Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes

Babahan, İlknur; Özmen, Ali; Orhan, Nil; Kazar, Didem; Değirmenci, Esin Hafize

doi:10.1016/j.bioorg.2014.01.003

Cited by 12 publications

(12 citation statements)

References 47 publications

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“…The 13 C NMR spectrum of LH 2 showed oxime carbon (HNC=NOH) and (HC=NOH) peaks at 137.06 and 137.06 ppm, whereas hydrazone imine (MeC=NNH) was seen at 165.45 ppm, as shown in our previous studies [30–32] . Aromatic carbons were between 126.34 and 107.05 ppm, whereas the carbons of methyl groups for indole were observed at 51.27 ppm.…”

Section: Resultssupporting

confidence: 78%

“…3‐Methoxy‐indole‐hydrazone glyoxime (LH 2 ) was synthesized from the starting materials (antiglyoximehydrazine [GH 2 ] and 3‐methoxy indole) using glacial acetic acid as the catalyst. The starting material antichloroglyoxime was explained in our previous work [30–32] . A cooled (5 °C) solution of 3‐methoxy indole (1 mmol) in ethanol was added dropwise into a cooled solution containing (1 mmol) GH 2 and 3–5 drops of CH 3 COOH with constant stirring.…”

Section: Methodsmentioning

confidence: 99%

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A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

Babahan

Özmen

Aksel

et al. 2020

Applied Organom Chemis

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In this study, a novel bidentate ligand containing oxime, hydrazone, and indole moieties and its BF2+‐bridged transition metal complexes [Ni(II), Cu(II), and Co(II)] were synthesized and their cytotoxic activities against prostate and breast cancer cells were investigated. The vic‐dioxime ligand bearing indole–hydrazone side groups was synthesized by reacting antiglyoximehydrazine (GH2) with 3‐methoxy indole. The ligand forms mononuclear complexes with a metal‐to‐ligand ratio of 1:2 with M = Co(II)(H2O)2, Ni(II), and Cu(II). These metal complexes were then reacted with BF3(C2H5)2O to obtain BF2+‐bridged transition metal complexes. The Co(II) complex of the ligand is proposed to be octahedral with water molecules as axial ligands, whereas the Ni(II) and Cu(II) complexes are proposed to be square planar. Spectral studies showed that the ligand bonded to the metal ion in a neutral bidentate fashion through the azomethine nitrogen atom and the imine oxime group. Structural assignments are supported by a combination of 1H nuclear magnetic resonance (NMR), 13C NMR, Fourier‐transform infrared, LC/MS, elemental analyses, and magnetic susceptibility testing. For determining the cytotoxic effects of the novel anticancer products, cancer cells were cultured. The antiproliferative effects were determined using the MCF‐7 breast cancer and PC‐3 prostate cancer cell lines. The antiproliferative effects of the products were analyzed and their apoptotic or necrotic effects were determined with the Hoechst/propidium iodide double staining method in both cancer cell lines. Paclitaxel was used as the positive control (1 μm). The results indicated that the newly synthesized compounds are effective on both cell lines between concentrations of 5 and 40 μm and show their effects by apoptotic mechanisms. Besides, these products were found to be more effective on the MCF‐7 cell line. The cytotoxic efficiency of the newly synthesized products was more than that of paclitaxel (depending on concentration), which is a chemotherapeutic agent used in cancer therapy.

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Section: Resultssupporting

confidence: 78%

Section: Methodsmentioning

confidence: 99%

A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

Babahan

Özmen

Aksel

et al. 2020

Applied Organom Chemis

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“…Recent interest in the chemistry of thiosemicarbazone ligands arises mainly from the potential from both azomethine nitrogen and thiolate sulphur donor atoms with variance coordination modes of either monodentate [ 1 ], bidentate [ 2 ], or tridentate [ 3 ]. This variance can be performed by introducing different substituents in order to form a selection of mononuclear [ 4 ] and polynuclear [ 5 ] complexes.…”

Section: Introductionmentioning

confidence: 99%

“…is variance can be performed by introducing different substituents in order to form a selection of mononuclear [4] and polynuclear [5] complexes. e versatility of thiosemicarbazone derivatives and its metal complexes allows for the design and development of bioactive compounds, including anticancer [6], antioxidant [7], and antibacterial [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-Ray Structure, Hirshfeld Surface Analysis, DFT Calculations, and Molecular Docking Studies of Nickel(II) Complex with Thiosemicarbazone Derivative

