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Electron‐Rich EDOT Linkers in Tetracationic bis‐Triarylborane Chromophores: Influence on Water Stability, Biomacromolecule Sensing, and Photoinduced Cytotoxicity

Please always quote using this URN: urn:nbn:de:bvb:20-opus-287241
  • 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 comparativeThree 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.show moreshow less

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Metadaten
Author: Matthias Ferger, Chantal Roger, Eva Köster, Florian Rauch, Sabine Lorenzen, Ivo Krummenacher, Alexandra Friedrich, Marta Košćak, Davor Nestić, Holger BraunschweigORCiD, Christoph Lambert, Ivo Piantanida, Todd B. Marder
URN:urn:nbn:de:bvb:20-opus-287241
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Chemistry – A European Journal
Year of Completion:2022
Volume:28
Issue:48
Article Number:e202201130
Source:Chemistry – A European Journal 2022, 28(48):e202201130: DOI: 10.1002/chem.202201130
DOI:https://doi.org/10.1002/chem.202201130
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:DNA/RNA sensors; boranes; fluorescent probes; singlet oxygen; theranostics
Release Date:2023/01/18
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International