Synthesis and the characterization of Schiff-base copper complexes: Reactivity with DNA, 4-NPP and BNPP

Kozlyuk, Natalia; Lopez, Tyler; Roth, Patrick; Acquaye, J. Henry

doi:10.1016/j.ica.2014.12.034

Cited by 11 publications

(15 citation statements)

References 74 publications

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“…Based on these results, the structures of the complexes were suggested to be as shown in Scheme 1. Similarly, copper (II)-Schiff base complexes with 1:1 molar ratio, having Cu(L)(OAc).CH3.OH formula, was reported in literature [33].…”

Section: Synthesis and General Characterizationsupporting

confidence: 56%

“…Geometry optimization gives more information about atomic arrangement, without crystal data, and also provides the most stable structure. It is well-known that acetate group behaves as both terminal and bridging, and both monodentate and bidentate ligand [33][34][35][36]. We attempt to optimize the monomeric [Cu(HL)(η 1 -acetato)] and [Cu(HL)(η 2 -acetato)] complexes.…”

Section: Geometry Optimization Of the Complexesmentioning

confidence: 99%

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DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

et al. 2019

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Abstract. Three new copper(II) complexes (1-3) with general formula [Cu(HL)CH3COO] of N-salicyl-β-amino alcohol Schiff bases containing, (S)-(+)-phenyl glycinol, (1S, 2R)-2-amino-1, 2-diphenylethanol and 1, 1, 3-triphenyl-(R)-(+)-2-amino propanol, were synthesized. Their structures were characterized by FTIR, LCMS, magnetic moment, molar conductance and elemental analysis data. DFT calculations proposed distorted square planar geometries for the complexes. The calculated IR spectra are in good agreement with the experimental IR spectra, confirming the proposed structures. Their interactions with calf thymus DNA were investigated and their binding constants Kb were found. Gel electrophoresis reveals that all complexes display significant nuclease activity against supercoiled pentry/d-topo plasmid DNA. Resumen. Tres nuevos complejos de cobre (II) (1-3) con la fórmula general [Cu (HL) CH3COO] de N-salicil-β-amino alcohol Schiff bases que contienen, (S) - (+) - fenilglicinol, (1S, 2R). Se sintetizaron -2-amino-1, 2-difeniletanol y 1, 1, 3-trifenil- (R) - (+) - 2-amino propanol. Sus estructuras se caracterizaron por FTIR, LCMS, momento magnético, conductancia molar y datos de análisis elemental. Los cálculos de DFT propusieron geometrías planas cuadradas distorsionadas para los complejos. Los espectros de IR calculados están en buena concordancia con los espectros de IR experimentales, confirmando las estructuras propuestas. Se investigaron sus interacciones con el ADN del timo de ternera y se encontraron sus constantes de unión Kb. La electroforesis en gel revela que todos los complejos muestran una actividad nucleasa significativa contra el ADN plasmídico pentry / d-topo superenrollado.

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Section: Synthesis and General Characterizationsupporting

confidence: 56%

Section: Geometry Optimization Of the Complexesmentioning

confidence: 99%

DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

et al. 2019

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“…[1][2][3][4] For this purpose, several photosensitizers, such as Photofrin, 5-aminolevulinic acid (ALA), Foscan, and Verteporn, have been clinically approved for the treatment of cancersa nd skin diseases with light irradiation. [7][8][9][10] Among the essential transitionm etals,c opperi st he third most abundant crucial transition metal ion in human tissuea nd plays important biological roles in the actives ite of cytochrome co xidase and as ac atalyst in oxidation-reduction reactions in many proteins. [7][8][9][10] Among the essential transitionm etals,c opperi st he third most abundant crucial transition metal ion in human tissuea nd plays important biological roles in the actives ite of cytochrome co xidase and as ac atalyst in oxidation-reduction reactions in many proteins.…”

Section: Introductionmentioning

confidence: 99%

“…[5,6] Recently,t oi mprove the selectivity and efficacy against canceri nP DT treatments, transition metal complexes have been considered. [7][8][9][10] Among the essential transitionm etals,c opperi st he third most abundant crucial transition metal ion in human tissuea nd plays important biological roles in the actives ite of cytochrome co xidase and as ac atalyst in oxidation-reduction reactions in many proteins. [11][12][13][14] Furthermore, comparedt op latinum and ruthenium complexes,copper complexes have demonstratedgood antitumor activity with fewer side effects.…”

