19176
DL-Buthionine-sulfoximine
synthetic, ≥99.0% (TLC), glutathione biosynthesis inhibitor, powder or crystals
Synonym(s):
DL-Buthionine (S,R)-sulfoximine, BSO, Buthionine sulfoximine, Butionine sulfoximine
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About This Item
Empirical Formula (Hill Notation):
C8H18N2O3S
CAS Number:
Molecular Weight:
222.31
Beilstein:
2367136
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
Product Name
DL-Buthionine-sulfoximine, ≥99.0% (TLC)
biological source
synthetic
Quality Level
Assay
≥99.0% (TLC)
form
powder or crystals
mp
215 °C
solubility
H2O: 50 mg/mL, clear to almost clear, colorless
storage temp.
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)
InChI key
KJQFBVYMGADDTQ-UHFFFAOYSA-N
Related Categories
Application
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
Biochem/physiol Actions
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).
Other Notes
Depletes glutathionine in isolated cells
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
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
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
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
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
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