b-AP15

ChemicalBook > CAS DataBase List > b-AP15

Product Name: b-AP15
CAS No.: 1009817-63-3
Chemical Name: b-AP15
Synonyms: LM-3077;CS-1719;b-AP15 USP/EP/BP;b-AP15 (NSC687852);NSC 687852 (b-AP15);NSC687852;NSC-687852;NSC 687852;(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)-4-piperidinone;(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one;3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propene-1-yl)-4-piperidone;(3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-1-prop-2-enoylpiperidin-4-one
CBNumber: CB92677395
Molecular Formula: C22H17N3O6
Formula Weight: 419.39
MOL File: 1009817-63-3.mol

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b-AP15 Property

Boiling point:: 670.4±55.0 °C(Predicted)
Density: 1.416±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: Soluble in DMSO (up to 35 mg/ml).
pka: -1.58±0.20(Predicted)
form: solid
color: Pale yellow
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 662140
Product name: DUB Inhibitor IV, b-AP15 - CAS 1009817-63-4 - Calbiochem
Purity: The DUB Inhibitor IV, b-AP15 controls the biological activity of DUB. This small molecule/inhibitor is primarily used for Protease Inhibitors applications.
Packaging: 10MG
Price: $216
Updated: 2024/03/01

Cayman Chemical

Product number: 11324
Product name: b-AP15
Purity: ≥98%
Packaging: 1mg
Price: $37
Updated: 2024/03/01

Cayman Chemical

Product number: 11324
Product name: b-AP15
Purity: ≥98%
Packaging: 5mg
Price: $72
Updated: 2024/03/01

Cayman Chemical

Product number: 11324
Product name: b-AP15
Purity: ≥98%
Packaging: 10mg
Price: $127
Updated: 2024/03/01

Cayman Chemical

Product number: 11324
Product name: b-AP15
Purity: ≥98%
Packaging: 25mg
Price: $266
Updated: 2024/03/01

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b-AP15 Chemical Properties,Usage,Production

Description

b-AP15 (1009817-63-3) abrogates the deubiquitinating activity of the 19S regulatory particle by inhibiting ubiquitin C-terminal hydrolase 5 (UCHL5) and ubiquitin-specific peptidase 14 (USP14) resulting in accumulation of polyubiquitin in cells. b-AP15 induces tumor cell apoptosis and tumor progression in four different solid tumor models in vivo.

Uses

(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one is a candidate cytotoxic agent for malignant cells.

in vitro

nsc 687852 blocked deubiquitylating activity of usp14 and uchl5 selectively without inhibiting proteasome activity. nsc 687852 decreased viability in multiple myeloma (mm) cell lines and patient mm cells, inhibited mm cell proliferation even in the presence of bone marrow stroma cells, and overcomed bortezomib resistance. anti-mm activity of nsc 687852 was associated with growth arrest through downregulating cdc2, cdc25c, and cyclin b1, as well as induction of caspase-dependent apoptosis and activation of unfolded protein response [1].

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)

in vivo

in vivo studies using distinct human mm xenograft models showed that nsc 687852 was well tolerated, inhibited tumor growth, and prolonged mouse survival. combination of nsc 687852 with suberoylanilide hydroxamic acid, lenalidomide, or dexamethasone was found to induce synergistic anti-mm activity [1].

References

1) D’Arcy et al. (2011), Inhibition of proteasome deubiquitinating activity as a new cancer therapy; Nature Medicine, 17 1636

b-AP15 Preparation Products And Raw materials

Raw materials

Preparation Products

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b-AP15 Suppliers

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1009817-63-3, b-AP15Related Search:

NSC781406 2,4-Thiazolidinedione,5-[(4-hydroxy-3-methoxyphenyl)methylene]- 4-Chloro-N,N-diisopropylbenzamide Pifithrin-μ 2-Pyridinecarbothioamide, N-2-pyridinyl- 1,3-Bis(4-aminophenyl)urea 5-(4-iodobenzylidene)rhodanine S3I-201 NSC228155 NSC632839hydrochloride NSC23005 Sodium HAMNO NSC 247030 5-[(4-chlorophenyl)methylidene]-1,3-thiazolidine-2,4-dione BAY 11-7082 TCID 1-[1-(4-Fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl]-2-(1-pyrrolidinyl)ethanone TIMTEC-BB SBB006342

b-AP15 (NSC687852)

4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-, (3E,5E)-

NSC 687852 (b-AP15)

LM-3077

(3E,5E)-3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-4-piperidinone

(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one

(3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-1-prop-2-enoylpiperidin-4-one

3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propene-1-yl)-4-piperidone

CS-1719

NSC687852;NSC-687852;NSC 687852

(3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)-4-piperidinone

b-AP15 USP/EP/BP

Deubiquitinase,Inhibitor,BAP15,inhibit,NSC687852,Apoptosis,DUBs,NSC-687852,B AP15,b-AP15,B-AP-15

1009817-63-3

Inhibitors