Osman

Silvarajoo

Hassim

et al. 2021

Bioinorganic Chemistry and Applications

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This article presents both experimental and computational study of a new Ni(II) complex, namely, bis{2-(2-trifluoromethylbenzylidene)hydrazine-1-carbothioamido-κ2N2, S}nickel(II) (abbreviate as NiL2). The complex was synthesized and well characterized using various spectroscopic methods. The single X-ray crystallographic study revealed a distorted square planar geometry around Ni(II) metal ion centre in which the angles deviated from ideal 90° with a maximum value of 6.57° occupied by nitrogen and sulphur donor atoms. The theoretical bond lengths and angles for the NiL2 complex were obtained by using the B3LYP level of density function theory (DFT) with LANL2DZ/6-311G (d, p) basis sets. These results showed very good agreement with the experimental X-ray values. The electrophilicity index (ω = 50.233 eV) shows that the NiL2 complex is a very strong electrophile. In addition, strong F⋯H/H⋯F interactions with 28.5% of the total Hirshfeld surface analyses in NiL2 were obtained indicating that the complex could bind with protein effectively. Furthermore, the new NiL2 complex was docked with plasma retinol-binding protein 4 (RBP4) (PDB id: 5NU7), which implied that the NiL2 complex bound to Tyrosine 133 and Aspartate 102 amino acids via N-H intermolecular hydrogen bonds.

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“…The syn form of isomer does not form complex with metal ions due to the steric hindrance. The planar structure of 1,2-dioximes is balanced by hydrogen bonding interactions is also considered as the reason of the recognizable steadiness and sole electronic specifications of vic-dioxime complexes [7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

The Novel bis-dioxime-based and Boronic acid-capped Groups Containing Fe(II) and Co(II) Complexes: Synthesis, Characterization, and Spectroscopy

Kılıç¹,

Erdoğan²,

Durğun³

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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In the present work, firstly the novel monoxime (1) and asymmetric dioxime ligand (LH2) (2) derived 4′-hydroxyvalerophenone as ketone was prepared under optimum reaction conditions. Then, the bis-dioxime-based and boronic acid-capped groups containing Fe(II) and Co(II) complexes [(L)2M(X)2(BA)2] (3-6) (L= Dioxime, M = Fe(II) or Co(II), X= Cl2 or H2O and BA = Butyl boronic acid (BBA) or Ferrocene boronic acid (FBA)) were synthesized into a two-necked round-bottom flask by direct interaction of the dioxime ligand (2), and different boronic acid with metal salts (FeCl2.4H2O or CoCl2) without special requirement of any additional chemical process. The prepared ligands and their Fe(II) and Co(II) complexes were characterized by melting points, FT-IR, UV-Vis, LC-MS, NMR spectra (1 H and 13 C), elemental analysis, as well as magnetic susceptibility measurements. The spectroscopic results demonstrate that the proposed Fe(II) and Co(II) complexes consist of six-coordinated species and possess the octahedral geometry. The FT-IR spectra of the Fe(II) and Co(II) complexes reveal the existence of the characteristic peaks at range from 1208 to 1217 cm-1 corresponding to (B-O) stretching.

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Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes

Cited by 12 publications

References 47 publications

A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

Synthesis, X-Ray Structure, Hirshfeld Surface Analysis, DFT Calculations, and Molecular Docking Studies of Nickel(II) Complex with Thiosemicarbazone Derivative

The Novel bis-dioxime-based and Boronic acid-capped Groups Containing Fe(II) and Co(II) Complexes: Synthesis, Characterization, and Spectroscopy

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Synthesis, characterization, and in vitro anti-neoplastic activity of novel vic-dioximes bearing thiosemicarbazone side groups and their mononuclear complexes

Cited by 12 publications

References 47 publications

A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF2+ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF2+ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

Synthesis, X-Ray Structure, Hirshfeld Surface Analysis, DFT Calculations, and Molecular Docking Studies of Nickel(II) Complex with Thiosemicarbazone Derivative

The Novel bis-dioxime-based and Boronic acid-capped Groups Containing Fe(II) and Co(II) Complexes: Synthesis, Characterization, and Spectroscopy

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A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells

A novel bidentate ligand containing oxime, hydrazone and indole moieties and its BF₂⁺ bridged transition metal complexes and their efficiency against prostate and breast cancer cells