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Aroylhydrazone Diorganotin Complexes Causes DNA Damage and Apoptotic Cell Death: From Chemical Synthesis to Biochemical Effects.

ABSTRACT: Under microwave irradiation, eighteen new aroylhydrazone diorganotin complexes (1a-9b) were produced through the reaction of aroylhydrazine, 2-ketobutyric acid, and the corresponding diorganotin. Fourier transform infrared spectroscopy, ¹H, ¹³C, and ¹¹⁹Sn nuclear magnetic resonance spectroscopies, high-resolution mass spectroscopy, X-ray crystallography, and thermogravimetric analysis (TGA) were performed to characterize the complexes. The in vitro anticancer activity for complexes were assessed using a CCK-8 assay on human cancer cells of HepG2, NCI-H460, and MCF-7. Complex 4b revealed more intensive anticancer activity against MCF-7 cells than the other complexes and cisplatin. Flow cytometry analysis and transmission electron microscope observation demonstrated that complex 4b mediated cell apoptosis of MCF-7 cells and arrested cell cycle in S phase. Western blotting analysis showed that 4b induced DNA damage in MCF-7 cells and led to apoptosis by the ATM-CHK2-p53 pathway. The single cell gel electrophoreses assay results showed that 4b induced DNA damage. The DNA binding activity of 4b was studied by UV-Visible absorption spectrometry, fluorescence competitive, viscosity measurements, gel electrophoresis, and molecular docking, and the results show that 4b can be well embedded in the groove and cleave DNA.

SUBMITTER: Jiang W

PROVIDER: S-EPMC8709053 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Aroylhydrazone Diorganotin Complexes Causes DNA Damage and Apoptotic Cell Death: From Chemical Synthesis to Biochemical Effects.

Jiang Wujiu W Tan Yuxing Y Peng Yiyuan Y

International journal of molecular sciences 20211216 24

Under microwave irradiation, eighteen new aroylhydrazone diorganotin complexes (1a-9b) were produced through the reaction of aroylhydrazine, 2-ketobutyric acid, and the corresponding diorganotin. Fourier transform infrared spectroscopy, 1H, 13C, and 119Sn nuclear magnetic resonance spectroscopies, high-resolution mass spectroscopy, X-ray crystallography, and thermogravimetric analysis (TGA) were performed to characterize the complexes. The in vitro ...[more]

PMID: 34948323

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Project description:Current antimicrobial drug discovery and advancement attempts are aimed to identify new complexes that can work effectively against the infections caused by microbes. The aim of present study was to synthesize new diorganotin(IV) complexes of N'-((8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene)-2-nitrobenzohydrazide (H2L1), N'-((8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene)-3-methoxybenzohydrazide (H2L2) and N'-((8-hydroxy-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)methylene)-4-methylbenzohydrazide (H2L3) Schiff base ligands with formula R2SnL1−3 (where R = Me, Et, Bu and Ph). Various spectral and physico-analytical techniques such as elemental analysis, FT-IR, multinuclear (1H, 13C, 119Sn) NMR, HRMS and XRD were utilized to structurally elucidate the prepared compounds. Based on the spectral data, it was concluded that ligands behave in a tridentate manner and coordinates to the central tin atom through ONO donor atoms. Furthermore, the synthesized compounds were examined for in vitro antimicrobial activity against four bacterial and two fungal strains. Among the examined compounds, Ph2SnL1 complex (MIC = 0.0095 µmol/mL) was found to be the most active. To rationalize the preferred mode of interactions of the most active compound, a molecular docking study of compound Ph2SnL1 was executed in the binding site of 3-oxoacyl-[acyl-carrier-protein] synthase 2 (FabF) of E. coli and sterol 14-alpha demethylase of C. albicans. Compound Ph2SnL1 inhibits the microbes effectively and it could be an effective and new candidate for the modulation of various infections. Graphical Abstract New diorganotin(IV) complexes (4–15) were prepared from tridentate Schiff base hydrazones (1–3). The compounds were examined for in vitro antimicrobial activity. Further, molecular docking study of the most potent compound Ph2SnL1 (7) was performed against the enzyme 3-oxoacyl-[acyl-carrier-protein] synthase 2 (FabF) of E. coli and sterol 14-alpha demethylase of C. albicans. Supplementary Information The online version contains supplementary material available at 10.1007/s11164-022-04860-0.

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Aroylhydrazone Diorganotin Complexes Causes DNA Damage and Apoptotic Cell Death: From Chemical Synthesis to Biochemical Effects.

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Aroylhydrazone Diorganotin Complexes Causes DNA Damage and Apoptotic Cell Death: From Chemical Synthesis to Biochemical Effects.

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