| Identification | Back Directory | [Name]
L-BUTHIONINE-(S,R)-SULFOXIMINE | [CAS]
83730-53-4 | [Synonyms]
L-BSO
nsc326231
L-BUTHIONINESULPHOXIMINE
L-BUTHIONINE-SULFOXIMINE
D-Buthionine Sulfoximine
Buthionine - sulfoxide iMine
L-BUTHIONINE-[S,R]-SULFOXIME
L-BUTHIONINE-S,R-SULPHOXIMINE
L-BUTHIONINE-(S,R)-SULFOXIMINE
L-BUTHIONINE (R,S)-SULFOXIMINE
-2-Amino-4-(butylsulfonimidoyl)
L-Buthionine-(S,R)-sulfoximine,99%
L-Buthionine-(S,R)-sulfoxiMine, 99% 1GR
(S)-2-Amino-4-(S-butylsulfonimidoyl)butyric acid
(2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid | [Molecular Formula]
C8H18N2O3S | [MDL Number]
MFCD00067000 | [MOL File]
83730-53-4.mol | [Molecular Weight]
222.31 |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
224-228 °C (dec.)
| [Boiling point ]
382.3±52.0 °C(Predicted) | [density ]
1.29 | [refractive index ]
1.6300 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL, clear, colorless to faintly yellow
| [form ]
Fine Powder | [color ]
White | [biological source]
synthetic (organic) | [Water Solubility ]
water: 50mg/mL, clear to slightly hazy, colorless to faintly yellow | [BRN ]
2367136 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily. | [CAS DataBase Reference]
83730-53-4 |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
A potent and specific inhibitor of alpha-glutamylcysteine synthetase | [Uses]
inhibitor of gamma-glutamylcysteine synthetase | [Uses]
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. 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-resistant tumors. | [Hazard]
A reproductive hazard.
| [Description]
L-Buthionine-(S,R)-sulfoximine 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. Administration of L-buthionine-(S,R)-sulfoximine 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, L-buthionine-(S,R)-sulfoximine has been shown to enhance the toxicity of various chemotherapeutic agents in drug-resistant tumors. | [Definition]
ChEBI: L-buthionine-(S,R)-sulfoximine is a 2-amino-4-(S-butylsulfonimidoyl)butanoic acid which has S-configuration. It is a inhibitor of gamma-glutamylcysteine synthetase and glutathione (GSH) biosynthesis and is capable of enhancing the apoptotic effects of several chemotherapeutic agents. It has a role as a ferroptosis inducer and an EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor. | [Biochem/physiol Actions]
Blocks cellular resistance to chemotherapy by inhibiting γ-glutamylcysteine synthetase, a key enzyme in glutathione biosynthesis. Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes. | [storage]
Store at -20°C | [References]
1) Lu?et al.?(2009),?Regulation of glutathione synthesis; Mol. Aspects Med.?30?42
2) Lee?et al.?(2008),?Adaptive response to GSH depletion and resistance to L-buthionine-(S,R)-sulfoximine; Mol. Cell Biochem.?12?174
3) Qiwei et al. (2016),?The effects of buthionine sulfoximine on the proliferation and apoptosis of biliary tract cancer cells induced by cisplatin and gemcitabine; Oncol. Lett.?11?474
4) Glasuer and Chandel (2014),?Targeting antioxidants for cancer therapy; Biochem. Pharmacol.?92?90 |
|
|