Efficient UV-induced charge separation and recombination in an 8-oxoguanine-containing dinucleotide(268 views visite) Zhang Y, Dood J, Beckstead AA, Li X-B, Nguyen KV, Burrows CJ, Improta R, Kohler B
P Natl Acad Sci Usa (ISSN: 0027-8424, 1091-6490, 0027-8424print), 2014 Sep 12; 111(32): 11612-11617.
Keywords 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,
Affiliations Affiliazioni: *** 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.
References Riferimenti: Gilbert, W., Origin of life: The RNA world (1986) Nature, 319 (6055), p. 61
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
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
Liu, Z., Dynamics and mechanism of cyclobutane pyrimidine dimer repair by DNA photolyase (2011) Proc Natl Acad Sci USA, 108 (36), pp. 14831-14836
Hub, W., Schneider, S., Dorr, F., Oxman, J. D., Lewis, F. D., Trans-stilbene amine exciplexes-behavior of the exciplex, solvent-separated radical ion-pair, and free-radical ions (1984) J Am Chem Soc, 106 (3), pp. 708-715
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
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
Schreier, W. J., Thymine dimerization in DNA is an ultrafast photoreaction (2007) Science, 315 (5812), pp. 625-629
Jayanth, N., Ramachandran, S., Puranik, M., Solution structure of the DNA damage lesion 8-oxoguanosine from ultraviolet resonance Raman spectroscopy (2009) J Phys Chem A, 113 (8), pp. 1459-1471
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
Steenken, S., Purine-bases, nucleosides, and nucleotides: Aqueous solution redox chemistry and transformation reactions of their radical cations and e' and OH adducts (1989) Chem Rev, 89 (3), pp. 503-520
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
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
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
Tomasi, J., Mennucci, B., Cammi, R., Quantum mechanical continuum solvation models (2005) Chem Rev, 105 (8), pp. 2999-3093
Zhao, Y., Truhlar, D. G., Density functionals with broad applicability in chemistry (2008) Acc Chem Res, 41 (2), pp. 157-167
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
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
Efficient UV-induced charge separation and recombination in an 8-oxoguanine-containing dinucleotide
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.
Efficient UV-induced charge separation and recombination in an 8-oxoguanine-containing dinucleotide
Kim YH, Shin SW, Pellicano R, Fagoonee S, Choi IJ, Kim YI, Park B, Choi JM, Kim SG, Choi J, Park JY, Oh S, Yang HJ, Lim JH, Im JP, Kim JS, Jung HC, Ponzetto A, Figura N, Malfertheiner P, Choi IJ, Kook MC, Kim YI, Cho SJ, Lee JY, Kim CG, Park B, Nam BH, Bae SE, Choi KD, Choe J, Kim SO, Na HK, Choi JY, Ahn JY, Jung KW, Lee J, Kim DH, Chang HS, Song HJ, Lee GH, Jung HY, Seta T, Takahashi Y, Noguchi Y, Shikata S, Sakai T, Sakai K, Yamashita Y, Nakayama T, Leja M, Park JY, Murillo R, Liepniece-karele I, Isajevs S, Kikuste I, Rudzite D, Krike P, Parshutin S, Polaka I, Kirsners A, Santare D, Folkmanis V, Daugule I, Plummer M, Herrero R, Tsukamoto T, Nakagawa M, Kiriyama Y, Toyoda T, Cao X, Corral JE, Mera R, Dye CW, Morgan DR, Lee YC, Lin JT, Garcia Martin R, Matia Cubillo A, Lee SH, Park JM, Han YM, Ko WJ, Hahm KB, Leontiadis GI, Ford AC, Ichinose M, Sugano K, Jeong M, Park JM, Han YM, Park KY, Lee DH, Yoo JH, Cho JY, Hahm KB, Bang CS, Baik GH, Shin IS, Kim JB, Suk KT, Yoon JH, Kim YS, Kim DJ * Helicobacter pylori Eradication for Prevention of Metachronous Recurrence after Endoscopic Resection of Early Gastric Cancer(211 visite) N Engl J Med (ISSN: 0028-4793, 0028-4793linking, 1533-4406electronic), 2015 Jun; 30642104201566393291: 749-756. Impact Factor:59.558 DettagliEsporta in BibTeXEsporta in EndNote