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The effect of methylation on the excited state dynamics of aminouracils (78 visite)

Gustavsson T, Improta R, Banyasz A, Vaya I, Markovitsi D

J Photochem Photobiol A Chem (ISSN: 1010-6030), 2012 Apr 15; 234: 37-43.

Tipo di articolo: Journal Article,

Impact factor: 2.416

Impact factor a 5 anni: 2.691


Parole chiave: Dna, Excited State, Femtosecond, Fluorescence Upconversion, Nucleobases, Td-Dft, Time-Resolved Fluorescence,

Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84859538922&partnerID=40&md5=898683f4b373b5ad4d870d0e959a0cd9

The excited state properties of two amino substituted uracils, 5-aminouracil (5AU) and 5-dimethylaminouracil (5DMAU) have been studied by steady-state and time-resolved fluorescence spectroscopy. In addition, the electronic transitions corresponding to photon absorption and emission were calculated using the TD-DFT/PCM method (with PBE0 and CAM-B3LYP functionals), explicitly including water molecules of the first solvent shell. The fluorescence decays, recorded by fluorescence upconversion, reveal that the emitting states of both molecules are substantially longer-lived than that of uracil. However, while the 5AU fluorescence decays on a picosecond timescale, the 5DMAU fluorescence contains a weak, long-lived component, continuing beyond 100 ps. Calculations show that the excited state deactivation of 5AU is governed by the existence of a minimum on the ππ* excited state potential energy surface. For 5DMAU, on the other hand, a very long-lived but weakly fluorescent intramolecular charge transfer (ICT) state, involving a significant charge transfer between the dimethylamino group and the pyrimidine ring, is found. This stable ICT state is characterized by a rotation of the dimethylamino group towards a quasi-perpendicular geometry. © 2012 Elsevier B.V. All rights reserved.
*** IBB - CNR ***

CNRS, IRAMIS, URA 2453, 91191 Gif-sur-Yvette, France

Istituto Biostrutture e Bioimmagini, CNR, Via Mezzocannone 16, I-80134 Napoli, Italy
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Contiene: [X]      Estesa  

