83730-53-4 Usage
Description
L-Buthionine-(S,R)-sulfoximine 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 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
Different sources of media describe the Uses of 83730-53-4 differently. You can refer to the following data:
1. A potent and specific inhibitor of alpha-glutamylcysteine synthetase
2. inhibitor of gamma-glutamylcysteine synthetase
3. 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.
4. L-Buthionine-(S,R)-sulfoximine is a potent and specific inhibitor of alpha-glutamylcysteine synthetase.
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 83730-53-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,3,7,3 and 0 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 83730-53:
(7*8)+(6*3)+(5*7)+(4*3)+(3*0)+(2*5)+(1*3)=134
134 % 10 = 4
So 83730-53-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)
83730-53-4Relevant articles and documents
Methionine and buthionine sulfoximines: Syntheses under mild and safe imidation/oxidation conditions
Buglioni, Laura,Bizet, Vincent,Bolm, Carsten
supporting information, p. 2209 - 2213 (2014/07/21)
Methionine and buthionine sulfoximines (MSO and BSO) are non-natural amino acids known to inhibit the biosynthesis of glutathione (GSH). The current syntheses of these biologically active molecules involve harsh reaction conditions and the use of hazardou
