Home Research Locations About us Organization Staff Contacts Education Login Documents IT
Projects highlights

INCIPIT

ISTAPCA (871 views)

Euro-BioImaging

Instruct-IT

Fondazione Veronesi

Fondo Europeo Pesca (280 views)

 INMiND (942 views)

 PRIN (1047 views)

 eHealthNet (869 views)

  Ponrec (825 views)

MFAG Grant (896 views)

(20 views)


Links

 |<  < >  >| 

    Export to BibTeX    Export to EndNote

Ultrafast Excited-State Deactivation of 8-Hydroxy-2′-deoxyguanosine Studied by Femtosecond Fluorescence Spectroscopy and Quantum-Chemical Calculations (59 views)

Changenet-Barret P, Gustavsson T, Improta R, Markovitsi D

J Phys Chem A (ISSN: 1089-5639, 1520-5215electronic), 2015; 119(23): 6131-6139.

Abstract
The fluorescence properties of the 8-hydroxy-2′-deoxyguanosine (8-oxo-dG) in aqueous solution at pH 6.5 are studied by steady-state spectroscopy and femtosecond fluorescence up-conversion and compared with those of 2′-deoxyguanine (dG) and 2′-deoxyguanine monophosphate (dGMP). The steady-state fluorescence spectrum of 8-oxo-dG is composed of a broad band that peaks at 356 nm and extends over the entire visible spectral region, and its fluorescence quantum yield is twice that of dG/dGMP. After excitation at 267 nm, the initial fluorescence anisotropy at all wavelengths is lower than 0.1, giving evidence of an ultrafast internal conversion (<100 fs) between the two lowest excited ππ∗ states (Lb and La). The fluorescence decays of 8-oxo-dG are biexponential with an average lifetime of 0.7 ± 0.1 ps, which is about two times longer than that of dGMP. In contrast with dGMP, only a moderate dynamical shift (∼1400 vs 10 000 cm-1) of the fluorescence spectra of 8-oxo-dG is observed on the time scale of a few picoseconds without modification of the spectral shape. PCM/TD-DFT calculations, employing either the PBE0 or the M052X functionals, provide absorption spectra in good agreement with the experimental one and show that the deactivation path is similar to that proposed for dGMP, with a fast motion toward an energy plateau, where the purine ring keeps an almost planar geometry, followed by decay to S0, via out-of-the plane motion of amino substituent. © 2015 American Chemical Society.

Affiliations ▼
*** IBB - CNR Affiliation

CNRS, IRAMIS, Laboratoire Francis Perrin, Gif sur Yvette, France

Consiglio Nazionale Delle Ricerche, Istituto di Biostrutture e Bioimmagini, Naples, Italy

Laboratoire d'Optique et Biosciences, Ecole Polytechnique, INSERM, Palaiseau cedex, France

Details ▼
Impact factor: 2.883, 5-year impact factor: 2.709

Paper type: Journal Article,

Keywords: Biomolecules, Fluorescence, Fluorescence Spectroscopy, Geometry, Quantum Chemistry, Quantum Theory, Femtosecond Fluorescence, Fluorescence Anisotropy, Fluorescence Properties, Fluorescence Quantum Yield, Quantum Chemical Calculations, Steady State Fluorescences, Steady State Spectroscopy, Visible Spectral Regions, Excited States,

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84935884627&partnerID=40&md5=c89096d8210080e59a1053ce491c1deb

References ▼
Cadet, J., Douki, T., Ravanat, J.-L., Oxidatively Generated Damage to the Guanine Moiety of DNA: Mechanistic Aspects and Formation in Cells (2008) Acc. Chem. Res., 41, p. 107

Kanvah, S., Joseph, J., Schuster, G.B., Barnett, R.N., Cleveland, C.L., Landman, U., Oxidation of DNA: Damage to Nucleobases (2010) Acc. Chem. Res., 43, pp. 280-287

Markus, T.Z., Daube, S.S., Naaman, R., Fleming, A.M., Muller, J.G., Burrows, C.J., Electronic Structure of DNA - Unique Properties of 8-Oxoguanosine (2009) J. Am. Chem. Soc., 131, pp. 89-95

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, pp. 14586-14589

Zhang, Y., Dood, J., Beckstead, A.A., Li, X.-B., Nguyen, K.V., Burrows, C.J., Improta, R., Kohler, B., Efficient UV-Induced Charge Separation and Recombination in an 8-Oxoguanine Containing Dinucleotide (2014) Proc. Natl. Acad. Sci. U.S.A., 111, pp. 11612-11617

Giorgi, T., Lena, S., Mariani, P., Cremonini, M.A., Masiero, S., Pieraccini, S., Rabe, J.P., Gottarelli, G., Supramolecular Helices via Self-Assembly of 8-Oxoguanosines (2003) J. Am. Chem. Soc., 125, pp. 14741-14749

