Electron-Rich EDOT Linkers in Tetracationic bis-Triarylborane Chromophores: Influence on Water Stability, Biomacromolecule Sensing, and Photoinduced Cytotoxicity.
DNA/RNA sensors
boranes
fluorescent probes
singlet oxygen
theranostics
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 Aug 2022
26 Aug 2022
Historique:
received:
12
04
2022
pubmed:
2
6
2022
medline:
1
9
2022
entrez:
1
6
2022
Statut:
ppublish
Résumé
Three novel tetracationic bis-triarylboranes with 3,4-ethylenedioxythiophene (EDOT) linkers, and their neutral precursors, showed significant red-shifted absorption and emission compared to their thiophene-containing analogues, with one of the EDOT-derivatives emitting in the NIR region. Only the EDOT-linked trixylylborane tetracation was stable in aqueous solution, indicating that direct attachment of a thiophene or even 3-methylthiophene to the boron atom is insufficient to provide hydrolytic stability in aqueous solution. Further comparative analysis of the EDOT-linked trixylylborane tetracation and its bis-thiophene analogue revealed efficient photo-induced singlet oxygen production, with the consequent biological implications. Thus, both analogues bind strongly to ds-DNA and BSA, very efficiently enter living human cells, accumulate in several different cytoplasmic organelles with no toxic effect but, under intense visible light irradiation, they exhibit almost instantaneous and very strong cytotoxic effects, presumably attributed to singlet oxygen production. Thus, both compounds are intriguing theranostic agents, whose intracellular and probably intra-tissue location can be monitored by strong fluorescence, allowing switching on of the strong bioactivity by well-focused visible light.
Identifiants
pubmed: 35647673
doi: 10.1002/chem.202201130
pmc: PMC9543662
doi:
Substances chimiques
Thiophenes
0
Water
059QF0KO0R
Singlet Oxygen
17778-80-2
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202201130Subventions
Organisme : Croatian Science Foundation
ID : IP-2018-01-5475
Organisme : Deutscher Akademischer Austauschdienst
Organisme : Deutsche Forschungsgemeinschaft
ID : MA4471/10-1
Organisme : Julius-Maximilians-Universität Würzburg
Informations de copyright
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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