(-)-Chaetominine

(-)-Chaetominine is a cytotoxic alkaloid originally isolated from Chaetomium sp. IFB-E015. It inhibits the growth of K562 leukemia and SW1116 colon cancer cells (IC50s = 20 and 28 nM, respectively). (-)-Chaetominine induces apoptosis of K562 cells via upregulation of the Bax/Bcl-2 ratio, decreasing mitochondrial membrane potential, inducing mitochondrial cytochrome C release, and activation of caspase-3 and caspase-9. It also decreases doxorubicin efflux mediated by multidrug resistance-associated protein 1 (MRP1) and restores sensitivity to doxorubicin (Cay-15007) in resistant K562 cells.Formal Name: (2S,4R,5aS,9cS)-4,5,5a,9c-tetrahydro-5a-hydroxy-2-methyl-4-(4-oxo-3(4H)-quinazolinyl)-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione. CAS Number: 918659-56-0. Molecular Formula: C22H18N4O4. Formula Weight: 402.4. Purity: >95%. Formulation: (Request formulation change), A solid. SMILES: O=C1N([C@H]2C)[C@]3([H])[C@](C4=CC=CC=C4N3C2=O)(O)C[C@H]1N5C=NC(C=CC=C6)=C6C5=O. InChi Code: InChI=1S/C22H18N4O4/c1-12-18(27)26-16-9-5-3-7-14(16)22(30)10-17(20(29)25(12)21(22)26)24-11-23-15-8-4-2-6-13(15)19(24)28/h2-9,11-12,17,21,30H,10H2,1H3/t12-,17+,21-,22-/m0/s1. InChi Key: GEURDGODABUDHB-TYTLQBBQSA-N.