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B2640

DL-Buthionine-(S,R)-sulfoximine

Name: <SC>DL</SC>-Buthionine-(<I>S</I>,<I>R</I>)-sulfoximine
Brand: SIGMA

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:

5072-26-4

Molecular Weight:

222.31

UNSPSC Code:

12161501

PubChem Substance ID:

24278264

NACRES:

NA.77

MDL number:

MFCD00070309

Assay:

≥98% (TLC)

Form:

powder

Quality level:

200

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Product Name

DL-Buthionine-(S,R)-sulfoximine,

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

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

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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Certificates of Analysis (COA)

Lot/Batch Number

0000517274

0000498015

0000443005

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Brain-derived neurotrophic factor released from engineered mesenchymal stem cells attenuates glutamate- and hydrogen peroxide-mediated death of staurosporine-differentiated RGC-5 cells.

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)

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)

Buthionine sulfoximine is a multitarget inhibitor of trypanothione synthesis in Trypanosoma cruzi.

Citlali Vázquez et al.

FEBS letters, 591(23), 3881-3894 (2017-11-12)

Buthionine sulfoximine (BSO) induces decreased glutathione (GSH) and trypanothione [T(SH)2 ] pools in trypanosomatids, presumably because only gamma-glutamylcysteine synthetase (γECS) is blocked. However, some BSO effects cannot be explained by exclusive γECS inhibition; therefore, its effect on the T(SH)2 metabolism

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Global Trade Item Number

SKU	GTIN
B2640-500MG	04061833427002
B2640-1G	04061833426999
B2640-5G	04061833427019

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