Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate and monodentate pseudohalides

Milenković, Milica R.; Bacchi, Alessia; Cantoni, Giulia; Vilipić, Jovana; Sladić, Dušan; Vujčić, Miroslava; Gligorijević, Nevenka; Jovanović, Katarina; Radulović, Siniša; Anđelković, Katarina

doi:10.1016/j.ejmech.2013.07.039

Cited by 30 publications

(17 citation statements)

References 22 publications

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“…However, studies on the antitumoral activity for Ni(II) complexes with other ligands are available in the literature (Tan et al, 2010;Milenković et al, 2013). Tan et al (2010) observed that quercetin-Ni(II) complex induced apoptosis in dose-dependent cell lines of liver carcinoma (HepG2), human hepatoma (SMMC7721) and lung adenocarcinoma (A549).…”

Section: Discussionmentioning

confidence: 99%

“…According to the authors, the antitumoral activity consisted of the selective binding of the complex with DNA, triggering a series of events that led to cell death. Milenković et al (2013) studied the activity of three square planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino) benzylidene] hydrazinecarboxylate and monodentate pseudohalides. They observed that all the complexes had cytotoxic activity in relation to the six tumor cell lines that were tested.…”

Section: Discussionmentioning

confidence: 99%

“…The activity of some metal complexes against tumors using both in vitro and in vivo protocols is already known and recognized worldwide (Immel et al, 2011;Côrte-Real et al, 2013;Palanimuthu et al, 2013;Tan et al, 2010;Milenković et al, 2013). Studies have reported the characterization and stability of some InsP 6 complexes with transition metal ions, including Ni(II) (De Carli et al, 2006Quirrenbach et al, 2009).…”

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 97%

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Cytotoxic effect of inositol hexaphosphate and its Ni(II) complex on human acute leukemia Jurkat T cells

Lima

Kanunfre

Andrade

et al. 2015

Toxicology in Vitro

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Inositol hexaphosphate (InsP6) is present in cereals, legumes, nuts and seed oils and is biologically active against some tumor and cancer cells. Herein, this study aimed at evaluating the cellular toxicity, antiproliferative activity and effects on cell cycle progression of free InsP6 and InsP6-Ni(II) of leukemic T (Jurkat) and normal human cells. Treatments with InsP6 at concentrations between 1.0 and 4.0mM significantly decreased the viability of Jurkat cells, but showed no cytotoxic effect on normal human lymphocytes. Treatment with InsP6-Ni(II) complex at concentrations between 0.05 and 0.30 mM showed an anti-proliferative dose and a time-dependent effect, with significantly reduced cell viability of Jurkat cells but showed no cytotoxic effect on normal human lymphocytes as compared to the control. Ni(II) free ion was toxic to normal cells while InsP6-Ni(II) had no cytotoxic effect. The InsP6-Ni(II) complex potentiated (up to 10×) the antiproliferative effect of free InsP6 on Jurkat cells. The cytometric flow assay showed that InsP6 led to an accumulation of cells in the G0/G1 phase of the cell cycle, accompanied by a decrease in the number of cells in S and G2/M phases, whereas InsP6-Ni(II) has led to an accumulation of cells in the S and G2/M phases. Our findings showed that InsP6-Ni(II) potentiates cytotoxic effects of InsP6 on Jurkat cells and may be a potential adjuvant in the treatment of cancer.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Contents Lists Available At Sciencedirectmentioning

confidence: 97%

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Cytotoxic effect of inositol hexaphosphate and its Ni(II) complex on human acute leukemia Jurkat T cells

Lima

Kanunfre

Andrade

et al. 2015

Toxicology in Vitro

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“…Acylhydrazones of 2-(diphenylphosphino)benzaldehyde with "soft" phosphorus and structural properties and biological activity [2][3][4][5][6]. In square-planar complexes of Ni(II) with 2-(diphenylphosphino)benzaldehyde benzoylhydrazone the ligand is coordinated in a monoanionic form through the PNO donor set while monodentate ligands (CH 3 COO -, Cl -, C≡C-C 6 H 5 -, C≡C-tBu -) occupy the fourth coordination place [2].…”

Section: Introductionmentioning

confidence: 99%

“…In this complex the condensation derivative of 2-(diphenylphosphino)benzaldehyde and semioxamazide lost the hydrazonic proton and coordinated to Ni(II) as tridentate via PNO atoms, with a cyanate anion occupying the fourth coordination place [4]. In square-planar Ni(II) complexes with the condensation derivative of 2-(diphenylphosphino)benzaldehyde and ethyl carbazate (L1) (ethyl (2E)-2- [2-(diphenylphosphino)benzylidene]hydrazinecarboxylate) the monoanionic ligand is coordinated through the phosphorus, imine nitrogen and carbonyl oxygen atoms while the fourth coordination place is occupied with one of three different pseudohalides: cyanate, thiocyanate or azide [5]. Also, square-planar azido, isothiocyanato and cyanato Ni(II) complexes of 2-(diphenylphosphino)benzaldehyde 4-phenylsemicarbazone (L2) were reported [6].…”

Section: Introductionmentioning

confidence: 99%

Experimental and theoretical investigation of octahedral and square-planar isothiocyanato complexes of Ni(II) with acylhydrazones of 2-(diphenylphosphino)benzaldehyde

et al. 2015

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Synthesis of Para‐Acetylated Functionalized Ni(II)‐POCOP Pincer Complexes and Their Cytotoxicity Evaluation Against Human Cancer Cell Lines

Sánchez‐Mora,

Briñez,

Pico

et al. 2024

Chemistry & Biodiversity

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A series of three Ni(II)‐POCOP complexes para‐functionalized with an acetoxyl fragment were synthesized. All complexes (2a‐c) were fully characterized through standard analytical techniques. The molecular structure of complex 2b was unambiguously determined by single‐crystal X‐ray diffraction, revealing that the metal center is situated in a slightly distorted square‐planar environment. Additionally, the acetoxy fragment at the para‐position of the phenyl ring was found to be present. The in vitro cytotoxic activity of all complexes was assessed on six human cancer cell lines. Notably, complex 2b exhibited selective activity against K‐562 (chronic myelogenous leukemia) and MCF‐7 (mammary adenocarcinoma) with IC50 values of 7.32 ± 0.60 μM and 14.36 ± 0.02 μM, respectively. Furthermore, this compound showed negligible activity on the healthy cell line COS‐7, highlighting the potential therapeutic application of 2b. The cytotoxic evaluations were further complemented with molecular docking calculations to explore the potential biological targets of complex 2b, revealing interactions with cluster differentiation protein 1a (CD1A, PDB: 1xz0) for K‐562 and with the progesterone receptor for MCF‐7.

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Synthesis, characterization and biological activity of three square-planar complexes of Ni(II) with ethyl (2E)-2-[2-(diphenylphosphino)benzylidene]hydrazinecarboxylate and monodentate pseudohalides

Cited by 30 publications

References 22 publications

Cytotoxic effect of inositol hexaphosphate and its Ni(II) complex on human acute leukemia Jurkat T cells

Cytotoxic effect of inositol hexaphosphate and its Ni(II) complex on human acute leukemia Jurkat T cells

Experimental and theoretical investigation of octahedral and square-planar isothiocyanato complexes of Ni(II) with acylhydrazones of 2-(diphenylphosphino)benzaldehyde

Synthesis of Para‐Acetylated Functionalized Ni(II)‐POCOP Pincer Complexes and Their Cytotoxicity Evaluation Against Human Cancer Cell Lines

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