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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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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. |
format | Online Article Text |
id | pubmed-10510718 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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