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B2640

Sigma-Aldrich

DL-Buthionine-(S,R)-sulfoximine

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About This Item

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

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Buthionine sulfoximine increases the toxicity of nifurtimox and benznidazole to Trypanosoma cruzi
Faundez M, et al.
Antimicrobial Agents and Chemotherapy, 49(1), 126-130 (2005)
Experimental inhibition of a key cellular antioxidant affects vocal communication
Messina S, et al.
Functional Ecology, 1101-1110 (2017)
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)
Jone López-Erauskin et al.
Brain : a journal of neurology, 135(Pt 12), 3584-3598 (2012-12-20)
A common process associated with oxidative stress and severe mitochondrial impairment is the opening of the mitochondrial permeability transition pore, as described in many neurodegenerative diseases. Thus, inhibition of mitochondrial permeability transition pore opening represents a potential target for inhibiting
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