The Cu/ligand stoichiometry effect on the coordination behavior of aroyl hydrazone with copper(II): Structure, anticancer activity and anticancer mechanism

Deng, Jungang; Gou, Yanzi; Chen, Wei; Xiang, Fu; Deng, Hongbo

doi:10.1016/j.bmc.2016.03.033

Cited by 39 publications

(11 citation statements)

References 52 publications

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“…Aroylhydrazones are an attractive class of ligands exhibiting coordination versatility toward a wide range of metals, particularly 3d transition metal ions (Bernhardt et al, 2006;Deng et al, 2016;Peng et al, 2017). Remarkable chelating ability together with synthetic accessibility led to the exploration of aroylhydrazones as potential metal-chelating drugs (Link et al, 2003;Bernhardt et al, 2007).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of the mixed methanol and ethanol solvate of bis{3,4,5-trimethoxy-N′-[1-(pyridin-2-yl)ethylidene]benzohydrazidato}zinc(II)

Znovjyak¹,

Fritsky²,

Sliva³

et al. 2020

Acta Cryst E

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The unit cell of the title compound, [Zn(C17H18N3O4)2]·CH4O·C2H6O, contains two complex molecules related by an inversion centre, plus one methanol and one ethanol solvent molecule per complex molecule. In each complex, two deprotonated pyridine aroylhydrazone ligands {3,4,5-trimethoxy-N′-[1-(pyridin-2-yl)ethylidene]benzohydrazide} coordinate to the ZnII ion through the N atoms of the pyridine group and the ketamine, and, additionally, through the O atom of the enolate group. In the crystal, dimers are formed by π–π interactions between the planar ligand moieties, which are further connected by C...O and C...C interactions. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H...H (44.8%), H...C/C...H (22.2%), H...O/O...H (18.7%) and C...C (3.9%) interactions.

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Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of the mixed methanol and ethanol solvate of bis{3,4,5-trimethoxy-N′-[1-(pyridin-2-yl)ethylidene]benzohydrazidato}zinc(II)

Znovjyak¹,

Fritsky²,

Sliva³

et al. 2020

Acta Cryst E

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“…They can easily form stable complexes with transition metal ions and can exhibit interesting photophysical and biological properties [8]. They exhibit biological activities such as antibacterial [9], antioxidant [10], antifungal [11], antitubercular [12], antiinflammatory [13] and anticancer [14].…”

Section: Introductionmentioning

confidence: 99%

Anticancer activity studies of novel metal complexes of ligands derived from polycyclic aromatic compound via greener route

Kumbar

Patil

Toragalmath³

et al. 2020

Journal of Organometallic Chemistry

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“…Due to the apparent permeability of copper compounds through the membrane of a cancer cell, it accumulates in the targeted tumor. In recent times, a series of copper complexes are found active as potent drugs towards the anticancer activity both in vitro and in vivo …”

Section: Introductionmentioning

confidence: 99%

Hexanuclear Zn(II) and Mononuclear Cu(II) Complexes containing imino phenol ligands: Exploitation of their Catalytic and Biological Perspectives

Mondal

Chatterjee

Tiwari

et al. 2019

Applied Organom Chemis

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A unique hexanuclear zinc(II) (1) and two mononuclear copper(II) (2 and 3) complexes anchored with imino phenol ligand HL 1 and HL 2 were synthesized with good yield and purity (where HL 1 = 4-tert-butyl-2,6-bis((mesitylimino) methylphenol and HL 2 = 5-tert-butyl-2-hydroxy-3-((mesitylimino)methyl) benzaldehyde). These complexes were characterized by utilizing various spectroscopic protocols like NMR, FTIR, UV as well as ESI-Mass spectrometry, elemental analysis and single crystal X-ray diffraction studies. Their potential to bind calf thymus DNA (CT-DNA) was tested utilizing different techniques such as UV-visible and fluorescence spectroscopy. The experiment implies that they interact with CT-DNA via non-intercalative mode with moderate capabilities (K b~1 0 4 M −1 ). On the other hand, these complexes have high capabilities to quench the fluorescence of bovine serum albumin (BSA) following the static pathway. In addition, they are active catalysts for the oxidation reaction of 3,5-di-tert-butylcatechol (3,5-DTBC) to 3,5-di-tert-butylquinone (3,5-DTBQ) under aerobic condition. From the recorded EPR signals of all complexes, it has been concluded that the oxidation reaction proceeds via ligand oriented radical pathway instead of metal based redox participation. Kinetic studies using 1-3 indicate that it follows Michaelis-Menten type of equation with moderate to high turnover number (k cat ). Apart from these aspects, complexes 1-3 were screened for their cytotoxic behavior towards HeLa cells (human cervical carcinoma) and found quite active with comparable IC 50 values to cisplatin.

show abstract

The Cu/ligand stoichiometry effect on the coordination behavior of aroyl hydrazone with copper(II): Structure, anticancer activity and anticancer mechanism

Cited by 39 publications

References 52 publications

Crystal structure of the mixed methanol and ethanol solvate of bis{3,4,5-trimethoxy-N′-[1-(pyridin-2-yl)ethylidene]benzohydrazidato}zinc(II)

Crystal structure of the mixed methanol and ethanol solvate of bis{3,4,5-trimethoxy-N′-[1-(pyridin-2-yl)ethylidene]benzohydrazidato}zinc(II)

Anticancer activity studies of novel metal complexes of ligands derived from polycyclic aromatic compound via greener route

Hexanuclear Zn(II) and Mononuclear Cu(II) Complexes containing imino phenol ligands: Exploitation of their Catalytic and Biological Perspectives

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