BSO (L-Buthionine-(S,R)-sulfoximine)

For research use only.

Catalog No.S9728 Synonyms: L-Buthionine sulfoximine

2 publications

BSO (L-Buthionine-(S,R)-sulfoximine) Chemical Structure

CAS No. 83730-53-4

BSO (L-Buthionine-(S,R)-sulfoximine, L-Buthionine sulfoximine) is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase (γ-glutamylcysteine synthetase, γ-GCS) and depletes cellular glutathione levels. The IC50 of BSO on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.

Selleck's BSO (L-Buthionine-(S,R)-sulfoximine) has been cited by 2 publications

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Biological Activity

Description

BSO (L-Buthionine-(S,R)-sulfoximine, L-Buthionine sulfoximine) is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase (γ-glutamylcysteine synthetase, γ-GCS) and depletes cellular glutathione levels. The IC50 of BSO on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.

In vitro

BSO (L-Buthionine-(S,R)-sulfoximine) synergistically enhanced BCNU activity against melanoma cell lines and human tumors. BSO (50 μM) treatment for 48 hr results in a 95% decrease in ZAZ and M14 melanoma cell line GSH levels, and a 60% decrease in GST enzyme activity. GST-μ protein and mRNA levels are significantly reduced in both cell lines. GST-π expression is unaffected. BSO enhancement of alkylator action may be related in part to down regulation of GST.[1]

In vivo

LButhionine-S,R-sulfoximine (L-S,R-BSO) substantially inhibits GSH production at a greater degree and causes a higher toxicity to guinea pigs than mice, implying that mice may have an additional protective mechanism against oxidative stress injury. Indeed, administration of L-S,R-BSO to mice inhibits tissue GSH production while increasing ascorbate levels. L-S,R-BSO also increases tissue ascorbate levels in mice fed a ascorbate and dehydroascorbatefree diet suggesting activation of ascorbate synthesis, which is further confirmed by increased urinary ascorbate excretion.[2]

Protocol

Cell Research:

[1]

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  • Cell lines: ZAZ, M14 melanoma cell line
  • Concentrations: 50 μM
  • Incubation Time: 6 h, 24 h, 48 h, 72 h
  • Method:

    The effect of BSO treatment on glutathione content (GSH + GSSG) is determined on cells plated in 24-well plates at the same density as in the thymidine incorporation assay. GSH is measured at time zero, and at 6, 24, 48, and 72 hr by a modified Tietze method. GSH standard curves are obtained by dissolving 5 mg GSH in 25 ml 0.01 N HCl and running determinations on serial dilutions. Cell supernatants are prepared by freezethawing cells resuspended to 107 cells per ml in 0.01 M NaP04 + 0.005 M EDTA buffer (pH 7.5) three times, and centrifuging for 30 min at 30,000g at 4℃. GSH levels are determined from the rate of change in optical density at 412 nm, 25℃.


    (Only for Reference)
Animal Research:

[2]

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  • Animal Models: Swiss-Webster mice, guinea pigs
  • Dosages: 2.5 mM/kg, 1.25 mM/kg, 0.625 mM/kg
  • Administration: SC
    (Only for Reference)

Solubility (25°C)

In vitro Water 40 mg/mL (179.92 mM)
DMSO Insoluble
Ethanol Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 222.31
Formula

C8H18N2O3S

CAS No. 83730-53-4
Storage powder
in solvent
Synonyms L-Buthionine sulfoximine

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Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID