Synthesis, crystal structures and antitumor activity of two platinum(II) complexes with methyl hydrazinecarbodithioate derivatives of indolin-2-one

Li, Youshan; Peng, Bin; Ma, Liang; Cao, Sheng‐Li; Bai, Lulu; Yang, Chao-Rui; Wan, Chong‐Qing; Yan, Hao-Jie; Ding, Pan-Pan; Li, Zhongfeng; Liao, Ji; Meng, Yingying; Wang, Hailong; Li, Jing; Xu, Xingzhi

doi:10.1016/j.ejmech.2016.12.050

Cited by 20 publications

(9 citation statements)

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“…Classic platinum(II) complexes are characterised by a high probability of serious side effects and resistance which results in a lack of therapeutic effect. This fact motivated researchers to look for more efficient, less toxic, and higher-specific platinum(II) complexes 24 .…”

Section: Discussionmentioning

confidence: 99%

A novel series of pyrazole-platinum(II) complexes as potential anti-cancer agents that induce cell cycle arrest and apoptosis in breast cancer cells

Czarnomysy

Surażyński

Muszyńska

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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Six novel compounds of platinum(II) with pyrazole derivatives PtPz1–PtPz6 were synthesised and characterised (PtPz1 - [Pt2N-hydroksymethyl-3,5-dimethylpyrazole4(berenil)2]Cl4; PtPz2 - [Pt23,5-dimethylpyrazole4(berenil)2]Cl4; PtPz3 - [Pt23,4-dimethylpyrazole4(berenil)2]Cl4; PtPz4 - [Pt2pyrazole4(berenil)2]Cl4; PtPz5- [Pt25-methylpyrazole4(berenil)2]Cl4; PtPz6 - [Pt2N-ethylpyrazole4(berenil)2]Cl4). The cytotoxic activity of these complexes against MCF-7 and MDA-MB-231 breast cancer cell lines was determined using the MTT assay. Evaluation of apoptosis induction was done with the Annexin V-fluorescein isothiocyanate/propidium iodide assay. In addition, using a flow cytometer, we determined the influence of test compounds on the cell cycle and caspase-3, -8, and -9 activity. The obtained results of caspase activity were confirmed by cell imaging. Moreover, using the flow cytometer, the effects of the test compounds on mitochondrial potential change were assessed. The test results showed that novel pyrazole-platinum(II) complexes exhibited stronger anti-proliferative activity against two breast cancer cell lines than reference cisplatin. Compounds PtPz1, PtPz2, and PtPz3 with methyl substituents at the pyrazole ring showed stronger activity than pyrazole or ethylpyrazole containing complexes. Studies have shown that inhibition of cell survival occurs by arresting the G1 cell cycle and inducing apoptosis. Our analysis associated with the response of MCF-7 and MDA-MB-231 cells to treatment with PtPz1–PtPz6 showed that it leads the cells through the external and intrinsic (mitochondrial) apoptotic pathway via indirect DNA damage.

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Section: Discussionmentioning

confidence: 99%

A novel series of pyrazole-platinum(II) complexes as potential anti-cancer agents that induce cell cycle arrest and apoptosis in breast cancer cells

Czarnomysy

Surażyński

Muszyńska

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Some derivatives have attracted much attentions because they are regarded as new anticancer agents [4][5][6][7]. Recently, our group synthesized two platinum(II) complexes with methyl hydrazinecarbodithioate derivatives of indolin-2-one, which can non-covalently bind to DNA with high affinity and exhibit cytotoxicity against cancer cells by inducing apoptosis [8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Qin

Cao

2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 10 H 8 FN 3 OS 2 , monoclinic, P2 1 /c (no. 14), a = 6.2909(2) Å, CCDC no.: 1557525The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. Source of materialThe title compound was obtained via condensation of 5-fluoroindoline-2,3-dione (0.3 g, 2 mmol) with methyl hydrazinecarbodithioate (0.2 g, 2 mmol) in 8 mL methanol at room temperature for 12 h. The mixture was isolated by column chromatography on silica gel with dichloromethane/methanol = 98:2 (v/v) as eluent to give the title compound methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate (yield 65%; m.p.

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“…According to Hathaway, G factor decides the presence and absence of interaction between copper centers. The calculated G factor of the present complex greater than 4 implies an absence of interaction between the copper centers [ 46 , 47 , 48 , 49 ]. The ESR parameters g ‖ , g ⊥ , A ‖ and A ⊥ of the complex and the energies of d-d transitions are used to evaluate the orbital reduction parameters (K ‖, K ⊥ ) [ 50 ].…”

Section: Resultsmentioning

confidence: 99%

“…The magnitude of hypochromism and red shift determines the binding strength and intrinsic binding constant K b for complexes with CT-DNA. Therefore, by considering the obtained results, hypochromism with a red shift evidences an intercalation binding mode established between the π∗ orbital of the ligand and π orbital of base pairs in DNA results in reduction of π–π∗ transition energy [ 48 , 49 ]. On the other hand, the coupling π orbital with partially filled electrons, thus decreases the transition probabilities, which leads to hypochromism and further results in the red shift.…”

Section: Resultsmentioning

confidence: 99%

Bivalent Ni(II), Co(II) and Cu(II) complexes of [(E)-[(2-methyl-1,3-thiazol-5-yl)methylidene]amino]thiourea: synthesis, spectral characterization, DNA and in-vitro anti-bacterial studies

Yallur

Krishna

Challa

2021

Heliyon

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The present work describes the preparation of bivalent Ni(II), Co(II) and Cu(II) complexes of [(E)-[(2-methyl-1,3-thiazol-5-yl)methylidene]amino]thiourea (MTHC) by mixing in 1:2 ratio of corresponding metal salt and Schiff base ligand in ethanolic medium. The prepared ligand and its complexes are confirmed using elemental analysis, magnetic moments, FT-IR, NMR, electronic and ESR spectroscopy techniques. The spectroscopic data reveals that metal complexes are in square planar in nature. In DNA binding studies, the higher intrinsic binding constants (K b ) of Ni(II), Co(II) and Cu(II) complexes are 2.713 × 10 6 M −1 , 5.529 × 10 6 M −1 and 2.950 × 10 6 M −1 respectively, evident that complexes are avid binder with DNA base pairs. The moderate anti-bacterial activity (in-vitro) against staphylococcus epidermidis, Bacillus subtilis, Pseudomonas aeruginosa and Escherichia coli bacterial culture may be due to the high electron density of ligand which prevents the charge reduction of metal ion. In the presence and absence of H 2 O 2, it is notified that there is no appreciable DNA cleavage activity of Ni(II) and Co(II) complexes except Cu(II) complex which is due to aprotonation in the medium.

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Synthesis, crystal structures and antitumor activity of two platinum(II) complexes with methyl hydrazinecarbodithioate derivatives of indolin-2-one

Cited by 20 publications

References 27 publications

A novel series of pyrazole-platinum(II) complexes as potential anti-cancer agents that induce cell cycle arrest and apoptosis in breast cancer cells

A novel series of pyrazole-platinum(II) complexes as potential anti-cancer agents that induce cell cycle arrest and apoptosis in breast cancer cells

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂

Bivalent Ni(II), Co(II) and Cu(II) complexes of [(E)-[(2-methyl-1,3-thiazol-5-yl)methylidene]amino]thiourea: synthesis, spectral characterization, DNA and in-vitro anti-bacterial studies

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Synthesis, crystal structures and antitumor activity of two platinum(II) complexes with methyl hydrazinecarbodithioate derivatives of indolin-2-one

Cited by 20 publications

References 27 publications

A novel series of pyrazole-platinum(II) complexes as potential anti-cancer agents that induce cell cycle arrest and apoptosis in breast cancer cells

A novel series of pyrazole-platinum(II) complexes as potential anti-cancer agents that induce cell cycle arrest and apoptosis in breast cancer cells

Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2

Bivalent Ni(II), Co(II) and Cu(II) complexes of [(E)-[(2-methyl-1,3-thiazol-5-yl)methylidene]amino]thiourea: synthesis, spectral characterization, DNA and in-vitro anti-bacterial studies

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Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C₁₀H₈FN₃OS₂