(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
CAS: 1009817-63-3
Molecular Formula: C22H17N3O6
(3E,5E)-3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-4-piperidinone - Names and Identifiers
(3E,5E)-3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-4-piperidinone - Physico-chemical Properties
| Molecular Formula | C22H17N3O6 |
| Molar Mass | 419.39 |
| Density | 1.416±0.06 g/cm3(Predicted) |
| Boling Point | 670.4±55.0 °C(Predicted) |
| Solubility | Soluble in DMSO (up to 35 mg/ml). |
| Appearance | solid |
| Color | Pale yellow |
| pKa | -1.58±0.20(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| In vitro study | b-AP15 inhibits two 19S regulatory granule-associated deubiquitinating enzymes, Ubiquitin C- terminal hydrolase 5(UCHL5) and ubiquitin-Specific Peptidase 14(USP14), results in the accumulation of poly-ubiquitin. b-AP15 resulted in UbG76V-YFP receptor accumulation with an IC50 of 0.8 μm, a dose-dependent effect indicating impaired degradation by the damaged proteasome. b-AP15 (1 μm) action on human colon cancer HCT-116 cells results in rapid accumulation of multimeric ubiquitinated protein. b-AP15(2.2 μm) increased the number of cyclin-dependent kinases CDKN1A and cdknnib, and tumor suppressor gene TP53 in HCT-116 cells in a dose-dependent manner, but does not change the amount of ornithine decarboxylase 1(ODC1). b-AP15(1 μm) acts on HCT-116 cells, resulting in cell cycle arrest in G2/M phase, which, in turn, leads to accumulation of cell cycle inhibitors. b-AP15 treatment increases the number of hypodiploid cells and, correspondingly, the number of apoptotic markers, including activated caspase-3,caspase-cleaved poly-ADP-ribose polymerase (PARP) and cytokeratin -18(CK18). hTERT-RPE1 was more toxic to b-AP15 cells than immortalized epithelial cells (HCT-116) or peripheral blood mononuclear cells. b-AP15 inhibition of deubiquitin activity using a variety of substrates, including Ub-AMC, Ub-GFP22, ubiquitinated p53-binding protein homologs (HDM2), and K48-and K63-linked ubiquitin tetramer chains. b-AP15 is a UPS inhibitor that induces cell death by inducing a cathepsin-D-dependent lysosomal apoptosis pathway. b-AP15 elicits characteristic UPS defects including accumulation of ubiquitin conjugates, cell cycle inhibitors such as p21,p27, and the tumor suppressor gene p53. b-AP15 inhibition of the deubiquitination enzyme activity of cysteine DUBs, USP14 is slightly more sensitive than uchl5. b-AP15 acts on cells overexpressing anti-apoptotic Bcl-2 protein and cells lacking p53 gene to induce apoptosis. b-AP15 (1 μm) inhibited ATP-induced release of IL-1β from LPS-induced peritoneal macrophages. b-AP15(1 μm) action on THP-1 cells reduced the level of cell death induced by Nigericin treatment. b-AP15(1 μm) treatment of LPS-induced THP-1 cells significantly reduced the number of ASC spots formed after treatment with Nigericin. |
| In vivo study | b-AP15 (5 mg/kg) treatment of severe combined immunodeficiency (SCID) mice with squamous cell carcinoma transplanted tumor, with significant anti tumor activity. b-AP15(5 mg/kg) treatment of mice carrying HCT-116 colon cancer xenografts significantly delayed tumor onset. |
(3E,5E)-3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-4-piperidinone - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.384 ml | 11.922 ml | 23.844 ml |
| 5 mM | 0.477 ml | 2.384 ml | 4.769 ml |
| 10 mM | 0.238 ml | 1.192 ml | 2.384 ml |
| 5 mM | 0.048 ml | 0.238 ml | 0.477 ml |
Last Update：2024-01-02 23:10:35
(3E,5E)-3,5-Bis[(4-nitrophenyl)methylene]-1-(1-oxo-2-propen-1-yl)-4-piperidinone - Introduction
b-AP15(NSC 687852) is a compound with the property of targeting deubiquitination. It acts by selectively inhibiting the deubiquitin proteases USP14 and UCHL5. This compound is widely used to study intracellular protein degradation pathways, especially the protein ubiquitin degradation pathway.
The preparation of b-AP15 is obtained by chemical synthesis, but the specific preparation conditions and procedures may vary by manufacturer or research laboratory.
Regarding safety information, b-AP15 toxicity and side effects are still being studied. It should be operated with caution and in accordance with laboratory safety operating procedures. It is recommended to read the Safety Data Sheet (MSDS) and instructions for use of the relevant substances in detail before conducting experiments to understand the risks and safety measures of their use. Prior to use, appropriate laboratory safety practices should be followed and personal protective equipment such as laboratory suits, gloves and goggles should be worn.
Please note that b-AP15 is a compound used for research purposes and should not be used to diagnose or treat any disease. b-AP15 should be used in accordance with professional and legal guidance and in a suitable laboratory environment.
The preparation of b-AP15 is obtained by chemical synthesis, but the specific preparation conditions and procedures may vary by manufacturer or research laboratory.
Regarding safety information, b-AP15 toxicity and side effects are still being studied. It should be operated with caution and in accordance with laboratory safety operating procedures. It is recommended to read the Safety Data Sheet (MSDS) and instructions for use of the relevant substances in detail before conducting experiments to understand the risks and safety measures of their use. Prior to use, appropriate laboratory safety practices should be followed and personal protective equipment such as laboratory suits, gloves and goggles should be worn.
Please note that b-AP15 is a compound used for research purposes and should not be used to diagnose or treat any disease. b-AP15 should be used in accordance with professional and legal guidance and in a suitable laboratory environment.
Last Update：2024-04-09 21:21:28
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Spot supply
Product Name: (3E,5E)-1-Acryloyl-3,5-bis(4-nitrobenzylidene)piperidin-4-one Visit Supplier Webpage Request for quotationCAS: 1009817-63-3
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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