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 activity
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 synt...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Association of Pharmaceutical Teachers of India
2025
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| Online Access: | http://psasir.upm.edu.my/id/eprint/118575/ http://psasir.upm.edu.my/id/eprint/118575/1/118575.pdf |
| _version_ | 1848867547007418368 |
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| author | Elsalami, Rabia Mrehil Rullah, Kamal Kassab, Yaman Walid Qureshi, Mohammad Javed Ahmad, Waqas Mahadi, Mahani Hassan, Masriana Zin, Noraziah Mohamad Kalifa Kafo, Anwar Salm Yee, Chin Chai Mohamad, Najwa |
| author_facet | Elsalami, Rabia Mrehil Rullah, Kamal Kassab, Yaman Walid Qureshi, Mohammad Javed Ahmad, Waqas Mahadi, Mahani Hassan, Masriana Zin, Noraziah Mohamad Kalifa Kafo, Anwar Salm Yee, Chin Chai Mohamad, Najwa |
| author_sort | Elsalami, Rabia Mrehil |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | 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. |
| first_indexed | 2025-11-15T14:38:13Z |
| format | Article |
| id | upm-118575 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T14:38:13Z |
| publishDate | 2025 |
| publisher | Association of Pharmaceutical Teachers of India |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-1185752025-07-18T06:59:52Z http://psasir.upm.edu.my/id/eprint/118575/ 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 activity Elsalami, Rabia Mrehil Rullah, Kamal Kassab, Yaman Walid Qureshi, Mohammad Javed Ahmad, Waqas Mahadi, Mahani Hassan, Masriana Zin, Noraziah Mohamad Kalifa Kafo, Anwar Salm Yee, Chin Chai Mohamad, Najwa 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. Association of Pharmaceutical Teachers of India 2025 Article PeerReviewed text en cc_by_nc_sa_4 http://psasir.upm.edu.my/id/eprint/118575/1/118575.pdf Elsalami, Rabia Mrehil and Rullah, Kamal and Kassab, Yaman Walid and Qureshi, Mohammad Javed and Ahmad, Waqas and Mahadi, Mahani and Hassan, Masriana and Zin, Noraziah Mohamad and Kalifa Kafo, Anwar Salm and Yee, Chin Chai and Mohamad, Najwa (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 activity. Indian Journal of Pharmaceutical Education and Research, 59 (2). pp. 810-825. ISSN 0019-5464 https://ijper.org/10.5530/ijper.20255518 10.5530/ijper.20255518 |
| spellingShingle | Elsalami, Rabia Mrehil Rullah, Kamal Kassab, Yaman Walid Qureshi, Mohammad Javed Ahmad, Waqas Mahadi, Mahani Hassan, Masriana Zin, Noraziah Mohamad Kalifa Kafo, Anwar Salm Yee, Chin Chai Mohamad, Najwa 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 activity |
| title | 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 activity |
| title_full | 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 activity |
| title_fullStr | 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 activity |
| title_full_unstemmed | 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 activity |
| title_short | 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 activity |
| title_sort | 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 activity |
| url | http://psasir.upm.edu.my/id/eprint/118575/ http://psasir.upm.edu.my/id/eprint/118575/ http://psasir.upm.edu.my/id/eprint/118575/ http://psasir.upm.edu.my/id/eprint/118575/1/118575.pdf |