Synthesis and use of dioxime ligands for treatment of leukemia and colon cancer cells

Babahan, İlknur; Özmen, Ali; Aslan, Kadir

doi:10.1002/aoc.3752

Cited by 11 publications

(3 citation statements)

References 39 publications

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“…Several techniques were employed to grow good crystals of the compounds for x‐ray diffraction but were unsuccessful. Therefore, other techniques which have been extensively employed by other researchers in the establishment of the geometry of metal(II) compounds were employed.…”

Section: Resultsmentioning

confidence: 99%

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Omaka¹,

Ekennia²,

Njoku³

et al. 2018

Applied Organom Chemis

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Benzothiazole moiety has gained a lot of attention because of its importance as essential pharmacophore in the development of metal based drugs. Nickel (II) and copper(II) complexes of a benzothiazole based ligand, 2,2'-bibenzo[d]thiazole (L 1 ), synthesized by the reaction of benzothiazole-2-carbonylchloride and o-aminothiophenol, is reported. The compounds were characterised by elemental and percentage metal analyses, spectroscopic (FTIR and UV-vis), 1 H and 13 C NMR, Mass spectra, thermal, magnetic moment and molar conductance analyses. The mass spectra, elemental and percentage metal composition of the metal complexes gave a 2:1 ligand to metal stoichiometric mole ratio. The spectral data showed that the ligand was coordinated to the metal ions through the nitrogen atoms of the benzothiazole moiety. The electronic spectra and magnetic susceptibility measurements showed that the nickel and copper complexes adopted square planar geometries. The ligand and its metal(II) complexes were screened against some drug resistant microbes and were found to exhibit varied degree of antimicrobial activities. The nickel complex was more active compared to ciprofloxacin against Staphylococcus aureus and Bacillus cereus. Similarly, the antioxidant potential of the ligand was evaluated. The ligand is a better ferrous ion chelating agent compared to 1,10-phenanthroline and 2,2-bipyridine. The ligand and its complexes exhibited good antimicrobial and Fe 2+ chelating properties making them probable compounds of interest in antibiotic and antioxidant drug researches.

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Section: Resultsmentioning

confidence: 99%

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Omaka¹,

Ekennia²,

Njoku³

et al. 2018

Applied Organom Chemis

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“…[8] The exceptional stability and unique electronic properties of these complexes can be attributed to their planar structure, stabilized by hydrogen bonding. [9] It has been widely used for various purposes due to the high stability of metal complexes prepared from vic-dioxime ligand. The geometrical isomers of vic-dioximes and their derivatives are syn-, anti-, and amphi-structures usually, the stability order of these is anti-> amphi-> syn-configuration, vic-dioximes, and monoximes are amphoteric materials containing basic C=N groups and weakly acidic OH groups.…”

Section: Introductionmentioning

confidence: 99%

“…One of the striking features of this ligand class and its complexes is that it exhibits a wide range of pharmacological activities, including antibacterial, antioxidant, antifungal, and antidepressant. [4,9,12] It has attracted the attention of many scientists and research groups around the world due to its numerous biological studies of vic-dioxime compounds and their metal complexes. [13][14][15] These findings led us to synthesize a novel vic-dioxime ligand (1) and associated (2), ( 3), ( 4), (5), and ( 6) metal complexes, we also examined the antimicrobial and antioxidant behavior of these new types of compounds.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Cu(II), Ni(II), Ti(IV), VO(IV), and Zn(II) Metal Complexes Derived from Novel vic‐Dioxime and Investigation of Their Antioxidant and Antibacterial Activities

Alhafez

Savcı

Alan

et al. 2022

Chemistry & Biodiversity

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In this work, novel vic-dioxime ligand (LH 2 ) containing bound to the N 4 -oxime core moiety and its complexes with Cu(II), Ni(II), Ti(IV), VO(IV), and Zn(II) salts have been studied. The structure of the ligand and its complexes were successfully synthesized and characterized using NMR ( 1 H and 13 C), LC/MS/MS spectrometer, FT-IR and UV/ VIS spectroscopy, melting point, and magnetic susceptibility measurements. Vic-dioxime ligand (LH 2 ) (1) and its metal complexes ([Cu(LH) 5), and [Zn(LH) 2 ] (6), respectively) were tested for them in-vitro antibacterial and antioxidant activities. According to the metal chelating results of the study, it was determined that compounds (1), ( 2), ( 3), and ( 6) showed very good activity, and especially compound (2), had a stronger metal chelating capacity due to ligand dissociation from the synthesized metal complexes, which then would chelate Fe(II) in the experimental setting. When microorganisms were evaluated in terms of the % viability effect, it was observed that all compounds had activity against C. Albicans and S. Cerevisiae at rates similar to antibiotics.

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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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Synthesis and use of dioxime ligands for treatment of leukemia and colon cancer cells

Cited by 11 publications

References 39 publications

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Preparation of Cu(II), Ni(II), Ti(IV), VO(IV), and Zn(II) Metal Complexes Derived from Novel vic‐Dioxime and Investigation of Their Antioxidant and Antibacterial Activities

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

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Synthesis and use of dioxime ligands for treatment of leukemia and colon cancer cells

Cited by 11 publications

References 39 publications

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Preparation of Cu(II), Ni(II), Ti(IV), VO(IV), and Zn(II) Metal Complexes Derived from Novel vic‐Dioxime and Investigation of Their Antioxidant and Antibacterial Activities

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

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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