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Indian Journal of Pharmaceutical Education and ResearchAn Official Publication of Association of Pharmaceutical Teachers of India (APTI)
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Investigating the Dual-Action Potential of (Z)-6-methoxy 2-(naphthalen-1-ylmethylene) Benzofuran-3(2H)-one (AU-23): A Novel Synthetic Aurone Derivative with Antibacterial and Anti-Inflammatory Activ

1, 2, 3, 4, 5, 1, 6, 7, 6, 7, 1

  1. 1Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Cyberjaya, Cyberjaya, MALAYSIA.
  2. 2Department of Pharmaceutical Chemistry, Drug Discovery and Synthetic Chemistry Research Group, Kulliyyah of Pharmacy, International Islamic University Malaysia, Bandar Indera Mahkota, Kuantan, Pahang, MALAYSIA.
  3. 3Department of Pharmacy practice, College of Pharmacy, National University of Science and Technology, Bousher, Muscat, Sultanate of OMAN.
  4. 4Department of Pharmaceutics, College of Pharmacy, National University of Science and Technology, Bousher, Muscat, Sultanate of OMAN.
  5. 5Discipline of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Penang, MALAYSIA.
  6. 6Department of Pathology, Faculty of Medicine and Health Science, Universiti Putra Malaysia, Serdang, Selangor, MALAYSIA.
  7. 7Center for Diagnostic, Therapeutics and Investigative Studies, Faculty of Health Sciences, Universiti Kebangsaan Malaysia, Kuala Lumpur, MALAYSIA.
  8. 8School of Pharmacy, Faculty of Health and Medical Sciences, University of Taylor, Subang Jaya, Selangor, MALAYSIA.
  9. 9College of Pharmacy, Al-Bayan University, Baghdad, IRAQ.

CORRESPONDENCE

Dr. Najwa Mohamad

Department of Pharmaceutical Sciences, Faculty of Pharmacy University of Cyberjaya, MALAYSIA.

najwa@cyberjaya.edu.my

Received: 22-10-2023; Revised: 14-03-2024; Accepted: 23-10-2024.

Volume 59, Issue 2 · pp. 810-825 · 2025 · DOI: 10.5530/ijper.20255518

ABSTRACT

Aim/Background: Aurone is a well-known, naturally occurring, minor flavonoid with significant biological properties. However, their low abundance in nature limits their application in the medical field. In this study, we investigated the antimicrobial and anti-inflammatory properties of a novel synthetic aurone, (Z)-6-methoxy-2-(naphthalen-1-ylmethylene) benzofuran-3(2H)-one (AU-23).Materials and Methods: AU-23 was synthesized via multistep synthesis reactions involving the oxidative cyclization of 2’-hydroxychalcones. AU-23 was tested for antibacterial, minimum inhibitory concentration and antibiofilm activity against several ATCC strains using agar well diffusion, broth-micro dilution and XTT assay methods respectively.Results: At various concentrations, it selectively inhibited the growth of four strains (P. aeruginosa ATCC 9027, methicillin-resistant S. aureus (MRSA) ATCC 33591, methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 25923 and methicillin-resistant S. aureus (MRSA) ATCC 43300). Moreover, it was observed that AU-23 had a bactericidal effect on sensitive strains of MSSA ATCC 25923 and P. aeruginosa ATCC 9027, as well as a bacteriostatic effect on MRSA ATCC 33591 and MRSA ATCC 43300. AU-23 also displayed effective antibiofilm activity against monomicrobial biofilms but not against polymicrobial biofilms. The findings of PCR study revealed that AU-23 downregulates the expression of pro-inflammatory cytokines and mediators (i.e., IL-6, IL-1β, iNOS and TNF-α), as well as crucial pattern recognition receptors (TLR4 and CD14) in LPS-stimulated RAW 264.7 cells. Molecular docking studies demonstrated that the ability of AU-23 to bind to the mouse TLR4/MD-2 complex was comparable to that of dexamethasone.Conclusion: the results of several studies conducted, suggests that AU-23 has the potential to function as an effective dual-action agent with antimicrobial and anti-inflammatory properties.

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    Elsalami, R. M., Rullah, K., Kassab, Y. W., Qureshi, M. J., Ahmad, W., Mahadi, M., Hassan, M., Zin, N. M., Kafo, A. S. K., Yee, C. C., & Mohamad, N. (2025). Investigating the Dual-Action Potential of (Z)-6-methoxy 2-(naphthalen-1-ylmethylene) Benzofuran-3(2H)-one (AU-23): A Novel Synthetic Aurone Derivative with Antibacterial and Anti-Inflammatory Activ. Indian Journal of Pharmaceutical Education and Research, 59(2), 810-825. https://doi.org/10.5530/ijper.20255518

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    © 2025 Author(s)

    This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 License, which permits unrestricted use, distribution and reproduction in any medium, provided the original author and source are credited. CC BY 4.0