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L-Buthionine-(S,R)-sulfoximine
Cat. No. IC23133
CAS. No. 83730-53-4
Key Features and Details
Category
Inhibitor&Activator
Purity
≥99.0%
Formula
C8H18N2O3S
Product Details
Product Name
L-Buthionine-(S,R)-sulfoximine
CAS No.
83730-53-4
Molecular Weight
222.31
Synonyms
L-Buthionine sulfoximine; L-BSO
Formula
C8H18N2O3S
Appearance
Solid
Purity
≥99.0%
SMILES
N[C@H](C(O)=O)CCS(CCCC)(=O)=N
Product Overview
Description
L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.
In Vitro Activity
L-Buthionine-(S,R)-sulfoximine (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-π protein and mRNA levels are significantly reduced in both cell lines. L-Buthionine-(S,R)-sulfoximine (BSO) induces oxidative stress in a cell by irreversibly inhibiting g-glutamylcysteine synthetase, an essential enzyme for the synthesis of glutathione (GSH).
L-Buthionine-(S,R)-sulfoximine (BSO) induces ferroptosis in cancer cells.
In Vivo Activity
BSO causes an elevated frequency of DNA deletions during mouse development. BSO treatment reduced GSH concentration in mouse fetuses by 55% and 70% at 2 mM and 20 mM BSO doses, respectively, compared to untreated mice. Co-treatment with 2 mM BSO and 20 mM NAC depleted GSH to a similar extent as 2 mM BSO, consistent with the function of BSO to inhibit the g-GCS enzyme indispensable for GSH synthesis. Like GSH, cysteine levels dropped following BSO treatment.
Storage & Handling
Storage
-20 °C, sealed storage, away from moisture
*In solvent : -80 °C, 6 months; -20 °C, 1 month (sealed storage, away from moisture)
Shipping
Room temperature in continental US; may vary elsewhere.
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