9-Methoxyellipticine
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MedKoo CAT#: 464404

CAS#: 10371-86-5

Description: 9-Methoxyellipticine is an alkaloid and a derivative of the DNA intercalating agent ellipticine that has been found in O. maculata and has anticancer activity. 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). 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). It also increases survival in a variety of rodent tumor models.


Chemical Structure

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9-Methoxyellipticine
CAS# 10371-86-5

Theoretical Analysis

MedKoo Cat#: 464404
Name: 9-Methoxyellipticine
CAS#: 10371-86-5
Chemical Formula: C18H16N2O
Exact Mass: 276.1263
Molecular Weight: 276.339
Elemental Analysis: C, 78.24; H, 5.84; N, 10.14; O, 5.79

Price and Availability

Size Price Availability Quantity
1.0mg USD 400.0 2 Weeks
5.0mg USD 1060.0 2 Weeks
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Synonym: 9-Methoxyellipticine; 9 Methoxyellipticine; NSC 69187; NSC69187; NSC-69187; Methoxy-9-ellipticine;

IUPAC/Chemical Name: 9-methoxy-5,11-dimethyl-6H-pyrido[4,3-b]carbazole

InChi Key: BKRMCDAOAQWNTG-UHFFFAOYSA-N

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

SMILES Code: COC1=CC=C2C(C3=C(N2)C(C)=C(C=CN=C4)C4=C3C)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 276.339 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Xu YH, Li W, Rao Y, Huang ZS, Yin S. Pyridocarbazole alkaloids from Ochrosia borbonica: lipid-lowering agents inhibit the cell proliferation and adipogenesis of 3T3-L1 adipocyte via intercalating into supercoiled DNA. Chin J Nat Med. 2019 Sep;17(9):663-671. doi: 10.1016/S1875-5364(19)30080-9. PMID: 31526501.

2: Abe T. [Synthesis of indole compounds using multifunctional synthons]. Yakugaku Zasshi. 2013;133(1):99-106. Japanese. doi: 10.1248/yakushi.12-00233. PMID: 23292026.

3: Carroll AR, Addepalli R, Fechner G, Smith J, Guymer GP, Forster PI, Quinn RJ. Alkaloids from the Australian rainforest tree Ochrosia moorei. J Nat Prod. 2008 Jun;71(6):1063-5. doi: 10.1021/np070655e. Epub 2008 Apr 16. PMID: 18412397.

4: Liu CY, Knochel P. Preparation of polyfunctional aryl azides from aryl triazenes. A new synthesis of ellipticine, 9-methoxyellipticine, isoellipticine, and 7-carbethoxyisoellipticine. J Org Chem. 2007 Sep 14;72(19):7106-15. doi: 10.1021/jo070774z. Epub 2007 Aug 18. PMID: 17705535.

5: Salim AA, Garson MJ, Craik DJ. New indole alkaloids from the roots of Ochrosia acuminata. J Nat Prod. 2004 Oct;67(10):1719-21. doi: 10.1021/np049812p. PMID: 15497947.

6: Sentagne C, Meunier B, Paillous N. DNA cleavage photoinduced by new water- soluble zinc porphyrins linked to 9-methoxyellipticine. J Photochem Photobiol B. 1992 Oct 15;16(1):47-59. doi: 10.1016/1011-1344(92)85152-k. PMID: 1469512.

7: Ding L, Etemad-Moghadam G, Cros S, Auclair C, Meunier B. Syntheses and in vitro evaluation of water-soluble "cationic metalloporphyrin-ellipticine" molecules having a high affinity for DNA. J Med Chem. 1991 Mar;34(3):900-6. doi: 10.1021/jm00107a005. PMID: 2002470.

8: Ding L, Etemad-Moghadam G, Meunier B. Oxidative cleavage of DNA mediated by hybrid metalloporphyrin-ellipticine molecules and functionalized metalloporphyrin precursors. Biochemistry. 1990 Aug 28;29(34):7868-75. doi: 10.1021/bi00486a013. PMID: 2148113.

9: Honda T, Kato M, Inoue M, Shimamoto T, Shima K, Nakanishi T, Yoshida T, Noguchi T. Synthesis and antitumor activity of quaternary ellipticine glycosides, a series of novel and highly active antitumor agents. J Med Chem. 1988 Jul;31(7):1295-305. doi: 10.1021/jm00402a007. PMID: 3385725.

10: Braham Y, Meunier G, Meunier B. Mise en évidence d'une biotransformation oxydante de la méthoxy-9-ellipticine. Comparaison avec le cas de l'hydroxy-9-ellipticine [Demonstration of an oxidative biotransformation of 9-methoxyellipticine. Comparison with the case of 9-hydroxyellipticine]. C R Acad Sci III. 1987;304(11):301-6. French. PMID: 3103875.

11: Meunier G, Meunier B. Peroxidase-catalyzed O-demethylation reactions. Quinone-imine formation from 9-methoxyellipticine derivatives. J Biol Chem. 1985 Sep 5;260(19):10576-82. PMID: 4030757.

12: Roy M, Monsarrat B, Cros S, Lecointe P, Rivalle C, Bisagni E. Cytochrome P-450-mediated O-demethylation of two ellipticine derivatives. Differential effect of the murine Ah locus phenotype. Drug Metab Dispos. 1985 Jul- Aug;13(4):497-502. PMID: 2863116.

13: Kouamo K, Creche J, Chénieux JC, Rideau M, Viel C. Alkaloid Production by Ochrosia elliptica Cell Suspension Cultures. J Plant Physiol. 1985 Mar;118(3):277-83. doi: 10.1016/S0176-1617(85)80229-7. Epub 2012 Jan 2. PMID: 23196012.

14: Kouadio K, Chenieux JC, Rideau M, Viel C. Antitumor alkaloids in callus cultures of Ochrosia elliptica. J Nat Prod. 1984 Sep-Oct;47(5):872-4. doi: 10.1021/np50035a022. PMID: 6512537.

15: Meunier G, Paoletti C, Meunier B. Mise en évidence de la réaction de O-déméthylation catalysée par une peroxydase: application au cas de la méthoxy-9 ellipticine [Demonstration of the O-demethylation reaction catalyzed by a peroxidase: application to 9-methoxyellipticine]. C R Acad Sci III. 1984;299(15):629-32. French. PMID: 6440666.

16: DeMarini DM, Cros S, Paoletti C, Lecointe P, Hsie AW. Mutagenicity and cytotoxicity of five antitumor ellipticines in mammalian cells and their structure-activity relationships in Salmonella. Cancer Res. 1983 Aug;43(8):3544-52. PMID: 6344986.