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Solvent effects on the steady-state absorption and fluorescence spectra of uracil, thymine and 5-fluorouracil (87 visite)

Gustavsson T, Sarkar N, Banyasz A, Markovitsi D, Improta R

Photochem Photobiol (ISSN: 0031-8655), 2007 May; 83(3): 595-599.

Tipo di articolo: Journal Article, , Impact factor: 2.172, Impact factor a 5 anni: 2.305, Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-34249819657&partnerID=40&md5=04e2ffcd9677021fb7246517d2bad942

Parole chiave: Fluorouracil, Solvent, Thymine, Chemistry, Conference Paper, Electricity, Hydrogen Bond, Spectrofluorometry, Ultraviolet Spectrophotometry, Electrostatics, Hydrogen Bonding, Spectrometry, Fluorescence,

Affiliazioni: *** IBB - CNR ***
Laboratoire Francis Perrin, CEA/DSM/DRECAM/SPAM - CNRS URA 2453, CEA Saclay, F-91191 Gif-sur-Yvette, France
Dipartimento di Chimica, Universita Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, I-80126 Napoli, Italy
Istituto di Biostrutture e Bioimmagini-CNR, Via Mezzocannone 6, I-80134 Napoli, Italy
Department of Chemistry, Indian Institute of Technology, Kharagpur, PIN 721 302, WB, India


Riferimenti: Crespo-Hernández, C.E., Cohen, B., Hare, P.M., Kohler, B., Ultrafast excited-state dynamics in nucleic acids (2004) Chem. Rev., 104, pp. 1977-202

Improta, R., Barone, V., Absorption and fluorescence spectra of uracil in the gas phase and in aqueous solution: A TD-DFT quantum mechanical study (2004) J. Am. Chem. Soc., 126, pp. 14320-14321

Matsika, S., Radiationless decay of excited states of uracil through conical intersections (2004) J. Phys. Chem. a, 108, pp. 7584-7590

Matsika, S., Three-state conical intersections in nucleic acid bases (2005) J. Phys. Chem. a, 109, pp. 7538-7545

Zgierski, M.Z., Patchkovskii, S., Fujiwara, T., Lim, E.C., On the origin of the ultrafast internal conversion of electronically excited pyrimidine bases (2005) J. Phys. Chem. a, 109, pp. 9384-9387

Ismail, N., Blancafort, L., Olivucci, M., Kohler, B., Robb, M.A., Ultrafast decay of electronically excited singlet cytosine via a π,π* to nO,π* state switch (2002) J. Am. Chem. Soc., 124, pp. 6818-6819

Blancafort, L., Robb, M.A., Key role of a threefold state crossing in the ultrafast decay of electronically excited cytosine (2004) J. Phys. Chem. a, 108, pp. 10609-10614

Blancafort, L., Cohen, B., Hare, P.M., Kohler, B., Robb, M.A., Singlet excited-state dynamics of 5-fluorocytosine and cytosine: An experimental and computational study (2005) J. Phys. Chem. a, 109, pp. 4431-4436

Marian, C.M., A new pathway for the rapid decay of electronically excited adenine (2005) J. Chem. Phys., 122, pp. 1043141-10431413

Marian, C., Nolting, D., Weinkauf, R., The electronic spectrum of protonated adenine: Theory and experiment (2005) Phys. Chem. Chem. Phys., 7, pp. 3306-3316

Nielsen, S.B., Sølling, T.I., Are conical intersections responsible for the ultrafast processes of adenine, protonated adenine, and the corresponding nucleosides? (2005) ChemPhysChem, 6, pp. 1276-1281

Perun, S., Sobolewski, A.L., Domcke, W., Photostability of 9H-adenine: Mechanisms of the radiationless deactivation of the lowest excited singlet states (2005) Chem. Phys., 313, pp. 107-112

Clark, L.B., Tinoco Jr., I., Correlations in the ultraviolet spectra of the purine and pyrimidine bases (1965) J. Am. Chem. Soc., 87, pp. 11-15

Becker, R.S., Kogan, G., Photophysical properties of nucleic acid components. 1. the pyrimidines: Thymine, uracil, N,N-dimethyl derivatives, and thymidine (1980) Photochem. Photobiol., 31, pp. 5-13

Georghiou, S., Gerke, L.S., Excited-state properties of thymidine and their relevance to its heterogeneous emission in double-stranded DNA (1999) Photochem. Photobiol., 69, pp. 646-652

Häupl, T., Windolph, C., Jochum, T., Brede, O., Hermann, R., Picosecond fluorescence of nucleic acid bases (1997) Chem. Phys. Lett., 280, pp. 520-524

Canuel, C., Mons, M., Piuzzi, F., Tardivel, B., Dimicoli, I., Elhanine, M., Excited states dynamics of DNA and RNA bases: Characterization of a stepwise deactivation pathway in the gas phase (2005) J. Chem. Phys., 122, pp. 0743161-0743166

