Cargando…

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

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 n...

Descripción completa

Detalles Bibliográficos
Autores principales: Jimidar, Claire Cheyenne, Grunenberg, Jörg, Karge, Bianka, Fuchs, Hazel Leanne Sarah, Brönstrup, Mark, Klahn, Philipp
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9299139/
https://www.ncbi.nlm.nih.gov/pubmed/34713944
http://dx.doi.org/10.1002/chem.202103525
_version_ 1784750884740136960
author Jimidar, Claire Cheyenne
Grunenberg, Jörg
Karge, Bianka
Fuchs, Hazel Leanne Sarah
Brönstrup, Mark
Klahn, Philipp
author_facet Jimidar, Claire Cheyenne
Grunenberg, Jörg
Karge, Bianka
Fuchs, Hazel Leanne Sarah
Brönstrup, Mark
Klahn, Philipp
author_sort Jimidar, Claire Cheyenne
collection PubMed
description 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
format Online
Article
Text
id pubmed-9299139
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-92991392022-07-21 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 Jimidar, Claire Cheyenne Grunenberg, Jörg Karge, Bianka Fuchs, Hazel Leanne Sarah Brönstrup, Mark Klahn, Philipp Chemistry Communications 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 John Wiley and Sons Inc. 2021-11-08 2022-01-10 /pmc/articles/PMC9299139/ /pubmed/34713944 http://dx.doi.org/10.1002/chem.202103525 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Jimidar, Claire Cheyenne
Grunenberg, Jörg
Karge, Bianka
Fuchs, Hazel Leanne Sarah
Brönstrup, Mark
Klahn, Philipp
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9299139/
https://www.ncbi.nlm.nih.gov/pubmed/34713944
http://dx.doi.org/10.1002/chem.202103525
work_keys_str_mv AT jimidarclairecheyenne maskedaminotrimethyllockh2ntmlsystemsnewmolecularentitiesforthedevelopmentofturnonfluorophoresandtheirapplicationinhydrogensulfideh2simaginginhumancells
AT grunenbergjorg maskedaminotrimethyllockh2ntmlsystemsnewmolecularentitiesforthedevelopmentofturnonfluorophoresandtheirapplicationinhydrogensulfideh2simaginginhumancells
AT kargebianka maskedaminotrimethyllockh2ntmlsystemsnewmolecularentitiesforthedevelopmentofturnonfluorophoresandtheirapplicationinhydrogensulfideh2simaginginhumancells
AT fuchshazelleannesarah maskedaminotrimethyllockh2ntmlsystemsnewmolecularentitiesforthedevelopmentofturnonfluorophoresandtheirapplicationinhydrogensulfideh2simaginginhumancells
AT bronstrupmark maskedaminotrimethyllockh2ntmlsystemsnewmolecularentitiesforthedevelopmentofturnonfluorophoresandtheirapplicationinhydrogensulfideh2simaginginhumancells
AT klahnphilipp maskedaminotrimethyllockh2ntmlsystemsnewmolecularentitiesforthedevelopmentofturnonfluorophoresandtheirapplicationinhydrogensulfideh2simaginginhumancells