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Vinyl Ether/Tetrazine Pair for the Traceless Release of Alcohols in Cells
- Source :
- Digital.CSIC. Repositorio Institucional del CSIC, instname, Zaguán. Repositorio Digital de la Universidad de Zaragoza, RIUR. Repositorio Institucional de la Universidad de La Rioja, RIUR: Repositorio Institucional de la Universidad de La Rioja, Universidad de La Rioja (UR), Angewandte Chemie International Edition
- Publication Year :
- 2017
-
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.
- Subjects :
- Vinyl Compounds
Fluorophore
Tetrazoles
Electrons
010402 general chemistry
01 natural sciences
Article
Catalysis
Tetrazine
chemistry.chemical_compound
fluorescent probes
Cell Line, Tumor
medicine
Humans
Organic chemistry
Moiety
Protecting group
Duocarmycin
heterocycles
Cycloaddition Reaction
Molecular Structure
010405 organic chemistry
General Medicine
Hep G2 Cells
General Chemistry
Vinyl ether
Prodrug
0104 chemical sciences
caged compounds
Kinetics
ethers
chemistry
Alcohols
drug delivery
Quantum Theory
Bioorthogonal chemistry
medicine.drug
Subjects
Details
- Database :
- OpenAIRE
- Journal :
- Digital.CSIC. Repositorio Institucional del CSIC, instname, Zaguán. Repositorio Digital de la Universidad de Zaragoza, RIUR. Repositorio Institucional de la Universidad de La Rioja, RIUR: Repositorio Institucional de la Universidad de La Rioja, Universidad de La Rioja (UR), Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....e2d9e0fa16cb8f3cd405c585f518fb54