A bacterial metabolite with antibacterial and anticancer activities
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Echinosporin

Item No. 31416

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,4aS,5S,7aS)-1,4a,5,7a-tetrahydro-5-hydroxy-8-oxo-1,5-(epoxymethano)cyclopenta[c]pyran-3-carboxamide
CAS Number
79127-35-8
Synonyms
  • NSC 357683
  • XK-213
Molecular Formula
C10H9NO5
Formula Weight
223.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleMethanol: solubleWater: soluble
SMILES
O[C@@]12[C@]3([H])[C@@](C=C2)([H])[C@H](OC1=O)OC(C(N)=O)=C3
InChi Code
InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)/t4-,5-,8-,10-/m0/s1
InChi Key
OXSZHYWOGQJUST-PDXIVQBHSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $401

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    Product Description

    Echinosporin is a bacterial metabolite originally isolated from Streptomyces echinosporus that has antibacterial and anticancer activities.1,2,3 It is active against P. vulgaris, S. typhosa, S. sonnei, E. coli, and B. subtilis (MICs = 100, 100, 100, 200, and 400 µg/ml, respectively).1 Echinosporin induces cell cycle arrest at the G2/M phase and apoptosis in, as well as inhibits proliferation of, HCT-15 human colorectal cancer cells (IC50s = 1.7, 1.75, and 247 µM, respectively).2 It inhibits tumor growth in murine P388 leukemia and Meth 1 fibrosarcoma models when administered at doses ranging from 10 to 80 mg/kg.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sato, T., Kawamoto, I., Oka, T., et al. A new antibiotic echinosporin (XK-213) - producing organism, isolation and characterization. J. Antibiot. (Tokyo) 35(3), 266-271 (1982).

    2. Cui, C.B., Liu, H.B., Gu, J.Y., et al. Echinosporins as new cell cycle inhibitors and apoptosis inducers from marine-derived Streptomyces albogriseolus. Fitoterapia 78(3), 238-240 (2007).

    3. Morimoto, M., and Imai, R. Antitumor activity of echinosporin. J. Antibiot. (Tokyo) 38(4), 490-495 (1985).