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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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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
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author Wohlrábová, Lucie
Okoročenkova, Jana
Palao, Eduardo
Kužmová, Erika
Chalupský, Karel
Klán, Petr
Slanina, Tomáš
author_facet Wohlrábová, Lucie
Okoročenkova, Jana
Palao, Eduardo
Kužmová, Erika
Chalupský, Karel
Klán, Petr
Slanina, Tomáš
author_sort Wohlrábová, Lucie
collection PubMed
description [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.
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spelling pubmed-105107182023-09-21 Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n) Wohlrábová, Lucie Okoročenkova, Jana Palao, Eduardo Kužmová, Erika Chalupský, Karel Klán, Petr Slanina, Tomáš Org Lett [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. American Chemical Society 2023-09-05 /pmc/articles/PMC10510718/ /pubmed/37668439 http://dx.doi.org/10.1021/acs.orglett.3c02511 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Wohlrábová, Lucie
Okoročenkova, Jana
Palao, Eduardo
Kužmová, Erika
Chalupský, Karel
Klán, Petr
Slanina, Tomáš
Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)
title Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)
title_full Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)
title_fullStr Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)
title_full_unstemmed Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)
title_short Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H(2)S(n)
title_sort sulfonothioated meso-methyl bodipy shows enhanced uncaging efficiency and releases h(2)s(n)
url 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
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