Streptonigrin

Streptonigrin is a phenylpyridylquinoline originally isolated from S. flocculus with diverse biological activities. Streptonigrin (2.5-12.5 µM) induces DNA cleavage by calf thymus topoisomerase II in a concentration-dependent manner. It induces phage production in S. typhimurium when used at concentrations ranging from 1 to 10 µg/ml. Streptonigrin (10 µg/ml) inhibits DNA synthesis in and reduces survival of S. typhimurium bacteria. Streptonigrin is bactericidal against E. coli in an iron-dependent manner, an effect that is blocked by the iron chelators deferoxamine (Cay-14595) and orthophenanthroline. Streptonigrin (40 nM) is cytotoxic to human HT-29 colon carcinoma cells but not to BE colon carcinoma cells in which NAD(P)H:quinone oxidoreductase is not expressed. Streptonigrin (0.001-0.1 µg/ml) inhibits mitosis and induces chromatin breaks in human leukocytes in a concentration-dependent manner. In vivo, streptonigrin (0.05 mg/kg, i.p.) increases the mean survival time in rats infected with Rauscher virus.Formal Name: (4R)-5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methyl-2-pyridinecarboxylic acid. CAS Number: 3930-19-6. Synonyms: NSC 45383, NSC 56748, NSC 83950. Molecular Formula: C25H22N4O8. Formula Weight: 506.5. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Chloroform:Methanol (1:1): 2 mg/ml. SMILES: NC1=C(OC)C(C(C=CC(C2=C(N)C(C3=CC=C(OC)C(OC)=C3O)=C(C)C(C(O)=O)=N2)=N4)=C4C1=O)=O. InChi Code: InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34). InChi Key: PVYJZLYGTZKPJE-UHFFFAOYSA-N. Origin: Bacterium/Streptomyces flocculus.