Evodiamine, a dual catalytic inhibitor of type I and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells

Pan, Xiaobei; Hartley, Janet M.; Hartley, John A.; White, Kenneth; Wang, Zhengtao; Bligh, S. W. Annie

doi:10.1016/j.phymed.2012.02.003

Cited by 53 publications

(35 citation statements)

References 29 publications

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“…The extract was dried on anhydrous Na 2 SO 4 , the EtOAc was removed and the crude product was purified by column chromatography to afford the pure target compounds. The characterization data for these compounds was as follows: (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). Yellowish product 1.22 g, yield 53.8%, m.p.…”

Section: Synthesis Of N13-substituted Evodiamine Derivatives: Generalmentioning

confidence: 99%

“…(5 (6). This compound was obtained by the hydrolysis of 9-(2,2-diethoxyethyl)evodiamine (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Into a solution of 2-18 (1.26 g, 3.0 mmol) in ethanol (20 mL) was added 10% hydrochloric acid (10 mL), and the mixture was stirred for 4-5 h at room temperature, while monitored by TLC.…”

Section: Synthetic Procedures For 3-1-3-3mentioning

confidence: 99%

“…It was demonstrated by Hu [4] and Linag [1] that evodiamine possesses a wide range of biological activities related to anti-inflammatory, anti-obesity and antitumor properties. In particular, both the strong cytotoxicity of evodiamine against human cancer cells and the underlining mechanisms of growth inhibition, apoptosis induction and suppression of invasion and metastasis have attracted much attention [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. Moreover, it was demonstrated that evodiamine sensitized chemoresistant breast cancer cells to adriamycin without obvious cytotoxicity against normal human peripheral blood cells [4,23], which indicated the potential of evodiamine for clinical application.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines

Song

Chen

et al. 2013

Molecules

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Abstract:Attempting to improve the anticancer activity and solubility of evodiamine in simulated gastric fluid (SGF) and simulated intestinal fluid (SIF) solutions, thirty-eight N13-substituted evodiamine derivatives were designed, synthesized and tested for antitumor activities against six kinds of human cancer cell lines, namely prostate cancer (DU-145 and PC-3), lung cancer (H460), breast cancer (MCF-7), colon cancer (HCT-5) and glioblastoma (SF-268). The solubility of these compounds in SGF and SIF solutions was evaluated, and apoptosis induced by 2-2, 2-3, 2-16 and 3-2 was determined. The results showed: (1) among all compounds examined, 2-16 showed the highest antitumor activity and a broader spectrum of activity, with IC 50 values ranging from 1-2 µM; (2) their solubility was obviously improved; (3) 2-3, 2-16 and 3-2 had a significant impact inducing apoptosis in some cancer cell lines. The preliminary structure-activity relationships of these derivatives were discussed.

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Section: Synthesis Of N13-substituted Evodiamine Derivatives: Generalmentioning

confidence: 99%

Section: Synthetic Procedures For 3-1-3-3mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines

Song

Chen

et al. 2013

Molecules

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“…In recent years, extensive attention has been drawn to some major compounds of ZJW with regard to the anticancer effects (Tang et al 2009;Jantova et al 2007;Kang et al 2005;Pan et al 2012). Our previous studies (Wang et al 2008;Wang et al 2009) have shown that berberine and evodiamine have synergistic inhibitory effects on SMMGC-7721 cells, and ZJW is more powerful than C. Chinese Frach and E. rutaecarpa (Juss.)…”

Section: Introductionmentioning

confidence: 99%

In vitro anti-proliferative effects of Zuojinwan on eight kinds of human cancer cell lines

et al. 2013

Cytotechnology

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Zuojinwan (ZJW), a famous Chinese medicinal formula, contains two medicinal herbs Coptis chinese Frach and Evodia rutaecarpa (Juss.) Benth in the ratio of 6: 1. The inhibitory effects of ZJW on eight kinds of human cancer cell lines including SMMC-7721, BEL-7402, BEL-7404, HepG2, A549, NCI-H446, NCI-H460 and HCT-116 cells were evaluated, and the possible mechanism was investigated. The growths of the eight kinds of cancer cells were inhibited by ZJW assessed through MTT assay. Flow cytometry assay revealed a sub-G1 peak with reduced DNA content was formed. The cell cycle was arrested in the G0/G1 phase in ZJW-treated SMMC-7721 and HepG2 cells, and in the S phase for NCI-H460 cells. Significant DNA damage was produced by ZJW assessed with single-cell gel electrophoresis assay. Morphological changes were also observed. Caspase-3 and -9 activities were increased following ZJW treatment. Western blot analysis showed that Bax and Bak protein levels were increased after ZJW treatment, while Bcl-2 and Bcl-xl protein levels were decreased. Our results suggest that ZJW has significant anti-cancer activities due to induction of mitochondria-dependent apoptosis pathway. Therefore, ZJW has the potential to be a novel chemotherapy drug to treat hepatoma, lung cancer and colon cancer by suppressing tumor growth.

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“…Evodiamine is an alkaloid extracted from Evodia rutecarpa used as an anticancer, anti-inflammatory and antiobesity agent [20]. This compound was initially classified as a topo I inhibitor, but then it was proposed that evodiamine could also bind to topoisomerase II [21]. …”

Section: Introductionmentioning

confidence: 99%

Effects of camptothecin derivatives and topoisomerase dual inhibitors on Trypanosoma cruzi growth and ultrastructure

Lacombe

Zuma

Silva

et al. 2014

J Negat Results BioMed

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BackgroundTrypanosoma cruzi is the etiological agent of Chagas’ disease that is an endemic disease in Latin America and affects about 8 million people. This parasite belongs to the Trypanosomatidae family which contains a single mitochondrion with an enlarged region, named kinetoplast that harbors the mitochondrial DNA (kDNA). The kinetoplast and the nucleus present a great variety of essential enzymes involved in DNA replication and topology, including DNA topoisomerases. Such enzymes are considered to be promising molecular targets for cancer treatment and for antiparasitic chemotherapy. In this work, the proliferation and ultrastructure of T. cruzi epimastigotes were evaluated after treatment with eukaryotic topoisomerase I inhibitors, such as topotecan and irinotecan, as well as with dual inhibitors (compounds that block eukaryotic topoisomerase I and topoisomerase II activities), such as baicalein, luteolin and evodiamine. Previous studies have shown that such inhibitors were able to block the growth of tumor cells, however most of them have never been tested on trypanosomatids.ResultsConsidering the effects of topoisomerase I inhibitors, our results showed that topotecan decreased cell proliferation and caused unpacking of nuclear heterochromatin, however none of these alterations were observed after treatment with irinotecan. The dual inhibitors baicalein and evodiamine decreased cell growth; however the nuclear and kinetoplast ultrastructures were not affected.ConclusionsTaken together, our data showed that camptothecin is more efficient than its derivatives in decreasing T. cruzi proliferation. Furthermore, we conclude that drugs pertaining to a certain class of topoisomerase inhibitors may present different efficiencies as chemotherapeutical agents.

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Evodiamine, a dual catalytic inhibitor of type I and II topoisomerases, exhibits enhanced inhibition against camptothecin resistant cells

Cited by 53 publications

References 29 publications

Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines

Design, Synthesis and Evaluation of N13-Substituted Evodiamine Derivatives against Human Cancer Cell Lines

In vitro anti-proliferative effects of Zuojinwan on eight kinds of human cancer cell lines

Effects of camptothecin derivatives and topoisomerase dual inhibitors on Trypanosoma cruzi growth and ultrastructure

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