Manzamine A

Manzamine A is a beta-carboline alkaloid with diverse activities that has been found in marine sponges, including X. ashmorica. It is an inhibitor of glycogen synthase kinase 3beta (GSK3beta) and cyclin-dependent kinase 5 (CDK5, IC50s = 10.2 and 1.5 µM, respectively). It inhibits the growth of L5178y mouse lymphoma cells with an ED50 value of 1.8 µg/mL. In an agar diffusion assay, manzamine A inhibits the growth of B. subtilis and S. aureus, but not E. coli bacteria. It reduces the reverse transcriptase (RT) activity in supernatant from HIV-1-infected peripheral blood mononuclear cells (PBMCs, EC50 = 4.2 µM). In vivo, manzamine A (100 µmol/kg, i.p.) has antimalarial activity and reduces the amount of P. berghei in infected mice by over 90% relative to the control.Formal Name: (1R,4S,9Z,13S,13aR,20aR,21aR)-2,3,5,6,7,8,11,12,15,16,17,18,20a,21-tetradecahydro-24-(9H-pyrido[3,4-b]indol-1-yl)-1,13-etheno-4,21a-methano-1H-azocino[1',2':1,5]pyrrolo[3,2-e]azacyclopentadecin-13(13aH)-ol. CAS Number: 104196-68-1. Synonyms: Keramamine A. Molecular Formula: C36H44N4O. Formula Weight: 548.8. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble. SMILES: [H][C@@]1(N2CCCC/C=C\1)C[C@@]3(C4)[C@]2([H])[C@]5(O)CC/C=C/CCCC[N@@]4CC[C@@]3([H])C(C6=C(NC7=C8C=CC=C7)C8=CC=N6)=C5. InChi Code: InChI=1S/C36H44N4O/c41-36-18-10-4-1-2-5-11-20-39-22-17-30(35(25-39)23-26-13-7-3-6-12-21-40(26)34(35)36)29(24-36)32-33-28(16-19-37-32)27-14-8-9-15-31(27)38-33/h1,4,7-9,13-16,19,24,26,30,34,38,41H,2-3,5-6,10-12,17-18,20-23,25H2/b4-1+,13-7-/t26-,30-,34+. InChi Key: FUCSLKWLLSEMDQ-SHIWRGCWSA-N.