The Influence of Biodegradable Gemini Surfactants, N,N’-bis(1-Decyloxy-1-Oxopronan-2-yl)-N,N,N’,N’ Tetramethylpropane-1,3-Diammonium Dibromide and N,N’-bis(1-Dodecyloxy-1-Oxopronan-2-yl) N,N,N’,N’-Tetramethylethane-1,2-Diammonium Dibromide, on Fungal Biofilm and Adhesion

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  • Obłąk Ewa
    Institute of Genetics and Microbiology, University of Wroclaw
  • Piecuch Agata
    Institute of Genetics and Microbiology, University of Wroclaw
  • Dworniczek Ewa
    Department of Microbiology, Wroclaw Medical University
  • Olejniczak Teresa
    The Faculty of Food Science, Department of Chemistry, Wrocław University of Environmental and Life Sciences

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A group of biodegradable alanine-derived gemini quaternary ammonium salts (bromides and chlorides) with various alkyl chains and spacer lengths was tested for anti-adhesive and anti-biofilm activity. The strongest antifungal activity was exhibited by bromides with 10 and 12 carbon atoms within hydrophobic chains (N,N’-bis(1-decyloxy-1-oxopronan-2-yl)-N,N,N’,N’-tetramethylpropane-1,3-diammonium dibromide and N,N’-bis(1-dodecyloxy-1-oxopronan-2-yl)-N,N,N’,N’-tetramethylethane-1,2-diammonium dibromide). It was also demonstrated that these gemini surfactants enhanced the sensitivity of Candida albicans to azoles (itraconazole and fluconazole) and polyenes (amphotericin B and nystatine). Gemini quaternary ammonium salts effectively inhibited fungal cell adhesion to polystyrene and silicone surface. These compounds reduced C. albicans filamentation and eradicated C. albicans and Rhodotorula mucilaginosa biofilms, as it was shown in crystal violet and fluorescent staining. None of the tested compounds were cytotoxic against yeast mitochondrial metabolism.

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