Department of Chemistry, College of Science, University Ha'il, Ha'il 81451, Saudi Arabia.
Department of Science, Institute for Information Technologies, University of Kragujevac, Jovana Cvijića bb, 34000 Kragujevac, Serbia.
Int J Mol Sci. 2023 Jul 25;24(15):11910. doi: 10.3390/ijms241511910.
Thiosemicarbazones and their transition metal complexes are biologically active compounds and anticancer agents with versatile structural properties. In this contribution, the structural features and stability of four pyridoxal-thiosemicarbazone (PLTSC) complexes with Fe, Co, Ni, and Cu were investigated using the density functional theory and natural bond orbital approach. Special emphasis was placed on the analysis of the donor atom-metal interactions. The geometry of compounds and crystallographic structures were further examined by Hirshfeld surface analysis, and the main intermolecular interactions were outlined. It has been shown that the geometry and the number of PLTSC units in the structure determine the type and contribution of the specific interactions. The binding of all four complexes to bovine and human serum albumin was investigated through spectrofluorometric titration. The dependency of the thermodynamic parameters on the present metal ion and geometry was explained by the possible interactions through molecular docking simulations. The binding of complexes to DNA, as one of the possible ways the compounds could induce cell death, was examined by molecular docking. The cytotoxicity was measured towards HCT116, A375, MCF-7, A2780, and MCF5 cell lines, with Cu-PLTSC being the most active, as it had the highest affinity towards DNA and proteins.
噻唑烷酮及其过渡金属配合物是具有多种结构性质的生物活性化合物和抗癌剂。在本研究中,采用密度泛函理论和自然键轨道方法研究了四种与 Fe、Co、Ni 和 Cu 配位的吡哆醛缩氨硫脲(PLTSC)配合物的结构特征和稳定性。特别强调了对供体原子-金属相互作用的分析。通过 Hirshfeld 表面分析进一步研究了化合物的几何形状和晶体结构,并概述了主要的分子间相互作用。结果表明,化合物的几何形状和结构中 PLTSC 单元的数量决定了特定相互作用的类型和贡献。通过光谱荧光滴定法研究了所有四种配合物与牛和人血清白蛋白的结合。通过分子对接模拟解释了热力学参数与金属离子和几何形状的依赖性,这是可能的相互作用的结果。通过分子对接研究了配合物与 DNA 的结合,作为化合物可能诱导细胞死亡的一种可能途径。用噻唑烷酮及其过渡金属配合物对 HCT116、A375、MCF-7、A2780 和 MCF5 细胞系进行了细胞毒性测定,Cu-PLTSC 是最活跃的,因为它对 DNA 和蛋白质具有最高的亲和力。