Streptonigrin

• CAT Number: R002167
• CAS Number: 3930-19-6
• Molecular Formula: C25H22N4O8
• Molecular Weight: 506.5
• Purity: ≥95%
• Storage: 2-8°C
• IUPAC Name: 5-amino-6-(7-amino-6-methoxy-5,8-dioxoquinolin-2-yl)-4-(2-hydroxy-3,4-dimethoxyphenyl)-3-methylpyridine-2-carboxylic acid
• InChI: 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)
• InChIKey: PVYJZLYGTZKPJE-UHFFFAOYSA-N
• SMILES: CC1=C(C(=C(N=C1C(=O)O)C2=NC3=C(C=C2)C(=O)C(=C(C3=O)N)OC)N)C4=C(C(=C(C=C4)OC)OC)O

Streptonigrin (Cat No.:R002167) is a naturally occurring antitumor antibiotic derived from Streptomyces flocculus. This naphthoquinone antibiotic exhibits broad-spectrum biological activity and has been studied for its potential as an anticancer agent. Streptonigrin induces DNA damage and inhibits DNA synthesis in tumor cells by generating reactive oxygen species (ROS). It has demonstrated effectiveness against various cancer types. However, due to its significant toxicity and challenging synthesis, it is primarily used in laboratory research to investigate DNA damage and cancer cell death mechanisms rather than in clinical applications.

Reference

Targeting NAD(P)H:quinone oxidoreductase (NQO1) in pancreatic cancer. Lewis A.M. Mol. Carcinogen. 2005, 43, 215.Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells. Gu B. & DeAngelis L.M. Anticancer Drugs 2005, 16, 167.The effect of metal ions on the electrochemistry of the antitumor antibiotic streptonigrin. Anderberg P.I. J. Inorg. Biochem. 2004, 98, 720.