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In silico and biological exploration of greenly synthesized curcumin-incorporated isoniazid Schiff base and its ruthenium complexes

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Abstract

In the present investigation, ultrasound-mediated three Knoevenagel condensates have been prepared from biologically active curcumin and different aldehydes. Curcumin Schiff bases have been prepared by reacting these Knoevenagel condensates with isoniazid. Ruthenium Schiff base complexes are synthesized and octahedral geometry of these complexes are confirmed by various analytical techniques like elemental analysis, molar conductive measurements, and spectroscopic techniques like UV–Vis, FT-IR, NMR, EPR, and ESI mass. Moreover, optimized geometry and DFT calculation have been done using Gaussian 09 W software and the quantum mechanical calculation of these complexes is also performed. Pharmacokinetic behavior of the synthesized compounds is examined using SWISS ADME, PASS online, and molinspiration online software. Based on this, in vivo and in vitro pharmaceutical investigations are carried out and it is found that all the complexes possess potent biological activity than the ligand. All the synthesized compounds are docked against 1BNA and 4fm9 colon cancer receptors. Interestingly, intercalative binding efficacy of the synthesized compounds is confirmed by using UV–visible absorption titration and viscosity measurements against CT-DNA.

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The data sets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

The author (Jeyaraman Porkodi) shows her gratitude to Tamil Nadu State Council for Science and Technology for providing the fund to undergo this research. She also thanks the Management and the Principal of The Standard Fireworks Rajaratnam College for Women, Sivakasi, for providing necessary support like Schrodinger Maestro 12.0 and Gaussian 09W software and other facilities towards the completion of this funded project. We also thank the Management and Principal of Virudhunagar Hindu Nadars’ Senthikumara Nadar College, Virudhunagar, for their moral support and providing the instrumental facilities. We thank Prof. Dr. P. Natarajan, Department of Pharmaceutical chemistry, Sankaralingam Bhuvaneswari College of Pharmacy, Annaikuttam, Sivakasi, for the in vivo and in vitro studies.

Funding

This work was supported by Tamil Nadu State Council for Science and Technology (C.No. TNSCST/STP/AR/2018–2019/9302). The author Dr. J. Porkodi has received research support from the above funding agency.

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Authors and Affiliations

  1. Post Graduate and Research Centre of Chemistry, The Standard Fireworks Rajaratnam College for Women (Autonomous), Sivakasi, India

    Porkodi Jeyaraman

  2. Research Department of Chemistry, VHNSN College, Virudhungar, India

    Samuel Michael & Raman Natrajan

  3. Department of Chemistry, St. Xavier’s College, Palayamkottai, India

    Anto Arockia Raj Adaikalam

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  1. Porkodi Jeyaraman
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  2. Samuel Michael
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  3. Raman Natrajan
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  4. Anto Arockia Raj Adaikalam
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection, and analysis were performed by Dr. J. Porkodi], Mr. M. Samuel, and Dr. A. Anto Arockia Raj under the guidance of Dr. N. Raman. The first draft of the manuscript was written by Dr. J. Porkodi, and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Porkodi Jeyaraman.

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Jeyaraman, P., Michael, S., Natrajan, R. et al. In silico and biological exploration of greenly synthesized curcumin-incorporated isoniazid Schiff base and its ruthenium complexes. Struct Chem 34, 1115–1132 (2023). https://doi.org/10.1007/s11224-022-02065-0

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