Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells
Angewandte Chemie - International Edition
John Wiley & Sons Ltd.
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Jiménez-Moreno, E., Guo, Z., Oliveira, B., Albuquerque, I., Kitowski, A., Guerreiro, A., Boutureira, O., et al. (2017). Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells. Angewandte Chemie - International Edition, 56 (1), 243-247. https://doi.org/10.1002/anie.201609607
The cleavage of a protecting group from a protein or drug under bioorthogonal conditions enables accurate spatiotemporal control over protein or drug activity. Disclosed herein is that vinyl ethers serve as protecting groups for alcohol-containing molecules and as reagents for bioorthogonal bond-cleavage reactions. A vinyl ether moiety was installed in a range of molecules, including amino acids, a monosaccharide, a fluorophore, and an analogue of the cytotoxic drug duocarmycin. Tetrazine-mediated decaging proceeded under biocompatible conditions with good yields and reasonable kinetics. Importantly, the nontoxic, vinyl ether duocarmycin double prodrug was successfully decaged in live cells to reinstate cytotoxicity. This bioorthogonal reaction presents broad applicability and may be suitable for in vivo applications.
caged compounds, drug delivery, ethers, fluorescent probes, heterocycles
European Commission; China Scholarship Council; FCT Portugal; MINECO (CTQ2015-70524-R and RYC-2013-14706); EPSRC; Royal Society; European Research Council (TagIt)
European Commission Horizon 2020 (H2020) ERC (676832)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (702574)
European Commission Horizon 2020 (H2020) Marie Sk?odowska-Curie actions (701473)
External DOI: https://doi.org/10.1002/anie.201609607
This record's URL: https://www.repository.cam.ac.uk/handle/1810/262471
Attribution 4.0 International, Attribution 4.0 International, Attribution 4.0 International, Attribution 4.0 International