Excited State Pathways Leading to Formation of Adenine Dimers

Journal of Physical Chemistry Letters

Volumn 7, Issue 11, 2016, Pages 2020-2023

  Banyasz, Akos ^a   Martinez Fernandez, Lara ^b,d   Ketola, Tiia Maaria ^a,c   Munoz Losa, Aurora ^a   Esposito, Luciana ^b   Markovitsi, Dimitra ^a   Improta, Roberto ^b  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b CNR   (Italy)

^c CP Kelco Oy   (Finland)

^d UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION INTERMEDIATES;

DEOXYADENOSINE; TIME QUANTUM; TIME-SCALES; UV INDUCED;

EXCITED STATES;

ADENINE;

CHEMISTRY; DIMERIZATION; QUANTUM THEORY; ULTRAVIOLET RADIATION;

ADENINE; DIMERIZATION; QUANTUM THEORY; ULTRAVIOLET RAYS;

EID: 84973547172     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/acs.jpclett.6b00660     Document Type: Article

References (20)

1. Porschke, D. Analysis of a Specific Photoreaction in Oligodeoxyadenylic and Polydeoxyadenylic Acids J. Am. Chem. Soc. 1973, 95, 8440-8446 10.1021/ja00806a040
2. Porschke, D. Specific Photoreaction in Polydeoxyadenylic Acid Proc. Natl. Acad. Sci. U. S. A. 1973, 70, 2683-2686 10.1073/pnas.70.9.2683
3. Kumar, S.; Sharma, N. D.; Davies, R. J. H.; Phillipson, D. W.; McCloskey, J. A. The Isolation and and Characterization of a New Type of Dimeric Adenine Photoproduct in UV-Irradiated Deoxyadenylates Nucleic Acids Res. 1987, 15, 1199-1216 10.1093/nar/15.3.1199
4. Sharma, N. D.; Davies, R. J. H. Extent of Formation of a Dimeric Adenine Photoproduct in Polynucleotides and DNA J. Photochem. Photobiol., B 1989, 3, 247-258 10.1016/1011-1344(89)80066-1
5. Kumar, S.; Joshi, P. C.; Sharma, N. D.; Bose, S. N.; Davies, R. J. H.; Takeda, N.; McCloskey, J. A. Adenine Photodimerization in Deoxyadenylate Sequences-Elucidation of the Mechanism through Structural Studies of a Major D(ApA) Photoproduct Nucleic Acids Res. 1991, 19, 2841-2847 10.1093/nar/19.11.2841
6. Clingen, P. H.; Jeremy, R.; Davies, H. Quantum Yields of Adenine Photodimerization in Poly(Deoxyadenylic Acid) and DNA J. Photochem. Photobiol., B 1997, 38, 81-87 10.1016/S1011-1344(96)07420-9
7. Wang, Y. S.; Taylor, J. S.; Gross, M. L. Isolation and Mass Spectrometric Characterization of Dimeric Adenine Photoproducts in Oligodeoxynucleotides Chem. Res. Toxicol. 2001, 14, 738-745 10.1021/tx010009u
8. Wang, Y. S.; Taylor, J. S.; Gross, M. L. Fragmentation of Photomodified Oligodeoxynucleotides Adducted with Metal Ions in an Electrospray-Ionization Ion-Trap Mass Spectrometer J. Am. Soc. Mass Spectrom. 2001, 12, 1174-1179 10.1016/S1044-0305(01)00302-6
9. Banyasz, A.; Douki, T.; Improta, R.; Gustavsson, T.; Onidas, D.; Vayá, I.; Perron, M.; Markovitsi, D. 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 10.1021/ja304069f
10. Cadet, J.; Mouret, S.; Ravanat, J.-L.; Douki, T. Photoinduced Damage to Cellular DNA: Direct and Photosensitized Reactions Photochem. Photobiol. 2012, 88, 1048-1065 10.1111/j.1751-1097.2012.01200.x
11. Richa; Sinha, R. P.; Häder, D.-P. Physiological Aspects of UV-Excitation of DNA Top. Curr. Chem. 2015, 356, 203-248 10.1007/128-2014-531
12. Zhao, Y.; Truhlar, D. G. Density Functionals with Broad Applicability in Chemistry Acc. Chem. Res. 2008, 41, 157-167 10.1021/ar700111a
13. Tomasi, J.; Mennucci, B.; Cammi, R. Quantum Mechanical Continuum Solvation Models Chem. Rev. 2005, 105, 2999-3093 10.1021/cr9904009
14. Esposito, L.; Banyasz, A.; Douki, T.; Perron, M.; Markovitsi, D.; Improta, R. Effect of C5-Methylation of Cytosine on the Photoreactivity of DNA: A Joint Experimental and Computational Study of TCG Trinucleotides J. Am. Chem. Soc. 2014, 136, 10838-10841 10.1021/ja5040478
15. Improta, R. Photophysics and Photochemistry of Thymine Deoxy-Dinucleotide in Water: A Pcm/Td-Dft Quantum Mechanical Study J. Phys. Chem. B 2012, 116, 14261-14274 10.1021/jp3093385
16. Marguet, S.; Markovitsi, D. Time-Resolved Study of Thymine Dimer Formation J. Am. Chem. Soc. 2005, 127, 5780-5781 10.1021/ja050648h
17. Marguet, S.; Markovitsi, D.; Talbot, F. One and Two Photon Ionization of DNA Single and Double Helices Studied by Laser Flash Photolysis at 266 Nm J. Phys. Chem. B 2006, 110, 11037-11039 10.1021/jp062578m
18. Candeias, L. P.; Steenken, S. Ionization of Purine Nucleosides and Nucleotides and Their Components by 193-nm Laser Photolysis in Aqueous Solution: Model Studies for Oxidative Damage of DNA J. Am. Chem. Soc. 1992, 114, 699-704 10.1021/ja00028a043
19. -) in Aqueous Solution J. Phys. Chem. Ref. Data 1988, 17, 513-886 10.1063/1.555805
20. Clivio, P.; Fourrey, J.-L.; Gasche, J.; Favre, A. DNA Photodamage Mechanistic Studies: Characterization of a Thietane Intermediate in a Model Reaction Relevant to ″6-4 Lesions″ J. Am. Chem. Soc. 1991, 113, 5481-5483 10.1021/ja00014a065