Journal
CHEMBIOCHEM
Volume 15, Issue 7, Pages 955-959Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201300806
Keywords
activity-based probes; cathepsins; coumarins; fluorescent probes; inhibitors; peptidyl vinyl sulfones
Funding
- Gender Equality Center of the Bonn-Rhein-Sieg University of Applied Sciences
- Jurgen Manchot Foundation, Dusseldorf, Germany
- Czech Grant Agency [P302/11/1481]
- [RVO 61388963]
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A coumarin-tetrahydroquinoline hydride 8 was synthesized as a chemical tool for fluorescent labeling. The rigidified tricyclic coumarin structure was chosen for its suitable fluorescence properties. The connection of 8 with a vinyl sulfone building block was accomplished by convergent synthesis thereby leading to the coumarin-based, tripeptidomimetic activity-based probe 10, containing a Gly-Phe-Gly motif. Probe 10 was evaluated as inactivator of the therapeutically relevant human cysteine cathepsins S, L, K, and B: it showed particularly strong inactivation of cathepsin S. The detection of recombinant and native cathepsin S was demonstrated by applying 10 to in-gel fluorescence imaging.
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