Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 2, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202103525
Keywords
H2S imaging; lactams; molecular release; trimethyl lock; turn-on fluorescence
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Funding
- Ministry of Science and Culture (MWK) of Lower Saxony, Germany
- DFG [KL3012/2-1]
- Fonds der Chemischen Industrie
- Projekt DEAL
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This article discusses the development of a novel amino trimethyl lock system for the release of fluorophores, which was successfully applied for imaging H2S in human cells in vitro.
Masked trimethyl lock (TML) systems as molecular moieties enabling the bioresponsive release of compounds or dyes in a controlled temporal and spatial manner have been widely applied for the development of drug conjugates, prodrugs or molecular imaging tools. Herein, we report the development of a novel amino trimethyl lock (H2N-TML) system as an auto-immolative molecular entity for the release of fluorophores. We designed Cou-TML-N-3 and MURh-TML-N-3, two azide-masked turn-on fluorophores. The latter was demonstrated to selectively release fluorescent MURh in the presence of physiological concentrations of the redox-signaling molecule H2S in vitro and was successfully applied to image H2S in human cells
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