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Synthesis, biological activities and docking studies of novel 2,4-dihydroxybenzaldehyde based Schiff base

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Abstract

The present study describes the synthesis and characterization of a series of novel Schiff bases derived from 2,4-dihydroxybenzaldehyde. The biological activities of the newly synthesized compounds were examined by investigating their antioxidant, antibacterial, antifungal, enzyme inhibition and DNA interaction potential. The potential of these compounds as an antioxidant was determined by 2,2-diphenylpicrylhydrazyl radical scavenging method. The antibacterial and antifungal activities of these compounds were assayed by the disk diffusion method, while the enzyme inhibition studies were carried out against acetylcholinesterase and butyrylcholinesterase. The aforementioned studies revealed that the newly synthesized Schiff bases can be used as potential inhibitors for cholinesterase. In addition, the molecular docking studies also agreed well with the experimental results with better interaction patterns in the cases of acetylcholinesterase and butyrylcholinesterase. The DNA binding interactions in these synthesized compounds was studied by the UV–Vis absorption titration method and the results of calculated thermodynamic parameters such as binding constant (K) and free energy change (ΔG) were calculated accordingly. Most of these Schiff bases displayed relatively higher positive values for K and larger negative values for ΔG, indicating efficient binding of these Schiff bases with the DNA. During the course of this study, we also carried out the computational analysis for the determination of the mode of binding of these compounds with the DNA structure.

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Acknowledgment

The authors gratefully acknowledged Dr. Safeer Ahmed, Quaid-i-Azam University Islamabad, Pakistan, for his help in the NMR analysis and Dr. Sajid Mahmood, University of Gujrat (UOG), Gujrat, Pakistan for biological studies. The authors extend their sincere appreciations to the Deanship of Scientific Research at King Saud University for its funding this Prolific Research Group (PRG-1437-34).

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Authors and Affiliations

  1. Department of Chemistry, University of Gujrat, Gujrat, 50700, Pakistan

    Shahzad Murtaza, Kiran Iftikhar, Saima Shamim, Zobia Razzaq & Khadija Naseem

  2. Institute of Chemistry, University of the Punjab, Lahore, Pakistan

    Aadil Abbas

  3. Department of Pharmacology, Faculty of Pharmacy, University of Sargodha, Sargodha, Pakistan

    Muhammad Shoaib Akhtar

  4. Botany and Microbiology Department, College of Science, King Saud University, P.O. Box: 2445, Riyadh, 11451, Saudi Arabia

    Abdallah Mohamed Elgorban

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  1. Shahzad Murtaza
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Correspondence to Shahzad Murtaza.

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Murtaza, S., Abbas, A., Iftikhar, K. et al. Synthesis, biological activities and docking studies of novel 2,4-dihydroxybenzaldehyde based Schiff base. Med Chem Res 25, 2860–2871 (2016). https://doi.org/10.1007/s00044-016-1711-y

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