Synthesis and Biological Activity of 5‐Aza‐ellipticine Derivatives.

Moody, Deborah L.; Dyba, Marcin; Kosakowska-Cholody, Teresa; Tarasova, Nadya I.; Michejda, Christopher J.

doi:10.1002/chin.200735192

Cited by 2 publications

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“…Several derivatives of ellipticine have been investigated (Moody et al 2007;Miller et al 2012;Deane et al 2013;Iacopetta et al 2017). We previously reported two novel ellipticine derivatives, N-methyl-5-demethyl ellipticine and 2-methyl-N-methyl-5-demethyl ellipticinium iodide that both were potent topoisomerase II-targeting compounds (Vann et al 2016b).…”

Section: Introductionmentioning

confidence: 99%

Structural modification of ellipticine derivatives with alkyl groups of varying length is influential on their effects on human DNA topoisomerase II: a combined experimental and computational study

et al. 2019

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The compounds reducing tumor cell viability and disrupting DNA topoisomerase reactions have been widely used in anticancer drug development. Ellipticine (5,carbazole) is a potent intercalating agent that interferes with nucleic acid processing through interaction with DNA topoisomerase II. Although ellipticine is a wellcharacterized compound, it is not a widely-accepted drug due to the adverse effects detected upon administration. We have previously reported two novel ellipticine derivatives, N-methyl-5-demethyl ellipticine (ET-1) and 2-methyl-N-methyl-5demethyl ellipticinium iodide (ET-2) as potent compounds targeting DNA topoisomerase II. This study covers an extended synthesis, characterization, and activity data for five new salts of N-methyl 5-demetyl ellipticine (Z-1, Z-2, Z-4, Z-5 and Z-6) having several organic halides and their effects on human topoisomerase II enzymes. Moreover, combined in silico studies were conducted for better understanding of modes of action of studied molecules at the binding pocket of target. Our results showed that three of the derivatives (Z-1, Z-2, and Z-6) have considerable effect on the catalytic activity of human topoisomerase II implying the influence of alkyl groups added to the parental structure of ellipticine.

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Section: Introductionmentioning

confidence: 99%

Structural modification of ellipticine derivatives with alkyl groups of varying length is influential on their effects on human DNA topoisomerase II: a combined experimental and computational study

et al. 2019

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“…Among nitrogen heterocycles, indole derivatives such as carbazole alkaloids display a wide variety of activities, including antibacterial, anti-inflammatory, psychotropic and anti-histamine properties [3][4][5][6][7]. Moreover, carbazoles show significant antitumor activity in cells derived from leukemia, melanoma, colon adenocarcinoma, kidney, brain and breast tumors [8][9][10][11][12][13][14][15]. For instance, a series of simple benzo[a]carbazoles has been shown to bind to estrogen receptor (ER) and inhibit breast cancer cell proliferation as well as the growth of mammary tumors in rats [16].…”

Section: Introductionmentioning

confidence: 99%

(6-Bromo-1,4-dimethyl-9<i>H</i>-carbazol-3-yl-methylene)-hydrazine (Carbhydraz) Acts as a GPER Agonist in Breast Cancer Cells

Sinicropi

Lappano

Caruso

et al. 2015

CTMC

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Estrogens control a wide number of aspects of human physiology and play a key role in multiple diseases, including cancer. Estrogens act by binding to and activating the cognate receptor (ER), however numerous studies have revealed that the G protein-coupled receptor named GPR30/GPER mediates also estrogen signals. As ER and GPER share the ability to bind to same compounds, the use of GPER-selective ligands has allowed a better understanding of the biological responses mediated by GPER. In the present study, we designed and synthesized two novel carbazole derivatives and then investigated their ability to interact with and activate the GPER-mediated transduction pathway in breast cancer cells. Both compounds did not activate the classical ER in MCF7 cells, whereas one of the two compounds synthesized triggered through GPER the rapid ERK activation in ER-negative SkBr3 cells, demonstrating a good affinity for GPER in docking studies. The characterization of this novel selective GPER agonist could represent a potential useful tool to provide further insights into the physiopathological role exerted by GPER.

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Synthesis and Biological Activity of 5‐Aza‐ellipticine Derivatives.

Cited by 2 publications

References 1 publication

Structural modification of ellipticine derivatives with alkyl groups of varying length is influential on their effects on human DNA topoisomerase II: a combined experimental and computational study

Structural modification of ellipticine derivatives with alkyl groups of varying length is influential on their effects on human DNA topoisomerase II: a combined experimental and computational study

(6-Bromo-1,4-dimethyl-9<i>H</i>-carbazol-3-yl-methylene)-hydrazine (Carbhydraz) Acts as a GPER Agonist in Breast Cancer Cells

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