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

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Martinez-fernandez L, Pepino AJ, Segarra-marti J, Jovaisaite J, Vaya I, Nenov A, Markovitsi D, Gustavsson T, Banyasz A, Garavelli M, Improta R
J Am Chem Soc (ISSN: 1520-5126electronic, 0002-7863linking), 2017 Jun 14; 139(23): 7780-7791.
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* Photoinduced long-lived charge transfer excited states in AT-DNA strands (45 visite)
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* Excited State Pathways Leading to Formation of Adenine Dimers (60 visite)
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* Synthetic approaches to nucleopeptides containing all the four nucleobases, and nucleic acid-binding studies on a mixed-sequence nucleo-oligolysine (91 visite)
Roviello GN, Musumeci D
Rsc Advances (ISSN: 2046-2069), 2016 Jun; 6: 63578-63585.
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* Quantum Mechanical Studies on the Photophysics and the Photochemistry of Nucleic Acids and Nucleobases (116 visite)
Improta R, Santoro F, Blancafort L
Chemical Reviews (ISSN: 0009-2665), 2016; 116(6): 3540-3593.
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* Excited States behavior of nucleobases in solution: insights from computational studies (85 visite)
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Topics In Current Chemistry (ISSN: 0340-1022), 2015; 355: 329-357.
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* Intramolecular vibrational redistribution in the non-radiative excited state decay of uracil in the gas phase: An ab initio molecular dynamics study (97 visite)
Carbonniere P, Pouchan C, Improta R
Phys Chem Chem Phys (ISSN: 1463-9076, 1463-3907, 1463-9084electronic), 2015; 17(17): 11615-11626.
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* Ultrafast Excited-State Deactivation of 8-Hydroxy-2′-deoxyguanosine Studied by Femtosecond Fluorescence Spectroscopy and Quantum-Chemical Calculations (90 visite)
Changenet-Barret P, Gustavsson T, Improta R, Markovitsi D
J Phys Chem A (ISSN: 1089-5639, 1520-5215electronic), 2015; 119(23): 6131-6139.
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* Relative stability of the La and Lb excited states in adenine and guanine: Direct evidence from TD-DFT calculations of MCD spectra (91 visite)
Santoro F, Improta R, Fahleson T, Kauczor J, Norman P, Coriani S
J Phys Chem Lett (ISSN: 1948-7185, 1948-7185electronic), 2014 Jun 5; 5(11): 1806-1811.
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Mode-specific vibrational relaxation of photoexcited guanosine 5'-monophosphate and its acid form: a femtosecond broadband mid-IR transient absorption and theoretical study (45 visite)
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Phys Chem Chem Phys (ISSN: 1463-9084electronic, 1463-9076linking), 2014 Jan 28; 16(4): 1487-1499.
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* Multi-pathway excited state relaxation of adenine oligomers in aqueous solution: A joint theoretical and experimental study (83 visite)
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* A joint experimental/theoretical study of the ultrafast excited state deactivation of deoxyadenosine and 9-methyladenine in water and acetonitrile (87 visite)
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* Electronic excited states responsible for dimer formation upon UV absorption directly by thymine strands: Joint experimental and theoretical study (101 visite)
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* Cation effect on the electronic excited states of guanine nanostructures studied by time-resolved fluorescence spectroscopy (98 visite)
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J Phys Chem C (ISSN: 1932-7447), 2012 Jul 12; 116(27): 14682-14689.
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* Barrierless photoisomerisation of the "simplest cyanine": Joining computational and femtosecond optical spectroscopies to trace the full reaction path (83 visite)
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* Excited state proton transfer is not involved in the ultrafast deactivation of Guanine-cytosine pair in solution (69 visite)
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* Interplay between "neutral" and "charge-transfer" excimers rules the excited state decay in adenine-rich polynucleotides (67 visite)
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* The Interplay between ππ*/nπ* excited states in gas-phase thymine: A quantum dynamical study (69 visite)
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Chemphyschem (ISSN: 1439-4235, 1439-7641, 1439-7641electronic), 2011 Jul 11; 12(10): 1957-1968.
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* Femtosecond fluorescence studies of DNA/RNA constituents (64 visite)
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J Phys Conf Ser (ISSN: 1742-6588), 2011; 261(1): 13-13.
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* Vibronic model for the quantum dynamical study of the competition between bright and charge-transfer excited states in single-strand polynucleotides: the adenine dimer case (72 visite)
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J Phys Chem A (ISSN: 1089-5639, 1520-5215electronic, 1089-5639linking), 2009 Dec 31; 113(52): 15346-15354.
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* PCM/TD-DFT study of the two lowest excited states of uracil derivatives in solution: The effect of the functional and of the cavity model (86 visite)
Improta R, Barone V
J Mol Struct Theochem (ISSN: 0166-1280), 2009 Nov 30; 914(1-3): 87-93.
