Synthesis and investigation of the anticancer effects of estrone-16-oxime ethers in vitro

Berényi, Ágnes; Minorics, Renáta; Iványi, Zoltán; Ocsovszki, Imre; Ducza, Eszter; Thole, Hubert; Messinger, Josef; Wölfling, János; Mótyán, Gergő; Mernyák, Erzsébet; Frank, Éva; Schneider, Gyula; Zupkó, István

doi:10.1016/j.steroids.2012.10.009

Cited by 59 publications

(40 citation statements)

References 35 publications

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“…These conjugates (11 a-x) were evaluated for their antiproliferative activity in a panel of five human cancer cell lines, namely MCF-7 (breast), A549 (lung), HeLa (cervix), DU-145 (prostate), and HT-29 (colon) by employing an MTT cell viability assay [40,41] with doxorubicin as the reference drug. The results are summarized in Table 1 and expressed as IC 50 values.…”

Section: Antiproliferative Activitymentioning

confidence: 99%

“…[40][41] Cells were were seeded at 1 10 4 cells/well in Dulbecco's modified Eagle's medium (DMEM) (200 mL), supplemented with 10 % fetal bovine serum (FBS) in each well of 96-well microculture plates, and incubated for 24 h at 37 8C in a CO 2 incubator. Compounds, diluted to the desired concentrations in culture medium, were added to the wells with respective vehicle control.…”

Section: Anticancer Activitymentioning

confidence: 99%

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Design and Synthesis of Imidazo[2,1‐b]thiazole–Chalcone Conjugates: Microtubule‐Destabilizing Agents

et al. 2014

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A series of chalcone conjugates featuring the imidazo[2,1-b]thiazole scaffold was designed, synthesized, and evaluated for their cytotoxic activity against five human cancer cell lines (MCF-7, A549, HeLa, DU-145 and HT-29). These new hybrid molecules have shown promising cytotoxic activity with IC50 values ranging from 0.64 to 30.9 μM. Among them, (E)-3-(6-(4-fluorophenyl)-2,3-bis(4-methoxyphenyl)imidazo[2,1-b]thiazol-5-yl)-1-(pyridin-2-yl)prop-2-en-1-one (11 x) showed potent antiproliferative activity with IC50 values ranging from 0.64 to 1.44 μM in all tested cell lines. To investigate the mechanism of action, the detailed biological aspects of this promising conjugate (11 x) were carried out on the A549 lung cancer cell line. The tubulin polymerization assay and immunofluoresence analysis results suggest that this conjugate effectively inhibits microtubule assembly in A549 cells. Flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase and leads to apoptotic cell death. This was further confirmed by Hoechst staining, activation of caspase-3, DNA fragmentation analysis, and Annexin V-FITC assay. Moreover, molecular docking studies indicated that this conjugate (11 x) interacts and binds efficiently with the tubulin protein.

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Section: Antiproliferative Activitymentioning

confidence: 99%

Section: Anticancer Activitymentioning

confidence: 99%

Design and Synthesis of Imidazo[2,1‐b]thiazole–Chalcone Conjugates: Microtubule‐Destabilizing Agents

et al. 2014

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“…The most potent compounds were found to induce apoptosis via the enhancement of tubulin polymerization or to cause disturbance in a cell cycle. Furthermore, 16-oximes of 13a-estrone proved to inhibit the proliferation of particular cancer cell lines effectively, with high selectivity for cancer cell lines 12 . As D-seco-and 13a-estrones have been reported to possess no estrogenic activity, but to exert growth-inhibitory action, we chose these compounds as candidates for the design of potentially cytostatic derivatives with selective biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin vitropharmacological evaluation ofN-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides ond-secoestrone scaffolds

Szabó

Bacsa

Wölfling

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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An efficient synthesis of several N-[(1-benzyl-1,2,3-triazol-4-yl)methyl]carboxamides in the 13b-and 13a-D-secoestrone series is reported. Novel triazoles were synthesized via the Cu(I)-catalyzed azide-alkyne cycloaddition of steroidal alkynyl carboxamides and p-substituted benzyl azides. Each of the products was evaluated in vitro by means of MTT assays for antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF-7, A431 and A2780). Some of them exhibited activities similar to those of the reference agent cisplatin. On change of the substitution pattern of the benzyl group of the azide, great differences in the cell growth-inhibitory properties were observed. The p-alkylbenzyl-substituted triazoles selectively exerted high cytostatic action against A2780 cells, with IC 50 values of 1 mM. We investigated the potential inhibitory action exerted on the human 17b-HSD1 activity of the new secosteroids. Three triazoles effectively suppressed the estrone to 17b-estradiol conversion with IC 50 values in low micromolar range.

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“…Non-toxic concentrations of digitoxin and digoxin inhibit growth and induce apoptosis in different human malignant cell lines, whereas highly proliferating normal cells are not affected. Although these compounds have no use as anticancer agents because of the cardiac side effects, the structure of these compounds can be used for the development of novel anticancer agents (Mijatovic and Kiss, 2013 (Minorics et al, 2012, Berényi et al, 2013, Kovács et al, 2014, Mernyák et al, 2014 et al, 1986, Alvarez et al, 1994, Genin et al, 2000, Zhou and Wang, 2012, Sahu et al, 2013. The introduction of a triazole ring at position 3 of the natural triterpene betulinic acid resulted in a set of compounds with considerable antiproliferative potency and proapoptotic capacity (Majeed et al, 2013).…”

Section: Role Of Steroids As Potential Anticancer Agentsmentioning

confidence: 99%

“…The most potent analogs inhibited DNA synthesis in Hela cells, changed the expression of endogenous factors regulating the G1-S transition (retinoblastoma protein, CDK4 and p16) and induced apoptosis (Berényi et al, 2013).…”

Section: Western Blotting Studiesmentioning

confidence: 99%

Characterization of antiproliferative activities of triazolyl-steroid derivatives

Molnár¹

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Synthesis and investigation of the anticancer effects of estrone-16-oxime ethers in vitro

Cited by 59 publications

References 35 publications

Design and Synthesis of Imidazo[2,1‐b]thiazole–Chalcone Conjugates: Microtubule‐Destabilizing Agents

Design and Synthesis of Imidazo[2,1‐b]thiazole–Chalcone Conjugates: Microtubule‐Destabilizing Agents

Synthesis andin vitropharmacological evaluation ofN-[(1-benzyl-1,2,3-triazol-4-yl)methyl]-carboxamides ond-secoestrone scaffolds

Characterization of antiproliferative activities of triazolyl-steroid derivatives

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