Copper(II) Complexes of Salicylaldehyde Hydrazones: Synthesis, Structure, and DNA Interaction

Wu, Lihong; Teng, Hao; Ke, Xianbing; Xu, Wenjin; Su, Jiangtao; Liang, Shucai; Hu, Xianming

doi:10.1002/cbdv.200790177

Cited by 29 publications

(11 citation statements)

References 46 publications

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“…The second terminal aromatic ring might act similarly, especially if it contains a hydroxy group. The amide group in the linker connected with an azomethine group with a nitrogen-nitrogen single bond (-(CO)-NH-N=CH-) is known to form coordination bonds with metals, i.e., copper cations [79][80][81]. We assumed that these three elements would provide the necessary interactions with the laccase substrate-binding pocket.…”

Section: Structure-activity Relationship (Sar)mentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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A series of hydrazide-hydrazones 1–3, the imine derivatives of hydrazides and aldehydes bearing benzene rings, were screened as inhibitors of laccase from Trametes versicolor. Laccase is a copper-containing enzyme which inhibition might prevent or reduce the activity of the plant pathogens that produce it in various biochemical processes. The kinetic and molecular modeling studies were performed and for selected compounds, the docking results were discussed. Seven 4-hydroxybenzhydrazide (4-HBAH) derivatives exhibited micromolar activity Ki = 24–674 µM with the predicted and desirable competitive type of inhibition. The structure–activity relationship (SAR) analysis revealed that a slim salicylic aldehyde framework had a pivotal role in stabilization of the molecules near the substrate docking site. Furthermore, the presence of phenyl and bulky tert-butyl substituents in position 3 in salicylic aldehyde fragment favored strong interaction with the substrate-binding pocket in laccase. Both 3- and 4-HBAH derivatives containing larger 3-tert-butyl-5-methyl- or 3,5-di-tert-butyl-2-hydroxy-benzylidene unit, did not bind to the active site of laccase and, interestingly, acted as non-competitive (Ki = 32.0 µM) or uncompetitive (Ki = 17.9 µM) inhibitors, respectively. From the easily available laccase inhibitors only sodium azide, harmful to environment and non-specific, was over 6 times more active than the above compounds.

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Section: Structure-activity Relationship (Sar)mentioning

confidence: 99%

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

et al. 2020

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“…[ 12 ] In addition, hydrazone-based copper complexes can be mentioned for their structural richness, as well as for their use to study the effects of structural and chemical factors that govern the exchange coupling between paramagnetic centres. [ 13 ] The design and preparation of pseudohalide-bridged dinuclear and polynuclear complexes remains an attractive area of investigation, since compounds with diverse architectures can be obtained with potential applications as magnetic materials. [ 14 ] The magnetic interactions between the metal centres of such complexes can be tuned by adjusting the chain length and bite angle of the bridging ligands.…”

Section: Introductionmentioning

confidence: 99%

End‐to‐End Thiocyanato‐Bridged Helical Chain Polymer and Dichlorido‐Bridged Copper(II) Complexes with a Hydrazone Ligand: Synthesis, Characterisation by Electron Paramagnetic Resonance and Variable‐Temperature Magnetic Studies, and Inhibitory Effects on Human Colorectal Carcinoma Cells

et al. 2012

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The reactions of the tridentate hydrazone ligand, N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide (HL), obtained by condensation of 2-acetylpyridine with acetic hyadrazide, with copper nitrate trihydrate in the presence of thiocyanate, or with CuCl2 produce two distinct coordination compounds, namely a one-dimensional helical coordination chain of [CuL(NCS)]n (1) units, and a doubly chlorido-bridged dinuclear complex [Cu2L2Cl2] (2) (where L=CH3C(O)=N–N=CCH3C5H4N). Single-crystal X-ray structural determination studies reveal that in complex 1, a deprotonated hydrazone ligand L− coordinates a copper(II) ion that is bridged to two neighbouring metal centres by SCN− anions, generating a one-dimensional helical coordination chain. In complex 2, two symmetry-related, adjacent copper(II) coordination entities are doubly chlorido-bridged, producing a dicopper entity with a Cu⋅⋅⋅Cu distance of 3.402 (1) Å. The two coordination compounds have been fully characterised by elemental analysis, spectroscopic techniques including IR, UV–vis and electron paramagnetic resonance, and variable-temperature magnetic studies. The biological effects of 1 and 2 on the viability of human colorectal carcinoma cells (COLO-205 and HT-29) were evaluated using an MTT assay, and the results indicate that these complexes induce a decrease in cell-population growth of human colorectal carcinoma cells with apoptosis.

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“…Absorption titration is an effective method to examine the binding mode of DNA with metal complexes . Therefore, the binding interaction of the complexes bearing acylhydrazone ligands with CT‐DNA was monitored by UV‐visible spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Copper(II) complexes of acylhydrazones: synthesis, characterization and DNA interaction

Gökçe

Güp

2013

Applied Organom Chemis

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Two new acylhydrazone copper(II) complexes of 4‐hydroxy‐N′‐[(1E)‐1‐(4‐methylphenyl)ethylidene]benzohydrazide (HL1) and 4 ethyl [4‐({(2E)‐2‐[1‐(4‐methylphenyl)ethylidene]hydrazinyl}carbonyl)phenoxy]acetate (HL2) have been synthesized and characterized. The structures of both acylhydrazone and copper(II) complexes were identified by elemental analysis, infrared spectra, UV–visible electronic absorption spectra, magnetic susceptibility measurements, TGA and powder X‐ray diffraction. DNA binding and DNA cleavage activities of the synthesized copper complexes were examined by using UV‐visible titration and agarose gel electrophoresis, respectively. The effect of complex concentration on the DNA cleavage reactions in the absence and presence of H2O2 was also investigated. The results indicate that all the complexes bind slightly to calf thymus DNA and cleavage pBR322 DNA. The mechanistic studies demonstrate that a hydrogen peroxide‐derived species and singlet oxygen (1O2) are the active oxidative species for DNA cleavage. Copyright © 2013 John Wiley & Sons, Ltd.

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Copper(II) Complexes of Salicylaldehyde Hydrazones: Synthesis, Structure, and DNA Interaction

Cited by 29 publications

References 46 publications

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

Synthesis and Structure-Activity Relationship Studies of Hydrazide-Hydrazones as Inhibitors of Laccase from Trametes versicolor

End‐to‐End Thiocyanato‐Bridged Helical Chain Polymer and Dichlorido‐Bridged Copper(II) Complexes with a Hydrazone Ligand: Synthesis, Characterisation by Electron Paramagnetic Resonance and Variable‐Temperature Magnetic Studies, and Inhibitory Effects on Human Colorectal Carcinoma Cells

Copper(II) complexes of acylhydrazones: synthesis, characterization and DNA interaction

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