Dual-Color Photoconvertible BODIPY Dyes Based on Visible-Light Photouncaging of Nitrobenzyl Moieties for Living-Cell Imaging,Advanced Optical Materials

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Dual-Color Photoconvertible BODIPY Dyes Based on Visible-Light Photouncaging of Nitrobenzyl Moieties for Living-Cell Imaging
Advanced Optical Materials ( IF 8.0 ) Pub Date : 2023-10-20 , DOI: 10.1002/adom.202302014
Heng Li ₁ , Qi Zhang ₁ , Xing Guo ₁ , Weibin Bu ₁ , Huiquan Zuo ₁ , Lijuan Jiao ₁ , Zhongxin Li ₁ , Changjiang Yu ₁ , Shaozhen Wang ₂ , Erhong Hao ₁

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Photoactivatable fluorophores are useful tools in live cell imaging due to precise spatial and temporal control. Herein, a tandem visible-light photodecaging and tautomerization strategy is proposed as an activation mechanism for the construction of photoconvertible boron dipyrromethenes (BODIPY) dyes, from which nitro-benzyloxy BODIPY derivatives are developed as a new class of visible light photoactivated fluorophores. Upon exposure to visible light, the nitro-benzyloxy moiety is released and the BODIPY moiety is converted to the keto-form BODIPY analog by tautomerization. The photoconversion process not only achieves over 50 nm blue shift of absorption/emission maxima but also provides bright fluorescence for both the pre- and post-activation forms. Mechanism studies indicate that no indications of radical species and singlet oxygen are involved in this unique photoconversion and both UV and visible light irradiation can efficiently activate this photoinduced release of the nitrobenzyl alcohol through photoexciting of BODIPY core rather than classical nitro-benzyloxy photocage. Cell and vesicle imaging is successfully performed using the new photoconversion dyes. The results show that these new photoconvertible dyes are highly efficient, universal, and non-cytotoxic, which are valuable for the development of promising photoactivated molecules.

中文翻译：

基于硝基苄基部分可见光光解的双色光转换 BODIPY 染料用于活细胞成像

由于精确的空间和时间控制，光活化荧光团是活细胞成像的有用工具。在此，提出了串联可见光光降解和互变异构策略作为构建光转换硼二吡咯亚甲基（BODIPY）染料的激活机制，由此开发了硝基苄氧基BODIPY衍生物作为一类新型可见光光激活荧光团。暴露于可见光后，硝基苄氧基部分被释放，并且 BODIPY 部分通过互变异构转化为酮式 BODIPY 类似物。光转换过程不仅实现了超过 50 nm 的吸收/发射最大值蓝移，而且还为激活前和激活后形式提供了明亮的荧光。机理研究表明，没有迹象表明自由基物种和单线态氧参与这种独特的光转化，并且紫外线和可见光照射都可以通过 BODIPY 核的光激发而不是经典的硝基苄氧基光笼有效激活硝基苯甲醇的光诱导释放。使用新型光转换染料成功地进行了细胞和囊泡成像。结果表明，这些新型光转换染料高效、通用且无细胞毒性，对于开发有前景的光活化分子具有重要价值。

更新日期：2023-10-20

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