Buthionine Sulfoximine

Cayman Chemical Item Number 14484

L-Buthionine-S,R-Sulfoximine; BSO; NSC 326231 (CAS 83730-53-4)

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Description

Buthionine sulfoximine (BSO) is an irreversible inhibitor of γ-glutamylcysteine synthetase (Ki <100 μM), the rate-limiting enzyme for L-glutathione (GSH) synthesis, that induces oxidative stress in cells by depleting GSH.1,2 Administration of BSO leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis.3,4 Whereas elevated glutathione levels are associated with tumor cell resistance, BSO has been shown to enhance the toxicity of various chemotherapeutic agents in drug-resistant tumors.5

1. Reliene, R., and Schiestl, R.H. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis 27(2) 240-244 (2006).

2. Griffith, O.W. Mechanism of action, metabolism, and toxicity of buthionine sulfoximine and its higher homologs, potent inhibitors of glutathione synthesis. J Biol Chem 257(22) 13704-13712 (1982).

3. Takahashi, K., Tatsunami, R., Oba, T., et al. Buthionine sulfoximine promotes methylglyoxal-induced apoptotic cell death and oxidative stress in endothelial cells. Biol Pharm Bull 33(4) 556-560 (2010).

4. Han, Y.H., Moon, H.J., You, B.R., et al. The effects of buthionine sulfoximine, diethyldithiocarbamate or 3-amino-1,2,4-triazole on propyl gallate-treated HeLa cells in relation to cell growth, reactive oxygen species and glutathione. Int J Mol Med 24(2) 261-268 (2009).

5. Lewis-Wambi, J.S., Kim, H.R., Wambi, C., et al. Buthionine sulfoximine sensitizes antihormone-resistant human breast cancer cells to estrogen-induced apoptosis. Breast Cancer Res 10(6) (2008).

Synonyms
  • L-Buthionine-S,R-Sulfoximine
  • BSO
  • NSC 326231
Formal Name 2S-​amino-​4-​(S-​butylsulfonimidoyl)-​butanoic acid
CAS Number 83730-53-4
Molecular Formula C8H18N2O3S
Formula Weight 222.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=S(CCCC)​(CC[C@H]​(N)​C(O)​=O)​=N
InCHI Code
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​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)​/t7-,14?/m0/s1
InCHI Key
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KJQFBVYMGADDTQ-CVSPRKDYSA-N

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Size Price Quantity Subtotal
250 mg $65.00 $0.00
500 mg $124.00 $0.00
1 g $234.00 $0.00
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Pricing updated 2015-05-26. Prices are subject to change without notice.

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