Darinaparsin

Darinaparsin is a dimethylated arsenic linked to glutathione. It is cytotoxic to DU145, LNCaP, and PC3 prostate cancer cells (IC50s = 5-10 µM) and patient-derived primary prostate cancer cells (IC50s = 2.5-20 µM), as well as Jurkat T cell lymphoma and L540 Hodgkin lymphoma cells (IC50s = 2.7 and 1.3 µM, respectively). It decreases the tumor-initiating subpopulation in DU145 and PC3 cells and halts the cell cycle in the G2/M phase. Darinaparsin decreases transcription of Gli-2, a transcription factor that mediates Sonic hedgehog signaling, when used at a concentration of 1.5 but not 3 µM. It decreases SHP1 phosphatase activity and increases ERK phosphorylation. Darinaparsin reduces tumor growth in DU145 and PC3 prostate cancer mouse xenograft models when administered at a dose of 100 mg/kg every other day.Formal Name: L-gamma-glutamyl-S-(dimethylarsino)-L-cysteinyl-glycine. CAS Number: 69819-86-9. Synonyms: Dimethylarsinic glutathione, ZIO 101. Molecular Formula: C12H22AsN3O6S. Formula Weight: 411.3. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: <100 µg/ml, DMSO: >10 mg/ml, Ethanol: <100 µg/ml, PBS (pH 7.2): >35 mg/ml. SMILES: OC(CNC([C@H](CS[As](C)C)NC(CC[C@H](N)C(O)=O)=O)=O)=O. InChi Code: InChI=1S/C12H22AsN3O6S/c1-13(2)23-6-8(11(20)15-5-10(18)19)16-9(17)4-3-7(14)12(21)22/h7-8H,3-6,14H2,1-2H3,(H,15,20)(H,16,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1. InChi Key: JGDXFQORBMPJGR-YUMQZZPRSA-N.