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Pseudopeptides with aldehyde or vinylsulfone warheads: Synthesis and antiproteasomal activity
R. Jorda, V. Molitorová, E. Pilařová, V. Vojáčková, E. Řezníčková, K. Svobodová, K. Pauk, A. Imramovský, V. Kryštof
Jazyk angličtina Země Spojené státy americké
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- aldehydy chemie farmakologie MeSH
- inhibitory proteasomu chemická syntéza chemie farmakologie MeSH
- lidé MeSH
- molekulární struktura MeSH
- nádorové buněčné linie MeSH
- peptidy chemie farmakologie MeSH
- proteasomový endopeptidasový komplex metabolismus MeSH
- sulfony chemie farmakologie MeSH
- vinylové sloučeniny chemie farmakologie MeSH
- vztah mezi dávkou a účinkem léčiva MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
The comparative study of new proteasome inhibitors based on salicylic acid-modified pseudo-tripeptides terminated with aldehyde or vinylsulfone is presented. We described the synthesis of 11 pairs of pseudopeptides and their properties related to the proteasome inhibition were determined. The effects of integrated amino acids (combinations of leucine, phenylalanine, tryptophan, proline, cyclohexylalanine or norleucine residues) on the activity of the proteasome were investigated. Compounds preferentially inhibited the chymotrypsin β5-subunit of the proteasome in cell-based assays compared with the β1- and β2-subunits, with IC50 values in mid-nanomolar ranges being obtained for the most active members. Our comparative study demonstrated that aldehydes were able to inhibit the proteasome in cells more effectively than vinylsulfones. These results were corroborated by the accumulation of polyubiquitinated proteins in treated cells, GFP accumulation in a reporter cell line and the ability of new compounds to induce apoptotic cell death.
Citace poskytuje Crossref.org
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- $a Jorda, Radek $u Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
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- $a The comparative study of new proteasome inhibitors based on salicylic acid-modified pseudo-tripeptides terminated with aldehyde or vinylsulfone is presented. We described the synthesis of 11 pairs of pseudopeptides and their properties related to the proteasome inhibition were determined. The effects of integrated amino acids (combinations of leucine, phenylalanine, tryptophan, proline, cyclohexylalanine or norleucine residues) on the activity of the proteasome were investigated. Compounds preferentially inhibited the chymotrypsin β5-subunit of the proteasome in cell-based assays compared with the β1- and β2-subunits, with IC50 values in mid-nanomolar ranges being obtained for the most active members. Our comparative study demonstrated that aldehydes were able to inhibit the proteasome in cells more effectively than vinylsulfones. These results were corroborated by the accumulation of polyubiquitinated proteins in treated cells, GFP accumulation in a reporter cell line and the ability of new compounds to induce apoptotic cell death.
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- $a Molitorová, Veronika $u Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
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- $a Pilařová, Eliška $u Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
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- $a Vojáčková, Veronika $u Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic
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- $a Imramovský, Aleš $u Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic. Electronic address: ales.imramovsky@upce.cz
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- $a Kryštof, Vladimír $u Department of Experimental Biology, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic; Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 5, 77900 Olomouc, Czech Republic. Electronic address: vladimir.krystof@upol.cz
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