鸦胆子苦醇

鸦胆子苦醇

中文名称鸦胆子苦醇
中文同义词BRUSATOL 鸦胆子苦醇;鸦胆苦醇;鸦胆子苦醇对照品;(1R,2S,3S,3AS,3A1R,4R,6AR,7AR,11AS,11BR)-甲基 1,2,9-三羟基-8,11A-二甲基-4-((3-甲基丁-2-烯酰基)氧基)-5,10-二氧代-2,3,3A,4,5,6A,7,7A,10,11,11A,11B-十二氢-1H-3,3A1-(环氧甲基)二苯并[DE,G]苯并吡喃-3-羧酸酯;鸦胆苦醇(鸦胆子苦醇);标准品对照品】BRUSATOL
英文名称brusatol
英文同义词13,20-Epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester;13,20-Epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicrasa-3-ene-21-oic acid methyl ester;Picras-3-en-21-oicacid,13,20-epoxy-3,11,12-trihydroxy-15-[(3-Methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-,Methyl ester, (11b,12a,15b)-;NSC 172924;Yatansin;Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-;Brustaol;Brusatol (NSC 172924)
CAS号14907-98-3
分子式C26H32O11
分子量520.53
EINECS号
相关类别植物提取物;标准品;对照品;中药对照品;标准品,对照品;标准品-对照品;精细化工;分析试剂标准品;20版药典新增;标准品,对照品;三萜
Mol文件14907-98-3.mol
结构式鸦胆子苦醇 结构式

鸦胆子苦醇 性质

沸点724.3±60.0 °C(Predicted)
密度1.46±0.1 g/cm3 (20 ºC 760 Torr)
储存条件-20°C
溶解度DMF:1mg/mL; DMSO:1mg/mL; DMSO:PBS (pH 7.2) (1:1):0.5 mg/mL
酸度系数(pKa)8.81±0.70(Predicted)
形态粉末
颜色白色至米色
旋光性 (optical activity)[α]/D +35 to +44°, c = 0.5 in acetone
LogP0.393 (est)

鸦胆子苦醇 用途与合成方法

Brusatol (NSC 172924),可分离自B. javanica果实,是一种NRF2抑制剂。
TargetValue
Nrf2
()

A potential therapeutic application of an Nrf2 inhibitor such as Brusatol (NSC 172924) is the downregulation of Nrf2 pathway components in cells harboring constitutively high levels of the transcription factor. Brusatol (NSC 172924) provokes the depletion of Nrf2 via a mechanism that is not dependent on Keap1 and the proteasomal and autophagic protein degradation systems. Brusatol (NSC 172924) provokes a rapid and transient depletion of Nrf2 protein, through a posttranscriptional mechanism, in mouse Hepa-1c1c7 hepatoma cells. Brusatol (NSC 172924) also inhibits Nrf2 in freshly isolated primary human hepatocytes. To explore the possible synergistic cytotoxicity of Brusatol (NSC 172924) in combination with CDDP, the study investigates the effects of Brusatol and CDDP cotreatment on CT-26 cell viability using an MTT assay. CT-26 cells are treated with various concentrations of Brusatol (0.05, 0.15, 0.45, 1.35, 4.05 and 12.15 μg/mL) and CDDP (0.05, 0.15, 0.45, 1.35, 4.05 and 12.15 μg/mL) for 48 h, either alone or in combination. Following treatment with Brusatol (NSC 172924) and CDDP for 48 h, the viability of CT-26 cells is reduced in a dose-dependent manner, with IC 50 values of 0.27±0.01 and 1.44±0.22 μg/mL, respectively. When Brusatol (NSC 172924) is combined with CDDP at a constant concentration ratio of 1:1, cell growth inhibition is markedly enhanced compared with single-agent treatment; the IC 50 value of Brusatol (NSC 172924) and CDDP cotreatment is 0.19±0.02 μg/mL.

To explore the anticancer effect of Brusatol in vivo, A549 xenografts grown in nude mice are used as a model. Nude mice are injected with A549 cells to induce tumor growth, followed by a single i.p. injection of 2 mg/kg Brusatol. Tumors are isolated 24 h or 48 h postinjection. Nrf2 protein levels are significantly decreased at 24 h or 48 h postinjection, indicating that Brusatol (NSC 172924) is able to reach the tumor tissue and inhibit the Nrf2 pathway. To measure tumor growth, two different experiments are performed. In the first experiment, once the tumor size reaches an average of 230 mm 3 , DMSO, Brusatol (NSC 172924) (2 mg/kg), Cisplatin (2 mg/kg), or Cisplatin (2 mg/kg) and Brusatol (2 mg/kg) combined treatment is i.p. injected every other day for a total of five times. Cisplatin or Brusatol (NSC 172924) alone does not inhibit tumor growth significantly, whereas in the combination group, tumor size is significantly reduced.

化学性质 
白色结晶性粉末,可溶于甲醇、乙醇、DMSO等有机溶剂,来源于鸦胆子Brucea javanica。
用途 
一种来源于植物的天然类西林类药物,通过抑制细胞蛋白的从头合成,在肿瘤培养中表现出广泛的细胞毒性。

安全信息

MSDS信息

更新日期产品编号产品名称CAS号包装价格
2024/01/16S7956鸦胆子苦醇
Brusatol
14907-98-32mg949.85元
2024/01/16S7956Brusatol14907-98-310mM (1mL in DMSO)1613.43元

鸦胆子苦醇 上下游产品信息

"鸦胆子苦醇"相关产品信息
鸦胆子苷L 鸦胆苦内酯B 鸦胆苦内酯C 鸦胆子素B 鸦胆子内脂A N/A 鸦胆子素A 鸦胆子素D 四氢吡喃-4-乙酸 ALFA-甲基谷氨酸 2-羟基-3,5,5-三甲基-2-环己烯-1-酮 十三烷二酸 乙酸二氢葛缕酯 八氢-2H-1-苯并吡喃-2-酮 壬二酸氢甲酯 2-四氢糠酸甲酯 (2-甲基丁氧代)乙酸-2-丙烯醇酯 鸦胆子内酯
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