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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
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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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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 |
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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 |
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