Gustavsson, T., Banyasz, A., Lazzarotto, E., Markovitsi, D., Scalmani, G., Frisch, M.J., Barone, V., Improta, R., Singlet excited-state behavior of uracil and thymine in aqueous solution: A combined experimental and computational study of 11 uracil derivatives (2006) J. Am. Chem. Soc., 128, pp. 607-619

Gustavsson, T., Sarkar, N., Lazzarotto, E., Markovitsi, D., Barone, V., Improta, R., Solvent effect on the singlet excited state dynamics of 5-fluorouracil in acetonitrile as compared to water (2006) J. Phys. Chem. B, 110, pp. 12843-12847

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

Hare, P.M., Crespo-Hernández, C.E., Kohler, B., Solvent-dependent photophysics of 1-cyclohexyluracil: Ultrafast branching in the initial bright state leads nonradiatively to the electronic ground state and a long-lived 1nπ* state (2006) J. Phys. Chem. B, 110, pp. 18641-18650

Markovitsi, D., Sharonov, A., Onidas, D., Gustavsson, T., The effect of molecular organisation in DNA oligomers studied by femtosecond fluorescence spectroscopy (2003) ChemPhysChem, 3, pp. 303-305

Markovitsi, D., Onidas, D., Gustavsson, T., Talbot, F., Lazzarotto, E., UV interaction with DNA bases: Collective behaviour of excited states in double helices (2005) J. Am. Chem. Soc., 127, pp. 17130-17131

Markovitsi, D., Talbot, F., Gustavsson, T., Onidas, D., Lazzarotto, E., Marguet, S., Complexity of excited state dynamics in DNA (2006) Nature, 441, pp. E7

Siano, D.B., Metzler, D.E., Band shapes of the electronic spectra of complex molecules (1969) J. Chem. Phys., 51, pp. 1856-1861

Clark, L.B., Peschel, G.G., Tinoco, I., Vapor spectra and heats of vaporization of some purine and pyrimidine bases (1965) J. Phys. Chem., 69, pp. 3615-3618

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

Crespo-Hern ndez, C. E., Cohen, B., Hare, P. M., Kohler, B., Ultrafast excited-state dynamics in nucleic acids (2004) Chem. Rev., 104, pp. 1977-202

Zgierski, M. Z., Patchkovskii, S., Fujiwara, T., Lim, E. C., On the origin of the ultrafast internal conversion of electronically excited pyrimidine bases (2005) J. Phys. Chem. a, 109, pp. 9384-9387

Marian, C. M., A new pathway for the rapid decay of electronically excited adenine (2005) J. Chem. Phys., 122, pp. 1043141-10431413

Nielsen, S. B., S lling, T. I., Are conical intersections responsible for the ultrafast processes of adenine, protonated adenine, and the corresponding nucleosides? (2005) ChemPhysChem, 6, pp. 1276-1281

Clark, L. B., Tinoco Jr., I., Correlations in the ultraviolet spectra of the purine and pyrimidine bases (1965) J. Am. Chem. Soc., 87, pp. 11-15

Becker, R. S., Kogan, G., Photophysical properties of nucleic acid components. 1. the pyrimidines: Thymine, uracil, N, N-dimethyl derivatives, and thymidine (1980) Photochem. Photobiol., 31, pp. 5-13

H upl, T., Windolph, C., Jochum, T., Brede, O., Hermann, R., Picosecond fluorescence of nucleic acid bases (1997) Chem. Phys. Lett., 280, pp. 520-524

Hare, P. M., Crespo-Hern ndez, C. E., Kohler, B., Solvent-dependent photophysics of 1-cyclohexyluracil: Ultrafast branching in the initial bright state leads nonradiatively to the electronic ground state and a long-lived 1n * state (2006) J. Phys. Chem. B, 110, pp. 18641-18650

Siano, D. B., Metzler, D. E., Band shapes of the electronic spectra of complex molecules (1969) J. Chem. Phys., 51, pp. 1856-1861

Clark, L. B., Peschel, G. G., Tinoco, I., Vapor spectra and heats of vaporization of some purine and pyrimidine bases (1965) J. Phys. Chem., 69, pp. 3615-3618

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



We report a comparison of the steady-state absorption and fluorescence spectra of three representative uracil derivatives (uracil, thymine and 5-fluorouracil) in alcoholic solutions. The present results are compared with those from our previous experimental and computational studies of the same compounds in water and acetonitrile. The effects of solvent polarity and hydrogen bonding on the spectra are discussed in the light of theoretical predictions. This comparative analysis provides a more complete picture of the solvent effects on the absorption and fluorescence properties of pyrimidine nucleobases, with special emphasis on the mechanism of the excited state deactivation. © 2007 American Society for Photobiology.
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