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Unraveling the Pharmaceutical Benefits of Freshly Prepared Amino Acid-Based Schiff Bases Via DFT, In Silico Molecular Docking and ADMET

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Abstract

A series of amino acid-based Schiff bases have been synthesized using a facile condensation between benzil (a diketone) and amino acid in the presence of a base. The formation of Schiff base compounds has been ensured by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and UV–Vis. spectra. Density Functional Theory (DFT) calculations have been explored in order to get intuition into the molecular structure and chemical reactivity of the compounds. The DFT, optimized structure of the compounds, has been used to attain the molecular docking studies with DNA structure to find the favorable mode of interaction. In silico ADME/Tox profile of the compounds has been predicted using pkCSM web tools, exhibiting suitable values of absorption, distribution, and metabolism. These obtained parameters are connected to bioavailability. In addition, toxicity, skin sensitization and cardiotoxicity (hERG) analysis have been performed for evaluating the drug-like character of the prepared Schiff bases. The findings obtained from this study may find applications in the field focusing on the production of efficient and harmless pharmacological drugs.

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Acknowledgements

The Authors express their gratitude to the Principal and Head of the Department of Chemistry, MSU College, Govindaperi, for providing necessary research facilities to complete this work successfully. The characterization facilities afforded by Manonmaniam Sundaranar University and IIT, Madras are gratefully acknowledged by all authors

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Authors and Affiliations

  1. Department of Chemistry, Manonmaniam Sundaranar University College, Tirunelveli, 627 414, Tamil Nadu, India

    Subramanian Ramasamy & Arun Thesingu Rajan

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  1. Subramanian Ramasamy
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  2. Arun Thesingu Rajan
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Contributions

R.S., and T.R.A., designed methodology, Formal analysis, Investigation and wrote manuscript.All authors read and approved the final manuscript.

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Correspondence to Arun Thesingu Rajan.

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Research Highlights

• A series of novel and innovative type amino acid derived Schiff bases are synthesized.

• Molecular structure of Schiff base ligands is optimized using DFT method.

• Molecular docking support for the intercalative mode of action with DNA.

• In silico ADMET profile of the Schiff bases has been examined.

• They act as potential cardiotoxicity (hERG) agents.

• Leads to develop more effective and harmless pharmacological drugs.

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Ramasamy, S., Rajan, A.T. Unraveling the Pharmaceutical Benefits of Freshly Prepared Amino Acid-Based Schiff Bases Via DFT, In Silico Molecular Docking and ADMET. J Fluoresc 32, 1873–1888 (2022). https://doi.org/10.1007/s10895-022-02987-2

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  • DOI: https://doi.org/10.1007/s10895-022-02987-2

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