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Collegamenti



Effect of amino substitution on the excited state dynamics of uracil (69 visite)

Banyasz A, Gustavsson T, Keszei E, Improta R, Markovitsi D

Photochem Photobiol Sci (ISSN: 1474-905x), 2008 Jul; 7(7): 765-768.

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

Impact factor: 2.144

Impact factor a 5 anni: 2.448


Parole chiave: 5 Amino 2, 4 Dihydroxypyrimidine, 5 Aminouracil Derivative, 6 Aminouracil, Pyrimidine Derivative, Anisotropy, Aqueous Solution, Article, Chemical Analysis, Chemical Reaction Kinetics, Fluorescence, Priority Journal, Waveform, Fluorescence Polarization, Time Factors, Water, Analogs, Chemistry,

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-46449125837&partnerID=40&md5=d45cf650b6821d6b29e602e44cbbb6fd

The excited state deactivation of two amino-substituted uracils, 5-aminouracil (5AU) and 6-aminouracil (6AU) in aqueous solution was studied by femtosecond fluorescence upconversion. The fluorescence of 6AU decays as fast as that of uracil with a unique time constant of about 100 femtoseconds. The fluorescence of 5AU exhibits a more complex behavior, fundamentally different from what we found in any other uracils: the decays are globally slower (up to several picoseconds) and depend strongly on the wavelength. This difference is attributed to the particular character of the amino group, affecting the out-of-plane motion of the 5-substituent which has been shown to be crucial for the ultrafast internal conversion occurring in uracils. Our observations indicate instead the formation of a transient fluorescent state which in turn is deactivated by a different relaxation process specific to the amino group. © The Royal Society of Chemistry and Owner Societies.
*** IBB - CNR ***

Laboratoire Francis Perrin, CEA/DSM/IRAMIS/SPAM - CNRS URA 2453, CEA Saclay, F-91191, Gif-sur-Yvette, France

Eötvös Lorand University Budapest, Department of Physical Chemistry, P.O. Box 32, 1518 Budapest 112, Hungary

Dipartimento di Chimica, Università Federico II, Complesso Universitario Monte S. Angelo, Via Cintia, I, 80126, Napoli, Italy

Istituto Biostrutture e Bioimmagini/CNR, V. Mezzocannone, 6, 80134, Napoli, Italy

E tv s Lorand University Budapest, Department of Physical Chemistry, P. O. Box 32, 1518 Budapest 112, Hungary
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

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

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

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

Merchán, M., Gonzalez-Luque, R., Climent, T., Serrano-Andres, L., Rodriguez, E., Reguero, M., Pelaez, D., Unified Model for the Ultrafast Decay of Pyrimidine Nucleobases (2006) J. Phys. Chem. B, 110, pp. 26471-26476

Zgierski, M.Z., Fujiwara, T., Kofron, W.G., Lim, E.C., Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: Photophysics of 5,6-trimethylenecytosine and 5,6-trimethyleneuracil (2007) Phys. Chem. Chem. Phys., 9, pp. 3206-3209

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

Subbarao, S.N., Bray, P.J., Nitrogen-14 nuclear quadrupole resonance study of several hydroxypyrimidines (1977) J. Chem. Phys., 67, pp. 1085-1090

Chandra, A.K., Uchimaru, T., Zeegers-Huyskens, T., Theoretical study on protonated and deprotonated 5-substituted uracil derivatives and their complexes with water (2002) J. Mol. Struct., 605, pp. 213-220

Whittleton, S.R., Hunter, K.C., Wetmore, S.D., Effects of Hydrogen Bonding on the Acidity of Uracil Derivatives (2004) J. Phys. Chem. a, 108, pp. 7709-7718

Palafox, M.A., Tardajos, G., Guerrero-Martinez, A., Rastogi, V.K., Mishra, D., Ojha, S.P., Kiefer, W., FT-IR, FT-Raman spectra, density functional computations of the vibrational spectra and molecular geometry of biomolecule 5-aminouracil (2007) Chem. Phys., 340, pp. 17-31

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

Alcolea Palafox, M., Tardajos, G., Guerrero-Martinez, A., Rastogi, V.K., Mishra, D., Ojha, S.P., Kiefer, W., FT-IR, FT-Raman spectra, density functional computations of the vibrational spectra and molecular geometry of biomolecule 5-aminouracil (2007) Chem. Phys., 340, pp. 17-31

Estrin, D.A., Paglieri, L., Corongiu, G., A density functional study of tautomerism of uracil and cytosine (1994) J. Phys. Chem., 98, pp. 5653-5660

