B2640

DL-Buthionine-(S,R)-sulfoximine

• Linear Formula: CH₃(CH₂)₃S(O)(=NH)CH₂CH₂CH(NH₂)CO₂H
• CAS Number: 5072-26-4
• Molecular Weight: 222.31
• MDL number: MFCD00070309
• UNSPSC Code: 12161501
• PubChem Substance ID: 24278264
• NACRES: NA.77

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• Assay: ≥98% (TLC)
• form: powder
• mp: 215 °C (dec.) (lit.)
• solubility: water: 50 mg/mL, clear to very slightly hazy, colorless to yellow
• 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

Description

General description

DL-buthionine-SR-sulfoximine (BSO) is an amino acid analogue, which acts as an inhibitor of γ-glutamylcysteine synthetase. BSO increases the sensitivity of Trypanosoma cruzi to antiparasitic drugs, such as nifurtimox or benznidazole.

Application

DL-Buthionine-(S,R)-sulfoximine has also been used:

• to induce oxidative stress in Starlings
• to deplete choroidal glutathione (GSH) in two-day-old rat pups
• to test its inhibitory effect on the enzymes, γ-glutamylcysteine synthetase and trypanothione synthetase (TryS) from T. cruzi

DL-Buthionine-(S,R)-sulfoximine has been used to deplete cellular glutathione levels in retinal ganglion cell 5 (RGC-5) cell line.

Biochem/physiol Actions

Depletes cellular glutathione and downregulates GST level.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves