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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/REAXYS Number:
2367136
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
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

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


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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
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)
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
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

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