Chartreusin

Chartreusin is an antibiotic originally isolated from S. chartreusis with diverse biological activities. It inhibits growth of S. aureus, B. subtilis, M. luteus, M. flavus, B. fragilis, C. difficile, C. perfringens, and P. acnes (MICs = 0.4-12.5 µg/ml). Chartreusin binds to DNA and induces electrophoretic shifts in both supercoiled and nicked plasmid DNA. It also inhibits strand-passing activity of topoisomerase II in a P4 unknotting assay. Chartreusin inhibits protein synthesis in chick embryo fibroblasts (CEFs) and mouse fibroblast 3T6 cells (IC50s = 7 and 70 µM, respectively). It is cytotoxic to human lung carcinoma A549 cells in vitro (IC50 = 95 nM) and increases median survival in P388 leukemia and B16 melanoma mouse tumor models when administered at a dose of 10 mg/kg per day.Formal Name: 10-[[6-deoxy-2-O-(6-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]oxy]-6-hydroxy-1-methyl-benzo[h][1]benzopyrano[5,4,3-cde][1]benzopyran-5,12-dione. CAS Number: 6377-18-0. Synonyms: Antibiotic X 465A, Lambdamycin, NSC 5159. Molecular Formula: C32H32O14. Formula Weight: 640.6. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: Acetone: soluble, DMSO: 10 mg/ml, Methanol: slightly soluble. lambdamax: 236, 268, 331, 400, 423 nm. SMILES: OC1=C(C(OC2=C3C(C(O4)=O)=C(C)C=C2)=O)C3=C4C5=C1C=CC=C5O[C@@H]6O[C@H](C)[C@H](O)[C@H](O)[C@H]6O[C@]7([H])[C@H](O)[C@@H](OC)[C@@H](O)[C@@H](C)O7. InChi Code: InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12-,21+,22+,24+,25-,27+,28-,31-,32+/m1/s1. InChi Key: PONPPNYZKHNPKZ-RYBWXQSLSA-N.