L-Buthionine-S,R-sulfoximine
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L-Buthionine-S,R-sulfoximine
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CAS No:
83730-53-4
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Formula:
C8H18N2O3S
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Chemical Name:
L-Buthionine-S,R-sulfoximine
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Synonyms:
Butanoic acid,2-amino-4-(S-butylsulfonimidoyl)-,(2S)-;(2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic acid;L-Buthionine sulfoximine;L-Buthionine-S,R-sulfoximine;NSC 326231;L-Buthionine-(R,S)-sulfoximine;(2S)-2-Amino-4-(butylsulfonimidoyl)butanoic acid
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CAS No:
Description
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.
Characteristics
113 Ų
1.29
224-228 °C (dec.)
382.3±52.0 °C(Predicted)
1.6300 (estimate)
H2O > 100 (mg/mL)|Acetate buffer, pH4 > 100 (mg/mL)|Carbonate buffer, pH9 > 100 (mg/mL)|0.1 N HCl > 100 (mg/mL)|0.1 N NaOH > 100 (mg/mL)|MeOH < 1 (mg/mL)|EtOH (95 %) < 1 (mg/mL)|CH3CN < 1 (mg/mL)|EtOAC < 1 (mg/mL)|CHC13 < 1 (mg/mL)|Dimethylacetamide < 1 (mg/mL)|DMSO < 1 (mg/mL)
146.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Safety Information
3
36/37/38
22-24/25
EK7713440
Xi
Bulk: Samples subjected to both light and dark conditions at room temperature showed no decomposition after 90 days. Samples kept at 50 °C in both light and dark conditions showed about 1% decomposition after 90 days. Solution: BSO was found to be stable in aqueous solution for 72 hours when stored at room temperature and under laboratory light.
L-Buthionine-S,R-sulfoximine Use and Manufacturing
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.
Computed Properties
Molecular Weight:222.31
XLogP3:-0.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:222.10381361
Monoisotopic Mass:222.10381361
Topological Polar Surface Area:113
Heavy Atom Count:14
Complexity:284
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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