L-Buthionine-(S,R)-sulfoximine

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.

White Crystalline Solid

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

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.

inhibitor of gamma-glutamylcysteine synthetase

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.

A reproductive hazard.

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.

Store at -20°C

[1] LU S C. Regulation of glutathione synthesis[J]. Molecular Aspects of Medicine, 2009, 30 1: Pages 42-59. DOI:10.1016/j.mam.2008.05.005
[2] HYANG-RIM LEE. Adaptive response to GSH depletion and resistance to L-buthionine-(S,R)-sulfoximine: involvement of Nrf2 activation.[J]. Molecular and Cellular Biochemistry, 2008: 23-31. DOI:10.1007/s11010-008-9853-y
[3] QI-WEI LI. The effects of buthionine sulfoximine on the proliferation and apoptosis of biliary tract cancer cells induced by cisplatin and gemcitabine.[J]. Oncology Letters, 2016, 11 1 1: 474-480. DOI:10.3892/ol.2015.3879
[4] ANDREA GLASAUER  Navdeep S C. Targeting antioxidants for cancer therapy[J]. Biochemical pharmacology, 2014, 92 1: Pages 90-101. DOI:10.1016/j.bcp.2014.07.017