An alkaloid with anticancer activity
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9-Methoxyellipticine

Item No. 31631

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole
CAS Number
10371-86-5
Synonyms
  • Methoxy-9-ellipticine
  • NSC 69187
Molecular Formula
C18H16N2O
Formula Weight
276.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
λmax
245, 276, 293 nm
SMILES
COC1=CC=C2C(C(C(C)=C3C(C=CN=C3)=C4C)=C4N2)=C1
InChi Code
InChI=1S/C18H16N2O/c1-10-15-9-19-7-6-13(15)11(2)18-17(10)14-8-12(21-3)4-5-16(14)20-18/h4-9,20H,1-3H3
InChi Key
BKRMCDAOAQWNTG-UHFFFAOYSA-N
Origin
Animal/Bleekeria sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $308

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    5 mg

    $1,078

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    Product Description

    9-Methoxyellipticine is an alkaloid and a derivative of the DNA intercalating agent ellipticine (hydrochloride) (Item No. 18742) that has been found in O. maculata and has anticancer activity.1,2 It intercalates into DNA and is an inhibitor of wild-type c-Kit and c-Kit containing the D816V activating mutation (c-KitD816V; IC50s = 0.8 and 0.6 µM, respectively).2,3 9-Methoxyellipticine inhibits proliferation of Ba/F3 cells in the presence of the c-Kit ligand SCF and Ba/F3 cells expressing c-KitD816V (IC50s = 0.5 and 0.3 µM, respectively).2 It also increases survival in a variety of rodent tumor models.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Svoboda, G.H., Poore, G.A., and Montfort, M.L. Alkaloids of Ochrosia maculata Jacq. (Ochrosia borbonica Gmel.). Isolation of the alkaloids and study of the antitumor properties of 9-methoxyellipticine. J. Pharm. Sci. 57(10), 1720-1725 (1968).

    2. Vendôme, J., Letard, S., Martin, F., et al. Molecular modeling of wild-type and D816V c-Kit inhibition based on ATP-competitive binding of ellipticine derivatives to tyrosine kinases. J. Med. Chem. 48(20), 6194-6201 (2005).

    3. Festy, B., Poisson, J., and Paoletti, C. A new DNA intercalating drug: Methoxy-9-ellipticine. FEBS Lett. 17(2), 321-323 (1971).