Square planar Au(III), Pt(II) and Cu(II) complexes with quinoline-substituted 2,2′:6′,2″-terpyridine ligands: From in vitro to in vivo biological properties

Two square-planar coordination compounds, namely [Cu(CPYA)Cl2] (1) and [Pd(CPYA)Cl2] (2), were prepared from the ligand 4-chloro-N-(pyridin-2-ylmethyl)aniline (CPYA) and two chloride salts, and were fully characterized, including by X-ray diffraction. Spectroscopic, electrophoretic and AFM studies revealed that the two isostructural compounds were interacting differently with DNA. In both cases, the initial interaction involves electrostatic contacts of the CPYA ligand in the minor groove (as suggested by molecular docking), but subsequent strong binding occurs with the palladium(II) complex 2, whereas the binding with the copper complex 1 is weaker and concentration dependent. The strong binding of 2 eventually leads to the cleavage of the double strand and the redox activity of 1 allows to oxidatively cleave the biomolecule. Graphic abstract

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“…S7). Similar bands were observed for other related copper(II) and palladium(II) complexes [20,[40][41][42][43][44][45].…”

Section: Molecular Dockingsupporting

confidence: 82%

DNA-interacting properties of two analogous square-planar cis-chlorido complexes: copper versus palladium

et al. 2021

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“…All media were supplemented with 10% fetal bovine serum and a 1% Pen/Strep solution (all media and supplements were from Thermo Fischer Scientific, Waltham, MA, USA). Cell cultures were maintained at 37 • C, in a humified atmosphere of 5% (v/v) CO 2 [103,104].…”

Section: Epr Spectroscopymentioning

confidence: 99%

“…After 24 h, culture media was replaced, and cells were exposed to different concentrations of complexes 1-3 or DMSO 0.1% (v/v) (vehicle control) or cisplatin (positive control) for 48 h (Figure S14). Cells exposed to cisplatin were used as a positive control [103,104]. After 48 h of incubation, the CellTiter 96 ® Aqueous Non-Radioactive Proliferation assay (Promega, Madison, WI, USA) was used to determine cellular viability through the production of formazan through the reduction of 3-(4,5dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, inner salt (MTS) by dehydrogenases present in metabolically active cells [103,104].…”

Section: Viability Assaysmentioning

confidence: 99%

“…Cells exposed to cisplatin were used as a positive control [103,104]. After 48 h of incubation, the CellTiter 96 ® Aqueous Non-Radioactive Proliferation assay (Promega, Madison, WI, USA) was used to determine cellular viability through the production of formazan through the reduction of 3-(4,5dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, inner salt (MTS) by dehydrogenases present in metabolically active cells [103,104]. The amount of formazan can be determined by its absorbance at 492 nm in an Infinite M200 microplate reader (Tecan, Mannedorf, Switzerland) [103,104].…”

Section: Viability Assaysmentioning

confidence: 99%

“…After 48 h of incubation, the CellTiter 96 ® Aqueous Non-Radioactive Proliferation assay (Promega, Madison, WI, USA) was used to determine cellular viability through the production of formazan through the reduction of 3-(4,5dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, inner salt (MTS) by dehydrogenases present in metabolically active cells [103,104]. The amount of formazan can be determined by its absorbance at 492 nm in an Infinite M200 microplate reader (Tecan, Mannedorf, Switzerland) [103,104]. The biological activity of the complexes was compared using the half maximal inhibitory concentration of cellular proliferation (IC 50 ) determined with Prism 8.2.1 software for windows (GraphPad Software, La Jolla, CA, USA).…”

Section: Viability Assaysmentioning

confidence: 99%

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Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity

et al. 2021

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Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)2-quin)2] (1), [VO(2,5-(Me)2-quin)2] (2) and [VO(2-Me-quin)2] (3). Complexes 1–3 demonstrated high catalytic activity in the oxidation of hydrocarbons with H2O2 in acetonitrile at 50 °C, in the presence of 2-pyrazinecarboxylic acid (PCA) as a cocatalyst. The maximum yield of cyclohexane oxidation products attained was 48%, which is high in the case of the oxidation of saturated hydrocarbons. The reaction leads to the formation of a mixture of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. When triphenylphosphine is added, cyclohexyl hydroperoxide is completely converted to cyclohexanol. Consideration of the regio- and bond-selectivity in the oxidation of n-heptane and methylcyclohexane, respectively, indicates that the oxidation proceeds with the participation of free hydroxyl radicals. The complexes show moderate activity in the oxidation of alcohols. Complexes 1 and 2 reduce the viability of colorectal (HCT116) and ovarian (A2780) carcinoma cell lines and of normal dermal fibroblasts without showing a specific selectivity for cancer cell lines. Complex 3 on the other hand, shows a higher cytotoxicity in a colorectal carcinoma cell line (HCT116), a lower cytotoxicity towards normal dermal fibroblasts and no effect in an ovarian carcinoma cell line (order of magnitude HCT116 > fibroblasts > A2780).

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Spectral studies, thermal investigations, and anticancer activity of some divalent metal complexes derived from 2‐(4‐bromophenylamino)acetohydrazide ligand

Emara

El‐Sayed

Khalaf‐Allah

et al. 2022

Applied Organom Chemis

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A series of biologically active metal complexes was yielded from the reactions of 2‐(4‐bromophenylamino)acetohydrazide ligand (HL) with Co(II), Ni(II), Cu(II), Cd(II) chlorides, CuBr2, Cu(CH3COO)2, and Cu(ClO4)2 salts. The structure and stereochemistry of the afforded complexes were elucidated by means of elemental analyses, molar conductance, magnetic susceptibility, thermal analyses (TG/DTG), and spectral techniques (mass, IR, UV‐Vis, and 1H NMR). Elemental analyses along with molar conductance data demonstrated that all metal complexes are nonelectrolyte and were formed with 1L:1M, 1L:2M, and 2L:1M stoichiometry. IR spectral data provided an evidence for the neutral bidentate behavior of the hydrazide ligand toward metal ions via carbonyl oxygen and amino nitrogen atoms (ON donor). Magnetic susceptibility along with electronic absorption spectral results authenticated that all complexes have an octahedral geometry except, CuCl2 complex (3), which possessed a square planar one. The hydrazide ligand and some of its synthesized metal complexes were screened in vitro for their antitumor and apoptotic activity. The results showed that CuBr2 complex (4) has promising anticancer activities against breast MCF7, liver HepG2, and colorectal HCT 116 cancerous cells through induction of proapoptotic gene (Bax) and inhibit the antiapoptotic gene (Bcl‐2), thus increase the Bax/Bcl‐2 ratio. Moreover, these newly synthesized compounds were most potent and can be used as a therapeutic chemoprevention against these cancerous cells compared with doxorubicin (DOX), the currently available anticancer drug against solid tumors.

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Square planar Au(III), Pt(II) and Cu(II) complexes with quinoline-substituted 2,2′:6′,2″-terpyridine ligands: From in vitro to in vivo biological properties

Cited by 49 publications

References 117 publications

DNA-interacting properties of two analogous square-planar cis-chlorido complexes: copper versus palladium

DNA-interacting properties of two analogous square-planar cis-chlorido complexes: copper versus palladium

Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity

Spectral studies, thermal investigations, and anticancer activity of some divalent metal complexes derived from 2‐(4‐bromophenylamino)acetohydrazide ligand

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