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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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250 MG

$117.00

1 G

$365.00

5 G

$1,260.00

$117.00

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About This Item

Empirical Formula (Hill Notation):
C8H18N2O3S
CAS Number:
5072-26-4
Molecular Weight:
222.31
NACRES:
NA.77
PubChem Substance ID:
57647786
UNSPSC Code:
12352202
MDL number:
MFCD00070309
Beilstein/REAXYS Number:
2367136

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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

100

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This Item
B25156443047634
DL-Buthionine-sulfoximine ≥99.0% (TLC)

Sigma-Aldrich

19176

DL-Buthionine-sulfoximine

L-Buthionine-sulfoximine ≥97% (TLC)

Sigma-Aldrich

B2515

L-Buthionine-sulfoximine

DL-Methionine sulfoxide ≥98.5% (NT)

Sigma-Aldrich

64430

DL-Methionine sulfoxide

Fmoc-Met-OH ≥98.0% (HPLC)

Sigma-Aldrich

47634

Fmoc-Met-OH

assay

≥99.0% (TLC)

assay

≥97% (TLC)

assay

≥98.5% (NT)

assay

≥98.0% (HPLC)

biological source

synthetic

biological source

synthetic (organic)

biological source

-

biological source

-

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

form

powder or crystals

form

powder

form

-

form

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

solubility

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

solubility

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

-

solubility

-

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[1]
  • investigate the effect of BSO on development of bovine embryos[2]
  • inhibit GSH in several studies[3][4]
  • investigate the effect of GSH synthesis on oocyte maturation[5]
It may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH[6]

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.[7] 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).[8]

Other Notes

Depletes glutathionine in isolated cells[9][10]

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN4733
BCCN4732
BCCN1185
BCCK0388
BCCJ2617

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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
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
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)
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