L-Buthionine-(S,R)-sulfoximine hydrochloride is a cell-permeable, potent, fast acting, orally active 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.

Product information

Molecular Weight: 258.77

Formula: C8H19ClN2O3S

Chemical Name: (2S)-2-amino-4-[butyl(imino)oxo-λ⁶-sulfanyl]butanoic acid hydrochloride

Smiles: Cl.CCCCS(=N)(=O)CC[C@H](N)C(O)=O

InChiKey: FMWPIVFRJOQKNQ-QNURJZHJSA-N

InChi: InChI=1S/C8H18N2O3S.ClH/c1-2-3-5-14(10,13)6-4-7(9)8(11)12;/h7,10H,2-6,9H2,1H3,(H,11,12);1H/t7-,14?;/m0./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

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:

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.

Products are for research use only. Not for human use.