Photophysical investigation of two emissive nucleosides exhibiting gigantic stokes shifts

Julie Stendevad, Mick Hornum, Daniel Wüstner, Jacob Kongsted*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

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.

Original languageEnglish
JournalPhotochemical and Photobiological Sciences
Volume18
Issue number7
Pages (from-to)1858-1865
Number of pages8
ISSN1474-905X
DOIs
Publication statusPublished - 17. Jun 2019

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Deoxycytidine
nucleosides
Nucleosides
analogs
shift
probes
biology
Quantum yield
molecular dynamics
density functional theory
Density functional theory
Molecular dynamics
optical properties
fluorescence
Optical properties
Fluorescence
simulation

Cite this

@article{b953e1cd9d9741569f760bbeb5e4ec0a,
title = "Photophysical investigation of two emissive nucleosides exhibiting gigantic stokes shifts",
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.",
author = "Julie Stendevad and Mick Hornum and Daniel W{\"u}stner and Jacob Kongsted",
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language = "English",
volume = "18",
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journal = "Photochemical & Photobiological Sciences",
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}

Photophysical investigation of two emissive nucleosides exhibiting gigantic stokes shifts. / Stendevad, Julie; Hornum, Mick; Wüstner, Daniel; Kongsted, Jacob.

In: Photochemical and Photobiological Sciences, Vol. 18, No. 7, 17.06.2019, p. 1858-1865.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Photophysical investigation of two emissive nucleosides exhibiting gigantic stokes shifts

AU - Stendevad, Julie

AU - Hornum, Mick

AU - Wüstner, Daniel

AU - Kongsted, Jacob

PY - 2019/6/17

Y1 - 2019/6/17

N2 - 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.

AB - 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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DO - 10.1039/c9pp00172g

M3 - Journal article

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JO - Photochemical & Photobiological Sciences

JF - Photochemical & Photobiological Sciences

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