Diorganotin(IV) complexes based on tridentate ONO ligands as potential anticancer agents

Wujiu Jiang; Qiqi Qin; Xiyuan Xiao; Yuxing Tan

doi:10.1016/j.jinorgbio.2022.111808

Diorganotin(IV) complexes based on tridentate ONO ligands as potential anticancer agents

J Inorg Biochem. 2022 Jul:232:111808. doi: 10.1016/j.jinorgbio.2022.111808. Epub 2022 Mar 31.

Authors

Wujiu Jiang¹, Qiqi Qin², Xiyuan Xiao², Yuxing Tan³

Affiliations

¹ Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, Hunan Provincial Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of XiangJiang River, College of Chemistry and Materials Science, Nanyue College, Hengyang Normal University, Hengyang, Hunan 421008, PR China. Electronic address: jiang59@hynu.edu.cn.
² Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, Hunan Provincial Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of XiangJiang River, College of Chemistry and Materials Science, Nanyue College, Hengyang Normal University, Hengyang, Hunan 421008, PR China.
³ Key Laboratory of Functional Metal-Organic Compounds of Hunan Province, Key Laboratory of Organometallic New Materials, College of Hunan Province, Hunan Provincial Engineering Research Center for Monitoring and Treatment of Heavy Metals Pollution in the Upper Reaches of XiangJiang River, College of Chemistry and Materials Science, Nanyue College, Hengyang Normal University, Hengyang, Hunan 421008, PR China. Electronic address: tanyuxing@hynu.edu.cn.

PMID: 35421767
DOI: 10.1016/j.jinorgbio.2022.111808

Abstract

Eight new diorganotin(IV) complexes (1a-2d), namely {[X-C₆H₄(O)C=N-N=C(Me)COO]R₂Sn(CH₃OH)}_n (1a, 2a), {[X-C₆H₄(O)C=N-N=C(Me)COO]R₂Sn(CH₃OH)}₂ (1b, 1c, 1d, 2b), and {[X-C₆H₄(O)C=N-N=C(Me)COO]R₂Sn}₂ (2c, 2d) (X = H-, p-Me-, p-OH-, p-NO₂-; R = o-Cl-C₆H₄CH₂- or o-Me-C₆H₄CH₂-), have been synthesized by microwave "one-pot" reaction with arylformylhydrazine, pyruvic acid, and the corresponding R₂SnCl₂. All the complexes have been characterized by FT-IR (Fourier transform infrared spectroscopy), multinuclear NMR (¹H, ¹³C, and ¹¹⁹Sn nuclear magnetic resonance spectroscopies), HRMS (high-resolution mass spectroscopy) and single-crystal X-ray structural analysis. The antiproliferative activity of all complexes was tested against the cancer cell lines NCI-H460, MCF-7 and HepG2. The diorganotin complex 1c has been shown to be more potent antitumor agents against HepG2 than other complexes and cisplatin. Flow cytometry analysis observation demonstrated that complex 1c mediated cell apoptosis of HepG2 cells and arrested cell cycle in the S phase. The single cell gel electrophoreses assay results show that the 1c induce DNA damage. The DNA binding activities of the 1c were studied by UV-visible absorption spectrometry, fluorescence competitive, circular dichroism measurements, and molecular docking, results shown 1c can be well embedded in the groove and cleave DNA.

Keywords: Anticancer activity; Apoptosis; Cell cycle; DNA damage; Organotin; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
DNA / metabolism
Ligands
Molecular Docking Simulation
Organotin Compounds* / chemistry
Spectroscopy, Fourier Transform Infrared

Substances

Antineoplastic Agents
Ligands
Organotin Compounds
DNA