Synthesis, anticancer evaluation and molecular docking study of some Arylidenehydrazono analogues

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Canadian Journal of Chemistry Pub Date : 2023-04-05 DOI:10.1139/cjc-2022-0276

M. Soliman, N. Mahmoud, Aml B. Mohamed, Howayda E. Khaled

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Abstract

A series of 2-(arylidenehydrazono)-5-(2-oxo-2-arylethyl)thiazolidin-4-one derivatives were synthesized, characterized by spectral analyses and evaluated for their in vitro antitumor activity. The IC50 determination of compounds was investigated on the human breast cancer cell line MCF-7. Among the series, compounds 3, 6, 10, 16, 17 and 24 showed remarkable anticancer activity with mean IC50 values 2.34, 0.73, 2.69, 3.40, 1.18 and 1.76 μg/ml respectively, against MCF-7 cancer cells. Compound 16 enhanced the concentration of caspase-9, inhibited the concentration of KI67 and showed a profound reduction in the amount of MMP9 secreted into the medium of MCF-7 treated cells. Furthermore, compound 16 revealed anti-angiogenic activity through down-regulation the concentration of VEGF in the medium of MCF-7 treated cells. Compound 16 exerted cytotoxic effects on MCF-7 tumor cells via anti-proliferative, apoptotic, antiangiogenic and antimetastatic activities. Molecular docking methodology was performed for the most effective anticancer compounds to rationalize the possible interactions with active site of VEGFR-2 enzyme.

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一些芳基二肼类似物的合成、抗癌评价及分子对接研究

合成了一系列2-(芳基肼)-5-(2-氧-2-芳基乙基)噻唑烷-4- 1衍生物，通过光谱分析对其进行了表征，并对其体外抗肿瘤活性进行了评价。研究了化合物在人乳腺癌细胞株MCF-7上的IC50测定。其中化合物3、6、10、16、17和24对MCF-7癌细胞的平均IC50值分别为2.34、0.73、2.69、3.40、1.18和1.76 μg/ml。化合物16提高了caspase-9的浓度，抑制了KI67的浓度，并显著降低了MCF-7处理细胞培养基中MMP9的分泌量。此外，化合物16通过下调MCF-7处理细胞培养基中VEGF的浓度显示出抗血管生成活性。化合物16对MCF-7肿瘤细胞具有抗增殖、抗凋亡、抗血管生成和抗转移作用。对最有效的抗癌化合物进行分子对接，以合理化其与VEGFR-2酶活性位点的可能相互作用。

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来源期刊

Canadian Journal of Chemistry 化学-化学综合

CiteScore

1.90

自引率

9.10%

发文量

审稿时长

1 months

期刊介绍： Published since 1929, the Canadian Journal of Chemistry reports current research findings in all branches of chemistry. It includes the traditional areas of analytical, inorganic, organic, and physical-theoretical chemistry and newer interdisciplinary areas such as materials science, spectroscopy, chemical physics, and biological, medicinal and environmental chemistry. Articles describing original research are welcomed.