C=C Bond Oxidative Cleavage of BODIPY Photocages by Visible Light.
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.
['Xu|Youwei|Y|http://orcid.org/0000-0002-4334-2030', 'Lin|Shanmeng|S|', 'He|Rongkun|R|', 'Zhang|Yichuan|Y|', 'Gao|Quan|Q|', 'Ng|Dennis K P|DKP|', 'Geng|Jin|J|']
D001895:Boron D001896:Boron Compounds D006367:HeLa Cells D006801:Humans D008027:Light D018384:Oxidative Stress
BODIPY photocages visible light C=C bond cleavage