Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells
- Jiménez-Moreno, E. 2
- Guo, Z. 2
- Oliveira, B.L. 2
- Albuquerque, I.S. 4
- Kitowski, A. 4
- Guerreiro, A. 4
- Boutureira, O. 2
- Rodrigues, T. 4
- Jiménez-Osés, G. 13
- Bernardes, G.J.L. 24
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1
Universidad de La Rioja
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2
University of Cambridge
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3
Universidad de Zaragoza
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4
Universidade de Lisboa
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ISSN: 1433-7851
Year of publication: 2017
Volume: 56
Issue: 1
Pages: 243-247
Type: Article
More publications in: Angewandte Chemie International
Related Projects
2015/00062/001
Abstract
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. © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.