Nickel(<scp>ii</scp>) and copper(<scp>ii</scp>) complexes constructed with N<sub>2</sub>S<sub>2</sub> hybrid benzamidine–thiosemicarbazone ligand: synthesis, X-ray crystal structure, DFT, kinetico-catalytic and in vitro biological applications

Vijayan, Paranthaman; Viswanathamurthi, Periasamy; Velmurugan, K.; Nandhakumar, Raju; Balakumaran, Manickam Dakshinamoorthi; Kalaichelvan, P. T.; Małecki, Jan Grzegorz

doi:10.1039/c5ra18568h

Cited by 41 publications

(14 citation statements)

References 68 publications

(53 reference statements)

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“…The angle O(4)‐Cu(1)‐O(9) (144.81°) was significantly less compared to 180°, indicating severe distortion from the octahedral geometry. The observed bond distances are related to the reported values [16,22–24] …”

Section: Resultssupporting

confidence: 68%

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

et al. 2021

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Four copper(II) complexes 1-4 of 3-acetylchromene-2-one and substituted 3-acetylchromene-2-one derived Schiff bases were synthesized and structurally characterized using analytical and spectral techniques. The molecular structure of complex 1 has been confirmed by single crystal X-ray diffraction studies, which revealed that ligand 3-acetylchromene-2-one-4 N-semicarbazone is coordinated to the metal as ONO pincer type ligand. Two nitrate molecules are coordinated to the copper ion through oxygen atoms, of which one nitrate molecule was found to coordinate via two oxygen atoms, thereby achieving six-coordination. Preliminary biological studies like DNA and protein binding analyses indicated the binding of the ligands and complexes to CT-DNA (Calf Thymus DNA) and BSA (Bovine Serum Albumin). We investigated the effects of complexes 1-4 against amyloid-β (Aβ) toxicity using transgenic Caenorhabditis elegans strains expressing muscle-and neuronal-specific human Aβ 1-42 . The results showed that the complexes 2-4 remarkably reduced the Aβ-induced paralysis phenotype, Aβ plaque deposition, and other Alzheimer's disease-associated functional deficits in C. elegans by their potent antioxidant and antiaggregative properties. Complexes 2-4 delayed Alzheimer's disease pathologies, providing a basis for further investigating these effects on higher models.

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Section: Resultssupporting

confidence: 68%

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

et al. 2021

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“…Cu(III) consequently draws the electron density from the negative ligands surrounding copper center and hence the charge on copper is less than +3 [14,[33][34][35][36][37]. Similar behavior was observed by earlier researchers in Ni(II) complexes with square planar geometry [38].…”

Section: Charge Distribution In the Cu(iii)-alkyl Complexessupporting

confidence: 82%

Structural Analysis and Reactivity of Tetramethylcopper(III) Complex towards Nitrogen Donor Ligands by Density Functional Theory

Balu

Kannappan

Kumar³

2016

Advances in Chemistry

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DFT studies are carried out on some ligand substitution reactions of tetramethylcuprate(III) (TMC) complex with five different nitrogen donor ligands as probe ligands. The geometry optimization of the possible nine model systems and the frequency calculations are carried out at DFT level using LANL2DZ basis set. The selected structural parameters of optimized model systems of Cu(III) complexes are reported and discussed. The change in the M-C bond distance in TMC due to substitution by probe ligands is explained. Natural population analysis (NPA) has been carried out for these complexes to establish the charge of copper in these complexes. A detailed population analysis of valence orbitals of copper complexes supports the existence of d8 configuration for metal in complexes and there is evidence for the transmission of electrons from the nitrogen donor atom to dxy, dx2-y2, and 4s orbitals. Bond order calculations have been performed for all the complexes to probe the interaction between Cu(III) and the ligand. The stability of the complexes is ascertained from the computed chemical hardness. In order to understand the nature of Cu(III)-L (L = N donors) and Cu(III)-Me bonds in different complexes, Energy Decomposition Analysis (EDA) has been carried out for all the complexes chosen in the theoretical study. Thermodynamic feasibility of these reactions is investigated in terms of free energy changes of these reactions.

