Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C

The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular mode...

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Bibliographic Details
Published in:Medicinal chemistry research 2015, Vol.24 (8), p.3157-3165
Main Authors: Makowski, Maciej, Lenartowicz, Paweł, Oszywa, Bartosz, Jewgiński, Michał, Pawełczak, Małgorzata, Kafarski, Paweł
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Original Research
Pharmacology/Toxicology
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Summary:The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular modeling, they are rather bound at the surface of the enzyme and are not submersed in its binding cavities.
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-015-1366-0