Shosha Mayada I, El-Ablack Fawzia Z, Saad Entsar A
Chemistry Department, Faculty of Science, Damietta University, Damietta, New-Damietta, 34517, Egypt.
Sci Rep. 2025 Jan 3;15(1):710. doi: 10.1038/s41598-024-81294-1.
To shed light on the significance of thiazole derivatives in the advancement of cancer medication and to contribute to therapeutic innovation, we have designed the synthesis and antiproliferative activity investigation of 5-(1,3-dioxoisoindolin-2-yl)-7-(4-nitrophenyl)-2-thioxo-3,7-dihydro-2H-pyrano[2,3-d] thiazole-6-carbonitrile, the structure of thiazole derivative was confirmed by spectroscopic techniques UV, IR and NMR. The cytotoxic activity (in vitro) of the new hybrid synthesized compound on five human cancer cell lines; human liver hepatocellular carcinoma (HepG-2), colorectal carcinoma (HCT-116), breast adenocarcinoma (MCF-7), and epithelioid carcinoma (Hela), and a normal human lung fibroblast (WI-38) was studied using MTT assay. The compound exhibited a strong cytotoxicity effect against HepG-2 and MCF-7. The interaction of the newly synthesized compound with calf-thymus DNA (CT-DNA) was investigated at pH 7.2 by using UV-Vis absorption measurements, also, molecular docking was carried out to investigate the DNA binding affinity of the proposed compound with the prospective target, DNA (PDB ID: 1d12). Finally, molecular docking was carried out to examine the binding patterns with the prospective target, DNA-Topo II complex (PDB-code: 3QX3). Results indicated that the investigated compound strongly binds to CT-DNA via intercalative mode, and correlated with those obtained from molecular docking and in agreement with that of in vitro cytotoxicity activity.
为了阐明噻唑衍生物在癌症药物研发中的重要性并推动治疗创新,我们设计了5-(1,3-二氧代异吲哚啉-2-基)-7-(4-硝基苯基)-2-硫代-3,7-二氢-2H-吡喃并[2,3-d]噻唑-6-腈的合成及抗增殖活性研究,其噻唑衍生物结构通过紫外、红外和核磁共振等光谱技术得以确认。使用MTT法研究了新合成的杂化化合物对五种人类癌细胞系(人肝细胞癌(HepG-2)、结肠直肠癌(HCT-116)、乳腺腺癌(MCF-7)和上皮样癌(Hela))以及正常人肺成纤维细胞(WI-38)的细胞毒性活性(体外)。该化合物对HepG-2和MCF-7表现出强烈的细胞毒性作用。通过紫外可见吸收测量研究了新合成的化合物在pH 7.2时与小牛胸腺DNA(CT-DNA)的相互作用,此外,还进行了分子对接以研究所提出化合物与预期靶点DNA(蛋白质数据银行ID:1d12)的DNA结合亲和力。最后,进行分子对接以检查与预期靶点DNA-拓扑异构酶II复合物(蛋白质数据银行编码:3QX3)的结合模式。结果表明,所研究的化合物通过插入模式与CT-DNA强烈结合,这与分子对接结果相关,并与体外细胞毒性活性结果一致。