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In our efforts to find new and selective thiazolidinone-based anti-<i>Candida</i> agents, we synthesized and tested 26 thiazolidinones against several <i>Candida</i> spp. and Gram-positive and Gram-negative bacteria. The compounds showed selective antifungal activity with potency similar to fluconazole and clotrimazole, while lacking strong antibacterial activity. Molecular docking and molecular dynamics studies were performed on <i>Candida</i> CYP51a1 and carbonic anhydrase (CA) enzymes to further suggest putative targets that could mediate the antifungal effects of these compounds. Finally, the compounds were tested in enzyme inhibition assays to assess their putative mechanism of action and showed promising <i>K</i>_I values in the 0.1–10 µM range against the <i>Candida glabrata</i> β-CA enzyme CgNce103.