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

Theo Rodat; Melanie Krebs; Alexander Döbber; Björn Jansen; Anja Steffen-Heins; Karin Schwarz; Christian Peifer

doi:10.1039/D0PP00097C

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

Theo Rodat,

‡^a Melanie Krebs,‡^a Alexander Döbber,^a Björn Jansen,^a Anja Steffen-Heins,^b Karin Schwarz^b and Christian Peifer

*^a

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* Corresponding authors

^a Institute of Pharmacy, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany
E-mail: cpeifer@pharmazie.uni-kiel.de

^b Institute of Human Nutrition and Food Science, Division of Food Technology, Kiel University, Heinrich-Hecht-Platz 10, 24118 Kiel, Germany

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.

This article is part of the themed collection: The World Congress on Light and Life, Barcelona 2019

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DOI: https://doi.org/10.1039/D0PP00097C
Article type: Paper
Submitted: 16 Mar 2020
Accepted: 23 Jul 2020
First published: 23 Jul 2020

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Photochem. Photobiol. Sci., 2020,19, 1319-1325

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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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Photochemical & Photobiological Sciences

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

Abstract

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

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