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C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light
Author(s) -
Xu Youwei,
Lin Shanmeng,
He Rongkun,
Zhang Yichuan,
Gao Quan,
Ng Dennis K. P.,
Geng Jin
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202101833
Subject(s) - bodipy , aldehyde , cleavage (geology) , chemistry , oxidative phosphorylation , photochemistry , cleave , fluorescence , bond cleavage , visible spectrum , hela , regioselectivity , ultraviolet light , combinatorial chemistry , organic chemistry , biochemistry , materials science , catalysis , in vitro , enzyme , physics , optoelectronics , quantum mechanics , fracture (geology) , composite material
Photocages for protection and the controlled release of bioactive compounds have been widely investigated. However, the vast majority of these photocages employ the cleavage of single bonds and high‐energy ultraviolet light. The construction of a photoactivation system that uses visible light to cleave unsaturated bonds still remains a challenge. Herein, we report a regioselective oxidative cleavage of C=C bonds from a boron‐dipyrrolemethene (BODIPY)‐based photocage by illumination at 630 nm, resulting in a free aldehyde and a thiol fluorescent probe. This strategy was demonstrated in live HeLa cells, and the generated α‐formyl‐BODIPY allowed real‐time monitoring of aldehyde release in the cells. In particular, it is shown that a mannose‐functionalized photocage can target HepG2 cells.