Anti-Cancer Activity, DFT and molecular docking study of new BisThiazolidine amide

IF 2.5 Q2 CHEMISTRY, MULTIDISCIPLINARY Results in Chemistry Pub Date : 2024-10-16 DOI:10.1016/j.rechem.2024.101835

Haider A. Omran , Ahmed A. Majed , Kawkab Hussein , Dawood S. Abid , Mostafa A. Abdel-Maksoud , Ahmed Elwahsh , Mohamed Aufy , Mohamed H. Kotob

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Abstract

In this study, a series of bis amide thiazolidine derivatives (Q1-Q6) were synthesized and their anticancer activity was evaluated against prostate (PC3) and breast (MCF7) cancer cells and normal cells line activity was evaluated against breast (MCF10), prostate (PNT1A) and living human cells (HUVEC) cancer cells. The thiazolidine rings were built from penicillamine and aromatic aldehydes (A1-A6), then converted to acetyl thiazolidines (B1-B6) using acetic anhydride, and finally linked with phenylene diamine to form the final compounds (Q1-Q6). Notably, compounds Q1 and Q3 displayed the highest activity against PC3, with IC50 values of 81 and 89 µg/ml, respectively. Docking simulations were performed for Q1, Q4, and Q5 against protein structures related to cancer (2FVD and 1SJ0). Additionally, DFT calculations were used to determine various molecular properties like HOMO/LUMO energies, band gap, and other descriptors, providing insights into the compounds’ stability and reactivity.

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新型双噻唑烷酰胺的抗癌活性、DFT 和分子对接研究

本研究合成了一系列双酰胺噻唑烷衍生物（Q1-Q6），并评估了它们对前列腺癌细胞（PC3）和乳腺癌细胞（MCF7）的抗癌活性，以及对乳腺癌细胞（MCF10）、前列腺癌细胞（PNT1A）和人类活细胞（HUVEC）的抗癌活性。噻唑烷环由青霉胺和芳香醛（A1-A6）形成，然后用乙酸酐转化为乙酰噻唑烷（B1-B6），最后与亚苯基二胺连接形成最终化合物（Q1-Q6）。值得注意的是，化合物 Q1 和 Q3 对 PC3 的活性最高，IC50 值分别为 81 微克/毫升和 89 微克/毫升。针对 Q1、Q4 和 Q5 与癌症相关的蛋白质结构（2FVD 和 1SJ0）进行了对接模拟。此外，还利用 DFT 计算确定了各种分子特性，如 HOMO/LUMO 能量、带隙和其他描述因子，从而深入了解了化合物的稳定性和反应性。

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