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.

中文翻译：

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BODIPY在基于单线态氧生成的生物学应用中笼养的适用性受到限制。

最近的研究报告称，硼二吡咯亚甲基（BODIPY）部分基于其对生物光学窗口中的波长辐射的响应，对于光药学中的笼罩应用很感兴趣。因此，在模型研究中，我们研究了介孔甲基-BODIPY笼蔽的CDK2抑制剂AZD5438，旨在评估BODIPY作为光敏保护基在光敏激酶抑制剂应用中的可用性。体外光化学分析和生物学表征揭示了BODIPY笼状抑制剂概念在水溶液中的溶解度和解笼方面的显着局限性。值得注意的是，我们为BODIPY笼蔽的化合物在辐照时产生单线态氧/自由基，然后对其进行光降解而提供了证据。因此，代替笼养，细胞中坏死的非特异性诱导表明BODIPY衍生物可用于光动力方法。