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Xanthines Studied via Femtosecond Fluorescence Spectroscopy

LIDYL, CEA, CNRS, Université Paris-Saclay, F-91191 Gif-sur-Yvette, France
Department of Medicinal Chemistry, University of Szeged, Dóm tér 8, 6720 Szeged, Hungary
Authors to whom correspondence should be addressed.
Present address: LOB, Ecole Polytechnique, CNRS, INSERM, Université Paris-Saclay, 91128 Palaiseau, France.
Academic Editor: Carlos E. Crespo-Hernández
Molecules 2016, 21(12), 1668;
Received: 14 October 2016 / Revised: 25 November 2016 / Accepted: 29 November 2016 / Published: 3 December 2016
(This article belongs to the Special Issue Experimental and Computational Photochemistry of Bioorganic Molecules)
Xanthines represent a wide class of compounds closely related to the DNA bases adenine and guanine. Ubiquitous in the human body, they are capable of replacing natural bases in double helices and give rise to four-stranded structures. Although the use of their fluorescence for analytical purposes was proposed, their fluorescence properties have not been properly characterized so far. The present paper reports the first fluorescence study of xanthine solutions relying on femtosecond spectroscopy. Initially, we focus on 3-methylxanthine, showing that this compound exhibits non-exponential fluorescence decays with no significant dependence on the emission wavelength. The fluorescence quantum yield (3 × 10−4) and average decay time (0.9 ps) are slightly larger than those found for the DNA bases. Subsequently, we compare the dynamical fluorescence properties of seven mono-, di- and tri-methylated derivatives. Both the fluorescence decays and fluorescence anisotropies vary only weakly with the site and the degree of methylation. These findings are in line with theoretical predictions suggesting the involvement of several conical intersections in the relaxation of the lowest singlet excited state. View Full-Text
Keywords: xanthines; femtosecond spectroscopy; fluorescence; electronic excited states xanthines; femtosecond spectroscopy; fluorescence; electronic excited states
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MDPI and ACS Style

Changenet-Barret, P.; Kovács, L.; Markovitsi, D.; Gustavsson, T. Xanthines Studied via Femtosecond Fluorescence Spectroscopy. Molecules 2016, 21, 1668.

AMA Style

Changenet-Barret P, Kovács L, Markovitsi D, Gustavsson T. Xanthines Studied via Femtosecond Fluorescence Spectroscopy. Molecules. 2016; 21(12):1668.

Chicago/Turabian Style

Changenet-Barret, Pascale, Lajos Kovács, Dimitra Markovitsi, and Thomas Gustavsson. 2016. "Xanthines Studied via Femtosecond Fluorescence Spectroscopy" Molecules 21, no. 12: 1668.

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