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ChemicalBook--->CAS DataBase List--->330450-45-8

330450-45-8

330450-45-8 Structure

330450-45-8 Structure
IdentificationBack Directory
[Name]

b-AP15
[CAS]

330450-45-8
[Synonyms]

b-AP15
NSC-687852
NSC687852 >=98% (HPLC)
(3Z,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)-piperidin-4-one
[Molecular Formula]

C22H17N3O6
[MDL Number]

MFCD25976718
[MOL File]

330450-45-8.mol
[Molecular Weight]

419.39
Hazard InformationBack Directory
[Enzyme inhibitor]

This deubiquitinase inhibitor (FW = 421.31 g/mol; CAS 1009817-63-3), also named 3,5-bis[ (4-nitrophenyl) methylene]-1- (1-oxo-2-propen-1-yl) - (3E,5E) -4-piperidinone, targets two proteasome-associated ubiquitin carboxyl-terminal hydrolase-14, or USP14, and Ubiquitin Carboxyl-terminal Hydrolase isozyme L5 UCHL5, IC50 = 2.1 μM, resulting in a rapid accumulation of high-molecular-weight ubiquitin conjugates and functional shutdown of proteasome. Interestingly, b-AP15 displays several differences with respect to bortezomib including insensitivity to over-expression of the anti-apoptotic mediator Bcl-2 and anti-tumor activity in solid tumor models. Inhibition of DUBs blocked the processing and release of interleukin IL-1β in both mouse and human macrophages. DUB activity was necessary for inflammasome association as DUB inhibition also impaired ASC oligomerization and caspase-1 activation without directly blocking caspase- 1 activity. These data reveal the requirement for DUB activity in a key reaction of the innate immune response and highlight the therapeutic potential of DUB inhibitors for chronic auto-inflammatory diseases. (See also Bortezomib, Eeeyarestatin I)
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