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Masked Amino Trimethyl Lock (H 2 N‐TML) Systems: New Molecular Entities for the Development of Turn‐On Fluorophores and Their Application in Hydrogen Sulfide (H 2 S) Imaging in Human Cells
Author(s) -
Jimidar Claire Cheyenne,
Grunenberg Jörg,
Karge Bianka,
Fuchs Hazel Leanne Sarah,
Brönstrup Mark,
Klahn Philipp
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103525
Subject(s) - chemistry , prodrug , turn (biochemistry) , combinatorial chemistry , fluorescence , hydrogen sulfide , lock (firearm) , in vitro , molecule , stereochemistry , biochemistry , organic chemistry , sulfur , mechanical engineering , physics , quantum mechanics , engineering
Abstract 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 (H 2 N‐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 H 2 S in vitro and was successfully applied to image H 2 S in human cells