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Issue 10, 2020
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Restricted suitability of BODIPY for caging in biological applications based on singlet oxygen generation

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Abstract

Recent studies report the boron-dipyrromethene (BODIPY) moiety to be interesting for caging applications in photopharmacology based on its response to irradiation with wavelengths in the biooptical window. Thus, in a model study, we investigated the meso-methyl-BODIPY caged CDK2 inhibitor AZD5438 and aimed to assess the usability of BODIPY as a photoremovable protecting group in photoresponsive kinase inhibitor applications. Photochemical analysis and biological characterisation in vitro revealed significant limitations of the BODIPY-caged inhibitor concept regarding solubility and uncaging in aqueous solution. Notably, we provide evidence for BODIPY-caged compounds generating singlet oxygen/radicals upon irradiation, followed by photodegradation of the caged compound system. Consequently, instead of caging, a non-specific induction of necrosis in cells suggests the potential usage of BODIPY derivatives for photodynamic approaches.

Graphical abstract: Restricted suitability of BODIPY for caging in biological applications based on singlet oxygen generation

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Supplementary files

Article information


Submitted
16 Mar 2020
Accepted
23 Jul 2020
First published
23 Jul 2020

Photochem. Photobiol. Sci., 2020,19, 1319-1325
Article type
Paper

Restricted suitability of BODIPY for caging in biological applications based on singlet oxygen generation

T. Rodat, M. Krebs, A. Döbber, B. Jansen, A. Steffen-Heins, K. Schwarz and C. Peifer, Photochem. Photobiol. Sci., 2020, 19, 1319
DOI: 10.1039/D0PP00097C

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