L-BUTHIONINE-(S,R)-SULFOXIMINE Chemical Properties

Melting point:

224-228 °C (dec.)

Boiling point:

382.3±52.0 °C(Predicted)

Density 

1.29

refractive index 

1.6300 (estimate)

storage temp. 

-20°C

solubility 

H₂O: 50 mg/mL, clear, colorless to faintly yellow

form 

Fine Powder

color 

White

biological source

synthetic (organic)

Water Solubility 

water: 50mg/mL, clear to slightly hazy, colorless to faintly yellow

BRN 

2367136

Stability:

Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily.

CAS DataBase Reference

83730-53-4

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

EK7713440

F 

10

HS Code 

29309090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

L-BUTHIONINE-(S,R)-SULFOXIMINE Usage And Synthesis

Description

L-Buthionine-(S,R)-sulfoximine is an irreversible inhibitor of γ-glutamylcysteine synthetase (K_i <100 μM), the rate-limiting enzyme for L-glutathione (GSH) synthesis, that induces oxidative stress in cells by depleting GSH. Administration of L-buthionine-(S,R)-sulfoximine leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis. Whereas elevated glutathione levels are associated with tumor cell resistance, L-buthionine-(S,R)-sulfoximine has been shown to enhance the toxicity of various chemotherapeutic agents in drug-resistant tumors.

Chemical Properties

White Crystalline Solid

Uses

inhibitor of gamma-glutamylcysteine synthetase

Uses

Buthionine sulfoximine (BSO) is an irreversible inhibitor of γ-glutamylcysteine synthetase (Ki <100 μM), the rate-limiting enzyme for L-glutathione (GSH) synthesis, that induces oxidative stress in cells by depleting GSH. Administration of BSO leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis. Whereas elevated glutathione levels are associated with tumor cell resistance, BSO has been shown to enhance the toxicity of various chemotherapeutic agents in drug-resistant tumors.

Uses

L-Buthionine-(S,R)-sulfoximine is a potent and specific inhibitor of alpha-glutamylcysteine synthetase.

Definition

ChEBI: L-buthionine-(S,R)-sulfoximine is a 2-amino-4-(S-butylsulfonimidoyl)butanoic acid which has S-configuration. It is a inhibitor of gamma-glutamylcysteine synthetase and glutathione (GSH) biosynthesis and is capable of enhancing the apoptotic effects of several chemotherapeutic agents. It has a role as a ferroptosis inducer and an EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor.

Hazard

A reproductive hazard.

Biochem/physiol Actions

Blocks cellular resistance to chemotherapy by inhibiting γ-glutamylcysteine synthetase, a key enzyme in glutathione biosynthesis. Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.

storage

Store at -20°C

References

1) Lu?et al.?(2009),?Regulation of glutathione synthesis; Mol. Aspects Med.?30?42 2) Lee?et al.?(2008),?Adaptive response to GSH depletion and resistance to L-buthionine-(S,R)-sulfoximine; Mol. Cell Biochem.?12?174 3) Qiwei et al. (2016),?The effects of buthionine sulfoximine on the proliferation and apoptosis of biliary tract cancer cells induced by cisplatin and gemcitabine; Oncol. Lett.?11?474 4) Glasuer and Chandel (2014),?Targeting antioxidants for cancer therapy; Biochem. Pharmacol.?92?90

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