Gustavsson, T., Improta, R., Markovitsi, D., DNA/RNA: Building Blocks of Life under UV Irradiation (2010) J. Phys. Chem. Lett., 1, pp. 2025-2030

Kohler, B., Nonradiative Decay Mechanisms in DNA Model Systems (2010) J. Phys. Chem. Lett., 1, pp. 2047-2053

Chen, H., Li, S., Ab Initio Study on Deactivation Pathways of Excited 9H-Guanine (2006) J. Chem. Phys., 124

Marian, C.M., The Guanine Tautomer Puzzle: Quantum Chemical Investigation of Ground and Excited States (2007) J. Phys. Chem. A, 111, pp. 1545-1553

Serrano-Andrès, L., Merchan, M., Borin, A.C., A Three-State Model for the Photophysics of Guanine (2008) J. Am. Chem. Soc., 130, pp. 2473-2484

Yamazaki, S., Domcke, W., Sobolewski, A.L., Nonradiative Decay Mechanisms of the Biologically Relevant Tautomer of Guanine (2008) J. Phys. Chem. A, 112, pp. 11965-11968

Shukla, M.K., Leszczynski, J., Hydration of Guanine: Electronic Singlet Excited States for Complexes with 19 and 27 Water Molecules (2009) Chem. Phys. Lett., 478, pp. 254-259

Lan, Z., Fabiano, E., Thiel, W., Photoinduced Nonadiabatic Dynamics of 9H-Guanine (2009) ChemPhysChem, 10, pp. 1225-1229

Karunakaran, K., Kleinermanns, K., Improta, R., Kovalenko, S.A., Photoinduced Dynamics of Guanosine Monophosphate in Water from Broad-Band Transient Absorption Spectroscopy and Quantum-Chemical Calculations (2009) J. Am. Chem. Soc., 131, pp. 5839-5850

Heggen, B., Lan, Z.G., Thiel, W., Nonadiabatic Decay Dynamics of 9H-Guanine in Aqueous Solution (2012) Phys. Chem. Chem. Phys., 14, pp. 8137-8146

Giussani, A., Segarra-Marti, J., Roca-Sanjuan, D., Merchan, M., Excitation of Nucleobases from a Computational Perspective I: Reaction Paths (2015) Top. Curr. Chem., 355, pp. 57-97

Mai, S., Richter, M., Marquetand, P., Gonzalez, L., Excitation of Nucleobases from a Computational Perspective II: Dynamics (2015) Top. Curr. Chem., 355, pp. 99-153

Improta, R., Barone, V., Excited States Behavior of Nucleobases in Solution: Insights from Computational Studies (2015) Top. Curr. Chem., 355, pp. 329-357

Culp, S.J., Cho, B.P., Kadlubar, F.F., Evans, F.E., Structural and Conformational Analyses of 8-Hydroxy-2′-Deoxyguanosine (1989) Chem. Res. Toxicol., 2, pp. 416-422

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, pp. 1459-1471

Onidas, D., Markovitsi, D., Marguet, S., Sharonov, A., Gustavsson, T., Fluorescence Properties of DNA Nucleosides and Nucleotides: A Refined Steady-State and Femtosecond Investigation (2002) J. Phys. Chem. B, 106, pp. 11367-11374

Gustavsson, T., Sharonov, A., Markovitsi, D., Thymine, Thymidine and Thymidine 5′-Monophosphate Studied by Femtosecond Fluorescence Upconversion Spectroscopy (2002) Chem. Phys. Lett., 351, pp. 195-200

Gustavsson, T., Baldacchino, G., Mialocq, J.-C., Pommeret, S., A Femtosecond Fluorescence Up-Conversion Study of the Dynamic Stokes Shift of the DCM Dye Molecule in Polar and Non-Polar Solvents (1995) Chem. Phys. Lett., 236, pp. 587-594

Horng, M.L., Gardecki, J.A., Papazyan, A., Maroncelli, M., Subpicosecond Measurements of Polar Solvation Dynamics: Coumarin 153 Revisited (1995) J. Phys. Chem., 99, pp. 17311-17337

Stokkum, I.H.M.V., Larsen, D.S., Grondelle, R.V., Global and Target Analysis of Time-Resolved Spectra (2004) Biochim. Biophys. Acta, 1657, pp. 82-104

Henry, E.R., Hofrichter, J., Singular Value Decomposition: Application to Analysis of Experimental Data (1992) Methods Enzymol., 210, pp. 129-192

Adamo, C., Barone, V., Toward Reliable Density Functional Methods Without Adjustable Parameters: The PBE0Model (1999) J. Chem. Phys., 110, pp. 6158-6170

Zhao, Y., Schultz, N.E., Truhlar, D.G., Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions (2006) J. Chem. Theory Comput., 2, pp. 364-382

