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. 2013:70:505-24.
doi: 10.1016/j.ejmech.2013.09.059. Epub 2013 Oct 17.

α- and β-hydrazino acid-based pseudopeptides inhibit the chymotrypsin-like activity of the eukaryotic 20S proteasome

Andrea Bordessa  1 , Massaba Keita, Xavier Maréchal, Lucia Formicola, Nathalie Lagarde, Jordi Rodrigo, Guillaume Bernadat, Cyril Bauvais, Jean-Louis Soulier, Laure Dufau, Thierry Milcent, Benoit Crousse, Michèle Reboud-Ravaux, Sandrine Ongeri
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α- and β-hydrazino acid-based pseudopeptides inhibit the chymotrypsin-like activity of the eukaryotic 20S proteasome

Andrea Bordessa et al. Eur J Med Chem. 2013.

Abstract

We describe the synthesis of a library of new pseudopeptides and their inhibitory activity of the rabbit 20S proteasome chymotrypsin-like (ChT-L) activity. We replaced a natural α-amino acid by an α- or a β-hydrazino acid and obtained inhibitors of proteasome up to a submicromolar range (0.7 μM for molecule 24b). Structural variations influenced the inhibition of the ChT-L activity. Models of inhibitor/20S proteasome complexes corroborated the inhibition efficacies obtained by kinetic studies.

Keywords: Chymotrypsin; Fluorine; Hydrazino acid; Proteasome inhibitors; Pseudopeptide; Trifluoromethyl.

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