biostudies-literatureUnknown22(10)Karimikia E<h4>Objectives</h4>In this study a series of novel colchicine-like β-acetamidoketones was designed and synthesized as potential tubulin inhibitors.<h4>Materials and methods</h4>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).<h4>Results</h4>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 <b>4f</b> 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 <b>4f</b>, colchicine and chalcone 1 were consistent with their antiproliferative activities. Molecular docking studies of <b>4f</b>, into the colchicine-binding site of tubulin exhibited possible mode of interaction between this compound and tubulin.<h4>Conclusion</h4>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 <i>para</i> 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.Iranian journal of basic medical sciences1138-1146https://www.ebi.ac.uk/biostudies/studies/S-EPMC6885397biostudies-literatureColchicine-like β-acetamidoketones as inhibitors of microtubule polymerization: Design, synthesis and biological evaluation of <i>in vitro</i> anticancer activity.PMC6885397Ghodsi RZarghi AGhandadi MOmid Malayeri SBehravan JKarimikia EfalseColchicine-like β-acetamidoketones as inhibitors of microtubule polymerization: Design, synthesis and biological evaluation of <i>in vitro</i> anticancer activity.<h4>Objectives</h4>In this study a series of novel colchicine-like β-acetamidoketones was designed and synthesized as potential tubulin inhibitors.<h4>Materials and methods</h4>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).<h4>Results</h4>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 <b>4f</b> 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 <b>4f</b>, colchicine and chalcone 1 were consistent with their antiproliferative activities. Molecular docking studies of <b>4f</b>, into the colchicine-binding site of tubulin exhibited possible mode of interaction between this compound and tubulin.<h4>Conclusion</h4>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 <i>para</i> 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.2019-01-01T00:00:00Z2019 Oct2025-04-27T00:52:52.813Z2025-04-06T18:02:02.304ZS-EPMC68853973199845410.22038/ijbms.2019.34760.8242