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1162656-22-5

中文名稱 4-乙基-2,6-雙(吡啶-3-基亞甲基)環(huán)己酮
英文名稱 MCB-613
CAS 1162656-22-5
分子式 C20H20N2O
分子量 304.39
MOL 文件 1162656-22-5.mol
更新日期 2024/09/13 14:46:00
1162656-22-5 結(jié)構(gòu)式 1162656-22-5 結(jié)構(gòu)式

基本信息

中文別名
MCB-613游離態(tài)
4-乙基-2,6-雙(吡啶-3-基亞甲基)環(huán)己酮
(2E,6E)-4-乙基-2,6-二(3-吡啶基亞甲基)環(huán)己酮
英文別名
CS-2522
MCB-613
4-ethyl-2,6-bis(pyridin-3-ylmethylene)cyclohexanone
(2E,6E)-4-Ethyl-2,6-bis(3-pyridinylmethylene)cyclohexanone
Cyclohexanone, 4-ethyl-2,6-bis(3-pyridinylmethylene)-, (2E,6E)-
(2E,6E)-4-ethyl-2,6-bis(pyridin-3-ylmethylidene)cyclohexan-1-one
所屬類別
生物化工:激動(dòng)劑抑制劑

物理化學(xué)性質(zhì)

沸點(diǎn)510.4±50.0 °C(Predicted)
密度1.159±0.06 g/cm3(Predicted)
儲(chǔ)存條件Sealed in dry,Room Temperature
溶解度insoluble in H2O; ≥13.2 mg/mL in DMSO with gentle warming; ≥9.26 mg/mL in EtOH with ultrasonic
酸度系數(shù)(pKa)4.36±0.12(Predicted)
形態(tài)固體
顏色Light yellow to yellow

安全數(shù)據(jù)

危險(xiǎn)性符號(hào)(GHS)GHS hazard pictograms
GHS07
警示詞警告
危險(xiǎn)性描述H302

常見問題列表

制備
以3-吡啶甲醛及對(duì)乙基環(huán)己酮為原料,通過Claisen-Schmidt縮合反應(yīng)得到雙吡啶α,β-不飽和酮中間體4-乙基-2,6-雙(吡啶-3-基亞甲基)環(huán)己酮。采用干燥的HCl作為縮合反應(yīng)的催化劑,操作簡(jiǎn)便,產(chǎn)率較高,均在85%以上。
1162656-22-5的合成
生物活性
MCB-613 是一種有效的類固醇受體共激活因子 (SRC) 小分子“刺激物” (SMS),超刺激 SRCs 的轉(zhuǎn)錄活性。 MCB-613 增加了 SRC 與其他共激活因子的相互作用,并顯著誘導(dǎo) ER 應(yīng)激與活性氧 (ROS) 的產(chǎn)生相結(jié)合。 MCB-613 是一種 SMS,通過過度刺激 SRC 致癌程序,靶向癌基因用作抗癌藥物。
體外研究

MCB-613 (6-8 μM; 24 hours) activates endogenous MMP13 mRNA expression in MDA-MB-231 cells. MCB-613 (2-10 μM; 4 hours) leads to proteasome dysfunction and ER stress, the induction of the markers for unfolded protein response (UPR), including the phosphorylation of eIF2α and IRE1α as well as the induction of ATF4 protein expression. MCB-613 (0-7 μM; 4 hours) affects SRC-3 KO and WT HeLa cell viability, SRC-3 WT HeLa cell is more affected by MCB-613 compared with KO cells.

RT-PCR

Cell Line: MDA-MB-231 cells
Concentration: 6 μM; 8 μM
Incubation Time: 24 hours
Result: Increased MMP13 mRNA expression.

Western Blot Analysis

Cell Line: HeLa cells
Concentration: 2 μM; 4 μM; 6 μM; 8 μM; 10 μM
Incubation Time: 24 hours
Result: Induced the p-eIF2α, p-IRE1α, and ATF-4 protein expression.

Cell Viability Assay

Cell Line: SRC-3 KO and WT HeLa cells
Concentration: 3 μM; 4 μM; 5 μM; 6 μM; 7 μM
Incubation Time: 24 hours
Result: Decreased SRC-3 KO and WT HeLa cell viability.
體內(nèi)研究

MCB-613 (intravenous injection; 20 mg/kg; 3 times/week; 7 weeks) significantly and dramatically stalls the growth of the tumor compared with the control group and causes no obvious animal toxicity

Animal Model: MCF-7 breast cancer mouse xenograft model (athymic nude mice by injecting MCF-7 cells into mammary fat pads)
Dosage: 20 mg/kg
Administration: Intravenous injection; 20 mg/kg; 3 times/week; 7 weeks
Result: Inhibited tumor growth in vivo.
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