Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 1, Pages 243-247Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609607
Keywords
caged compounds; ethers; heterocycles; drug delivery; fluorescent probes
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Funding
- European Commission (Marie Sklodowska-Curie ITN Protein Conjugates)
- European Commission (Marie Sklodowska-Curie IEF)
- European Commission (Marie Curie IEF)
- China Scholarship Council
- FCT Portugal
- MINECO [CTQ2015-70524-R, RYC-2013-14706]
- EPSRC
- European Research Council
- Engineering and Physical Sciences Research Council [EP/M003647/1] Funding Source: researchfish
- EPSRC [EP/M003647/1] Funding Source: UKRI
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The cleavage of a protecting group from a protein or drug under bioorthogonal conditions enables accurate spatio-temporal 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.
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