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Colchicine-like β-acetamidoketones as inhibitors of microtubule polymerization: Design, synthesis and biological evaluation of in vitro anticancer activity
2019
Journal:  
Iranian Journal of Basic Medical Sciences
Author:  
Abstract:

Objective(s): In this study a series of novel colchicine-like β-acetamidoketones was designed and synthesized as potential tubulin inhibitorsMaterials and Methods: The cytotoxicity of the novel synthesized β-acetamidoketones was assessed against two cancerous cell lines including MCF-7 (human breast cancer cells) and A549 (adenocarcinomic human alveolar basal epithelial cells) employing the MTT test. Tubulin polymerization test was done by using a commercial kit (Tubulin Polymerization Assay Kit).Results: In general, the cytotoxicity activities were highly dependent on the aromatic substitution pattern of phenyl ring at β position of β-acetamidoketones. Based upon, compound 4f possessing the same structural elements of colchicine and chalcone 1, revealed the most cytotoxicity more than the other β-acetamidoketone against the cancerous cell lines and showed moderate antitubulin effect. The tubulin inhibitory effect of 4f, colchicine and chalcone 1 were consistent with their antiproliferative activities. Molecular docking studies of 4f, into the colchicine-binding site of tubulin exhibited possible mode of interaction between this compound and tubulin.Conclusion: The structure activity relationship (SAR) data attained showed that the presence of trimethoxy phenyl attached to carbonyl group of β-acetamidoketones and a methoxy group at para position of the other ring are essential for cytotoxic activity. In general, the cytotoxicity activities were highly dependent on the aromatic substitution pattern of phenyl ring at β position of β-acetamidoketones.

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Iranian Journal of Basic Medical Sciences

Field :   Sağlık Bilimleri

Journal Type :   Uluslararası

Metrics
Article : 1.961
Cite : 737
2023 Impact : 0.06
Iranian Journal of Basic Medical Sciences