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Angewandte Chemie - International Edition

Volumn 47, Issue 2, 2008, Pages 406-409

Selective activity-based probes for cysteine cathepsins

(8) Watzke, Anja b Kosec, Gregor a Kindermann, Maik b Jeske, Volker b Nestler, Hans Peter b Turk, Vito a Turk, Boris a Ulrich Wendt, K a,b

a JO EF STEFAN INSTITUTE (Slovenia)

b SANOFI AVENTIS DEUTSCHLAND GMBH (Germany)

Author keywords

Enzymes; Fluorescent probes; Inhibitors; Medicinal chemistry

Indexed keywords

FLUORESCENCE; IMAGE ANALYSIS; PROBES; PROTEINS;

FLUORESCENT PROBES; MEDICINAL CHEMISTRY;

ENZYME INHIBITION;

CATHEPSIN; CYSTEINE; ENZYME INHIBITOR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; KINETICS; METABOLISM; TUMOR CELL LINE;

CATHEPSINS; CELL LINE, TUMOR; CYSTEINE; ENZYME INHIBITORS; HUMANS; KINETICS; MOLECULAR STRUCTURE;

EID: 38049057786 PISSN: 14337851 EISSN: None Source Type: Journal
DOI: 10.1002/anie.200702811 Document Type: Article

Times cited : (72)

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- 2 and 4 were synthesized by standard solid-phase peptide synthesis using the 2-chlorotrityl chloride resin. ABP 5 was generated using a combination of solid- and solution-phase chemistry
- ABPs 2 and 4 were synthesized by standard solid-phase peptide synthesis using the 2-chlorotrityl chloride resin. ABP 5 was generated using a combination of solid- and solution-phase chemistry. For details, see the Supporting Information.
- For details, see the Supporting Information
- ABPs¹

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- For the in vitro enzyme activity assay, the active cysteine proteases were dissolved in AHNP buffer (150 mM acetate/2-[4-(2-hydroxyethyl)-1- piperazinyl]ethanesulfonic acid (HEPES) pH 6.5, 300 mM NaCl; 0.001, pluronic, 5-100 mM cysteine depending on the enzyme) at a final concentration of 10 nM. The substrates 2, 4, and 5, dissolved in DMSO, were added at concentrations of 98 μM (2) and 24 μM (4 and 5, and fluorescence was measured with a Tecan SAFIRE II spectrometer. The final DMSO concentration in the assay did not exceed 1, v/v, Steady-state kinetics were fitted by nonlinear least-squares regression using v, A]V/(K M+1, A]/Ksi, A, where v is the initial velocity, V is the maximal rate, KM is the Michaelis-Menten constant, and Ksi is the constant for substrate inhibition
- si is the constant for substrate inhibition.

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- 50 = 19 000 nM (J. P. Falgueyret, S. Desmarais, R. Oballa, C. Black, W. Cromlish, K. Khougaz, S. Lamontagne, F. Masse, D. Riendeau, S. Toulmond, M. D. Percival, J. Med. Chem. 2005, 48, 7535-7543).
- 50 = 19 000 nM (J. P. Falgueyret, S. Desmarais, R. Oballa, C. Black, W. Cromlish, K. Khougaz, S. Lamontagne, F. Masse, D. Riendeau, S. Toulmond, M. D. Percival, J. Med. Chem. 2005, 48, 7535-7543).

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