Synthesis, crystal structures, and biological activity of aroylhydrazone di-m-chlorobenzyltin complexes

IF 2.7 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

JBIC Journal of Biological Inorganic Chemistry Pub Date : 2023-12-23 DOI:10.1007/s00775-023-02038-6

Wujiu Jiang, Pengfei Zhou, Le Chen, Weiwei Fu, Yuxing Tan

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Abstract

Six aroylhydrazone di-m-chlorobenzyltin complexes {[X-C₆H₄(O)C=N–N=C(Me)COO](MeOH)(m-Cl-C₆H₄CH₂)₂Sn}₂ (X = p-Me- (1), p-MeO- (2), p–t-Bu- (3), p-NO₂- (4), p-OH- (5) or o-OH- (6)) were synthesized and characterized by HRMS (high-resolution mass spectrometry), NMR (nuclear magnetic resonance spectroscopy), IR (Fourier transform infrared spectroscopy), and TGA (thermogravimetric analysis) techniques. The molecular structure of complexes 1–6 was confirmed by single-crystal X-ray crystallography. The structure of complexes showed a distorted pentagonal bipyramidal configuration around the tin atom center, and the ligands adopted a tridentate chelating mode. Fascinatingly, either one-dimensional infinite chain structures or two-dimensional network structures were observed in the complexes through hydrogen bonds. Complex 2 has the strongest inhibitory effect on MCF7 and HepG2 cell proliferation, its effect was superior to that of the positive control drug cisplatin. The interaction of ct-DNA (calf-thymus DNA) with complex 2 was explored using UV absorption (ultraviolet absorption) and fluorescence spectroscopy. Complex 2 exhibited a moderate affinity for ct-DNA through intercalation modes. The interaction of complex 2 with ct-DNA has also been supported by molecular docking studies.

Graphical abstract

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甲酰腙二间氯苄锡复合物的合成、晶体结构和生物活性。

通过 HRMS（高分辨率质谱）、NMR（核磁共振波谱）和 o-OH- (6) 等方法合成并表征了六种甲酰基腙二间氯苄锡配合物 {[X-C6H4(O)C=N-N=C(Me)COO](MeOH)(m-Cl-C6H4CH2)2Sn}2 (X = p-Me- (1)、p-MeO- (2)、p-t-Bu- (3)、p-NO2- (4)、2Sn}2 （X = p-Me- (1)、p-MeO- (2)、p-t-Bu- (3)、p-NO2- (4)、p-OH- (5) 或 o-OH- (6)）的合成，并通过 HRMS（高分辨率质谱）、NMR（核磁共振光谱）、IR（傅立叶变换红外光谱）和 TGA（热重分析）技术对其进行了表征。单晶 X 射线晶体学证实了复合物 1-6 的分子结构。配合物的结构以锡原子为中心呈扭曲的五角双锥构型，配体采用三叉螯合模式。有趣的是，通过氢键，在配合物中观察到了一维无限链结构或二维网络结构。复合物 2 对 MCF7 和 HepG2 细胞增殖的抑制作用最强，其效果优于阳性对照药物顺铂。利用紫外线吸收和荧光光谱分析了ct-DNA（小牛胸腺 DNA）与复合物 2 的相互作用。通过插层模式，复合物 2 与ct-DNA 的亲和力适中。分子对接研究也证实了复合物 2 与 ct-DNA 的相互作用。

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来源期刊

JBIC Journal of Biological Inorganic Chemistry 化学-生化与分子生物学

CiteScore

5.90

自引率

3.30%

发文量

审稿时长

3 months

期刊介绍： Biological inorganic chemistry is a growing field of science that embraces the principles of biology and inorganic chemistry and impacts other fields ranging from medicine to the environment. JBIC (Journal of Biological Inorganic Chemistry) seeks to promote this field internationally. The Journal is primarily concerned with advances in understanding the role of metal ions within a biological matrix—be it a protein, DNA/RNA, or a cell, as well as appropriate model studies. Manuscripts describing high-quality original research on the above topics in English are invited for submission to this Journal. The Journal publishes original articles, minireviews, and commentaries on debated issues.