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* The Excited States Decay Of The A-T Dna: A Pcm/Td-Dft Study In Aqueous Solution Of The (9-Methyl-Adenine) 2 (1-Methyl-Thymine) 2 Stacked Tetramer (76 visite)
Santoro F, Barone V, Improta R
J Am Chem Soc (ISSN: 0002-7863, 0002-2786, 1520-5126), 2009; 131(42): 15232-15245.
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* The decay from the dark nπ* excited state in uracil: An integrated CASPT2/CASSCF and PCM/TD-DFT study in the gas phase and in water (73 visite)
Mercier Y, Santoro F, Reguero M, Improta R
J Phys Chem B (ISSN: 1520-6106, 1520-5207, 1520-5207electronic), 2008 Sep 4; 112(35): 10769-10772.
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* Effect of amino substitution on the excited state dynamics of uracil (88 visite)
Banyasz A, Gustavsson T, Keszei E, Improta R, Markovitsi D
Photochem Photobiol Sci (ISSN: 1474-905x), 2008 Jul; 7(7): 765-768.
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* The excited states of adenine and thymine nucleoside and nucleotide in aqueous solution: A comparative study by time-dependent DFT calculations (83 visite)
Improta R, Barone V
Theor Chem Acc (ISSN: 1432-881x), 2008 Jul; 120(4-6): 491-497.
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* Assessing solvent effects on the singlet excited state lifetime of uracil derivatives: A femtosecond fluorescence upconversion study in alcohols and D2O (75 visite)
Gustavsson T, Bányász A, Sarkar N, Markovitsi D, Improta R
Chem Phys (ISSN: 0301-0104), 2008 Jun 23; 350(1-3): 186-192.
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* Can TD-DFT calculations accurately describe the excited states behavior of stacked nucleobases? The cytosine dimer as a test case (92 visite)
Santoro F, Barone V, Improta R
J Comput Chem (ISSN: 0192-8651, 1096-987xelectronic, 0192-8651linking), 2008 Apr 30; 29(6): 957-964.
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The Excited States Of Pi-Stacked 9-Methyl Adenine Oligomers: A Td-Dft Study In Aqueous Solution (71 visite)
Improta R
Physical Chemistry Chemical Physics, 2008; 10: 2656-2664.
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* Time-resolved fluorescence spectroscopy and molecular dynamics simulations point out the effects of pressure on the stability and dynamics of the porcine odorant-binding protein (104 visite)
Staiano M, Saviano M, Herman P, Grycznyski Z, Fini C, Varriale A, Parracino A, Kold AB, Rossi M, D'Auria S
Biopolymers (ISSN: 0006-3525, 0006-6352, 0006-3525print), 2008; 89(4): 284-291.
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* Excited state properties of sizable molecules in solution: From structure to reactivity (82 visite)
Santoro F, Barone V, Benzi C, Improta R
Theor Chem Acc (ISSN: 1432-881x), 2007 May; 117(5-6): 1073-1084.
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* Towards the understanding of the excited state dynamics of nucleic acids: Solvent and stacking effect on the photophysical behavior of nucleobases (79 visite)
Santoro F, Gustavsson T, Lami S, Barone V, Improta R
Aip Conf Proc (ISSN: 0094-243x), 2007; 963(2): 631-634.
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* Singlet excited state dynamics of uracil and thymine derivatives: A femtosecond fluorescence upconversion study in acetonitrile (70 visite)
Gustavsson T, Sarkar N, Lazzarotto E, Markovitsi D, Improta R
Chemical Physics Letters (ISSN: 0009-2614), 2006 Oct 5; 429(4-6): 551-557.
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* A state-specific polarizable continuum model time dependent density functional theory method for excited state calculations in solution (82 visite)
Improta R, Barone V, Scalmani G, Frisch MJ
J Chem Physj Chem Phys (ISSN: 0021-9606), 2006 Sep 7; 125(5): N/D-N/D.
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* Femtosecond study on the isomerization dynamics of NK88. I. Ground-state dynamics after photoexcitation (77 visite)
Nuernberger P, Vogt G, Gerber G, Improta R, Santoro F
J Chem Phys (ISSN: 0021-9606, 0021-9606print), 2006 Jul 28; 125(4): 44512-44544.
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* Femtosecond study on the isomerization dynamics of NK88. II. Excited-state dynamics (98 visite)
Vogt G, Nuernberger P, Gerber G, Improta R, Santoro F, Nuernberger P, Vogt G, Gerber G, Improta R, Santoro F
J Chem Physj Chem Phys (ISSN: 0021-9606), 2006 Jul 28; 125(4): 44512-44512.
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* A combined femtosecond fluorescence and TD-DFT study of uracil derivatives in aqueous solution (77 visite)
Gustavsson T, Lazzarotto E, Markovitsi D, Banyasz AA, Improta R, Scalmani G
Femtochemistry Vii Elsevier (ISSN: 9780-4445), 2006; N/D: 254-257.
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* A State-Specific Pcm Td-Dft Method For Equilibrium And Non-Equilibrium Excited State Calculations In Solution (108 visite)
Improta R, Barone V, Scalmani G, Frisch MJ
The Journal Of Chemical Physics (ISSN: 0897-690online, 0021-9606printed), 2006; 125(5): 54103-54103.
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37 Records (33 escludendo Abstract e Conferenze).
Impact factor totale: 206.562 (196.088 escludendo Abstract e Conferenze).
Impact factor a 5 anni totale: 210.22 (199.62 escludendo Abstract e Conferenze).

Interrogazione bibliografica effettuata: (([btitle] "Excited State" OR [btitle] "Femtosecond" OR [btitle] "Fluorescence Upconversion" OR [btitle] "Nucleobases" OR [btitle] "Time-Resolved Fluorescence") AND NOT [id] = 10621)







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