Journal
CHEMBIOCHEM
Volume 20, Issue 12, Pages 1541-1546Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201900098
Keywords
anti-inflammatory drugs; bioorthogonal decaging; inverse electron-demand Diels-Alder reaction; tetrazine; trans-cyclooctene
Funding
- EPSRC
- Herchel-Smith Fund
- FCT Portugal [IF/00624/2015]
- European Commission (Marie Sklodowska-Curie Fellowship) [702574]
- D. G. I. MINECO/FEDER [CTQ2015-70524-R, RYC-2013-14706]
- European Research Council Starting Grant (TagIt) [676832]
- EPSRC [1800475] Funding Source: UKRI
- Marie Curie Actions (MSCA) [702574] Funding Source: Marie Curie Actions (MSCA)
- European Research Council (ERC) [676832] Funding Source: European Research Council (ERC)
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In addition to its use for the study of biomolecules in living systems, bioorthogonal chemistry has emerged as a promising strategy to enable protein or drug activation in a spatially and temporally controlled manner. This study demonstrates the application of a bioorthogonal inverse electron-demand Diels-Alder (iEDDA) reaction to cleave trans-cyclooctene (TCO) and vinyl protecting groups from carboxylic acid-containing molecules. The tetrazine-mediated decaging reaction proceeded under biocompatible conditions with fast reaction kinetics (<2 min). The anti-inflammatory activity of ketoprofen was successfully reinstated after decaging of the nontoxic TCOprodrug in live macrophages. Overall, this work expands the scope of functional groups and the application of decaging reactions to a new class of drugs.
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