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Novel Schiff base metal complexes: synthesis, characterization, DNA binding, DNA cleavage and molecular docking studies

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Abstract

A novel Schiff base, 3-(((1H-1,2,4-triazol-3-yl)imino)methyl)-4H-chromen-4-one (L) was synthesized and used as ligand for the synthesis of Co(II), Ni(II), Cu(II), Zn(II) and Pd(II) complexes. The structural characterization of the ligand and its metal complexes was determined by using various physicochemical and spectroscopic methods. The IR data show that the Schiff base ligand acts as a bidentate donor coordinating through the oxygen atom of the chromone and nitrogen atom of the imine group. Based on all spectral data, tetrahedral geometry has been proposed for all the metal complexes except Cu(II) and Pd(II) complexes. However, square-planar geometry has been proposed for Cu(II) and Pd(II) complexes. DNA binding interaction of the ligand and its metal complexes was investigated by using UV–visible absorption, fluorescence and molecular docking studies. The binding constants were in the order of 104 M−1 suggesting good binding affinity towards CT-DNA. The DNA cleavage activity of the synthesized compounds was investigated by using agarose gel electrophoresis. In vitro antimicrobial activity of the synthesized compounds were screened against two gram-positive bacteria (Bacillus subtilis, Staphylococcus aureu) and two gram-negative bacteria (Escherichia coli, Proteus vulgaris) and one fungi strain Candida albicans using disc diffusion method. Antioxidant activity was carried out by DPPH radical scavenging method. In vitro anti-proliferative activity of the ligand and its metal complexes was also carried on the HEK-293, HeLa, IMR-32 and MCF-7 cancer cell lines using MTT assay.

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Acknowledgements

The authors wish to thank the Director, CMET, Hyderabad, for providing TG facility. The authors are thankful to the Department of Biochemistry, SV University, Tirupati, for providing antioxidant activity, Department of Biotechnology and University College of Pharmaceutical Sciences, Kakatiya University, Warangal, for antimicrobial and anti-proliferative activity studies. We also wish to thank the Ministry of Human Resource Development for granting the research fellowship to B. Mayuri.

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Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology, Warangal, Telangana, 506 004, India

    Mayuri Bheemarasetti, Kavitha Palakuri & Laxma Reddy Kotha

  2. Department of Biotechnology, National Institute of Technology, Warangal, Telangana, 506 004, India

    Shweta Raj & Prakash Saudagar

  3. Department of Pharmacology and Toxicology, Pharmaceutical Sciences, Kakatiya University, Warangal, Telangana, 506009, India

    Durgaiah Gandamalla & Narsimha Reddy Yellu

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  1. Mayuri Bheemarasetti
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Correspondence to Laxma Reddy Kotha.

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Bheemarasetti, M., Palakuri, K., Raj, S. et al. Novel Schiff base metal complexes: synthesis, characterization, DNA binding, DNA cleavage and molecular docking studies. J IRAN CHEM SOC 15, 1377–1389 (2018). https://doi.org/10.1007/s13738-018-1338-7

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