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

Research output: Contribution to JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)9900-9904
Number of pages5
JournalChemistry - A European Journal
Volume26
Issue number44
DOIs
Publication statusPublished - 6 Aug 2020

Keywords

  • bioorthogonal chemistry
  • Diels–Alder reactions
  • fluorescent probes
  • kinetics
  • nitrogen heterocycles

Fingerprint

Dive into the research topics of 'Fluorogenic Bifunctional trans-Cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics'. Together they form a unique fingerprint.

Cite this