Synthesis and Characterization of the Ligand Based on Benzimidazole and Its Copper Complex: DNA Binding and Antioxidant Activity

Wu, Huilu; Kou, Fan; Jia, Fei; Liu, Bin; Yuan, Jingkun; Bai, Ying

doi:10.1155/2011/105431

Cited by 12 publications

(14 citation statements)

References 53 publications

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“…To examine the intercalative binding skill of the surfactant copper(II) complexes, a competitive EB binding study to displace EB from its EB-DNA complex was performed with fluorescence experiments [28]. 3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide (EB) is a phenanthridine fluorescence dye and is a typical indicator of intercalation, forming soluble complexes with nucleic acids and emitting stringent fluorescence in the presence of tRNA due to the intercalation of the planar phenanthridinium ring between adjacent base pairs on the double helix.…”

Section: Competitive Binding Studiesmentioning

confidence: 99%

Effect of hydrophobicity on intercalative binding of some surfactant copper(II) complexes with tRNA

2014

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The binding interaction between tRNA and surfactant copper(II) complexes with imidazo[4,5-f][1, 10] phenanthroline, 6,7,8,9-tetrahydrodipyrido[3,2-a:2 0 ,4 0 -c] phenazine, and benzo[1]dipyrido[3,2-a 0 :2 0 ,3 0 -c]phenazine ligands has been studied using various physicochemical techniques. In the presence of tRNA, UV-Vis spectrum of surfactant complexes showed red shift of the absorption band along with significant hypochromicity indicating intercalation of surfactant complexes with tRNA. Competitive binding study with ethidium bromide shows that complexes exhibit the ability to displace the tRNA-bound EB indicating that these complexes bind to tRNA in strong competition with EB for the intercalative binding site. Observed changes in the circular dichroic spectra of tRNA in the presence of surfactant complexes support the strong binding of complexes with tRNA. CV and viscosity results also affirm this mode of binding. The results reveal that the extent of tRNA binding of the benzo[1]dipyrido[3,2-a 0 :2 0 ,3 0 -c] phenazine complex was greater than that of the other complexes. Binding to tRNA appears to be mainly intercalative in nature.

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Section: Competitive Binding Studiesmentioning

confidence: 99%

Effect of hydrophobicity on intercalative binding of some surfactant copper(II) complexes with tRNA

2014

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“…EB emits intense fluorescence in the presence of DNA due to its strong intercalation between the DNA base pairs which prevents it from solvent quenching. The addition of quencher ( Sul and complexes 1 – 7 ) to EB–DNA mixture leads to a reduction in the emission intensity as they replace the EB, indicating competitive DNA binding with EB . The reduction in emission intensity is completely due to the competitive replacement of EB intercalated to DNA, not due to any interaction of EB with Sul /complexes.…”

Section: Resultsmentioning

confidence: 98%

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Kumari

Nath

2017

Applied Organom Chemis

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Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac (Sul), coordinated with carboxylate oxygen, namely C23H25FO3SSn (1), C38H31FO3SSn (2), C32H43FO3SSn (3), C52H42F2O6S2Sn (4), C44H44S2Cl2O6F2Sn2 (5), C48H50F2O6S2Sn (6) and C56H66F2O6S2Sn (7), have been synthesized and characterized using analytical and spectroscopic (IR, 1H NMR, 13C NMR, 119Sn NMR and ESI‐MS) techniques. Optimized geometry and electronic structures of the complexes obtained from density functional theory calculations indicate that complexes 1, 2, 3 and 7 are tetra‐coordinated with monodentate carboxylates, 4 and 6 are hexa‐coordinated with highly distorted octahedral geometry, whereas 5 is penta‐coordinated with distorted trigonal bipyramidal geometry. Probable mode of DNA binding with ligand (Sul) and complexes 1–7 has been revealed via various biophysical techniques (UV–visible spectroscopy, fluorometry and circular dichroism). Intrinsic binding constants (Kb) obtained from UV–visible spectroscopy for Sul and complexes 1–7 are 3.69 × 104, and 7.3 × 103, 1.14 × 104, 1.47 × 104, 1.55 × 104, 1.49 × 104, 2.02 × 104, 1.17 × 104 M−1, respectively. The quenching constants (Ksv) using fluorometric titrations, calculated from competitive binding of ethidium bromide versus Sul/complexes with calf thymus DNA, also correspond to the above results. Circular dichroism spectral patterns of calf thymus DNA with Sul and complexes 1–7 have also been investigated. All the results reveal that the complexes bind with DNA through partial intercalative mode. pBr322 plasmid fragmentation has also been studied using gel electrophoresis, which shows the fragmentation of circular DNA by an increase in nicked form and also by the appearance of linear form with increasing concentration of drug or complexes.

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“…Bathochromism was also observed in the spectra of these complexes with increasing concentration as exemplified in Figure 1. This shift in wavelength can be attributed to strong intermolecular hydrogen bonding, a phenomenon which can be likened to the intercalative mode of bonding involving a strong - * stacking interaction between aromatic chromophores and DNA bases [38][39][40]. The molar conductivities of the complexes measured in DMSO (10 −3 M) was between 13.58 and 18.48 indicating the nonelectrolyte nature of these complexes [41][42][43].…”

Section: Electronic Absorption Spectra Conductivity and Magneticmentioning

confidence: 99%

Spectroscopic Characterization,In VitroCytotoxicity, and Antioxidant Activity of Mixed Ligand Palladium(II) Chloride Complexes Bearing Nucleobases

Tetteh

Dodoo

Appiah–Opong

et al. 2014

Journal of Inorganic Chemistry

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Mixed-ligand palladium(II) chloride complexes bearing the nucleobases, adenine (Ad), cytosine (Cyt), and guanine (Gua), have been synthesized and characterized by UV-vis spectrophotometric methods, magnetic susceptibility, molar conductivity, elemental analysis, FTIR, and 1 H-NMR. The complexes were found to have the composition cis-[PdCl 2 (Gua)(Cyt)], cis-[PdCl 2 (Ad)(Cyt)], and cis-[PdCl 2 (Ad)(Gua)]. A four-coordinated square-planar geometry is proposed for these Pd(II) complexes based on magnetic evidence and electronic spectra. The complexes as well as the free nucleobase ligands were tested for their in vitro cytotoxicity on human promyelocytic leukemia (HL60) and human histiocytic leukemia (U937) cell lines. cis-[PdCl 2 (Ad)(Gua)] showed IC 50 values of 11.29 ± 2.91 and 8.31 ± 1.44 M against HL60 and U937, respectively, which was higher than that of the positive control (curcumin) against U937. The complexes also showed significant antioxidant activity when tested against 2,2-diphenyl-1-picrylhydrazylradical (DPPH).

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Synthesis and Characterization of the Ligand Based on Benzimidazole and Its Copper Complex: DNA Binding and Antioxidant Activity

Cited by 12 publications

References 53 publications

Effect of hydrophobicity on intercalative binding of some surfactant copper(II) complexes with tRNA

Effect of hydrophobicity on intercalative binding of some surfactant copper(II) complexes with tRNA

Tri‐ and diorganotin(IV) derivatives of non‐steroidal anti‐inflammatory drug sulindac: Characterization, electronic structures (DFT), DNA binding and plasmid cleavage studies

Spectroscopic Characterization,In VitroCytotoxicity, and Antioxidant Activity of Mixed Ligand Palladium(II) Chloride Complexes Bearing Nucleobases

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