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Merck

SML1868

Sigma-Aldrich

鸦胆子苦醇

≥95% (HPLC)

别名:

(+)-鸦胆子苦醇, (11β,12α,15β)-13,20-环氧-3,11,12-三羟基-15-[(3-甲基-1-氧代-2-丁烯-1-基)氧]-2,16-二氧代-picras-3-烯-21-酸甲酯, NSC 172924, 鸦胆子苦醇

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About This Item

经验公式(希尔记法):
C26H32O11
CAS号:
分子量:
520.53
MDL號碼:
分類程式碼代碼:
12352200
NACRES:
NA.77

生物源

(Brucia javanica)

品質等級

化驗

≥95% (HPLC)

形狀

powder

光學活性

[α]/D +35 to +44°, c = 0.5 in acetone

儲存條件

desiccated

顏色

white to beige

溶解度

DMSO: 5 mg/mL, clear (warmed)

儲存溫度

−20°C

SMILES 字串

CC1=C(O)C(C[C@@]2(C)[C@@]1([H])C[C@]3([H])[C@]45[C@]2([H])[C@@H](O)[C@H](O)[C@](OC5)(C(OC)=O)[C@]4([H])[C@@H](OC(C=C(C)C)=O)C(O3)=O)=O

InChI

1S/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,12,14,17-21,29-31H,7-9H2,1-5H3/t12-,14+,17+,18+,19+,20+,21-,24-,25+,26-/m0/s1

InChI 密鑰

ZZZYHIMVKOHVIH-VILODJCFSA-N

應用

鸦胆子苦醇已被用于研究 Nrf2(核因子,红系 2 样 2)在肠缺血/再灌注诱导损伤中的保护作用。

生化/生理作用

鸦胆子苦醇促进 Nrf2(核因子,红系 2 样 2)泛素化和降解。鸦胆子苦醇上调多种核糖体成分的表达,控制大分子复合物功能。
鸦胆子苦醇是一种植物来源的天然苦木苦味素,在癌症培养物中表现出广泛的细胞毒性(IC 50 <1 μM, 457 个癌细胞系),通过抑制细胞蛋白的从头合成(在 A549 细胞中有效浓度 <50 nM),包括 NRF2

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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分析证书(COA)

Lot/Batch Number

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W Willingham et al.
Biochimica et biophysica acta, 654(2), 169-174 (1981-07-27)
The mechanism by which brusatol inhibits protein synthesis in rabbit reticulocytes has been investigated. When added to reticulocyte lysates, brusatol inhibits endogenous protein synthesis only after a lag of 2-4 min at 30 degrees C. During this period 80 S
Brusatol enhances the efficacy of chemotherapy by inhibiting the Nrf2-mediated defense mechanism.
Ren V, et al.
Proceedings of the National Academy of Sciences of the USA, 108(4), 201014275-201014275 (2011)
Transcription factors Nrf2 and NF-κB contribute to inflammation and apoptosis induced by intestinal ischemia-reperfusion in mice.
Meng Q T, et al.
International Journal of Molecular Medicine, 40(6), 1731-1740 (2017)
Application of mass spectrometry profiling to establish brusatol as an inhibitor of global protein synthesis.
Vartanian S, et al.
Molecular and Cellular Proteomics, 15(4), 1220-1231 (2016)
Steffan Vartanian et al.
Molecular & cellular proteomics : MCP, 15(4), 1220-1231 (2015-12-30)
The KEAP1/Nrf2 pathway senses and responds to changes in intracellular oxidative stress. Mutations that result in constitutive activation of Nrf2 are present in several human tumors, especially non-small cell lung cancer. Therefore, compounds that inhibit Nrf2 activity might be beneficial

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