Fluorogenic Bifunctional Trans-cyclooctenes as Efficient Tools for Investigating Click-to-Release Kinetics

Author(s):
Geus, M.A.R. de (0000-0002-1639-5890); Maurits, E. (0000-0001-9631-9152); Sarris, A.J.C.; Hansen, T. (0000-0002-6291-1569); Kloet, M.S.; Kamphorst, K.; Hoeve, W. ten; Robillard, M.S.; Pannwitz, A.; Bonnet, S.A. (0000-0002-5810-3657); Codée, J.D.C.; Filippov, D.V. (0000-0002-6978-7425); Overkleeft, H.S. (0000-0001-6992-4760); Kasteren, S.I. van (0000-0003-4369-6055)
Published
2020
Publication type
Article / Letter to editor

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 on 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 detection of both the click and release rates for any tetrazine at physiologically relevant concentrations.

Date issued
2020-03-10
Language
English
Is part of
Chemistry-a European Journal (2020), Vol. 26, no. 44, p. 9900-9904
hdl
1887/137785
doi
10.1002/chem.201905446
URL
https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201905446