DNA binding, molecular docking and apoptotic inducing activity of nickel(<scp>ii</scp>), copper(<scp>ii</scp>) and zinc(<scp>ii</scp>) complexes of pyridine-based tetrazolo[1,5-a]pyrimidine ligands

Haleel, Azees Khan; Arthi, P.; Reddy, N. Dastagiri; Veena, V.; Sakthivel, Natarajan; Arun, Y.; Perumal, Paramasivan T.; Rahiman, A. Kalilur

doi:10.1039/c4ra11197d

Cited by 40 publications

(15 citation statements)

References 57 publications

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“…-1 (Table 4) with similar binding affinity to reported copper tetrazole derivative complexes [26]. The 1-4 complexes with CT DNA interaction are through planar phenanthroline and pyridyl tetrazole ring likely via π-stacking interactions.…”

Section: Dna Binding Studiessupporting

confidence: 69%

Synthesis, Characterization of Mixed Cu(II) Pyridyl Tetrazoles and 1,10-Phenanthroline Complexes - DFT and Biological Activity

Himasekar¹,

Mustafa²,

Babu³

2019

Open Chem. J.

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Background: Mixed ligand copper complexes with 1,10-phenanthroline show good chemical nuclease activity and anticancer activity. Recently, tetrazole derivatives are also promising candidates for anticancer activity. Hence, it is significant to study the DNA binding and anticancer activity of two active N-donor ligands and their copper complexes. Objectives: The main objective of this study was to investigate the regioisomeric mixed ligand copper complexes response with calf thymus DNA binding and anti-toxic activity against MCF-7 cell line. Methods: The DNA binding interactions of complexes 1-4 with calf thymus DNA (CT-DNA) were monitored by UV/VIS spectroscopy. The absorption spectra of the Cu complexes are compared with and without CT-DNA at 400-450 nm. The cell proliferation was measured by using the standard 2,3-bis(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide (XTT) assay with four different concentrations of the compounds (5, 10, 50, and 100 mm) and cisplatin (as a positive control) was tested in triplicate for 48 h. The results obtained by the XTTassay are expressed as the average standard deviation of two experiments. The IC 50 values of the complexes exhibited differential and dose-dependent inhibitory activities on the growth of MCF-7 cancer cells. Results: Based on the elemental analysis, molar conductance, magnetic moments, mass, electronic, ESR and IR spectral data, the copper is coordinated by N-atoms of 1,10-phenanthroline and pyridyl tetrazole with octahedral structure. DFT calculations of HOMO and LUMO studies showed that electron density is localized on pyridyl tetrazole ring and phenanthroline ring. The calculated DNA binding constant (K b) values of 1-4 complexes are in the range 4.2-7.6 x10 4 M-1 (Table 4) with similar binding affinity to reported copper tetrazole derivative complexes. The 1-4 complexes with CT DNA interaction are through planar phenanthroline and pyridyl tetrazole ring likely via π-stacking interactions. The IC 50 values of complexes show excellent activity with 24(± 0.5); 18(± 0.5); 20(±0.5); (±0.5) and 38 (±0.8) for 1, 2, 3, 4 and cis platin complexes, respectively. After 72 h of the treatment of 1 on MCF-7 cell, IC 50 values hinder the cell growth upto 24(± 0.5) µg/ml at 5 µM concentration range (Fig. 5). It is apparent from IC 50 values that the order inhibition is 1 > 3 >2 > 4. Conclusion: Experimental results are highly encouraging to explore the mixed ligand regio isomeric copper complexes which have shown the parallel result with Cisplatin. By proper structural modification of pyridyl tetrazole ligand, substituent better anticancer agents can be prepared.

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Section: Dna Binding Studiessupporting

confidence: 69%

Synthesis, Characterization of Mixed Cu(II) Pyridyl Tetrazoles and 1,10-Phenanthroline Complexes - DFT and Biological Activity

Himasekar¹,

Mustafa²,

Babu³

2019

Open Chem. J.

