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Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment.

ABSTRACT: Four mononuclear bioefficient imine-based coordination complexes, [(L 1 ) 2 Cu], [(L 1 ) 2 Zn], [(L 2 )Cu(H 2 O)], and [(L 2 )Zn(H 2 O)], were synthesized using ligands [L 1 = 2-(((3-hydroxynaphthalen-2-yl)methylene)amino)-2-methylpropane-1,3-diol and L 2 = 4-(1-((1,3-dihydroxy-2-methylpropan-2-yl)imino)ethyl)benzene-1,3-diol]. The formation of the complexes was ascertained by elemental analysis, Fourier transform infrared, 1H NMR, 13C NMR, electrospray ionization-mass spectroscopy, electron paramagnetic resonance, and thermogravimetric analysis. The comparative binding propensity profiles of the above-synthesized complexes with the DNA/human serum albumin (HSA) were investigated via UV absorption, fluorescence, and Förster resonance energy-transfer studies. On the basis of extended conjugation and planarity, L 1 complexes exhibited superior bioactivity with greater calculated DNA binding constant values, (K b) 2.9444 × 103 [(L 1 ) 2 Cu] and 2.2693 × 103 [(L 1 ) 2 Zn], as compared to L 2 complexes, 1.793 × 103 [(L 2 )Cu(H 2 O)] and 9.801 × 102 [(L 2 )Zn(H 2 O)]. The competitive displacement assay of complexes was performed by means of fluorogenic dyes (EtBr and Hoechst), which corroborates the occurrence of minor groove binding because of the enhanced displacement activity with Hoechst 33258. The minor groove binding of the [(L 1 ) 2 Cu] complex is further confirmed by the molecular docking study. Moreover, the HSA study demonstrated effective static quenching of complexes with substantial K sv values. The [(L 1 ) 2 Cu] complex was found to have pronounced cleavage efficiency as evaluated from sodium dodecyl sulfate polyacrylamide gel electrophoresis electrophoresis. Furthermore, in vitro antioxidant activity against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals further proclaimed the remarkable bioefficiency of compounds, which make them promising as active chemotherapeutic agents.

SUBMITTER: Kabeer H

PROVIDER: S-EPMC6977212 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment.

Kabeer Hina H Hanif Summaiya S Arsalan Abdullah A Asmat Shamoon S Younus Hina H Shakir Mohammad M

ACS omega 20200106 2

Four mononuclear bioefficient imine-based coordination complexes, [(L 1 ) 2 Cu], [(L 1 ) 2 Zn], [(L 2 )Cu(H 2 O)], and [(L 2 )Zn(H 2 O)], were synthesized using ligands [L 1 = 2-(((3-hydroxynaphthalen-2-yl)methylene)amino)-2-methylpropane-1,3-diol ...[more]

PMID: 31984281

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Project description:New Schiff base ligand, derived from antiviral valacyclovir, and its novel Cr(III), Mn(II), Co(II), Ni(II), Cu(II), Zn(II) complexes have been synthesized. By using a variety of analytical and spectroscopic techniques, the type of bonding between the ligand and the metal ions in the recently formed complexes was clarified. The Schiff base ligand act as a bidentate and coordinated with the metal ions through the azomethine-N and the phenolic-O centers, in a mono-deprotonated form. Except for the Zn(II) complex, which displayed a tetrahedral geometry, all complexes displayed octahedral geometry. The TGA findings supported that the stability and decomposition properties of the metal complexes were entirely distinct from one another. The thermogram showed decomposition of all investigated metal complexes above 200 °C in three, four or five steps, and indicated the high thermal stability of these complexes. According to XRD patterns, the particles of these complexes were located at the nanoscale. Moreover, for all the samples analyzed, the TEM images showed uniform and homogeneous surface morphology. The biological activity revealing the high efficiencies of the screened complexes as antibacterial and antitumor agents. The antimicrobial activity of the ligand and its complexes was examined against a variety of pathogenic bacteria and fungi including Escherichia coli, Staphylococcus aureus and Candida albicans. The data obtained revealed that the metal ion in the complexes enhanced the antimicrobial activity compared to the free ligand. The high efficiencies toward S. aureus, E. coli, and C. albicans appeared by Cu(II) complex 23, Ni(II) complex 20, and Ni(II) complex 19, respectively. The antitumor activity of the ligand and its complexes was tested against Hepatocellular carcinoma cell line (HepG-2 cells), the residue 28 which produced after heating the Cu(II) complex 25 at 200 °C for 1 h, exhibited strong inhibition of HepG-2 cell growth. The results of the DNA cleavage investigation demonstrated the ability of investigated Cu(II) complex to degrade DNA. The docking findings showed strong interactions of both the ligand and its examined Cu(II) complex, revealing their ability to cleavage DNA and their potent inhibitory effects on tumor cells. The electrical conductivity study confirmed that the ligand and its investigated complexes had semiconducting properties.

Dataset Information

Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment.

Publications

Structural-Dependent N,O-Donor Imine-Appended Cu(II)/Zn(II) Complexes: Synthesis, Spectral, and in Vitro Pharmacological Assessment.

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