Cycleanine

Cycleanine is an alkaloid that has been found in T. subcordata and has anticancer and antimalarial activities. It selectively inhibits the growth of OVCAR-8, A2780, IGROV-1, and OVCAR-4 ovarian cancer cells (IC50s = 10, 7.6, 14, and 7.2 µM, respectively) over non-cancerous ovarian surface epithelial cells (IC50 = 35 µM). It also halts the cell cycle at the subG1 phase and induces apoptosis in OVCAR-8 cells. Cycleanine (25 and 50 mg/kg) reduces parasitemia and increases survival in a mouse model of infection with a chloroquine-resistant strain of P. berghei.Formal Name: (12aR,24aR)-2,3,12a,13,14,15,24,24a-octahydro-5,6,17,18-tetramethoxy-1,13-dimethyl-8,11:20,23-dietheno-1H,12H-[1,10]dioxacyclooctadecino[2,3,4-ij:11,12,13-i'j']diisoquinoline. CAS Number: 518-94-5. Synonyms: O,O-Dimethylisochondrodendrine, O-Methylnorcycleanine. Molecular Formula: C38H42N2O6. Formula Weight: 622.8. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Acetone: soluble, Dichloromethane: soluble, DMSO: soluble, Ethyl Acetate: soluble. SMILES: CN1[C@@](CC2=CC=C3C=C2)([H])C4=C(CC1)C=C(OC)C(OC)=C4OC5=CC=C(C[C@](N(CC6)C)([H])C7=C6C=C(OC)C(OC)=C7O3)C=C5. InChi Code: InChI=1S/C38H42N2O6/c1-39-17-15-25-21-31(41-3)35(43-5)37-33(25)29(39)19-23-7-11-28(12-8-23)46-38-34-26(22-32(42-4)36(38)44-6)16-18-40(2)30(34)20-24-9-13-27(45-37)14-10-24/h7-14,21-22,29-30H,15-20H2,1-6H3/t29-,30-/m1/s1. InChi Key: ANOXEUSGZWSCQL-LOYHVIPDSA-N. Origin: Plant/Stephania japonica (Thunb.) Miers..