19176

DL-Buthionin-sulfoximin

synthetic, ≥99.0% (TLC), glutathione biosynthesis inhibitor, powder or crystals

• Synonym(e): DL-Buthionine (S,R)-sulfoximine, BSO, Buthionine sulfoximine, Butionine sulfoximine
• Empirische Formel (Hill-System): C₈H₁₈N₂O₃S
• CAS-Nummer: 5072-26-4
• Molekulargewicht: 222.31
• NACRES: NA.77
• PubChem Substance ID: 57647786
• UNSPSC Code: 12352202
• MDL number: MFCD00070309
• Beilstein/REAXYS Number: 2367136

Eigenschaften

• Produktname: DL-Buthionin-sulfoximin, ≥99.0% (TLC)
• biological source: synthetic
• Quality Segment: 100
• assay: ≥99.0% (TLC)
• form: powder or crystals
• mp: 215 °C
• solubility: H₂O: 50 mg/mL, clear to almost clear, colorless
• storage temp.: 2-8°C
• SMILES string: CCCCS(=N)(=O)CCC(N)C(O)=O
• 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)
• InChI key: KJQFBVYMGADDTQ-UHFFFAOYSA-N

Beschreibung

Application

DL-Buthionine-sulfoximine is suitable for use to:

• examine whether the inhibition of glutathione by BSO enhances the apoptotic effect of estrogen on antihormone-resistant human breast cancer cells[1]
• investigate the effect of BSO on development of bovine embryos[2]
• inhibit GSH in several studies[3][4]
• investigate the effect of GSH synthesis on oocyte maturation[5]

It may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH

Biochem/physiol Actions

DL-Buthionine-sulfoximine inhibits the biosynthesis of Glutathione (GSH) in liver and other peripheral organs. It does not have any effect on GSH in the CNS.[6] It augments the antiproliferative action of reactive oxygen species (e.g., hydrogen peroxide), and agents that indirectly cause accumulation of reactive oxygen species (e.g., 2-methoxyestradiol, which increases intracellular superoxide anion).[7]

Other Notes

Depletes glutathionine in isolated cells[8][9]

Sicherheitshinweise

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves