DL-BUTHIONINE-[S,R]-SULFOXIMINE

Synonym(s):DL-Buthionine (S,R)-sulfoximine;BSO;Buthionine sulfoximine;Butionine sulfoximine

CAS NO.：5072-26-4
Empirical Formula: C8H18N2O3S
Molecular Weight: 222.31
MDL number: MFCD00070309
EINECS: 628-045-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-20 11:41:24

DL-BUTHIONINE-[S,R]-SULFOXIMINE Structural

What is DL-BUTHIONINE-[S,R]-SULFOXIMINE?

Chemical properties

White Crystalline Solid

The Uses of DL-BUTHIONINE-[S,R]-SULFOXIMINE

A potent and specific inhibitor of alpha-glutamyl cysteine synthetase

The Uses of DL-BUTHIONINE-[S,R]-SULFOXIMINE

Biological tool for depletion of glutathione.

The Uses of DL-BUTHIONINE-[S,R]-SULFOXIMINE

DL-Buthionine-sulfoximine is suitable for use to:

examine whether the inhibition of glutathione by BSO enhances the apoptotic effect of estrogen on antihormone-resistant human breast cancer cells
investigate the effect of BSO on development of bovine embryos
inhibit GSH in several studies
investigate the effect of GSH synthesis on oocyte maturation

It may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH

What are the applications of Application

D,L-Buthionine-(S,R)-sulfoximine is a gamma-GCSc inhibitor which decreases the proliferative response of T-lymphocytes

Definition

ChEBI: A sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl.

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.

Biochem/physiol Actions

DL-Buthionine-sulfoximine inhibits the biosynthesis of Glutathione (GSH) in liver and other peripheral organs. It does not have any effect on GSH in the CNS. It augments the antiproliferative action of reactive oxygen species (e.g., hydrogen peroxide), and agents that indirectly cause accumulation of reactive oxygen species (e.g., 2-methoxyestradiol, which increases intracellular superoxide anion).

Properties of DL-BUTHIONINE-[S,R]-SULFOXIMINE

Melting point:	215 °C (dec.)(lit.)
Boiling point:	382.3±52.0 °C(Predicted)
Density	1.29±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	H₂O: 50 mg/mL, clear, colorless
form	Fluffy Powder
color	White
Merck	13,1520
BRN	2367136
CAS DataBase Reference	5072-26-4(CAS DataBase Reference)

Safety information for DL-BUTHIONINE-[S,R]-SULFOXIMINE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.