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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

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Properties

Product Name

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

biological source

synthetic (organic)

Quality Segment

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.

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This Item	19176	SML0959	V105
Sigma-Aldrich B2640 DL-Buthionine-(S,R)-sulfoximine	Sigma-Aldrich 19176 DL-Buthionine-sulfoximine	Sigma-Aldrich SML0959 Bis-1,4-(4-methoxybenzenesulfonamidyl)naphthalene	Sigma-Aldrich V105 S(−)-Verapamil hydrochloride hydrate
description -	description ≥99.0% (TLC)	description ≥98% (HPLC)	description ≥98% (HPLC), powder
assay ≥98% (TLC)	assay ≥99.0% (TLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form powder or crystals	form powder	form powder
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. -
solubility water: 50 mg/mL, clear to very slightly hazy, colorless to yellow	solubility H₂O: 50 mg/mL, clear to almost clear, colorless	solubility DMSO: 20 mg/mL, clear	solubility ethanol: soluble, H₂O: >30 mg/mL
biological source synthetic (organic)	biological source synthetic	biological source -	biological source -

Pictograms

GHS07

Signal Word

Warning

Hazard Codes

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

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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