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Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H2S
Lucie Wohlrábová1, Jana Okoročenkova2,3, Eduardo Palao2,3
1Institute of Organic Chemistry and Biochemistry of the CAS, Flemingovo nám. 542/2, 160 00 Praha 6, Czech Republic.
Abstract:
meso-Methyl BODIPY photocages stand out for their absorption properties and easy chromophore derivatization. However, their low uncaging efficiencies often hinder applications requiring release of protected substrates in high amounts. In this study, we demonstrate that the sulfonothioated BODIPY group photocleaves a sulfonylthio group from the meso-methyl position with a 10-fold higher quantum yield than the most efficient leaving groups studied to date. Photocleavage, observed in solution and in cells, is accompanied by the spatiotemporally controlled photorelease of H2S. For this reason, sulfonothioated BODIPY may be applied in cell signaling, redox homeostasis, and metabolic regulation studies.
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