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
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
MDL number:
Beilstein/REAXYS Number:
2367136
Product Name
DL-Buthionine-sulfoximine, ≥99.0% (TLC)
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)
SMILES string
CCCCS(=N)(=O)CCC(N)C(O)=O
InChI key
KJQFBVYMGADDTQ-UHFFFAOYSA-N
biological source
synthetic
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
Quality Level
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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 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
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
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