| Summary: | Resistance of bacteria to multiple antibiotics is a significant health problem; hence, to continually respond to this challenge, different antibacterial agents must be constantly discovered. In this work, fluoroaryl-2,2′-bichalcophene derivatives were chemically synthesized and their biological activities were evaluated against <i>Staphylococcus aureus</i> (<i>S. aureus</i>). The impact of the investigated bichalcophene derivatives was studied on the ultrastructural level via scanning electron microscopy (SEM), molecular level via sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) method and on the biofilm inhibition via the electrochemical biosensors. Arylbichalcophenes’ antibacterial activity against <i>S. aureus</i> was affected by the presence and location of fluorine atoms. The fluorobithiophene derivative <b>MA-1156</b> displayed the best minimum inhibitory concentration (MIC) value of 16 µM among the tested fluoroarylbichalcophenes. Over a period of seven days, <i>S. aureus</i> did not develop any resistance against the tested fluoroarylbichalcophenes at higher concentrations. The impact of fluoroarylbichalcophenes was strong on <i>S. aureus</i> protein pattern showing high degrees of polymorphism. SEM micrographs of <i>S. aureus</i> cells treated with fluoroarylbichalcophenes displayed smaller cell-sizes, fewer numbers, arranged in a linear form and some of them were damaged when compared to the untreated cells. The bioelectrochemical measurements demonstrated the strong sensitivity of <i>S. aureus</i> cells to the tested fluoroarylbichalcophenes and an antibiofilm agent. Eventually, these fluoroarylbichalcophene compounds especially the <b>MA-1156</b> could be recommended as effective antibacterial agents.
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