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19176

Sigma-Aldrich

DL-Buthionine-sulfoximine

≥99.0% (TLC)

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:
5072-26-4
Molecular Weight:
222.31
Beilstein/REAXYS Number:
2367136
MDL number:
MFCD00070309
UNSPSC Code:
12352202
PubChem Substance ID:
57647786
NACRES:
NA.77

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

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

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
It may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
A Slivka et al.
Journal of neurochemistry, 50(5), 1391-1393 (1988-05-01)
Previous studies indicated that DL-buthionine sulfoximine (DL-BSO), an agent that inhibits the biosynthesis of GSH in liver and other peripheral organs, fails to suppress levels of GSH in the CNS. In the current study, preweanling mice responded to repeated injections
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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