L-Buthionine-(S,R)-Sulfoximine

L-Buthionine-(S,R)-sulfoximine is an irreversible inhibitor of gamma-glutamylcysteine synthetase (Ki = 25 µM). It inhibits the proliferation of ZAZ and M14 melanoma cells, as well as A2780 ovarian and MCF-7 breast cancer cells (IC50s = 4.9, 18, 8.5, and 26.5 µM, respectively). L-Buthionine-(S,R)-sulfoximine (100µM) induces ferroptosis in A172 and T98G glioblastoma cells. It increases reactive oxygen species (ROS) levels in HeLa cells when used at a concentration of 10 µM. L-Buthionine-(S,R)-sulfoximine (1 mM), in combination with methylglyoxal, induces apoptosis of bovine aortic endothelial cells (BAECs). It increases the number of eye spots in the retinal pigment epithelium, an indicator of DNA deletions, in mouse pups when administered to pregnant dams at concentrations of 2 and 20 mM in the drinking water. L-Buthionine-(S,R)-sulfoximine decreases cysteine and glutathione (GSH) levels in fetal mice when administered to pregnant dams.Formal Name: 2S-amino-4-(S-butylsulfonimidoyl)-butanoic acid. CAS Number: 83730-53-4. Synonyms: BSO, NSC 326231. Molecular Formula: C8H18N2O3S. Formula Weight: 222.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: PBS (pH 7.2): 5 mg/ml. SMILES: O=S(CCCC)(CC[C@H](N)C(O)=O)=N. InChi Code: 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)/t7-,14?/m0/s1. InChi Key: KJQFBVYMGADDTQ-CVSPRKDYSA-N.