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Photophysical investigation of two emissive nucleosides exhibiting gigantic stokes shifts

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Abstract

We report spectroscopic characterization of two emissive 2′-deoxycytidine analogues: 5-(5-phenylfuran-2-yl)-2′-deoxycytidine and 5-(1-phenyl-1H-pyrazol-3-yl)-2′-deoxycytidine. Their fluorescent properties were examined using a combined experimental and theory/simulation approach, where the latter was based on Born–Oppenheimer molecular dynamics and time-dependent density functional theory. The analogues were found to exhibit unusually large Stokes shifts in polar media (>100 nm), moderate fluorescence quantum yields, and their emissions were found to be very sensitive to the local dielectric environment. These two analogues of 2′-deoxycytidine thus hold a promising potential as probes in chemical biology. In addition, the accuracy of the theoretical models for determining the optical properties is validated, which opens up for a convenient way of assessing the potential of future probes.

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Authors and Affiliations

  1. Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, Odense M, DK-5230, Denmark

    Julie Stendevad, Mick Hornum & Jacob Kongsted

  2. Department of Biochemistry and Molecular Biology, University of Southern Denmark, Campusvej 55, Odense M, DK-5230, Denmark

    Daniel Wüstner

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  1. Julie Stendevad
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Correspondence to Jacob Kongsted.

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Electronic supplementary information (ESI) available: Modelling data, absorption spectra & additional charts. See DOI: 10.1039/C9PP00172G

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Stendevad, J., Hornum, M., Wüstner, D. et al. Photophysical investigation of two emissive nucleosides exhibiting gigantic stokes shifts. Photochem Photobiol Sci 18, 1858–1865 (2019). https://doi.org/10.1039/c9pp00172g

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