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Syntheses, in vitro, and in silico studies of rhodanine-based schiff bases as potential α-amylase inhibitors and radicals (DPPH and ABTS) scavengers

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Abstract

A two-step reaction method was used to synthesize a series of rhodanine-based Schiff bases (2–33) that were characterized using spectroscopic techniques. All compounds were assessed for α-amylase inhibitory and radical scavenging (DPPH and ABTS) activities. In comparison to the standard acarbose (IC50 = 9.08 ± 0.07 µM), all compounds demonstrated good to moderate α-amylase inhibitory activity (IC50 = 10.91 ± 0.08–61.89 ± 0.102 µM). Compounds also demonstrated significantly higher DPPH (IC50 = 10.33 ± 0.02–96.65 ± 0.03 µM) and ABTS (IC50 = 12.01 ± 0.12–97.47 ± 0.13 µM) radical scavenging activities than ascorbic acid (DPPH, IC50 = 15.08 ± 0.03 µM; ABTS, IC50 = 16.09 ± 0.17 µM). The limited structure-activity relationship (SAR) suggests that the position and nature of the substituted groups on the phenyl ring have a vital role in varying inhibitory potential. Among the series, compounds with an electron-withdrawing group at the para position showed the highest potency. Kinetic studies revealed that the compounds followed a competitive mode of inhibition. Molecular docking results are found to agree with experimental findings, showing that compounds reside in the active pocket due to the main rhodanine moiety.

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Acknowledgements

Dr. Samuel Attah Egu is thankful to The World Academy of Sciences, Trieste, Italy, for awarding a prestigious Fellowship for the year 2019-2020 under the ICCBS-TWAS Post Doc Fellowship program. The authors also thankfully acknowledge the financial support of Sindh Higher Education Commission (SHEC), Pakistan vide letter No. NO.DD/SHEC/1-14/2014, Project Code SHEC/SRSP/Med-3/15/2021-21.

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Authors and Affiliations

  1. Department of Pure and Industrial Chemistry, Kogi State University, Anyigba, Kogi, Nigeria

    Samuel Attah Egu

  2. H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

    Irfan Ali & Khalid Mohammed Khan

  3. Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia

    Khalid Mohammed Khan & Muhammad Taha

  4. Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraydah, 52571, Kingdom of Saudi Arabia

    Sridevi Chigurupati

  5. Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

    Urooj Qureshi, Uzma Salar & Zaheer Ul-Haq

  6. Department of Medical Laboratory Science, Fakeeh College for Medical Sciences, Jeddah, Kingdom of Saudi Arabia

    Shatha Ghazi Felemban

  7. Faculty of Pharmacy, AIMST University, 08100, Bedong, Kedah, Malaysia

    Vijayan Venugopal

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Egu, S.A., Ali, I., Khan, K.M. et al. Syntheses, in vitro, and in silico studies of rhodanine-based schiff bases as potential α-amylase inhibitors and radicals (DPPH and ABTS) scavengers. Mol Divers 27, 767–791 (2023). https://doi.org/10.1007/s11030-022-10454-0

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