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Issue 8, 2015
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DNA/protein binding, DNA cleavage, cytotoxicity, superoxide radical scavenging and molecular docking studies of copper(II) complexes containing N-benzyl-N′-aryl-N′′-benzoylguanidine ligands

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Abstract

Five copper(II) complexes containing N,N′,N′′-trisubstituted guanidine ligands were synthesized and characterized by elemental analyses and UV-Visible, FT-IR, EPR and mass spectroscopic techniques. The synthesized copper(II) complexes (1–5) bear the general formula [Cu{C6H5CONC(NR)NHCH2C6H5}2] where R = phenyl (1), 4-methylphenyl (2), 4-ethoxyphenyl (3), 2-methoxyphenyl (4) or 1-naphthyl (5). The four coordinated square planar geometry of the complexes was confirmed by the single crystal X-ray diffraction study. The interaction of the Cu(II) complexes with calf thymus DNA (CT DNA) was explored using absorption and fluorescence spectroscopic methods. The results revealed that the complexes have an affinity constant for DNA in the order of 104 M−1 and the mode of interaction is non-covalent intercalation. The DNA cleavage study showed that the complexes cleaved DNA without any external agent. The interaction of Cu(II) complexes with bovine serum albumin (BSA) was also studied using absorption and fluorescence techniques. The cytotoxic activity of the Cu(II) complexes was probed in vitro against human breast (MCF7) and lung (A549) cancer cell lines. The complexes were also tested against mouse embryonic fibroblast (NIH 3T3) cell lines. Complexes 1 and 3 have good cytotoxic activity which is comparable with the cyclophosphamide drug. The complexes were less cytotoxic towards normal cell lines showing that they affect only cancer cell lines. Superoxide radical scavenging property of the complexes was assessed using the NBT assay. Copper(II) complexes showed appreciable superoxide radical scavenging activity with IC50 values ranging from 1.53 to 5.62 μM. A further molecular docking technique was employed to understand the binding of the complexes toward the molecular target DNA and human DNA topoisomerase I.

Graphical abstract: DNA/protein binding, DNA cleavage, cytotoxicity, superoxide radical scavenging and molecular docking studies of copper(ii) complexes containing N-benzyl-N′-aryl-N′′-benzoylguanidine ligands

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Publication details

The article was received on 23 Dec 2014, accepted on 24 Jun 2015 and first published on 24 Jun 2015


Article type: Research Article
DOI: 10.1039/C4QI00234B
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Citation: Inorg. Chem. Front., 2015,2, 780-798
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    DNA/protein binding, DNA cleavage, cytotoxicity, superoxide radical scavenging and molecular docking studies of copper(II) complexes containing N-benzyl-N′-aryl-N′′-benzoylguanidine ligands

    K. Jeyalakshmi, Y. Arun, N. S. P. Bhuvanesh, P. T. Perumal, A. Sreekanth and R. Karvembu, Inorg. Chem. Front., 2015, 2, 780
    DOI: 10.1039/C4QI00234B

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