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Merck

SML1868

Sigma-Aldrich

Brusatol

≥95% (HPLC)

Sinónimos:

(+)-Brusatol, (11β,12α,15β)-13,20-Epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-picras-3-en-21-oic acid methyl ester, Brutasol, NSC 172924, Yatansin

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About This Item

Fórmula empírica (notación de Hill):
C26H32O11
Número de CAS:
Peso molecular:
520.53
Número MDL:
Código UNSPSC:
12352200
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

origen biológico

(Brucia javanica)

Nivel de calidad

Ensayo

≥95% (HPLC)

Formulario

powder

actividad óptica

[α]/D +35 to +44°, c = 0.5 in acetone

condiciones de almacenamiento

desiccated

color

white to beige

solubilidad

DMSO: 5 mg/mL, clear (warmed)

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

ZZZYHIMVKOHVIH-VILODJCFSA-N

Aplicación

Brusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.[1]

Acciones bioquímicas o fisiológicas

Brusatol (Brutasol) is a plant-derived natural quassinoid that exhibits broad cytotoxicity in cancer cultures (IC50 <1 μM against 457 cancer cell lines) by inhibiting de novo synthesis of cellular proteins (Effective conc. <50 nM in A549 cells), including NRF2.
Brusatol (Brutasol) is a plant-derived natural quassinoid that exhibits broad cytotoxicity.
Brusatol promotes Nrf2 (nuclear factor, erythroid 2 like 2 ) ubiquitination and degradation.[2] Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.[3]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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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
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)
Se-Been Jeon et al.
Journal of animal science and biotechnology, 14(1), 148-148 (2023-12-01)
Oxidative stress, caused by an imbalance in the production and elimination of intracellular reactive oxygen species (ROS), has been recognized for its detrimental effects on mammalian embryonic development. Luteolin (Lut) has been documented for its protective effects against oxidative stress
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)
Shakeel Mir et al.
Breast cancer research : BCR, 24(1), 48-48 (2022-07-15)
A pro-oxidant enzyme, NADPH oxidase 4 (Nox4) has been reported to be a critical downstream effector of TGFβ-induced myofibroblast transformation during fibrosis. While there are a small number of studies suggesting an oncogenic role of Nox4 derived from activated fibroblasts

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