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Synthesis and proteasome inhibition of N-allyl vinyl ester-based peptides

✍ Scribed by Anna Baldisserotto; Christian Franceschini; Franco Scalambra; Claudio Trapella; Mauro Marastoni; Fabio Sforza; Riccardo Gavioli; Roberto Tomatis

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
111 KB
Volume
16
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

Inhibition of the proteasome, the multicatalytic protease complex responsible for the turnover of many cellular proteins, represents an attractive target in the development of new drug therapies, proteasome inhibitors being potentially useful tools for the treatment of pathologies such as cancer, as well as inflammatory, immune and neurodegenerative diseases. Based on our previous development of a new class of inhibitors bearing a C‐terminal VE cluster able to interact with catalytic threonine, we report herein the synthesis and activity of new VE‐based peptide analogs bearing an additional allyl pharmacophore unit at the C‐ or N‐terminal position of the pseudotripeptide sequence. In the new series, the structural modification carried out to the prototype determine a decrease of proteasome inhibition. Copyright Β© 2010 European Peptide Society and John Wiley & Sons, Ltd.

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