-10293
22. Horke, D. A.; Roberts, G. M.; Lecointre, J.; Verlet, J. R. R. Velocity-Map Imaging at Low Extraction Fields Rev. Sci. Instrum. 2012, 83, 063101
23. Lecointre, J.; Roberts, G. M.; Horke, D. A.; Verlet, J. R. R. Ultrafast Relaxation Dynamics Observed through Time-Resolved Photoelectron Angular Distributions J. Phys. Chem. A 2010, 114, 11216
24. Horke, D. A.; Verlet, J. R. R. Time-Resolved Photoelectron Imaging of the Chloranil Radical Anion: Ultrafast Relaxation of Electronically Excited Electron Acceptor States Phys. Chem. Chem. Phys. 2011, 13, 19546-19552
25. Eppink, A. T. J. B.; Parker, D. H. Velocity Map Imaging of Ions and Electrons Using Electrostatic Lenses: Application in Photoelectron and Photofragment Ion Imaging of Molecular Oxygen Rev. Sci. Instrum. 1997, 68, 3477-3484
26. Roberts, G. M.; Nixon, J. L.; Lecointre, J.; Wrede, E.; Verlet, J. R. R. Toward Real-Time Charged-Particle Image Reconstruction Using Polar Onion-Peeling Rev. Sci. Instrum. 2009, 80, 053104
27. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Model J. Chem. Phys. 1999, 110, 6158-6170
28. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian09; Gaussian Inc.: Wallingford, CT, 2009.
29. Leang, S. S.; Zahariev, F.; Gordon, M. S. Benchmarking the Performance of Time-Dependent Density Functional Methods J. Chem. Phys. 2012, 136, 104101-104112
30. Mooney, C. R. S.; Horke, D. A.; Chatterley, A. S.; Simperler, A.; Fielding, H. H.; Verlet, J. R. R. Taking the Green Fluorescence out of the Protein: Dynamics of the Isolated GFP Chromophore Anion Chem. Sci. 2013, 4, 921-927
31. Gustavsson, T.; Sarkar, N.; Vaya, I.; Jimenez, M. C.; Markovitsi, D.; Improta, R. A Joint Experimental/Theoretical Study of the Ultrafast Excited State Deactivation of Deoxyadenosine and 9-Methyladenine in Water and Acetonitrile Photochem. Photobiol. Sci. 2013, 12, 1375-1386
32. Stuhldreier, M. C.; Temps, F. Ultrafast Photo-Initiated Molecular Quantum Dynamics in the DNA Dinucleotide D(Apg) Revealed by Broadband Transient Absorption Spectroscopy Faraday Discuss. 2013, 163, 173-188
33. Lan, Z.; Lu, Y.; Fabiano, E.; Thiel, W. QM/MM Nonadiabatic Decay Dynamics of 9H-Adenine in Aqueous Solution ChemPhysChem 2011, 12, 1989-1998
34. Mitrić, R.; Werner, U.; Wohlgemuth, M.; Seifert, G.; Bonačić-Koutecký, V. Nonadiabatic Dynamics within Time-Dependent Density Functional Tight Binding Method J. Phys. Chem. A 2009, 113, 12700-12705
35. Buchner, F.; Ritze, H.-H.; Lahl, J.; Lubcke, A. Time-Resolved Photoelectron Spectroscopy of Adenine and Adenosine in Aqueous Solution Phys. Chem. Chem. Phys. 2013, 15, 11402-11408
36. Chatterley, A. S.; Johns, A. S.; Stavros, V. G.; Verlet, J. R. R. Base-Specific Ionization of Deprotonated Nucleotides by Resonance Enhanced Two-Photon Detachment J. Phys. Chem. A 2013, 117, 5299-5305
37. Pluharova, E.; Schroeder, C.; Seidel, R.; Bradforth, S. E.; Winter, B.; Faubel, M.; Slavíček, P.; Jungwirth, P. Unexpectedly Small Effect of the DNA Environment on Vertical Ionization Energies of Aqueous Nucleobases J. Phys. Chem. Lett. 2013, 4, 3766-3769
38. Su, C.; Middleton, C. T.; Kohler, B. Base-Stacking Disorder and Excited-State Dynamics in Single-Stranded Adenine Homo-Oligonucleotides J. Phys. Chem. B 2012, 116, 10266-10274
39. Crespo-Hernandez, C. E.; Cohen, B.; Kohler, B. Base Stacking Controls Excited-State Dynamics in A·T DNA Nature 2005, 436, 1141-1144
40. Olaso-González, G.; Merchán, M.; Serrano-Andrés, L. The Role of Adenine Excimers in the Photophysics of Oligonucleotides J. Am. Chem. Soc. 2009, 131, 4368-4377
41. Gidden, J.; Bowers, M. T. Gas-Phase Conformational and Energetic Properties of Deprotonated Dinucleotides Eur. Phys. J. D 2002, 20, 409-419
42. Smith, V. R.; Samoylova, E.; Ritze, H. H.; Radloff, W.; Schultz, T. Excimer States in Microhydrated Adenine Clusters Phys. Chem. Chem. Phys. 2010, 12, 9632-9636
43. Doorley, G. W.; Wojdyla, M.; Watson, G. W.; Towrie, M.; Parker, A. W.; Kelly, J. M.; Quinn, S. J. Tracking DNA Excited States by Picosecond-Time- Resolved Infrared Spectroscopy: Signature Band for a Charge-Transfer Excited State in Stacked Adenine-Thymine Systems J. Phys. Chem. Lett. 2013, 4, 2739-2744