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“…Nuclear staining using acridine orange (AO)/EB and diamidino‐2‐phenylindole (DAPI) was measured by fluorescence microscopy according to the method previously described . HeLa and HepG2 cancer cells (1 × 10 6 in number) were cultured in six‐well plates at 37 °C in an incubator with fixed concentration of complexes 1 – 3 (50 μM) for 24 h. The cells were harvested and washed with ice‐cold PBS and 40 μl of AO/EB solution (1 part of 100 μg ml −1 AO in PBS; 1 part of 100 μg ml −1 EB in PBS) was added.…”

Section: Methodsmentioning

confidence: 99%

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

Vijayan

Viswanathamurthi

Sugumar

et al. 2016

Applied Organom Chemis

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N,N-[(diethylamino)(thiocarbonyl)]-substituted benzamidine ligands have been synthesized from the reaction of N,N-[(diethylamino)(thiocarbonyl)]benzimidoyl chloride with functionalized amines such as 2-aminophenol and 2-picolylamine. The reaction of N,N-[(diethylamino)(thiocarbonyl)]-2-hydroxyphenylbenzamidine (H 2 L 1 ) with ruthenium(II) precursor [RuHCl(CO)(PPh 3 ) 3 ] afforded complex 1 of the type [Ru(L 1 )(CO)(PPh 3 ) 2 ] in which the ligand coordinated in tridentate ONS mode. The reaction of H 2 L 1 with copper precursor [Cu(CH 3 COO)(PPh 3 ) 2 ] induced C═N bond cleavage of the ligand and afforded complex 3 of the type [Cu(1,1-DT) (Cl)(PPh 3 ) 2 ] (1,1-DT = 1,1-diethylthiourea) in which the ligand coordinated in a monodentate fashion. The ligand N,N-[(diethylamino)(thiocarbonyl)]-2picolylbenzamidine (HL 2 ) reacted with ruthenium(II) and copper(I) precursors to form complex 2 of the type [Ru(1,1-DT)(Cl 2 )(CO)(PPh 3 ) 2 ] and complex 3, respectively, in which the ligand underwent C═N cleavage and coordinated in a monodentate fashion via C═S group. In complexes 1 and 2, the two triphenylphosphine co-ligands coordinated in trans position whereas, in complex 3, the two triphenylphosphine co-ligands coordinated in cis position. All the compounds were characterized using infrared, UV-visible, ( 1 H, 13 C, 31 P) NMR, ESI-MS and elemental analyses. The molecular structures of ligand H 2 L 1 and complexes 1-3 were determined using X-ray crystallography, which confirmed the coordination mode of the ligands with metals. The crystal structure of complexes 1 and 2 revealed a distorted octahedral geometry around the ruthenium ion and the structure of complex 3 indicated a tetrahedral geometry around the copper ion. With the X-ray structures, density functional theory computations were carried out to determine the electronic structure of the compounds. The interactions of complexes 1-3 with calf thymus DNA and bovine serum albumin protein were investigated using UV-visible and fluorescence spectroscopic and viscometric methods. Catecholase-and phosphatase-like activities promoted by complexes 1-3 under physiological conditions have been studied. In vitro anticancer activities have been demonstrated by MTT assay, acridine orange/ethidium bromide and diamidino-2-phenylindole staining against various cancerous cell lines.

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Nickel(ii) and copper(ii) complexes constructed with N₂S₂ hybrid benzamidine–thiosemicarbazone ligand: synthesis, X-ray crystal structure, DFT, kinetico-catalytic and in vitro biological applications

Abstract: We report nickel(ii) and copper(ii) complexes containing the benzamidine–thiosemicarbazone ligand together with DFT, enzyme kinetics and in vitro biological applications such as DNA/BSA affinities and anticancer properties.

Cited by 41 publications

References 68 publications

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

Structural Analysis and Reactivity of Tetramethylcopper(III) Complex towards Nitrogen Donor Ligands by Density Functional Theory

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

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Nickel(ii) and copper(ii) complexes constructed with N2S2 hybrid benzamidine–thiosemicarbazone ligand: synthesis, X-ray crystal structure, DFT, kinetico-catalytic and in vitro biological applications

Abstract: We report nickel(ii) and copper(ii) complexes containing the benzamidine–thiosemicarbazone ligand together with DFT, enzyme kinetics and in vitro biological applications such as DNA/BSA affinities and anticancer properties.

Cited by 41 publications

References 68 publications

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

ONO‐Pincer‐Type Coumarin‐Based Copper(II) Metalates: Effect on Alzheimer's Disease Pathologies in Caenorhabditis elegans

Structural Analysis and Reactivity of Tetramethylcopper(III) Complex towards Nitrogen Donor Ligands by Density Functional Theory

Solvent‐assisted formation of ruthenium(II)/copper(I) complexes containing thiourea derivatives: Synthesis, crystal structure, density functional theory, enzyme mimetics and in vitro biological perspectives

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Nickel(ii) and copper(ii) complexes constructed with N₂S₂ hybrid benzamidine–thiosemicarbazone ligand: synthesis, X-ray crystal structure, DFT, kinetico-catalytic and in vitro biological applications