Here we report the synthesis and biological properties of peptide-based molecules bearing constrained analogues of phenylalanine at the C-terminal. Compounds were tested as proteasome subunits' inhibitors. Dehydro-peptides showed good inhibition, in particular against trypsin-like (T-L) proteasome activity while some C-terminal Tic-derivatives inhibit only caspase-like activity in enzymatic beta1 subunits with a certain degree of efficacy. The best analogues of the series demonstrated good resistance to proteolysis and a capacity to permeate the cell membrane.

C-terminal constrained phenylalanine as a pharmacophoric unit in peptide-based proteasome inhibitors

BALDISSEROTTO, Anna;MARASTONI, Mauro;LAZZARI, Ilaria;TRAPELLA, Claudio;GAVIOLI, Riccardo;TOMATIS, Roberto
2008

Abstract

Here we report the synthesis and biological properties of peptide-based molecules bearing constrained analogues of phenylalanine at the C-terminal. Compounds were tested as proteasome subunits' inhibitors. Dehydro-peptides showed good inhibition, in particular against trypsin-like (T-L) proteasome activity while some C-terminal Tic-derivatives inhibit only caspase-like activity in enzymatic beta1 subunits with a certain degree of efficacy. The best analogues of the series demonstrated good resistance to proteolysis and a capacity to permeate the cell membrane.
Baldisserotto, Anna; Marastoni, Mauro; Lazzari, Ilaria; Trapella, Claudio; Gavioli, Riccardo; Tomatis, Roberto
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11392/499064
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