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Efficient UV-induced charge separation and recombination in an 8-oxoguanine-containing dinucleotide (89 visite)

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.

Tipo di articolo: Journal Article, Research Support, Non-U. S. Gov'T, Non-P. H. S.,

Impact factor: 9.674

Impact factor a 5 anni: 10.563


Parole chiave: 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

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.
*** IBB - CNR ***

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.
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Zhang, Y., Ultrafast excited-state dynamics and vibrational cooling of 8-oxo-7, 8-dihydro-2'-deoxyguanosine in D2O (2013) J Phys Chem A, 117 (48), pp. 12851-12857

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

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Takaya, T., Su, C., De La Harpe, K., Crespo-Hern ndez, C. E., Kohler, B., UV excitation of single DNA and RNA strands produces high yields of exciplex states between two stacked bases (2008) Proc Natl Acad Sci USA, 105 (30), pp. 10285-10290

De La Harpe, K., Kohler, B., Observation of long-lived excited states in DNA oligonucleotides with significant base sequence disorder (2011) J Phys Chem Lett, 2 (3), pp. 133-138

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 (2013) J Am Chem Soc, 135 (28), pp. 10290-10293

Chen, J., Kohler, B., Base stacking in adenosine dimers revealed by femtosecond transient absorption spectroscopy (2014) J Am Chem Soc, 136 (17), pp. 6362-6372

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Zhang, Y., Improta, R., Kohler, B., Mode-specific vibrational relaxation of photoexcited guanosine 5'-monophosphate and its acid form: A femtosecond broadband mid-IR transient absorption and theoretical study (2014) Phys Chem Chem Phys, 16 (4), pp. 1487-1499

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

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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

Kobayashi, K., Tagawa, S., Direct observation of guanine radical cation deprotonation in duplex DNA using pulse radiolysis (2003) J Am Chem Soc, 125 (34), pp. 10213-10218

Steenken, S., Jovanovic, S. V., Bietti, M., Bernhard, K., The trap depth (in DNA) of 8-oxo-7, 8-dihydro-2'-deoxyguanosine as derived from electron-transfer equilibria in aqueous solution (2000) J Am Chem Soc, 122 (10), pp. 2373-2374

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

Kl n, 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

Daniels, M., Hauswirth, W., Fluorescence of the purine and pyrimidine bases of the nucleic acids in neutral aqueous solution at 300 k (1971) Science, 171 (3972), pp. 675-677

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

Rehm, D., Weller, A., Kinetics of fluorescence quenching by electron and H-atom transfer (1970) Isr J Chem, 8 (2), pp. 259-271

Su, C., Middleton, C. T., Kohler, B., Base-stacking disorder and excited-state dynamics in single-stranded adenine homo-oligonucleotides (2012) J Phys Chem B, 116 (34), pp. 10266-10274

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Vay, 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

Improta, R., Barone, V., Interplay between "neutral" and "charge-transfer" excimers rules the excited state decay in adenine-rich polynucleotides (2011) Angew Chem Int Ed Engl, 50 (50), pp. 12016-12019

Santoro, F., Improta, R., Avila, F., Segado, M., Lami, A., The interplay between neutral exciton and charge transfer states in single-strand polyadenine: A quantum dynamical investigation (2013) Photochem Photobiol Sci, 12 (8), pp. 1527-1543

Deibel, C., Strobel, T., Dyakonov, V., Role of the charge transfer state in organic donor-acceptor solar cells (2010) Adv Mater, 22 (37), pp. 4097-4111

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

Zhang, Y., Chen, J., Kohler, B., Hydrogen bond donors accelerate vibrational cooling of hot purine derivatives in heavy water (2013) J Phys Chem A, 117 (31), pp. 6771-6780

Vengris, M., Contrasting the excited-state dynamics of the photoactive yellow protein chromophore: Protein versus solvent environments (2004) Biophys J, 87 (3), pp. 1848-1857

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

Adamo, C., Barone, V., Toward reliable density functional methods without adjustable parameters: The PBE0 model (1999) J Chem Phys, 110 (13), pp. 6158-6170

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Scalmani, G., Geometries and properties of excited states in the gas phase and in solution: Theory and application of a time-dependent density functional theory polarizable continuum model (2006) J Chem Phys, 124 (9), p. 94107

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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3 Records (3 escludendo Abstract e Conferenze).
Impact factor totale: 22.734 (22.734 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 23.501 (23.501 escludendo Abstract e Conferenze).

Interrogazione bibliografica effettuata: (([btitle] "Base Pairing" OR [btitle] "Biogenesis" OR [btitle] "Electron Transport Radiation Effects" OR [btitle] "Guanine Analogs" OR [btitle] "Derivatives Chemistry") AND NOT [id] = 11565)







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