Activation by Glutathione in Hypoxic Environment of an Azo-based Rhodamine Activatable Photosensitizer. A Computational Elucidation.
DFT
Rhodamines
aPS
azo-compounds
glutathione
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
01 Mar 2022
01 Mar 2022
Historique:
received:
12
11
2021
pubmed:
19
1
2022
medline:
3
3
2022
entrez:
18
1
2022
Statut:
ppublish
Résumé
In the present paper, density functional theory (DFT) has been applied to the study of the activation mechanism of a new selenium azo-rhodamine (azoSeRho) in presence of the tripeptide thiol, glutathione (GSH), as potent activatable photosensitizer to be employed in photodynamic therapy. The introduction of the azo group into the conjugated system of the seleno-rhodamine dye and its reaction with GSH allow the selective formation of the active photosensitizer, SeRho. Furthermore, DFT calculations have allowed to shed light on the activation mechanism of the azoSeRho photosensitizer when molecular oxygen is present and hydrogen peroxide is formed. This study is the first theoretical investigation revealing how the reductive cleavage of the azo moiety by GSH occurs. Time-dependent DFT approach has been used to evaluate the chalcogen-substitution effect on the structures and photophysical properties of the azo derivatives and, then, on the activated photosensitizers.
Identifiants
pubmed: 35040535
doi: 10.1002/chem.202104083
doi:
Substances chimiques
Photosensitizing Agents
0
Rhodamines
0
Glutathione
GAN16C9B8O
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202104083Informations de copyright
© 2022 Wiley-VCH GmbH.
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