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
-
1
Universidad de La Rioja
info
-
2
University of Cambridge
info
-
3
Universidad de Zaragoza
info
-
4
Universidade de Lisboa
info
ISSN: 1433-7851
Any de publicació: 2017
Volum: 56
Número: 1
Pàgines: 243-247
Tipus: Article
Altres publicacions en: Angewandte Chemie International
Projectes relacionats
2015/00062/001
Resum
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.