B2640
DL-Buthionine-(S,R)-sulfoximine
synthetic (organic), ≥98% (TLC), γ-glutamylcysteine synthetase inhibitor, powder
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About This Item
Linear Formula:
CH3(CH2)3S(O)(=NH)CH2CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
222.31
UNSPSC Code:
12161501
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
DL-Buthionine-(S,R)-sulfoximine,
biological source
synthetic (organic)
Quality Level
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Articles
Discover Bioactive Small Molecules for ADME/Tox
Matthew M Harper et al.
Experimental eye research, 89(4), 538-548 (2009-06-16)
The purpose of this study was to determine the viability of cell-based delivery of brain-derived neurotrophic factor (BDNF) from genetically modified mesenchymal stem cells (MSCs) for neuroprotection of RGC-5 cells. RGC-5 cells were differentiated with the protein kinase inhibitor staurosporine
Glutathione: interorgan translocation, turnover, and metabolism
Griffith OW and Meister A
Proceedings of the National Academy of Sciences of the USA, 76(11), 5606-5610 (1979)
Experimental inhibition of a key cellular antioxidant affects vocal communication
Messina S, et al.
Functional Ecology, 1101-1110 (2017)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B2640-500MG | 04061833427002 |
| B2640-1G | 04061833426999 |
| B2640-5G | 04061833427019 |