Organotin(IV) complexes derived from Schiff base N’-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-3-carbohydrazone: Synthesis, in vitro cytotoxicities and DNA/BSA interaction

Yang, Yuanguang; Hong, Min; Xu, Lidan; Cui, Jichun; Chang, Guoliang; Li, Dacheng; Li, Chen-Zhong

doi:10.1016/j.jorganchem.2015.12.041

Cited by 64 publications

(28 citation statements)

References 54 publications

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“…In addition, complex 1 which possesses better planarity is more easily inserted in the base pairs of DNA in the cell lines The two complexes tend to be more effective towards HeLa tumor cells, exhibiting better activity against HeLa in comparison with A549, and complexes 1 and 2 demonstrate different anticancer activities against the same cell line. From the IC 50 values, we can see that the two dimethyltin(IV) complexes show higher in vitro cytotoxic activities than cisplatin against the two cancer cell lines, which is consistent with results reported in the literature …”

Section: Resultssupporting

confidence: 88%

“…Among the main‐group metal complexes, organotin complexes exhibit the most potent anticancer activities, and some organotin compounds are more effective than cisplatin in in vitro tests . Recent studies demonstrated that the interaction between some tri‐ and diorganotin(IV) complexes and DNA may damage DNA in cancer cells which leads to prevention of the multiplication of cancer cells and to cell death . Therefore, more accurate and in‐depth understanding about the interaction mode of metal complexes with DNA and the mechanism of anticancer drugs will be helpful in the development of metal‐based antitumor drugs.…”

Section: Introductionmentioning

confidence: 99%

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Dimethyltin(IV) complexes derived from hydroxamic acid and acylhydrazone ligands: Synthesis, DNA/bovine serum albumin interaction and cytotoxicity

Chang

Yan

et al. 2017

Applied Organom Chemis

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[(2-hydroxy-5-chlorophenyl)methylidene]benzoylhydrazone), were synthesized and characterized using elemental analyses, Fourier transform infrared and NMR ( 1 H, 13 C) spectroscopies and single-crystal X-ray diffraction. In complex 1 the geometry around the tin atom is a six-coordinated distorted octahedral configuration, while complex 2 exhibits five-coordinated distorted trigonal bipyramid geometry. Preliminary in vitro cytotoxicity studies with two human cancer cell lines (HeLa and A549) using MTT assay show that complex 1 is more potent than complex 2. The interactions of the two complexes with calf thymus DNA and bovine serum albumin were also investigated using UV-visible absorption spectral, thermal denaturation and viscosity measurements and docking analysis. Investigations indicate that the structures of the mixed ligands play an important role in the properties of the dimethyltin(IV) complexes, and, to some extent, the antitumor activities of the complexes are partly related to interactions with DNA and some proteins in cancer cells.

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Section: Resultssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Dimethyltin(IV) complexes derived from hydroxamic acid and acylhydrazone ligands: Synthesis, DNA/bovine serum albumin interaction and cytotoxicity

Chang

Yan

et al. 2017

Applied Organom Chemis

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“…Hydrazone compounds (-NH-N=C-) and their complexes have been widely studied due to their facile synthesis and potential biological activities [1][2][3][4][5]. During recent years, many hydrazone compounds and their complexes have displayed novel structures and extensive applications in luminescent probes, antibacterial and antitumor agents, fluorescence markers, optical materials, and anticonvulsant agent [6][7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

The Synthesis and Crystal Structure of Two New Hydrazone Compounds

Wang

Tai

2016

Crystals

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“…This confirmed the coordination of the oxygen and nitrogen donor atom of Schiff bases to the tin ion. Moreover, the signal of the HC=N proton in the spectra of tin(IV) compounds shifted to the downfield region due to the coordination of -NH to tin atom, which was a result of the formation of the C=N-N=C conjugated systems [46]. The downfield shift of the HC=N signal in the 13 C NMR spectra, due to electron density transfer from the Schiff bases to the acceptor (Sn atom), was consistent with that observed in earlier reports [47,48].…”

Section: Multinuclear ( 1 H 13 C and 119 Sn) Nmr Spectral Analysismentioning

confidence: 99%

Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

Yusof

Latif

Tahir

et al. 2020

Journal of Molecular Structure

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Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H 2 L1, H 2 L2 and H 2 L3) and 2,3-dihydroxybenzaldehyde (H 2 L4, H 2 L5 and H 2 L6) (where H 2 Ln = di-acids of Schiff base) are reported. The compounds were characterised by elemental analysis, FT-IR and multinuclear NMR (1 H, 13 C and 119 Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithiocarbazate] (2) and tin(IV) [S-benzyl-β-N-(2-hydroxy-3-methoxy benzylmethylene)dithiocarbazate] (3) were determined by X-ray single crystal diffraction analysis. X-ray crystallography showed the molecular geometries in homoleptic 2 and 3 to be quite similar in which the dinegative tridentate ligand coordinated the tin atoms via thiolate-S, phenoxide-O and imine-N atoms. The coordination geometries are based on an octahedron with like-atoms mutually trans. The *Revised Manuscript Click here to view linked References 2 experimental findings were validated by density functional theory (DFT) calculations at the B3LYP/LanL2DZ/6-311G(d,p) level of theory. All the tin(IV) compounds, except the insoluble compound 2 were screened for their in vitro cytotoxicity against a panel ten of cancer cell lines and one normal breast cell line (MCF-10A) by MTT assay. Interestingly, the cytotoxicity of five tin(IV) compounds against HT29, MCF7 and MIA was higher than the reference drug, cisplatin.

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Organotin(IV) complexes derived from Schiff base N’-[(1E)-(2-hydroxy-3-methoxyphenyl)methylidene]pyridine-3-carbohydrazone: Synthesis, in vitro cytotoxicities and DNA/BSA interaction

Cited by 64 publications

References 54 publications

Dimethyltin(IV) complexes derived from hydroxamic acid and acylhydrazone ligands: Synthesis, DNA/bovine serum albumin interaction and cytotoxicity

Dimethyltin(IV) complexes derived from hydroxamic acid and acylhydrazone ligands: Synthesis, DNA/bovine serum albumin interaction and cytotoxicity

The Synthesis and Crystal Structure of Two New Hydrazone Compounds

Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

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