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Universal Scaffold for an Activatable Photosensitizer with Completely Inhibited Photosensitivity
Author(s) -
Zhai Wenhao,
Zhang Yongkang,
Liu Ming,
Zhang Hao,
Zhang Junqing,
Li Changhua
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201907510
Subject(s) - photosensitivity , photosensitizer , phototoxicity , photodynamic therapy , biomarker , chemistry , cancer research , medicine , photochemistry , materials science , optoelectronics , biochemistry , in vitro , organic chemistry
Activatable photosensitizers (aPSs) sensitive to specific stimuli hold potential for targeting multiple disease biomarkers and are desirable for photodynamic therapy (PDT). Presented herein is the design of aPSs that can be activated and fully recover from an inhibited state in the presence of specific biomarker. A designed long‐wavelength D‐π‐A photosensitizer, PS Se‐I , with highly efficient photosensitivity for generation of 1 O 2 was used. Caging of the phenolate donor of PS Se‐I with a biomarker‐sensitive group provided ALP PS , and the drastic activation of its photosensitivity was demonstrated intracellularly. To enhance the flexibility of the design strategy, a clickable azide group was introduced into the scaffold to allow integration of more functionality. Modularly derived mito‐PN PS , equipped with a mitochondria‐targeting group and a specific peroxynitrite‐reactive trigger, was synthesized and demonstrated superior performance in cells. This strategy could lead to customization of aPSs applicable to a specific PDT.