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 (2013) Photochem. Photobiol. Sci., 12, pp. 1375-1386

Santoro, F., Barone, V., Gustavsson, T., Improta, R., Solvent Effect on the Singlet Excited-State Lifetimes of Nucleic Acid Bases: A Computational Study of 5-Fluorouracil and Uracil in Acetonitrile and Water (2006) J. Am. Chem. Soc., 128, pp. 16312-16322

Santoro, F., Improta, R., Fahleson, T., Kauczor, J., Norman, P., Coriani, S., Relative Stability of the La and Lb Excited States in Adenine and Guanine: Direct Evidence from TD-DFT Calculations of MCD Spectra (2014) J. Phys. Chem. Lett., 5, pp. 1806-1811

Improta, R., Quantum Mechanical Calculations Unveil the Structure and Properties of the Absorbing and Emitting Excited Electronic States of Guanine Quadruplex (2014) Chem. - Eur. J., 20, pp. 8106-8115

Tomasi, J., Mennucci, B., Cammi, R., Quantum Mechanical Continuum Solvation Models (2005) Chem. Rev., 105, pp. 2999-3093

Scalmani, G., Frisch, M.J., Mennucci, B., Tomasi, J., Cammi, R., Barone, V., 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

Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Petersson, G.A., (2009) Gaussian 09, , revision D.02

Gaussian, Inc.: Wallingford, CT

Kundu, L.M., Loppnow, G.R., Direct Detection of 8-Oxo-Deoxyguanosine Using UV Resonance Raman Spectroscopy (2007) Photochem. Photobiol., 83, pp. 600-602

Platt, J.R., Classification of Spectra of Cata-Condensed Hydrocarbons (1949) J. Chem. Phys., 17, pp. 484-495

Avila, F.J., Cerezo, J., Stendardo, E., Improta, R., Santoro, F., Insights for an Accurate Comparison of Computational Data to Experimental Absorption and Emission Spectra: Beyond the Vertical Transition Approximation (2013) J. Chem. Theory Comput., 9, pp. 2072-2082

Miannay, F.-A., Gustavsson, T., Banyasz, A., Markovitsi, D., Excited-State Dynamics of dGMP Measured by Steady-State and Femtosecond Fluorescence (2010) J. Phys. Chem. A, 114, pp. 3256-3263

Cheng, C.C.-W., Ma, C., Chan, C.T.-L., Hoa, K.Y.-F., Kwok, W.-M., The Solvent Effect and Identification of a Weakly Emissive State in Nonradiative Dynamics of Guanine Nucleosides and Nucleotides - A Combined Femtosecond Broadband Time-Resolved Fluorescence and Transient Absorption Study (2013) Photochem. Photobiol. Sci., 12, pp. 1351-1365

Clark, L.B., Electronic Spectra of Crystalline Guanosine: Transition Moment Directions of the Guanine Chromophore (1994) J. Am. Chem. Soc., 116, pp. 5265-5270

Fülscher, M.P., Serrano-Andrès, L., Roos, B.O., A Theoretical Study of the Electronic Spectra of Adenine and Guanine (1997) J. Am. Chem. Soc., 119, pp. 6168-6176

Jimenez, R., Fleming, G.R., Kumar, P.V., Maroncelli, M., Femtosecond Solvation Dynamics of Water (1994) Nature, 369, pp. 471-473


Related activities ▼
No results.

Related papers ▼
Insights into the anticancer properties of the first antimicrobialpeptide from Archaea (public domain) (21 views)

Related bibliography ▼

Content: [X]
Extended

Authors: [X]
AND Paper type: [X]

AND Start date: End date: [X]   AND Site:    AND  IBB affiliation

[Clear form]

<=2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018   ALL YEARS

Sort by: date    title    journal    authors      impact factor

* Photoinduced dynamics of guanosine monophosphate in water from broad-band transient absorption spectroscopy and quantum-chemical calculations (50 views)
Karunakaran V, Kleinermanns K, Improta R, Kovalenko SA
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2009; 131(16): 5839-5850.

View    Export to BibTeX    Export to EndNote    Upload PDF


1 Records (1 excluding Abstracts and Conferences).
Total impact factor: 8.58 (8.58 excluding Abstracts and Conferences).
Total 5-year impact factor: 8.805 (8.805 excluding Abstracts and Conferences).



Your bibliography query: (([btitle, keywords, abstract] BIOMOLECULES AND [btitle, keywords, abstract] FLUORESCENCE AND [btitle, keywords, abstract] SPECTROSCOPY)) AND NOT [id] = 52895



Last modified by Gennaro Angrisano on Thursday 01 October 2015, 17:36:09
59 views. Last viewed on Monday 13 November 2017, 21:01:28


Webmaster and developer: Marco Comerci
For problems and suggestions: adminibb.cnr.it
Last updated: Monday 20 November 2017, 11:36:46