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Sulfonothioated <i>meso</i>-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H<sub>2</sub>S<sub><i>n</i></sub>

Lucie Wohlrábová, Jana Okoročenkova, Eduardo Palao, Erika Kužmová, Karel Chalupský, Petr Klán, Tomáš Slanina

2023Organic Letters16 citationsDOIOpen Access PDF

Abstract

High Resolution Image Download MS PowerPoint Slide 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 H 2 S n . For this reason, sulfonothioated BODIPY may be applied in cell signaling, redox homeostasis, and metabolic regulation studies.

Topics & Concepts

BODIPYChemistryChromophoreQuantum yieldDerivatizationYield (engineering)RedoxPhotochemistryFluorescenceOrganic chemistryHigh-performance liquid chromatographyPhysicsMetallurgyMaterials scienceQuantum mechanicsNanoplatforms for cancer theranosticsLuminescence and Fluorescent MaterialsPhotochromic and Fluorescence Chemistry
Sulfonothioated <i>meso</i>-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H<sub>2</sub>S<sub><i>n</i></sub> | Litcius