Solvent-Dependent Stabilization of a Charge Transfer State is the Key to Ultrafast Triplet State Formation in an Epigenetic DNA Nucleoside.
DNA photophysics and photochemistry
charge transfer states
epigenetic nucleoside
intersystem crossing
triplet excited states
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
26 Jul 2021
26 Jul 2021
Historique:
received:
03
03
2021
pubmed:
17
4
2021
medline:
29
7
2021
entrez:
16
4
2021
Statut:
ppublish
Résumé
2'-Deoxy-5-formylcytidine (5fdCyd), a naturally occurring nucleoside found in mammalian DNA and mitochondrial RNA, exhibits important epigenetic functionality in biological processes. Because it efficiently generates triplet excited states, it is an endogenous photosensitizer capable of damaging DNA, but the intersystem crossing (ISC) mechanism responsible for ultrafast triplet state generation is poorly understood. In this study, time-resolved mid-IR spectroscopy and quantum mechanical calculations reveal the distinct ultrafast ISC mechanisms of 5fdCyd in water versus acetonitrile. Our experiment indicates that in water, ISC to triplet states occurs within 1 ps after 285 nm excitation. PCM-TD-DFT computations suggest that this ultrafast ISC is mediated by a singlet state with significant cytosine-to-formyl charge-transfer (CT) character. In contrast, ISC in acetonitrile proceeds via a dark
Identifiants
pubmed: 33860588
doi: 10.1002/chem.202100787
doi:
Substances chimiques
Nucleosides
0
Solvents
0
DNA
9007-49-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
10932-10940Subventions
Organisme : National Natural Science Foundation of China
ID : 21873030
Organisme : National Natural Science Foundation of China
ID : 11674101
Organisme : National Natural Science Foundation of China
ID : 91850202
Organisme : Shanghai Rising-Star Program
ID : 19QA1402800
Organisme : National Science Foundation
ID : CHE-1800471
Organisme : MICINN project
ID : PID2019-110091GB-I00
Informations de copyright
© 2021 Wiley-VCH GmbH.
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