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9-Methoxyellipticine Sale

(Synonyms: Methoxy-9-ellipticine, NSC 69187) 目录号 : GC48840

An alkaloid with anticancer activity

9-Methoxyellipticine Chemical Structure

Cas No.:10371-86-5

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产品描述

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.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

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-methoxyellipticineJ. 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 kinasesJ. Med. Chem.48(20)6194-6201(2005) 3.Festy, B., Poisson, J., and Paoletti, C.A new DNA intercalating drug: Methoxy-9-ellipticineFEBS Lett.17(2)321-323(1971)

Chemical Properties

Cas No. 10371-86-5 SDF
别名 Methoxy-9-ellipticine, NSC 69187
Canonical SMILES COC1=CC=C2C(C(C(C)=C3C(C=CN=C3)=C4C)=C4N2)=C1
分子式 C18H16N2O 分子量 276.3
溶解度 储存条件 -20°C
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1 mM 3.6193 mL 18.0963 mL 36.1925 mL
5 mM 0.7239 mL 3.6193 mL 7.2385 mL
10 mM 0.3619 mL 1.8096 mL 3.6193 mL
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Research Update

Peroxidase-catalyzed O-demethylation reactions. Quinone-imine formation from 9-Methoxyellipticine derivatives

J Biol Chem 1985 Sep 5;260(19):10576-82.PMID:4030757doi

Despite numerous reports on the N-demethylation reactions catalyzed by peroxidases, to our knowledge, O-demethylation reactions with the same enzymes seem to be still a questionable matter. Unexpectedly, a peroxidase system (horseradish peroxidase and hydrogen peroxide) is able to effect the O-demethylation of the cytotoxic agents 9-Methoxyellipticine and N2-methyl-9-methoxyellipticinium acetate. The reaction leads directly to the formation of the corresponding quinone-imine derivatives with the concomitant formation of one molecule of methanol per molecule of methoxy compound. One hydrogen peroxide molecule is consumed during the process. Experiments in H218O-enriched water clearly indicate that 18O is nearly quantitatively incorporated in the carbonyl group of the generated quinone-imine compound with the concomitant elimination of the methoxy group as methanol. So this peroxidase-catalyzed apparent O-demethylation in fact implies an oxidative demethoxylation step. This enzymatic reaction exhibits normal Michaelis-Menten saturation kinetics. Like the 9-hydroxylated ellipticines, both the 9-methoxylated ellipticines show a good affinity for the peroxidase itself (Km approximately 10 microM) but are slowly transformed to the corresponding quinone-imines. The Vmax values for methoxylated ellipticines are 10(-1)-10(-3) lower than those for hydroxylated compounds. This new route for the in vitro formation of electrophilic derivatives from the cytotoxic 9-Methoxyellipticine and N2-methyl-9-methoxyellipticinium might be considered as a novel possible metabolic pathway for these drugs, especially if we bear in mind the "bio-oxidative alkylation" process previously described for at least one of the corresponding hydroxylated ellipticine derivatives (see Bernadou, J., Meunier, B., Meunier, G., Auclair, C., and Paoletti, C. (1984) Proc. Natl. Acad. Sci. U.S.A. 81, 1297-1301; and Monsarrat, B., Maftouh, M., Meunier, G., Dugué, B., Bernadou, J., Armand, J. P., Picard-Fraire, C., Meunier, B., and Paoletti, C. (1983) Biochem. Pharmacol. 32, 3887-3890).

Microbial transformations of natural antitumor agents. 9. O-Demethylation of 9-Methoxyellipticine

J Nat Prod 1979 Nov-Dec;42(6):643-7.PMID:575547DOI:10.1021/np50006a010.

Microbial transformation studies were conducted with 9-Methoxyellipticine (1). Several microorganisms including Botrytis allii (NRRL 2502), Cunninghamella echinulata (NRRL 1386), C. echinulata (NRRL 3655), and Penicillium Brevicompactum (ATCC 10418) achieved O-demethylation of (1) in good yield. P. brevicompactum was used to prepare 9-hydroxyellipticine (4) from 1 for isolation and complete identification. High-performance liquid chromatography was used to verify the identity of the major metabolite (4) in other cultures.

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.PMID:17705535DOI:10.1021/jo070774z.

The preparation of polyfunctional aryl azides by the reaction of aryl triazenes with NaN3 in the presence of KHSO4 or BF3.OEt2/TFA (trifluoroacetic acid) has been described. A variety of functional groups (halides, esters, ketones, nitriles, aldehydes, and boronic esters) are tolerated under the Lewis acidic conditions. By using this methodology, the potent antitumor agents, ellipticine and 9-Methoxyellipticine, have been synthesized. In addition, isoellipticine and a related derivative, 7-carbethoxyisoellipticine, were also prepared.

Ellipticine derivatives

J Med Chem 1975 Jul;18(7):755-60.PMID:1151997DOI:10.1021/jm00241a023.

Several acyloxy and alkyl derivatives of ellipticine have been prepared. In addition, a modified synthesis leading to the hitherto unobtainable 8,9-dimethoxy- and 8,9-methylenedioxyellipticines is described. Some of the derivatives described herein exhibit antitumor activity. However, none of the compounds showed activity superior to that of the naturally occurring pyridocarbazoles, ellipticine and 9-Methoxyellipticine.

[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.PMID:3103875doi

Evidences for the formation of the glutathione-hydroxyellipticine adduct during the rat metabolism of 9-Methoxyellipticine are provided. These data suggest that such a cytotoxic molecule might behave as a pro-alkylating agent in vivo.