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Merck

19176

Sigma-Aldrich

DL-Buthionin-sulfoximin

≥99.0% (TLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C8H18N2O3S
CAS-Nummer:
Molekulargewicht:
222.31
Beilstein:
2367136
MDL-Nummer:
UNSPSC-Code:
12352202
PubChem Substanz-ID:
NACRES:
NA.77

Biologische Quelle

synthetic

Qualitätsniveau

Assay

≥99.0% (TLC)

Form

powder or crystals

mp (Schmelzpunkt)

215 °C

Löslichkeit

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

Lagertemp.

2-8°C

SMILES String

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)

InChIKey

KJQFBVYMGADDTQ-UHFFFAOYSA-N

Anwendung

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

Biochem./physiol. Wirkung

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).

Sonstige Hinweise

Depletes glutathionine in isolated cells

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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N Yamauchi et al.
Biology of reproduction, 61(3), 828-833 (1999-08-24)
The present study was conducted to examine effects of cysteamine in culture medium on progression of meiosis, glutathione (GSH) content, kinase activities (histone H1 kinase and mitogen-activated protein kinase), and male pronuclear formation after in vitro insemination of cumulus-denuded oocytes
Jong-Shyan Wang et al.
European journal of applied physiology, 95(4), 290-297 (2005-08-13)
Exercise is linked with intensity-dependent immune response. Intracellular redox status is important in programmed cell death. This study, by closely examining 18 sedentary men who exercised moderately and severely (ie. 60% and 80% VO2max, respectively) for 40 min, investigated how
Christine Syng-Ai et al.
Molecular cancer therapeutics, 3(9), 1101-1108 (2004-09-16)
Curcumin, a well-known dietary pigment derived from Curcuma longa, inhibited growth of several types of malignant cells both in vivo and in vitro. However, its mechanism of action still remains unclear. In this study, we have focused primarily on the
Sophia Fried et al.
Scientific reports, 10(1), 7599-7599 (2020-05-07)
Biliary atresia is a neonatal liver disease with extrahepatic bile duct obstruction and progressive liver fibrosis. The etiology and pathogenesis of the disease are unknown. We previously identified a plant toxin, biliatresone, responsible for biliary atresia in naturally-occurring animal models
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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