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Appraisal of antioxidant scavenging and antibiofilm capacities of pyrazolic, isoxazolic-based chalcones and aurones: Synthesis, molecular docking, simulation, and ADME properties
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DOI：10.1016/j.lddd.2025.100256.png)
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Abstract
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Background: The increasing prevalence of antimicrobial resistance underscores the urgent need for novel therapeutic agents. Objectives: This study reports the synthesis and characterization of pyrazolic and isoxazolic chalcones and aurones. Methods: The chalcones and aurones were confirmed via IR NMR, and EI-MS analyses. The newly synthesized derivatives were also screened for antioxidant, antibiofilm, and hemolytic activities. Results: Among the tested molecules, 3a stood out with the strongest DPPH radical-scavenging activity (86.11 +/- 1.14 %), while 5a (80.31 +/- 0.87 %) and 9a (79.43 +/- 1.43 %) also performed notably well. In the FRAP assay, 10b showed the highest reducing potential (53.6 +/- 0.58 %), followed closely by 11a (51.4 +/- 0.76 %). The antibiofilm experiments further highlighted the strength of these compounds; 10a produced the most pronounced inhibition against both E. coli (54.59 +/- 0.75 %) and B. subtilis (57.29 +/- 0.88 %), with 5a (51.15 +/- 0.33 %) and 10b (51.23 +/- 0.64 %) also showing meaningful activity. Hemolysis testing indicated that the compounds were generally safe, exhibiting low cytotoxicity within a narrow range of 0.94-4.36 %, with 9b showing the least hemolytic effect (0.94 +/- 0.01 %). Molecular docking with the B. subtilis LuxS protein identified strong binding affinities, especially for 10a, achieving a binding score of-8.7 kcal/mol and forming interactions with key catalytic residues such as Glu57, His58, and Cys128. Compounds 11a (- 8.6 kcal/mol) and 5a/10b (each-8.3 kcal/mol) also demonstrated strong binding tendencies. Molecular dynamics simulations (200 ns) affirmed complex stability, particularly for 10a and 11a. ADMET predictions indicated high intestinal absorption and BBB permeability with acceptable safety profiles. Conclusion: These findings support the potential of these derivatives, especially 10a, as lead candidates for therapeutic development against oxidative stress-related and bacterial diseases.
Keywords:
Chalcones
Aurones
Antioxidant activities
Antibiofilm
Hemolytic
Docking
Simulation
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