Constructing pH-Responsive and Tunable Azo-Phenol-Based o-Nitrobenzyl Photocages.

Tsung-Shing Andrew Wang, Ya-Wen Zhang, Huai-An Chen, Shiou-Ting Lin, Hsien-Ming Lee

Chemistry (Weinheim an der Bergstrasse, Germany) 2023 Jul 14

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Multiple triggered-release strategies are widely utilized to control the release of caged target molecules. Among them, photocages with conditional triggers provide extra layers of control in photorelease. In this work, a series of pH-responsive photocages was designed that could be triggered under irradiation and specific intracellular pH values. pH-sensitive phenolic groups were conjugated with o-nitrobenzyl (oNB) to form azo-phenolic NPX photocages with tunable pKa. These azo-phenol-based oNB photocages showed differentiable photoreleasing profiles at pH 5.0, 7.2 and 9.0. By attaching fluorogenic cargos, it was shown that one of the photocages, NPdiCl, could be used to differentiate between acidic pH 5.0 and neutral pH 7.2 in cells under artificial pH conditions. Finally, NPdiCl was identified as a promising pH-responsive photocage for photoreleasing cargo inside acidic tumor cells. © 2023 Wiley-VCH GmbH.

Citation

Tsung-Shing Andrew Wang, Ya-Wen Zhang, Huai-An Chen, Shiou-Ting Lin, Hsien-Ming Lee. Constructing pH-Responsive and Tunable Azo-Phenol-Based o-Nitrobenzyl Photocages. Chemistry (Weinheim an der Bergstrasse, Germany). 2023 Jul 14;29(40):e202300884