Marian, C.M., Schneider, F., Kleinschmidt, M., Tatchen, J., Electronic excitation and singlet-triplet coupling in uracil tautomers and uracil-water complexes. a quantum chemical investigation (2002) Eur. Phys. J. D: Atom. Mol. Opt. Phys., 20, pp. 357-367

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

Tóth, A., Billes, F., Ultraviolet spectroscopic study of the acid base equilibrium of pyrimidine derivatives. I. Uracil derivatives. (1968) Acta Chim. Acad. Sci. Hung., 56, pp. 229-250

Jimenez, R., Fleming, G.R., Kumar, P.V., Maroncelli, M., Femtosecond solvation dynamics of water (1994) Nature, 369, pp. 471-473

Pal, S.K., Peon, J., Zewail, A.H., Ultrafast decay and hydration dynamics of DNA bases and mimics (2002) Chem. Phys. Lett., 363, pp. 57-63

Migani, A., Bearpark, M.J., Olivucci, M., Robb, M.A., Photostability versus photodegradation in the excited-state intramolecular proton transfer of nitro enamines: Competing reaction paths and conical intersections (2007) J. Am. Chem. Soc., 129, pp. 3703-3713

Kitamura, T., Okita, M., Sasaki, Y., Ishikawa, H., Fujimoto, A., Amino-imino tautomerization reaction of the 4-aminopyrimidine/acetic acid system (2008) Spectrochim. Acta, Part a, 69, pp. 350-360

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

Merch n, M., Gonzalez-Luque, R., Climent, T., Serrano-Andres, L., Rodriguez, E., Reguero, M., Pelaez, D., Unified Model for the Ultrafast Decay of Pyrimidine Nucleobases (2006) J. Phys. Chem. B, 110, pp. 26471-26476

Zgierski, M. Z., Fujiwara, T., Kofron, W. G., Lim, E. C., Highly effective quenching of the ultrafast radiationless decay of photoexcited pyrimidine bases by covalent modification: Photophysics of 5, 6-trimethylenecytosine and 5, 6-trimethyleneuracil (2007) Phys. Chem. Chem. Phys., 9, pp. 3206-3209

Subbarao, S. N., Bray, P. J., Nitrogen-14 nuclear quadrupole resonance study of several hydroxypyrimidines (1977) J. Chem. Phys., 67, pp. 1085-1090

Chandra, A. K., Uchimaru, T., Zeegers-Huyskens, T., Theoretical study on protonated and deprotonated 5-substituted uracil derivatives and their complexes with water (2002) J. Mol. Struct., 605, pp. 213-220

Whittleton, S. R., Hunter, K. C., Wetmore, S. D., Effects of Hydrogen Bonding on the Acidity of Uracil Derivatives (2004) J. Phys. Chem. a, 108, pp. 7709-7718

Palafox, M. A., Tardajos, G., Guerrero-Martinez, A., Rastogi, V. K., Mishra, D., Ojha, S. P., Kiefer, W., FT-IR, FT-Raman spectra, density functional computations of the vibrational spectra and molecular geometry of biomolecule 5-aminouracil (2007) Chem. Phys., 340, pp. 17-31

Estrin, D. A., Paglieri, L., Corongiu, G., A density functional study of tautomerism of uracil and cytosine (1994) J. Phys. Chem., 98, pp. 5653-5660

Marian, C. M., Schneider, F., Kleinschmidt, M., Tatchen, J., Electronic excitation and singlet-triplet coupling in uracil tautomers and uracil-water complexes. a quantum chemical investigation (2002) Eur. Phys. J. D: Atom. Mol. Opt. Phys., 20, pp. 357-367

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

T th, A., Billes, F., Ultraviolet spectroscopic study of the acid base equilibrium of pyrimidine derivatives. I. Uracil derivatives. (1968) Acta Chim. Acad. Sci. Hung., 56, pp. 229-250

Pal, S. K., Peon, J., Zewail, A. H., Ultrafast decay and hydration dynamics of DNA bases and mimics (2002) Chem. Phys. Lett., 363, pp. 57-63

Nessun risultato.
Nessun risultato.


Contiene: [X]      Estesa  

Autori: [X]   E Tipo di lavoro: [X]

E Data iniziale: Data finale: [X]   E Sede:  E    Affiliazione IBB   [Pulisci modulo]



Nessun risultato.


Interrogazione bibliografica effettuata: (([btitle] "5 Amino 2" OR [btitle] "4 Dihydroxypyrimidine" OR [btitle] "5 Aminouracil Derivative" OR [btitle] "6 Aminouracil" OR [btitle] "Pyrimidine Derivative") AND NOT [id] = 48597)





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