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Title: Synthesis and extended activity of triazole-containing macrocyclic protease inhibitors
Authors: Pehere, Ashok D.
Pietsch, Markus
Gütschow, Michael
Neilsen, Paul M.
Pedersen, Daniel Sejer
Nguyen, Steven
Zvarec, Ondrej
Sykes, Matthew J.
Callen, David F.
Abell, Andrew D.
Keywords: DRNTU::Engineering::Materials
Issue Date: 2013
Source: Pehere, A. D., Pietsch, M., Gütschow, M., Neilsen, P. M., Pedersen, D. S., Nguyen, S., et al. (2013). Synthesis and extended activity of triazole-containing macrocyclic protease inhibitors. Chemistry - A European Journal, 19(24), 7975-7981.
Series/Report no.: Chemistry - a European journal
Abstract: Peptide-derived protease inhibitors are an important class of compounds with the potential to treat a wide range of diseases. Herein, we describe the synthesis of a series of triazole-containing macrocyclic protease inhibitors pre-organized into a β-strand conformation and an evaluation of their activity against a panel of proteases. Acyclic azido–alkyne-based aldehydes are also evaluated for comparison. The macrocyclic peptidomimetics showed considerable activity towards calpain II, cathepsin L and S, and the 20S proteasome chymotrypsin-like activity. Some of the first examples of highly potent macrocyclic inhibitors of cathepsin S were identified. These adopt a well-defined β-strand geometry as shown by NMR spectroscopy, X-ray analysis, and molecular docking studies.
ISSN: 0947-6539
DOI: 10.1002/chem.201204260
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:MSE Journal Articles

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