Section: Introductionmentioning

confidence: 99%

Photocytotoxic Copper(II) Complexes with Schiff‐Base Scaffolds for Photodynamic Therapy

Lin

Chiu

Hsu

et al. 2018

Chemistry A European J

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Photodynamic therapy (PDT) is a promising and minimally invasive method for the treatment of superficial diseases, and photosensitizers with high phototoxicity indices (defined as (IC )/(IC )) are essential for the development of ideal photosensitizing properties for this technology. Herein, we report a series of photocytotoxic copper(II) complexes [Cu( QYMP)(dppn)] ( QYMP=N,N,O-tridentate Schiff-base derivatives, dppn=benzo[i]dipyrido[3,2-a;2',3'-c]phenazine), the structures of which have been confirmed by mass spectrometry and FTIR spectroscopy. X-ray crystallography revealed that the CuN O core of the [Cu( QYMP)(dppn)](ClO ) complex (3) has a distorted square-pyramidal geometry. Phototoxicity indices of 329 against human squamous cell carcinoma (SCC15) and 296 against basal cell carcinoma (BCC) cell lines have been determined with [Cu( QYMP)(dppn)](ClO ) (4). This can be attributed to the formation of reactive oxygen species, cell apoptosis, and caspase-3 activation, indicating high potential of complex 4 as a photosensitizer candidate in PDT. Thus, copper complexes bearing suitable Schiff-base ligands with a dppn co-ligand may be considered for the design of efficient metal-based anticancer agents for PDT.

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“…This is mainly due to their ease of preparation, good solubility in common solvents, structural diversities, magnetic, spectral, redox, and catalytic properties [3][4][5][6][7][8]. Transition metal complexes contain oxygen and nitrogen donor Schiff base ligands, which can be modified by choosing the appropriate amine precursors and the ring may serve in coordination field [9]. Also, Schiff bases and their corresponding metal complexes have continued to enjoy extensive interest owing to their structural diversity and potential wide applications such as anticancer, anti-convulsant, antitumor, antifungal, antibacterial, anti-tubercular, antioxidant, antimalarias, antiElectronic supplementary material The online version of this article (doi:10.1007/s10973-015-4838-z) contains supplementary material, which is available to authorized users.…”

Section: Introductionmentioning

confidence: 99%

Elaborated studies on nano-sized homo-binuclear Mn(II), Fe(III), Co(II), Ni(II), and Cu(II) complexes derived from N2O2 Schiff base, thermal, molecular modeling, drug-likeness, and spectral

Shah

Abou‐Melha

Saad

et al. 2015

J Therm Anal Calorim

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A series of new homo-binuclear nano Mn(II), Fe (III), Co(II), Ni(II), and Cu(II) complexes were synthesized using a Schiff base ligand derived by condensation of p-phenylenediamine with 2-hydroxy-1-naphthaldehyde. The prepared complexes were characterized using elemental, thermal analyses, FTIR, 1 HNMR, 13 CNMR, UV-Vis, XRD, SEM, molar conductance, and magnetic moment measurements. FTIR spectral studies revealed the interaction of the ligand as bi-negative tetra-dentate towards Mn(II) and Fe(III) atoms, whereas the ligand molecule coordinates in neutral tetra-dentate mode towards Co(II), Ni(II), and Cu (II) ions. The geometries proposed are mainly octahedral configuration surrounds the central atoms referring to the electronic spectral data and magnetic measurements. The calculations abstracted from XRD patterns propose the nano-sized complexes. The SEM images show the nanosized appearance of the particles except for the Ni(II)-complex. Thermo-gravimetric analysis was used to ensure the nature of the presence of solvent molecules attaching to the complexes. Molecular modeling was performed to assert the structural formula proposed for the ligand and some of its complexes. Also, drug-likeness was theoretically estimated to display the probable biological activity of the free ligand through a theoretical comparison with known drugs.

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Synthesis and the characterization of Schiff-base copper complexes: Reactivity with DNA, 4-NPP and BNPP

Cited by 11 publications

References 74 publications

DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

Photocytotoxic Copper(II) Complexes with Schiff‐Base Scaffolds for Photodynamic Therapy

Elaborated studies on nano-sized homo-binuclear Mn(II), Fe(III), Co(II), Ni(II), and Cu(II) complexes derived from N2O2 Schiff base, thermal, molecular modeling, drug-likeness, and spectral

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