Synthesis, crystal structure, DNA interaction and anticancer activity of novel organotin cinnamate complexes

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2025-05-27 DOI:10.1016/j.molstruc.2025.142814

Jingni Wang , Meifen Wei , Zhiyu Pan , Wen Zhong , Shaofeng Chen , Shijie Lin , Wei Tian

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引用次数: 0

Abstract

Four dibutyltin cinnamate complexes (1a∼4a) and four tricyclohexyltin cinnamate complexes (1b∼4b) were successfully synthesized and were characterized by various techniques including Fourier-transform infrared spectroscopy (FT-IR), multinuclear nuclear magnetic resonance (¹H, ¹³C, and ¹¹⁹Sn), and thermogravimetric analysis (TGA). The crystal structures of these eight complexes were thoroughly determined. Among them, the dibutyltin cinnamate complexes (1a∼4a) exhibited a tetranuclear trapezoidal structure, while the tricyclohexyltin cinnamate complexes (1b∼4b) displayed a monomeric structure. The supramolecular structures were observed in 1b, 3a, 3b, 4a, and 4b All complexes were tested for their inhibitory activity against human cell lines A549, HepG2, and MDA-MB-231. The results showed that the 4a complex demonstrated the most significant inhibitory effect on HepG2 cells, with an IC₅₀ value of 0.08 ± 0.02 μM. Preliminary studies indicated that complex 4a induced apoptosis in HepG2 cells, accompanied by G2 phase cell cycle arrest. The DNA binding activity of 4a was investigated using ultraviolet-visible, fluorescence competition assays, and molecular docking, revealing that 4a can effectively intercalate the DNA groove.

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新型肉桂酸有机锡配合物的合成、晶体结构、DNA相互作用及抗癌活性

成功合成了4个肉桂酸二丁基锡配合物（1a ~ 4a）和4个肉桂酸三环己基锡配合物（1b ~ 4b），并通过傅里叶变换红外光谱（FT-IR）、多核核磁共振（1H、13C和119Sn）和热重分析（TGA）等多种技术对其进行了表征。对这8种配合物的晶体结构进行了全面测定。其中，肉桂酸二丁基锡配合物（1a ~ 4a）为四核梯形结构，而肉桂酸三环己基锡配合物（1b ~ 4b）为单体结构。在1b， 3a, 3b， 4a和4b中观察到超分子结构，并检测了所有复合物对人细胞系A549， HepG2和MDA-MB-231的抑制活性。结果表明，4a复合物对HepG2细胞的抑制作用最为显著，IC50值为0.08±0.02 μM。初步研究表明复合物4a可诱导HepG2细胞凋亡，并伴有G2期细胞周期阻滞。利用紫外可见、荧光竞争和分子对接等方法研究4a的DNA结合活性，发现4a能有效嵌入DNA凹槽。

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来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.