C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light
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AbstractPhotocages 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 alpha-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.
Acceptance Date10/06/2021
All Author(s) ListYouwei Xu, Shanmeng Lin, Rongkun He, Yichuan Zhang, Quan Gao, Dennis K. P. Ng, Jin Geng
Journal nameChemistry - A European Journal
Year2021
Month8
Day5
Volume Number27
Issue Number44
PublisherWiley
Pages11268 - 11272
ISSN0947-6539
eISSN1521-3765
LanguagesEnglish-United States