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Merck

19176

Sigma-Aldrich

DL-Buthionine-sulfoximine

≥99.0% (TLC)

Sinónimos:

DL-Buthionine (S,R)-sulfoximine, BSO, Buthionine sulfoximine, Butionine sulfoximine

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About This Item

Fórmula empírica (notación de Hill):
C8H18N2O3S
Número de CAS:
Peso molecular:
222.31
Beilstein:
2367136
Número MDL:
Código UNSPSC:
12352202
ID de la sustancia en PubChem:
NACRES:
NA.77

origen biológico

synthetic

Nivel de calidad

Ensayo

≥99.0% (TLC)

Formulario

powder or crystals

mp

215 °C

solubilidad

H2O: 50 mg/mL, clear to almost clear, colorless

temp. de almacenamiento

2-8°C

cadena SMILES

CCCCS(=N)(=O)CCC(N)C(O)=O

InChI

1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)

Clave InChI

KJQFBVYMGADDTQ-UHFFFAOYSA-N

Aplicación

DL-Buthionine-sulfoximine is suitable for use to:
  • examine whether the inhibition of glutathione by BSO enhances the apoptotic effect of estrogen on antihormone-resistant human breast cancer cells
  • investigate the effect of BSO on development of bovine embryos
  • inhibit GSH in several studies
  • investigate the effect of GSH synthesis on oocyte maturation
It may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH

Acciones bioquímicas o fisiológicas

DL-Buthionine-sulfoximine inhibits the biosynthesis of Glutathione (GSH) in liver and other peripheral organs. It does not have any effect on GSH in the CNS. It augments the antiproliferative action of reactive oxygen species (e.g., hydrogen peroxide), and agents that indirectly cause accumulation of reactive oxygen species (e.g., 2-methoxyestradiol, which increases intracellular superoxide anion).

Otras notas

Depletes glutathionine in isolated cells

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órganos de actuación

Respiratory system

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

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Evaluation of hepatotoxicity and nephrotoxicity of natural food colorants in mice depleted of glutathione by DL-buthionine sulfoximine.
Kawazoe S, et al.
Journal of Health Science, 46, 56-58 (2000)
Joan S Lewis-Wambi et al.
Breast cancer research : BCR, 10(6), R104-R104 (2008-12-09)
Estrogen deprivation using aromatase inhibitors is one of the standard treatments for postmenopausal women with estrogen receptor (ER)-positive breast cancer. However, one of the consequences of prolonged estrogen suppression is acquired drug resistance. Our group is interested in studying antihormone
Yuka Hirai et al.
Biological & pharmaceutical bulletin, 29(5), 1064-1067 (2006-05-03)
2-Methoxyestradiol (2-ME), an endogenous metabolite of 17beta-estradiol, induces the intracellular accumulation of superoxide anion (O2*-) and buthionine sulfoximine (BSO) is an inhibitor of glutathione (GSH) synthesis. We have examined the combination anticancer effect of 2-ME and BSO accompanied with hydrogen
M A Baker et al.
Analytical biochemistry, 190(2), 360-365 (1990-11-01)
By combining the least complicated and expedient methods of sample handling with the sensitivity and specificity of the GSH assay by enzymatic recycling and the small volumes and software capabilities of microtiter plate technology we have devised a rapid, sensitive
M Takahashi et al.
Biology of reproduction, 49(2), 228-232 (1993-08-01)
The purpose of this investigation was to determine the effect of beta-mercaptoethanol (beta-ME) and cysteamine, low-molecular-weight thiol compounds, on the development and intracellular glutathione content of bovine embryos obtained by in vitro fertilization of in vitro-matured oocytes. Embryos developed to

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