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 KloetKiki KamphorstWolter Ten HoeveMarc S Robillard Andrea Pannwitz Sylvestre A Bonnet Jeroen D C Codée Dmitri V Filippov Herman S Overkleeft Sander Izaäk van Kasteren

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2020)

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.

Keyphrases

electron transfer
molecular docking
dna binding
fluorescent probe
solid phase extraction
transcription factor
metal organic framework