Issue 10, 2020

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

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

Supplementary files

Article information

Article type
Paper
Submitted
21 رجب 1441
Accepted
02 ذو الحجة 1441
First published
02 ذو الحجة 1441

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

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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