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Efficient UV-induced charge separation and recombination in an 8-oxoguanine-containing dinucleotide (63 views)

Zhang Y, Dood J, Beckstead AA, Li X-B, Nguyen KV, Burrows CJ, Improta R, Kohler B

Proc Natl Acad Sci U S A (ISSN: 0027-8424, 1091-6490, 0027-8424print), 2014 Sep 12; 111(32): 11612-11617.

Abstract
During the early evolution of life, 8-oxo-7,8-dihydro-2'-deoxyguanosine (O) may have functioned as a proto-flavin capable of repairing cyclobutane pyrimidine dimers in DNA or RNA by photoinduced electron transfer using longer wavelength UVB radiation. To investigate the ability of O to act as an excited-state electron donor, a dinucleotide mimic of the FADH(2) cofactor containing O at the 5'-end and 2'-deoxyadenosine at the 3'-end was studied by femto-second transient absorption spectroscopy in aqueous solution. Following excitation with a UV pulse, a broadband mid-IR pulse probed vibrational modes of ground-state and electronically excited molecules in the double-bond stretching region. Global analysis of time- and frequency-resolved transient absorption data coupled with ab initio quantum mechanical calculations reveal vibrational marker bands of nucleobase radical ions formed by electron transfer from O to 2'-deoxyadenosine. The quantum yield of charge separation is 0.4 at 265 nm, but decreases to 0.1 at 295 nm. Charge recombination occurs in 60 ps before the O radical cation can lose a deuteron to water. Kinetic and thermodynamic considerations strongly suggest that all nucleobases can undergo ultrafast charge separation when p-stacked in DNA or RNA. Interbase charge transfer is proposed to be a major decay pathway for UV excited states of nucleic acids of great importance for photostability as well as photoredox activity.

Affiliations ▼
*** IBB - CNR Affiliation

Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717

and kohler@chemistry.montana.edu burrows@chem.utah.edu robimp@unina.it.

Consiglio Nazionale delle Ricerche, Istituto di Biostrutture e Bioimmagini, 80136 Naples, Italy kohler@chemistry.montana.edu burrows@chem.utah.edu robimp@unina.it.

Details ▼
Impact factor: 9.809, 5-year impact factor: 10.727

Paper type: Journal Article, Research Support, Non-U. S. Gov'T, Non-P. H. S.,

Keywords: Base Pairing, Biogenesis, Electron Transport Radiation Effects, Guanine Analogs, Derivatives Chemistry, Kinetics, Models, Chemical, Oligonucleotides Chemistry Radiation Effects, Photochemical Processes, Quantum Theory, Spectrophotometry, Atomic, Spectroscopy, Fourier Transform Infrared, Thermodynamics, Ultraviolet Rays, Dna Charge Transfer States, Dna Photophysics, Ab Initio Calculations, Photoreactivation, Time-Resolved Vibrational Spectroscopy, 8 Hydroxyguanine, Deoxyadenosine, Dinucleotide, Absorption, Absorption Spectroscopy, Aqueous Solution, Article, Density Functional Theory, Excitation, Infrared Spectroscopy, Priority Journal, Quantum Mechanics, Quantum Yield, Time Resolved Infrared Spectroscopy, Ultraviolet Radiation,

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84905962353&partnerID=40&md5=237f66cc34985fd467e59658a5bdad9d

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Nguyen, K.V., Burrows, C.J., A prebiotic role for 8-oxoguanosine as a flavin mimic in pyrimidine dimer photorepair (2011) J Am Chem Soc, 133 (37), pp. 14586-14589

Stover, J.S., Ciobanu, M., Cliffel, D.E., Rizzo, C.J., Chemical and electrochemical oxidation of C8-arylamine adducts of 2'-deoxyguanosine (2007) J Am Chem Soc, 129 (7), pp. 2074-2081

