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Enhanced Antimicrobial Efficacy of Sulfones and Sulfonamides via Cage-Like Silsesquioxane Incorporation
Autorzy
Rok wydania
2025
Czasopismo
Numer woluminu
64
Strony
6460-6469
DOI
10.1021/acs.inorgchem.4c05156
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
This work introduces a novel class of hybrid antimicrobial agents by integrating sulfone and sulfonamide functionalities with polyhedral oligomeric silsesquioxanes (POSSs). By employing efficient synthetic protocols, we have successfully prepared both sulfone (ethylvinylsulfone-POSS and phenylethylsulfone-POSS) and sulfonamide (benzenesulfonamide-POSS, p-toluenesulfonamide-POSS, 3-fluorobenzenesulfonamide-POSS, and 2-naphthalenesulfonamide-POSS) derivatives with high yields (73–90%). All derivatives were examined using Fourier transform infrared spectroscopy, multinuclear (1H, 13C, 19F, and 29Si) NMR spectroscopy, MALDI-ToF MS spectrometry, and elemental analysis. Additionally, the crystal structure of the p-toluenesulfonamide-POSS hybrid was revealed. The unique cage-like POSS structure not only imparts enhanced thermal and chemical stability, a common feature of silsesquioxane-based hybrids, but also boosts the lipophilic character of these compounds, thereby facilitating their interaction with microbial membranes. This interaction, likely resulting in membrane disruption and cell lysis, translates into potent antimicrobial activity (against Escherichia coli, Pseudomonas aeruginosa, Enterococcus hirae, Staphylococcus aureus, and Candida albicans)─especially against Gram-positive bacteria─at remarkably low minimum inhibitory concentrations in the range from 125 to 3000 μM. In turn, E. hirae and S. aureus were more susceptible compared to Gram-negative bacteria and C. albicans. The strategic incorporation of POSSs into these sulfur-based moieties represents a significant breakthrough, opening new avenues for the development of advanced antimicrobial coatings and therapeutic agents in the fight against antibiotic resistance.
Słowa kluczowe
Anions, Antimicrobial agents, Bacteria, Reaction products, Sulfones
Licencja otwartego dostępu
Licencja na prawach której można swobodnie kopiować, rozprowadzać, zmieniać i remiksować objęty prawem autorskim utwór (Utwór-przedmiot prawa autorskiego) pod warunkiem podania imienia i nazwiska autora utworu pierwotnego oraz źródła pochodzenia utworu.
Pełny tekst licencji: https://creativecommons.org/licenses/by/3.0/pl/legalcode
Adres publiczny
http://dx.doi.org/10.1021/acs.inorgchem.4c05156
Strona internetowa wydawcy
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