L-Buthionine-(S,R)-sulfoximine

• CAT Number: R000634
• CAS Number: 83730-53-4
• Molecular Formula: C8H18N2O3S
• Molecular Weight: 222.303
• Purity: ≥95%
• Synonyms: (2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid; L-Buthionine Sulfoximine; NSC 326231
• Storage: -20°C
• IUPAC Name: (2S)-2-amino-4-(butylsulfonimidoyl)butanoic acid
• InChI: 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)/t7-,14?/m0/s1
• InChIKey: KJQFBVYMGADDTQ-CVSPRKDYSA-N
• SMILES: CCCCS(=N)(=O)CCC(C(=O)O)N

Buthionine sulfoximine (BSO; CAS 83730-53-4) is an irreversible inhibitor of γ-<wbr />glutamylcysteine synthetase (Ki <100 μM), the rate-<wbr />limiting enzyme for L-<wbr />glutathione (GSH) synthesis, that induces oxidative stress in cells by depleting GSH. Administration of BSO leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis. Whereas elevated glutathione levels are associated with tumor cell resistance, BSO has been shown to enhance the toxicity of various chemotherapeutic agents in drug-<wbr />resistant tumors.

Reference

1.Reliene, Ramune, and Robert H. Schiestl. "Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice." Carcinogenesis 27.2 (2006): 240-244.
2.Griffith, O. W. "Mechanism of action, metabolism, and toxicity of buthionine sulfoximine and its higher homologs, potent inhibitors of glutathione synthesis." Journal of Biological Chemistry 257.22 (1982): 13704-13712.
3.Takahashi, Kyohei, et al. "Buthionine sulfoximine promotes methylglyoxal-induced apoptotic cell death and oxidative stress in endothelial cells." Biological and Pharmaceutical Bulletin 33.4 (2010): 556-560.
4.Han, Yong Hwan, 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." International journal of molecular medicine 24.2 (2009): 261-268.
5.Lewis-Wambi, Joan S., et al. "Buthionine sulfoximine sensitizes antihormone-resistant human breast cancer cells to estrogen-induced apoptosis." Breast Cancer Research 10.6 (2008): R104.