Crespo-Hernández, C.E., Cohen, B., Hare, P.M., Kohler, B., Ultrafast excited-state dynamics in nucleic acids (2004) Chem Rev, 104 (4), pp. 1977-2019

Kuimova, M.K., Monitoring the direct and indirect damage of DNA bases and polynucleotides by using time-resolved infrared spectroscopy (2006) Proc Natl Acad Sci USA, 103 (7), pp. 2150-2153

Schreier, W.J., Thymine dimerization in DNA is an ultrafast photoreaction (2007) Science, 315 (5812), pp. 625-629

Van Stokkum, I.H.M., Larsen, D.S., Van Grondelle, R., Global and target analysis of time-resolved spectra (2004) Biochim Biophys Acta, 1657 (2-3), pp. 82-104

Parker, A.W., Lin, C.Y., George, M.W., Towrie, M., Kuimova, M.K., Infrared characterization of the guanine radical cation: Finger printing DNA damage (2010) J Phys Chem B, 114 (10), pp. 3660-3667

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 (1992) J Am Chem Soc, 114 (2), pp. 699-704

Doorley, G.W., Tracking DNA excited states by picosecond-time-resolved infrared spectroscopy: Signature band for a charge-transfer excited state in stacked adenine-thymine systems (2013) J Phys Chem Lett, 4 (16), pp. 2739-2744

Stuhldreier, M.C., Temps, F., Ultrafast photo-initiated molecular quantum dynamics in the DNA dinucleotide d(ApG) revealed by broadband transient absorption spectroscopy (2013) Faraday Discuss, 163, pp. 173-188

Bucher, D.B., Pilles, B.M., Carell, T., Zinth, W., Charge separation and charge delocalization identified in long-living states of photoexcited DNA (2014) Proc Natl Acad Sci USA, 111 (12), pp. 4369-4374

Klán, P., Wirz, J., (2009) Photochemistry of Organic Compounds: From Concepts to Practice, , Wiley Chichester United Kingdom

Kao, Y.T., Ultrafast dynamics of flavins in five redox states (2008) J Am Chem Soc, 130 (39), pp. 13132-13139

Seidel, C.A.M., Schulz, A., Sauer, M.H.M., Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies (1996) J Phys Chem, 100 (13), pp. 5541-5553

Moser, C.C., Keske, J.M., Warncke, K., Farid, R.S., Dutton, P.L., Nature of biological electron transfer (1992) Nature, 355 (6363), pp. 796-802

Cantor, C.R., Warshaw, M.M., Shapiro, H., Oligonucleotide interactions. 3. Circular dichroism studies of the conformation of deoxyoligonucleotides (1970) Biopolymers, 9 (9), pp. 1059-1077

Vayá, I., Gustavsson, T., Miannay, F.A., Douki, T., Markovitsi, D., Fluorescence of natural DNA: From the femtosecond to the nanosecond time scales (2010) J Am Chem Soc, 132 (34), pp. 11834-11835

Lange, A.W., Herbert, J.M., Both intra-and interstrand charge-transfer excited states in aqueous B-DNA are present at energies comparable to, or just above, the 1' excitonic bright states (2009) J Am Chem Soc, 131 (11), pp. 3913-3922

Jailaubekov, A.E., Hot charge-transfer excitons set the time limit for charge separation at donor/acceptor interfaces in organic photovoltaics (2013) Nat Mater, 12 (1), pp. 66-73

De Koning, M.C., Simple and efficient solution-phase synthesis of oligonucleotides using extractive work-up (2006) Org Process Res Dev, 10 (6), pp. 1238-1245


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16 Records (14 excluding Abstracts and Conferences).
Total impact factor: 86.626 (79.558 excluding Abstracts and Conferences).
Total 5-year impact factor: 89.689 (81.659 excluding Abstracts and Conferences).



Your bibliography query: (([btitle, keywords, abstract] BASE AND [btitle, keywords, abstract] PAIRING)) AND NOT [id] = 11565



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