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Exploring tricycle acridines as prospective urease inhibitors: synthesis via microwave assistance, in vitro evaluation, kinetic profiling, and molecular docking investigations

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Abstract

The current research deals with the microwave-assisted green synthesis of two acridine-based libraries and in vitro urease inhibitory activities. The first library is based on 9-phenyl acridine 1–13 derivatives, while the second is based on 10H-acridin-9-one 14–33 derivatives. All compounds were characterized using FTIR, EI-MS, 1H-NMR, and CHNX techniques. As a result of in vitro evaluation of the synthesized derivatives, most compounds showed potent inhibitory activity against urease with IC50 values ranging from 0.91 to 11.84 µM. Thiourea was used as the standard (IC50 = 19.43 ± 0.18 µM). The structure–activity relationship (SAR) was established to identify key relationships between studied compounds' chemical structure and biological activity. The kinetic studies revealed a competitive mode of inhibition by the compounds. In addition, molecular docking and MD simulation studies were conducted to determine the different interactions between the ligands (compounds) and the enzyme’s active site for the retention time of the ligand into the active pocket of the protein. Thus, it is well-known that inhibiting the urease enzyme activity effectively treats infections caused by Helicobacter pylori. This study has identified that these synthetic acridines may serve as promising lead candidates as urease inhibitors.

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Acknowledgements

The authors acknowledge the financial support of the Pakistan Academy of Sciences, Islamabad, Pakistan, PAS Project No. 111.

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Authors and Affiliations

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

    Mehwish Manzoor, Mehwish Solangi, Fouzia Naz & Khalid Mohammed Khan

  2. PCSIR Laboratories Complex, Karachi, Shahrah-E-Dr. Salimuzzaman Siddiqui, Karachi, 75280, Pakistan

    Shahnaz Perveen

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

    Uzma Salar

  4. Center for Advanced Drug Research, COMSATS University Islamabad, Abbottabad Campus, Abbottabad, 22060, Pakistan

    Jamshed Iqbal, Zahid Hussain & Aqeel Imran

  5. Department of Chemistry, COMSATS University Islamabad, Lahore Campus, Lahore, Punjab, 54000, Pakistan

    Jamshed Iqbal & Zahid Hussain

  6. Department of Pharmacy, COMSATS University Islamabad, Lahore Campus, Lahore, Punjab, 54000, Pakistan

    Aqeel Imran

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

    Muhammad Taha

  8. Pakistan Academy of Sciences, 3-Constitution Avenue Sector G-5/2, Islamabad, Pakistan

    Khalid Mohammed Khan

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  1. Mehwish Manzoor
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Contributions

MM: design, methodology, synthesis, data acquisition, characterization of target compounds, and manuscript writing. MS and FN: writing-review and editing the original draft, spectroscopic data, and manuscript final draft validation. SP: supervised the whole project and authenticated the final draft of the manuscript. US: validation of characterization of spectral data and initial draft of the manuscript. JI, ZH, and AI: performed in vitro urease bioactivity, enzyme kinetics studies, and molecular docking of all compounds. MT: involved in the conceptualization of this research work and the finalization of the manuscript. KMK: conceptualization, overall supervision of the whole project, formal analysis, review, editing, funding acquisition, and authentication of the final draft of the manuscript.

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Correspondence to Jamshed Iqbal or Khalid Mohammed Khan.

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Manzoor, M., Solangi, M., Perveen, S. et al. Exploring tricycle acridines as prospective urease inhibitors: synthesis via microwave assistance, in vitro evaluation, kinetic profiling, and molecular docking investigations. J IRAN CHEM SOC 21, 1163–1183 (2024). https://doi.org/10.1007/s13738-024-02990-3

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