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Synthesis, characterization, biological screening and molecular docking studies of 2-aminonicotinaldehyde (ANA) and its metal complexes

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Abstract

The biological and optical importance of the o-aminoaldehyde family of ligands inspired us to evaluate the coordination properties and biological activities of 2-aminonicotinaldehyde (ANA). Here, we report the synthesis, characterization, biological screening and molecular docking studies of ANA and its metal complexes of Ni(II), Pd(II), Co(II) and Cu(II) using various analytical and spectroscopic techniques. The single crystal X-ray diffraction studies of ANA explain the solid-state assembly and an interesting supramolecular herring bone stacking pattern by classical N–H···O/N intra/inter molecular and non-classical C–H···O/N intermolecular H-bonding. ANA and its metal complexes were screened for in vitro anticancer, antimicrobial and anti-oxidant activities. Anticancer activity was tested against HeLa, MCF-7 and HEK293 human cancer cell lines. The [Ni(ANA)2Cl2] complex showed good activity against HeLa and MCF-7, the [Pd(ANA)2Cl2] and [Cu(ANA)2Cl2] complexes against HeLa, and the [Co(ANA)2Cl2] complex against MCF-7. In antimicrobial screening, the [Co(ANA)2Cl2] and [Cu(ANA)2Cl2] complexes were proved to be potent antibacterial and antifungal agents. The anti-oxidant activity of these complexes was investigated through DPPH radical assay, and it was found that all the complexes have good radical scavenging capability. Molecular docking studies were also carried for all the metal complexes against EGFR as a target protein by using Autodock, and the results strongly correlated with the anticancer activity.

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Acknowledgements

I am very grateful to Dr. Munirathinam, IISC Bangalore, for providing the single-crystal XRD facility. I am grateful to the Ministry of Human Resource Development (MHRD), India for awarding a research fellowship to me.

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Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology, Warangal, 506004, India

    Ramaiah Konakanchi & Laxma Reddy Kotha

  2. Department of Chemistry, Lal Bahadur College, Warangal, 506007, India

    Ramachary Mallela

  3. Department of Chemistry, Kakatiya University, Warangal, 506009, India

    Ramu Guda

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  1. Ramaiah Konakanchi
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  2. Ramachary Mallela
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  4. Laxma Reddy Kotha
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Correspondence to Laxma Reddy Kotha.

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Konakanchi, R., Mallela, R., Guda, R. et al. Synthesis, characterization, biological screening and molecular docking studies of 2-aminonicotinaldehyde (ANA) and its metal complexes. Res Chem Intermed 44, 27–53 (2018). https://doi.org/10.1007/s11164-017-3089-y

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