Ungeremine

Ungeremine is a betaine-type alkaloid that has been found in C. zeylanicum and has diverse biological activities. It is an inhibitor of acetylcholinesterase (AChE, IC50 = 0.35 µM). Ungeremine acts as a topoisomerase poison, inducing double-strand breaks in DNA by stabilizing the linkage between topoisomerase IIbeta and DNA. It inhibits the relaxation of supercoiled DNA by human topoisomerase I and -IIalpha and E. coli topoisomerase I and -IV (IC50s = 6.1, 25.8, 15, and 7.3 µM, respectively). Ungeremine inhibits the growth of HL-60, MOLT-4, K562, U937, and LXFL 529L cells (IC50s = 1.3, 0.7, 0.8, 2.5, and 1.2 µM, respectively). It is cytotoxic to a variety of drug-sensitive and -resistant cancer cells (IC50s = 4.89-6.45 and 3.67-75.24 µM, respectively) and induces ferroptosis, necroptosis, apoptosis, and autophagy in CCRF-CEM leukemia cells. Ungeremine (60 mg/kg twice per week) also reduces tumor growth in a GXF251L mouse xenograft model.Formal Name: 4,5-dihydro-2-hydroxy-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridinium. CAS Number: 2121-12-2. Synonyms: Lycobetaine. Molecular Formula: C16H12NO3. Formula Weight: 266.3. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: Methanol: 10 mg/ml. lambdamax: 262, 277, 369 nm. SMILES: OC1=CC2=C(C(CC3)=C1)[N+]3=CC4=CC5=C(OCO5)C=C24. InChi Code: InChI=1S/C16H11NO3/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17/h3-7H,1-2,8H2/p+1. InChi Key: DFQOXFIPAAMFAU-UHFFFAOYSA-O. Origin: Plant/Lycoris radiata.