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“…Molecular docking studies were made using the AutoDock Vina software to understand the drug–DNA interactions to analyse the potential binding mode of compound . The X‐ray crystal structure of B‐DNA (PDB ID: 1BNA) dodecamer d(CGCGAATTCGCG)2 was obtained from the Protein Data Bank (http://www.rcsb.org/pdb).…”

Section: Methodsmentioning

confidence: 99%

Study of interfacial charge transfer in nanosemiconductor–molecule composites

Jayabharathi

Prabhakaran

Karunakaran

et al. 2016

J of Physical Organic Chem

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Interaction of sol-gel synthesized Ce-Ag-codoped ZnO (CSZO) nanocrystals with (E)-1-(naphthalen-1-yl)-2-styryl-1Hphenanthro [9,10-d]imidazole has been analysed. The synthesized nanocrystals and their composites with naphthyl styryl phenanthrimidazole have been characterized using scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy, X-ray diffractometry, X-ray photoelectron spectroscopy (XPS) lifetime and Fourier transform infrared spectroscopy and cyclic voltammetry. XPS shows doped silver and cerium in Ag 0 and Ce 4+ states, respectively . SEM and TEM images of CSZO nanoparticles show that they appear to be 3D trapezoid and cocoon-like shape. The selected area electron diffraction pattern supports the nanocrystalline character of the synthesized material. The percentages of doping of cerium and silver in CSZO are 0.54 (at.) and 0.34 (at.), respectively. From the energy levels of the materials used in the imidazole-CSZO composite, the dominant CT direction has been analysed. Theoretical investigation shows that the binding energy and energy gap of the imidazole composites are highly dependent on the nature of the silver oxide cluster and that charge transfer in the imidazole-Ag 4 O 4 composite is faster than the same in other composites. Molecular docking technique has also been carried out to understand the imidazole-DNA interactions. Figure 7. (a) Lifetime spectra of NSPI and NSPI-Ce-Ag-ZnO composites. (b) Cyclic voltammogram of NSPI and NSPI-Ce-Ag-ZnO composite. (c) FT-IR spectra of NSPI, bare pristine ZnO and NSPI-Ce-Ag-ZnO composite INTERFACIAL CHARGE TRANSFER IN NANOSEMICONDUCTOR-MOLECULE COMPOSITES

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“…All geometrical optimizations were carried out at the DFT (B3LYP) [58,59] level of theory with 6-31+G* basis set for C, N, O, S, Cl, Br, H and DZpdf [60] for the copper center using Gaussian 09 program [61]. In order to check the binding modes of the copper nucleases, three DNA sequences were used in the verified docking studies: d(5'-ATATATATATAT-3')2 (assigned as DNA1) which is AT-rich sequence, d(5'-CGCGCGCGCGCG-3')2 (assigned as DNA2) which is GC-rich sequence and d(5'-CGCGAATTCGCG-3')2 (assigned as DNA3) which not only contains AT base pair but also contains CG one and is mostly used in molecular docking studies [62][63][64][65]. Three DNAs adopted in this study are B-DNA , which were built by 3DNA [66].…”

Section: Initial Structuresmentioning

confidence: 99%

Theoretical studies on binding modes of copper-based nucleases with DNA

Liu

Zhu

Tang

2016

Journal of Molecular Graphics and Modelling

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DNA binding, molecular docking and apoptotic inducing activity of nickel(ii), copper(ii) and zinc(ii) complexes of pyridine-based tetrazolo[1,5-a]pyrimidine ligands

Abstract: The biological activity of metal(ii) complexes of tetrazolo[1,5-a]pyrimidine ligands show that the copper(ii) complexes may act as promising anticancer agents.

Cited by 40 publications

References 57 publications

Synthesis, Characterization of Mixed Cu(II) Pyridyl Tetrazoles and 1,10-Phenanthroline Complexes - DFT and Biological Activity

Synthesis, Characterization of Mixed Cu(II) Pyridyl Tetrazoles and 1,10-Phenanthroline Complexes - DFT and Biological Activity

Study of interfacial charge transfer in nanosemiconductor–molecule composites

Theoretical studies on binding modes of copper-based nucleases with DNA

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