Boronic Acid-substituted Benzimidazole Derivatives and Their Supramolecular Hybrid System Formed with Glutathione-functionalized Graphene Quantum Dots: Synthesis, Antimicrobial Activities and Molecular Docking Calculations

This study presents novel functional molecules containing benzimidazole units, which are known to have biological properties, as well as phenylboronic acid units attached to the benzimidazole core. These structures were prepared for the first time and conjugated to glutathione-functionalized graphene quantum dots (G-GQDs) to form supramolecular hybrids through π-π stacking. The newly developed compounds showed varying degrees of antimicrobial activity against a panel of human pathogens: Escherichia coli, Staphylococcus aureus, Candida albicans, and Aspergillus brasiliensis. The G-GQD-functionalized derivatives were more efficient in inhibiting microbial growth, particularly against antibiotic-resistant Staphylococcus. This study introduces a new direction in antimicrobial research for G-GQD-functionalized benzimidazole derivatives as effective alternatives to conventional antibiotics. Molecular docking calculations revealed a strong correlation between antimicrobial activity and the high binding affinity of the phenylboronic acid-substituted benzimidazole derivatives to specific protein targets (5M18, 2QZX, 4LE8, 2H6T, and 2Q85). The analysis emphasized the impact of substituent positioning on enzyme inhibition, illustrating how structural modifications influenced inhibitory activity. Integrating experimental and computational findings, our study highlights key structure-activity relationships in benzimidazole derivatives and identifies promising candidates for further studies on enzyme inhibition and antimicrobial research. (Figure presented.)