An antibiotic
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10'-Desmethoxystreptonigrin

Item No. 28065

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-amino-6-(7-amino-5,8-dihydro-6-methoxy-5,8-dioxo-2-quinolinyl)-4-(2-hydroxy-3-methoxyphenyl)-3-methyl-2-pyridinecarboxylic acid
CAS Number
136803-89-9
Molecular Formula
C24H20N4O7
Formula Weight
476.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
NC1=C(OC)C(C(C=CC(C2=C(N)C(C3=CC=CC(OC)=C3O)=C(C)C(C(O)=O)=N2)=N4)=C4C1=O)=O
InChi Code
InChI=1S/C24H20N4O7/c1-9-14(10-5-4-6-13(34-2)20(10)29)15(25)19(28-17(9)24(32)33)12-8-7-11-18(27-12)22(31)16(26)23(35-3)21(11)30/h4-8,29H,25-26H2,1-3H3,(H,32,33)
InChi Key
ULSNCNUVHUNMCF-UHFFFAOYSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $248

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    2.5 mg

    $922

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    Product Description

    10’-Desmethoxystreptonigrin is an antibiotic originally isolated from Streptomyces and a derivative of the antibiotic streptonigrin.1 It is active against a variety of bacteria, including S. aureus, S. faecalis, E. coli, K. pneumoniae, and P. vulgaris (MICs = 0.4, 1.6, 3.1, 3.1, and 0.4 µg/ml, respectively).2 10’-Desmethoxystreptonigrin is cytotoxic to HCT116 colon and A2780 ovarian cancer cells (IC50s = 0.004 and 0.001 µg/ml, respectively), as well as HCT116 cells resistant to etoposide (Item No. 12092) and teniposide (Item No. 14425) and cisplatin-resistant A2780 cells (IC50s = 0.003, 0.001, and 0.01 µg/ml, respectively). 10’-Desmethoxystreptonigrin is also an inhibitor of p21ras farnesylation (IC50 = 21 nM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakajima, M., Takahashi, H., Shimada, Y., et al. Novel antibiotic 10'-demethoxystreptonigrin and its manufacture with Streptomyces otagonensis. (1991).

    2. Liu, W.C., Barbacid, M., Bulgar, M., et al. 10'-Desmethoxystreptonigrin, a novel analog of streptonigrin. J. Antibiot. (Tokyo) 45(4), 454-457 (1992).