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A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging
Fluorescent probes that light‐up upon reaction with complementary bioorthogonal reagents are superior tools for no‐wash fluorogenic bioimaging applications. In this work, a thorough study is presented on a set of seventeen structurally diverse coumarin–tetrazine probes that produce fluorescent dyes...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497033/ https://www.ncbi.nlm.nih.gov/pubmed/32339341 http://dx.doi.org/10.1002/chem.202001290 |
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author | Galeta, Juraj Dzijak, Rastislav Obořil, Jan Dračínský, Martin Vrabel, Milan |
author_facet | Galeta, Juraj Dzijak, Rastislav Obořil, Jan Dračínský, Martin Vrabel, Milan |
author_sort | Galeta, Juraj |
collection | PubMed |
description | Fluorescent probes that light‐up upon reaction with complementary bioorthogonal reagents are superior tools for no‐wash fluorogenic bioimaging applications. In this work, a thorough study is presented on a set of seventeen structurally diverse coumarin–tetrazine probes that produce fluorescent dyes with exceptional turn‐on ratios when reacted with trans‐cyclooctene (TCO) and bicyclononyne (BCN) dienophiles. In general, formation of the fully aromatic pyridazine‐containing dyes resulting from the reaction with BCN was found superior in terms of fluorogenicity. However, evaluation of the probes in cellular imaging experiments revealed that other factors, such as reaction kinetics and good cell permeability, prevail over the fluorescence turn‐on properties. The best compound identified in this study showed excellent performance in live cell‐labeling experiments and enabled no‐wash fluorogenic imaging on a timescale of seconds. |
format | Online Article Text |
id | pubmed-7497033 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74970332020-09-25 A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging Galeta, Juraj Dzijak, Rastislav Obořil, Jan Dračínský, Martin Vrabel, Milan Chemistry Full Papers Fluorescent probes that light‐up upon reaction with complementary bioorthogonal reagents are superior tools for no‐wash fluorogenic bioimaging applications. In this work, a thorough study is presented on a set of seventeen structurally diverse coumarin–tetrazine probes that produce fluorescent dyes with exceptional turn‐on ratios when reacted with trans‐cyclooctene (TCO) and bicyclononyne (BCN) dienophiles. In general, formation of the fully aromatic pyridazine‐containing dyes resulting from the reaction with BCN was found superior in terms of fluorogenicity. However, evaluation of the probes in cellular imaging experiments revealed that other factors, such as reaction kinetics and good cell permeability, prevail over the fluorescence turn‐on properties. The best compound identified in this study showed excellent performance in live cell‐labeling experiments and enabled no‐wash fluorogenic imaging on a timescale of seconds. John Wiley and Sons Inc. 2020-07-14 2020-08-06 /pmc/articles/PMC7497033/ /pubmed/32339341 http://dx.doi.org/10.1002/chem.202001290 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Full Papers Galeta, Juraj Dzijak, Rastislav Obořil, Jan Dračínský, Martin Vrabel, Milan A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging |
title | A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging |
title_full | A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging |
title_fullStr | A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging |
title_full_unstemmed | A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging |
title_short | A Systematic Study of Coumarin–Tetrazine Light‐Up Probes for Bioorthogonal Fluorescence Imaging |
title_sort | systematic study of coumarin–tetrazine light‐up probes for bioorthogonal fluorescence imaging |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497033/ https://www.ncbi.nlm.nih.gov/pubmed/32339341 http://dx.doi.org/10.1002/chem.202001290 |
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