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B2640

Sigma-Aldrich

DL-Buthionine-(S,R)-sulfoximine

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About This Item

Fórmula lineal:
CH3(CH2)3S(O)(=NH)CH2CH2CH(NH2)CO2H
Número de CAS:
5072-26-4
Peso molecular:
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

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
Ingrid Kratzer et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 38(14), 3466-3479 (2018-03-07)
Exposure of the developing brain to toxins, drugs, or deleterious endogenous compounds during the perinatal period can trigger alterations in cell division, migration, differentiation, and synaptogenesis, leading to lifelong neurological impairment. The brain is protected by cellular barriers acting through
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