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

Mark A.R. de Geus; Elmer Maurits; Alexi J.C. Sarris; Thomas Hansen; Max S. Kloet; Kiki Kamphorst; Wolter ten Hoeve; Marc S. Robillard; Andrea Pannwitz; Sylvestre A. Bonnet; Jeroen D.C. Codée; Dmitri V. Filippov; Herman S. Overkleeft; Sander I. van Kasteren

doi:10.1002/chem.201905446

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

Mark A.R. de Geus, Elmer Maurits, Alexi J.C. Sarris, Thomas Hansen, Max S. Kloet, Kiki Kamphorst, Wolter ten Hoeve, Marc S. Robillard, Andrea Pannwitz, Sylvestre A. Bonnet, Jeroen D.C. Codée, Dmitri V. Filippov, Herman S. Overkleeft, Sander I. van Kasteren^*

^*Corresponding author for this work

Chemistry and Pharmaceutical Sciences

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

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.

Original language	English
Pages (from-to)	9900-9904
Number of pages	5
Journal	Chemistry - A European Journal
Volume	26
Issue number	44
DOIs	https://doi.org/10.1002/chem.201905446
Publication status	Published - 6 Aug 2020

Funding

S.I.V.K. was the recipient of an ERC Starting Grant from the European Research Council (ERC-2014-StG-639005). A.J.C.S., D.V.F., H.S.O., and S.I.V.K. were funded by the Institute of Chemical Immunology (NWO Zwaartekracht). The authors thank SURFsara for use of the Lisa supercomputer and kindly acknowledge Mark Somers for technical support.

Funders	Funder number
Institute of Chemical Immunology
Horizon 2020 Framework Programme	639005
European Research Council
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

Keywords

bioorthogonal chemistry
Diels–Alder reactions
fluorescent probes
kinetics
nitrogen heterocycles

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1002/chem.201905446

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de Geus, M. A. R., Maurits, E., Sarris, A. J. C., Hansen, T., Kloet, M. S., Kamphorst, K., ten Hoeve, W., Robillard, M. S., Pannwitz, A., Bonnet, S. A., Codée, J. D. C., Filippov, D. V., Overkleeft, H. S., & van Kasteren, S. I. (2020). Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics. Chemistry - A European Journal, 26(44), 9900-9904. https://doi.org/10.1002/chem.201905446

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title = "Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics",

abstract = "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.",

keywords = "bioorthogonal chemistry, Diels–Alder reactions, fluorescent probes, kinetics, nitrogen heterocycles",

author = "\{de Geus\}, \{Mark A.R.\} and Elmer Maurits and Sarris, \{Alexi J.C.\} and Thomas Hansen and Kloet, \{Max S.\} and Kiki Kamphorst and \{ten Hoeve\}, Wolter and Robillard, \{Marc S.\} and Andrea Pannwitz and Bonnet, \{Sylvestre A.\} and Cod{\'e}e, \{Jeroen D.C.\} and Filippov, \{Dmitri V.\} and Overkleeft, \{Herman S.\} and \{van Kasteren\}, \{Sander I.\}",

year = "2020",

month = aug,

day = "6",

doi = "10.1002/chem.201905446",

language = "English",

volume = "26",

pages = "9900--9904",

journal = "Chemistry - A European Journal",

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de Geus, MAR, Maurits, E, Sarris, AJC, Hansen, T, Kloet, MS, Kamphorst, K, ten Hoeve, W, Robillard, MS, Pannwitz, A, Bonnet, SA, Codée, JDC, Filippov, DV, Overkleeft, HS & van Kasteren, SI 2020, 'Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics', Chemistry - A European Journal, vol. 26, no. 44, pp. 9900-9904. https://doi.org/10.1002/chem.201905446

TY - JOUR

T1 - Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics

AU - de Geus, Mark A.R.

AU - Maurits, Elmer

AU - Sarris, Alexi J.C.

AU - Hansen, Thomas

AU - Kloet, Max S.

AU - Kamphorst, Kiki

AU - ten Hoeve, Wolter

AU - Robillard, Marc S.

AU - Pannwitz, Andrea

AU - Bonnet, Sylvestre A.

AU - Codée, Jeroen D.C.

AU - Filippov, Dmitri V.

AU - Overkleeft, Herman S.

AU - van Kasteren, Sander I.

PY - 2020/8/6

Y1 - 2020/8/6

N2 - 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.

AB - 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.

KW - bioorthogonal chemistry

KW - Diels–Alder reactions

KW - fluorescent probes

KW - kinetics

KW - nitrogen heterocycles

UR - https://www.scopus.com/pages/publications/85085689851

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DO - 10.1002/chem.201905446

M3 - Article

AN - SCOPUS:85085689851

SN - 0947-6539

VL - 26

SP - 9900

EP - 9904

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 44

ER -

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

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UN SDGs

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