A Coumarin- Labeled Vinyl Sulfone as Tripeptidomimetic Activity- Based Probe for Cysteine Cathepsins

0429455 - ÚOCHB 2015 RIV DE eng J - Článek v odborném periodiku
Mertens, M. D. - Schmitz, J. - Horn, Martin - Furtmann, N. - Bajorath, J. - Mareš, Michael - Gütschow, M.
A Coumarin- Labeled Vinyl Sulfone as Tripeptidomimetic Activity- Based Probe for Cysteine Cathepsins.
Chembiochem. Roč. 15, č. 7 (2014), s. 955-959. ISSN 1439-4227. E-ISSN 1439-7633
Grant CEP: GA ČR(CZ) GAP302/11/1481
Institucionální podpora: RVO:61388963
Klíčová slova: activity-based probes * cathepsins * coumarins * fluorescent probes * inhibitors * peptidyl vinyl sulfones
Kód oboru RIV: CE - Biochemie
Impakt faktor: 3.088, rok: 2014

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.
Trvalý link: http://hdl.handle.net/11104/0234605