L-BUTHIONINE-(S,R)-SULFOXIMINE

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

The Uses of L-BUTHIONINE-(S,R)-SULFOXIMINE

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

The Uses of L-BUTHIONINE-(S,R)-SULFOXIMINE

inhibitor of gamma-glutamylcysteine synthetase

The Uses of L-BUTHIONINE-(S,R)-SULFOXIMINE

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.

What are the applications of Application

L-Buthionine sulfoximine is a glutathione-synthesis inhibitor that activates oxidative stress

What are the applications of Application

L-Buthionine-(S,R)-Sulfoximine is an irreversible inhibitor of γ-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