J 2023

Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H2Sn

WOHLRABOVA, Lucie; Jana OKOROČENKOVA; Eduardo PALAO UTIEL; Erika KUZMOVA; Karel CHALUPSKY et al.

Basic information

Original name

Sulfonothioated meso-Methyl BODIPY Shows Enhanced Uncaging Efficiency and Releases H2Sn

Authors

WOHLRABOVA, Lucie; Jana OKOROČENKOVA; Eduardo PALAO UTIEL; Erika KUZMOVA; Karel CHALUPSKY; Petr KLÁN and Tomáš SLANINA

Edition

Organic Letters, WASHINGTON, American Chemical Society, 2023, 1523-7060

Other information

Language

English

Type of outcome

Article in a journal

Country of publisher

United States of America

Confidentiality degree

is not subject to a state or trade secret

References:

URL

Marked to be transferred to RIV

Yes

RIV identification code

RIV/00216224:14310/23:00132247

Organization

Přírodovědecká fakulta – Repository – Repository

DOI

https://doi.org/10.1021/acs.orglett.3c02511

UT WoS

001062605500001

EID Scopus

2-s2.0-85171393041

Keywords in English

HYDROGEN-SULFIDE; CYTOTOXICITY; MITOCHONDRIA; ENERGY

Links

EF17_043/0009632, research and development project. 857560, interní kód Repo. RECETOX RI, large research infrastructures.
Changed: 20/6/2025 00:50, RNDr. Daniel Jakubík

Abstract

In the original language

meso-Met h y l 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-met h y l 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 photo-release of H2Sn. For this reason, sulfonothioated BODIPY may be applied in cell signaling, redox homeostasis, and metabolic regulation studies.
Displayed: 3/5/2026 11:39