D,L-Buthionine-(S,R)-sulfoximine

• CAT Number: R000046
• CAS Number: 5072-26-4
• Molecular Formula: C8H18N2O3S
• Molecular Weight: 222.303
• Purity: ≥95%
• Synonyms: 2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid; S-(3-Amino-3-carboxypropyl)-S-butylsulfoximine; Buthionine Sulfoximine; NSC 381100
• Target: gamma-glutamylcysteine synthetase inhibitor
• Storage: -20°C
• IUPAC Name: 2-amino-4-(butylsulfonimidoyl)butanoic acid
• InChI: InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)
• InChIKey: KJQFBVYMGADDTQ-UHFFFAOYSA-N
• SMILES: CCCCS(=N)(=O)CCC(C(=O)O)N

Buthionine Sulphoximine, also known as NSC-326231, is a gamma-glutamylcysteine synthetase inhibitor potentially for the treatment of solid tumors.

Reference

1:[Effect of D,L-buthionine-S,R-sulfoximine on the ratio of glutathione forms and the growth of tatar buckwheat calli]. Nigmatullina LR, Rumiantseva NI, Kostiukova IuA.Ontogenez. 2014 Jan-Feb;45(1):50-62. Russian. PMID: 25720265 2:Buthionine sulfoximine and 1,25-dihydroxyvitamin D induce apoptosis in breast cancer cells via induction of reactive oxygen species. Bohl LP, Liaudat AC, Picotto G, Marchionatti AM, Narvaez CJ, Welsh J, Rodriguez VA, Tolosa de Talamoni NG.Cancer Invest. 2012 Oct;30(8):560-70. Epub 2012 Aug 29. PMID: 22931489 3:[Mechanisms of 232Th effects on Chlorella vulgaris Beljer and modifications of it/’s toxic effect with caffeine and buthionine sulfoximine]. Evseeva TI, Maĭstrenko TA, Geras/’kin SA, Belykh ES.Radiats Biol Radioecol. 2006 Nov-Dec;46(6):741-8. Russian. PMID: 17323704 4:Zonisamide inhibits nitric oxide synthase activity induced by N-methyl-D-aspartate and buthionine sulfoximine in the rat hippocampus. Noda Y, Mori A, Packer L.Res Commun Mol Pathol Pharmacol. 1999;105(1-2):23-33. PMID: 10850366 5:Potentiation of benzo[a]pyrene-induced pulmonary and forestomach tumorigenesis in mice by D,L-buthionine-S,R-sulfoximine-mediated tissue glutathione depletion. Srivastava SK, Xia H, Pal A, Hu X, Guo J, Singh SV.Cancer Lett. 2000 May 29;153(1-2):35-9. PMID: 10779627 6:d,l-buthionine-(S,R)-sulfoximine potentiates in vivo the therapeutic efficacy of doxorubicin against multidrug resistance protein-expressing tumors. Vanhoefer U, Cao S, Minderman H, Toth K, Skenderis BS 2nd, Slovak ML, Rustum YM.Clin Cancer Res. 1996 Dec;2(12):1961-8. PMID: 9816155 Free Article7:Quantitation of the diastereoisomers of L-buthionine-(R,S)-sulfoximine in human plasma: a validated assay by capillary electrophoresis. Sandor V, Flarakos T, Batist G, Wainer IW, Lloyd DK.J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):123-31. PMID: 8925065 8:Cytotoxicity of antitumor platinum complexes with L-buthionine-(R,S)-sulfoximine and/or etanidazole in human carcinoma cell lines sensitive and resistant to cisplatin. Brooks SE, Korbut TT, Dupuis NP, Holden SA, Teicher BA.Cancer Chemother Pharmacol. 1995;36(5):431-8. PMID: 7634385 9:The effect of L-buthionine-[S,R]-sulfoximine on the pancreas in mice. A model of weakening glutathione-based defense mechanisms. Lüthen RE, Neuschwander-Tetri BA, Niederau C, Ferrell LD, Grendell JH.Int J Pancreatol. 1994 Aug;16(1):31-6. PMID: 7528760 10:Effect of buthionine sulfoximine on PtII and PtIV drug accumulation and the formation of glutathione conjugates in human ovarian-carcinoma cell lines. Mistry P, Loh SY, Kelland LR, Harrap KR.Int J Cancer. 1993 Nov 11;55(5):848-56. PMID: 8244583