Constructing pH‐Responsive and Tunable Azo‐Phenol‐Based o‐Nitrobenzyl Photocages

Author:

Wang Tsung‐Shing Andrew1ORCID,Zhang Ya‐Wen1,Chen Huai‐An2,Lin Shiou‐Ting1,Lee Hsien‐Ming2ORCID

Affiliation:

1. Department of Chemistry and Center for Emerging Material and Advanced Devices National Taiwan University Taipei 10617 Taiwan (R.O.C.

2. Institute of Chemistry, Academia Sinica Taipei 11529 Taiwan (R.O.C.

Abstract

AbstractMultiple 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.

Funder

National Taiwan University

Center for Emerging Material and Advanced Devices, National Taiwan University

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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