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Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)

[Image: see text] 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 sulfonot...

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Detalles Bibliográficos
Autores principales: Wohlrábová, Lucie, Okoročenkova, Jana, Palao, Eduardo, Kužmová, Erika, Chalupský, Karel, Klán, Petr, Slanina, Tomáš
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10510718/
https://www.ncbi.nlm.nih.gov/pubmed/37668439
http://dx.doi.org/10.1021/acs.orglett.3c02511
Descripción
Sumario:[Image: see text] 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.