A phenylpyridylquinoline with diverse biological activities
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Streptonigrin

Item No. 27952

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in 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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Streptonigrin is a phenylpyridylquinoline originally isolated from S. flocculus with diverse biological activities.1,2,3,4,5,6 Streptonigrin (2.5-12.5 μM) induces DNA cleavage by calf thymus topoisomerase II in a concentration-dependent manner.1 It induces phage production in S. typhimurium when used at concentrations ranging from 1 to 10 μg/ml.2 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 (Item No. 14595) and orthophenanthroline.3 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.4 Streptonigrin (0.001-0.1 μg/ml) inhibits mitosis and induces chromatin breaks in human leukocytes in a concentration-dependent manner.5 In vivo, streptonigrin (0.05 mg/kg, i.p.) increases the mean survival time in rats infected with Rauscher virus.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yamashita, Y., Kawada, S., Fujii, N., et al. Induction of mammalian DNA topoisomerase II dependent DNA cleavage by antitumor antibiotic streptonigrin. Cancer Res. 50(18), 5841-5844 (1990).

    2. Levine, M., and Borthwick, M. The action of streptonigrin on bacterial DNA metabolism and on induction of phage production in lysogenic bacteria. Virology 21(4), 568-574 (1963).

    3. Yeowell, H.N., and White, J.R. Iron requirement in the bactericidal mechanism of streptonigrin. Antimicrob. Agents Chemother. 22(6), 961-968 (1982).

    4. Beall, H.D., Liu, Y., Siegel, D., et al. Role of NAD(P)H:quinone oxidoreductase (DT-diaphorase) in cytotoxicity and induction of DNA damage by streptonigrin. Biochem. Pharmacol. 51(5), 645-652 (1996).

    5. Cohen, M.M., Shaw, M.W., and Craig, A.P. The effects of streptonigrin on cultured human leukocytes. Proc. Natl. Acad. Sci. USA 50(1), 16-24 (1963).

    6. McBride, T.J., Oleson, J.J., and Woolf, D. The activity of streptonigrin against the Rauscher murine leukemia virus in vivo. Cancer Res. 26(4), 727-732 (1966).