(3E,5E)-3,5-雙(4-硝基亞芐基)哌啶-4-酮
| 中文名稱 | (3E,5E)-3,5-雙(4-硝基亞芐基)哌啶-4-酮 |
|---|---|
| 中文同義詞 | (3E,5E)-3,5-雙(4-硝基亞芐基)哌啶-4-酮;化合物RA-9;化合物RA-9,10 MM DMSO 溶液 |
| 英文名稱 | RA-9 |
| 英文同義詞 | 4-Piperidinone, 3,5-bis[(4-nitrophenyl)methylene]-, (3E,5E)-;RA-9 UPS inhibitor;Unfolded,RA-9,cancer,RA 9,DUBs,Inhibitor,Apoptosis,Response,Deubiquitinase,cells,inhibit,Protein,ovarian,RA9,survival;RA-9, 10 mM in DMSO;(3E,5E)-3,5-Bis[(4-nitrophenyl)methylene]-4-piperidinone |
| CAS號 | 919091-63-7 |
| 分子式 | C19H15N3O5 |
| 分子量 | 365.34 |
| EINECS號 | |
| 相關類別 | |
| Mol文件 | 919091-63-7.mol |
| 結(jié)構式 |  |
(3E,5E)-3,5-雙(4-硝基亞芐基)哌啶-4-酮 性質(zhì)
| 熔點 | 230-233 °C(Solv: ethyl ether (60-29-7); acetonitrile (75-05-8)) |
|---|---|
| 沸點 | 588.5±50.0 °C(Predicted) |
| 密度 | 1.414±0.06 g/cm3(Predicted) |
| 儲存條件 | Store at -20°C |
| 溶解度 | DMSO：4.17 mg/mL（11.41 mM；超聲加熱并加熱至 80°C） |
| 酸度系數(shù)(pKa) | 5.13±0.20(Predicted) |
| 形態(tài) | 固體 |
| 顏色 | 淺黃至黃色 |
| InChI | 1S/C19H15N3O5/c23-19-15(9-13-1-5-17(6-2-13)21(24)25)11-20-12-16(19)10-14-3-7-18(8-4-14)22(26)27/h1-10,20H,11-12H2/b15-9+,16-10+ |
| InChIKey | YUYPWAMLWZVHAE-KAVGSWPWSA-N |
| SMILES | O=C(/C(CNC/1)=C/C2=CC=C([N+]([O-])=O)C=C2)C1=C\C3=CC=C([N+]([O-])=O)C=C3 |
RA-9 是一種具有細胞滲透性的蛋白酶體相關的 deubiquitinating enzymes (DUBs) 的強效選擇性抑制劑，具有良好的毒性和抗癌活性。RA-9 可在卵巢癌細胞系中選擇性地誘導凋亡。
| Target | Value |
|
DUBs
() |
RA-9 (10-30 μM; 48 hours) inhibits growth of ovarian cancer cell lines and primary cultures.
RA-9 (1.25-5 μM; 18 hours) causes cell cycle arrest and caspase-mediated apoptosis in ovarian cancer cells.
RA-9 (5 μM; 0-24 hours) induces ER-stress responses in ovarian cancer cells.
RA-9 (5 μM; over 24 hours) treatment results with time-dependent accumulation of the cleaved formed of PARP noticeable as early as 8 hours.
Cell Viability Assay
| Cell Line: | Cisplatin-sensitive ovarian cancer cell lines TOV-21G and ES-2, Cisplatin-resistant ovarian cancer cell lines HEY and OVCAR-3, primary ovarian cancer cells |
| Concentration: | 10, 20, 30 μM |
| Incubation Time: | 48 hours |
| Result: | Compromised the viability of ovarian cancer cells in a dose-dependent fashion. |
Cell Cycle Analysis
| Cell Line: | ES-2 cells |
| Concentration: | 1.25, 5 μM |
| Incubation Time: | 18 hours |
| Result: | Resulted in a dose-dependent increase in the fraction of ES-2 cells in the G2-M cell cycle phase. |
Western Blot Analysis
| Cell Line: | ES-2, SKOV-3 and TOV-21G ovarian cancer cells |
| Concentration: | 5 μM |
| Incubation Time: | 0-24 h |
| Result: | Caused a time-dependent increase in the steady levels of the early ER-stress marker GRP-78, as well as the late ER-stress markers IRE1-α and Ero1L-α. |
RA-9 (5 mg/kg; i.p; one-day on, two-days off) inhibits human ovarian cancer cell growth in vivo and prolongs survival in a mouse model for ovarian cancer.
| Animal Model: | Six-week-old female immunodeficient (NCr nu/nu) mice |
| Dosage: | 5 mg/kg |
| Administration: | I.p; one-day on, two-days off |
| Result: | Significant reduction in tumor burden at day 12. |
安全信息
| WGK Germany | WGK 3 |
|---|---|
| 存儲類別 | 11 - 可燃固體 |
| 危險性類別 | 急性毒性 類別4 經(jīng)口 |
| 更新日期 | 產(chǎn)品編號 | 產(chǎn)品名稱 | CAS號 | 包裝 | 價格 |
|---|---|---|---|---|---|
| 2026/07/06 | S0884 | (3E,5E)-3,5-雙(4-硝基亞芐基)哌啶-4-酮 RA-9 | 919091-63-7 | 5mg | 794.58元 |
| 2026/07/06 | S0884 | (3E,5E)-3,5-雙(4-硝基亞芐基)哌啶-4-酮 RA-9 | 919091-63-7 | 25mg | 2432.03元 |