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Co(II), Ni(II), Cu(II) and Zn(II) complexes of Schiff base ligands: synthesis, characterization, DFT, in vitro antimicrobial activity and molecular docking studies

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Abstract

Three Schiff base ligands [H2L1–H2L3] containing nitrogen/oxygen donor atoms and their Co(II), Ni(II), Cu(II) and Zn(II) complexes were synthesized by stirring metal acetates with Schiff base ligands obtained from condensation reaction of 2-amino-6-chloro-4-nitrophenol with 5-chloro salicylaldehyde/3,5-dibromo salicylaldehyde/3-methoxy-5–nitro salicylaldehyde. The structural traits of the synthesized compounds were done by using elemental analysis, spectroscopic techniques (UV–Vis, 1H and 13C NMR, FT-IR), mass spectrometry and some physical studies (XRD, TGA). According to spectral data, ligands behave as a tridentate (ONO) and formed complexes with octahedral geometry. The thermogravimetric analysis revealed that metal complexes decay in multi-steps leaving metal oxide as an end product. Powder XRD study suggested crystalline nature of the compounds. The energy gap (HOMO–LUMO) and molecular electrostatic potential calculation were computed by using DFT/B3LYP/6-31G** basis set. Derived ligands and complexes were explored for in vitro antimicrobial potential toward two gram-positive bacteria, two gram-negative bacteria, i.e., S. aureus, B. subtilis, P. aeruginosa, E. coli, and two fungal strains, i.e., A. niger, C. albicans, through serial dilution method taking ciprofloxacin and fluconazole as standard. The investigated results showed that complexes are more potent than free Schiff base ligands. The Cu(L2)(H2O)3 (0.0115 μmol/mL) and Zn(L2)(H2O)3 (0.0115 μmol/mL) complexes were found to be more active among all the investigated compounds. Additionally, molecular docking studies were also performed for some compounds in the active site of DNA Gyrase enzyme (PDB code: 1AJ6), suggesting good hydrophobic interactions of compounds with the enzyme.

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Acknowledgements

The author Mr. Sanjeev Kumar (SRF) (File No. 09/752(0095)/2019-EMR-I) is highly thankful to CSIR, New Delhi, India, for the grant of fellowship and thankful to Dr. A.P.J. Abdul Kalam Central Instrumentation Laboratory and Department of Chemistry, GJUS&T, Hisar, for providing good facilities to perform this research work.

Funding

Author Sanjeev Kumar (SRF) (File No. 09/752(0095)/2019-EMR-I), acknowledges the CSIR, New Delhi, India, for financial assistance in form of Senior Research Fellowship.

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Authors and Affiliations

  1. Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, 125001, India

    Sanjeev Kumar, Jai Devi & Sonika Asija

  2. Computational Chemistry and Drug Discovery Division, Quanta Calculus Pvt. Ltd, Kushinagar, 274203, India

    Amit Dubey

  3. Department of Pharmacology, Saveetha Dental College and Hospital, Saveetha Institute of Medical and Technical Sciences, Tamil Nadu, Chennai, 600077, India

    Amit Dubey

  4. Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Shoolini University, Solan, 173229, India

    Deepak Kumar

  5. Department of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, 125001, India

    Deepak Kumar Jindal

  6. School of Pharmaceutical Sciences, Delhi Pharmaceutical Sciences and Research University, New Delhi, 110017, India

    Archana Sharma

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Contributions

SK helped in writing—original draft; analysis, validation; conceptualization; data curation; methodology; software; visualization. JD performed formal analysis; supervision; validation. AD contributed to writing—original draft, validation, software. DG developed software. DKJ, AS and SA helped in formal analysis.

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Correspondence to Jai Devi.

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Kumar, S., Devi, J., Dubey, A. et al. Co(II), Ni(II), Cu(II) and Zn(II) complexes of Schiff base ligands: synthesis, characterization, DFT, in vitro antimicrobial activity and molecular docking studies. Res Chem Intermed 49, 939–965 (2023). https://doi.org/10.1007/s11164-022-04941-0

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