Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics

The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans‐cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we re...

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Autores principales: de Geus, Mark A. R., Maurits, Elmer, Sarris, Alexi J. C., Hansen, Thomas, Kloet, Max S., Kamphorst, Kiki, ten Hoeve, Wolter, Robillard, Marc S., Pannwitz, Andrea, Bonnet, Sylvestre A., Codée, Jeroen D. C., Filippov, Dmitri V., Overkleeft, Herman S., van Kasteren, Sander I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496853/
https://www.ncbi.nlm.nih.gov/pubmed/32154603
http://dx.doi.org/10.1002/chem.201905446
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author de Geus, Mark A. R.
Maurits, Elmer
Sarris, Alexi J. C.
Hansen, Thomas
Kloet, Max S.
Kamphorst, Kiki
ten Hoeve, Wolter
Robillard, Marc S.
Pannwitz, Andrea
Bonnet, Sylvestre A.
Codée, Jeroen D. C.
Filippov, Dmitri V.
Overkleeft, Herman S.
van Kasteren, Sander I.
author_facet de Geus, Mark A. R.
Maurits, Elmer
Sarris, Alexi J. C.
Hansen, Thomas
Kloet, Max S.
Kamphorst, Kiki
ten Hoeve, Wolter
Robillard, Marc S.
Pannwitz, Andrea
Bonnet, Sylvestre A.
Codée, Jeroen D. C.
Filippov, Dmitri V.
Overkleeft, Herman S.
van Kasteren, Sander I.
author_sort de Geus, Mark A. R.
collection PubMed
description The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans‐cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO‐linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations.
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spelling pubmed-74968532020-09-25 Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics de Geus, Mark A. R. Maurits, Elmer Sarris, Alexi J. C. Hansen, Thomas Kloet, Max S. Kamphorst, Kiki ten Hoeve, Wolter Robillard, Marc S. Pannwitz, Andrea Bonnet, Sylvestre A. Codée, Jeroen D. C. Filippov, Dmitri V. Overkleeft, Herman S. van Kasteren, Sander I. Chemistry Full Papers The inverse electron demand Diels–Alder pyridazine elimination reaction between tetrazines and allylic substituted trans‐cyclooctenes (TCOs) is a key player in bioorthogonal bond cleavage reactions. Determining the rate of elimination of alkylamine substrates has so far proven difficult. Here, we report a fluorogenic tool consisting of a TCO‐linked EDANS fluorophore and a DABCYL quencher for accurate determination of both the click and release rate constants for any tetrazine at physiologically relevant concentrations. John Wiley and Sons Inc. 2020-06-03 2020-08-06 /pmc/articles/PMC7496853/ /pubmed/32154603 http://dx.doi.org/10.1002/chem.201905446 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-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 Full Papers
de Geus, Mark A. R.
Maurits, Elmer
Sarris, Alexi J. C.
Hansen, Thomas
Kloet, Max S.
Kamphorst, Kiki
ten Hoeve, Wolter
Robillard, Marc S.
Pannwitz, Andrea
Bonnet, Sylvestre A.
Codée, Jeroen D. C.
Filippov, Dmitri V.
Overkleeft, Herman S.
van Kasteren, Sander I.
Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
title Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
title_full Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
title_fullStr Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
title_full_unstemmed Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
title_short Fluorogenic Bifunctional trans‐Cyclooctenes as Efficient Tools for Investigating Click‐to‐Release Kinetics
title_sort fluorogenic bifunctional trans‐cyclooctenes as efficient tools for investigating click‐to‐release kinetics
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7496853/
https://www.ncbi.nlm.nih.gov/pubmed/32154603
http://dx.doi.org/10.1002/chem.201905446
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