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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

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.

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. Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.

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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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)
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
Guangqin Zhu et al.
Hereditas, 159(1), 21-21 (2022-05-14)
Ferroptosis, a novel manner of cell death depended on iron ion, contributed to goat mammary epithelial cell dysfunction. Interleukin-6 (IL-6) is a major pro-inflammatory factor during many inflammation-related diseases including mastitis, and a quite recently identified ferroptosis inducer. This study
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)
Katsuya Iuchi et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 125, 109928-109928 (2020-02-01)
An increasing number of metal-based compounds, including arsenic trioxide, auranofin, and cisplatin, have been reported to have antitumor activity. Their beneficial effects are controlled by a transcription factor, nuclear factor (erythroid-derived 2)-like 2 (NRF2). In response to oxidative stress, NRF2

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