The synthesis, antifungal and apoptotic effects of triazole-oxadiazoles against Candida species

KAYA ÇAVUŞOĞLU B., Yurtta L., CANTÜRK Z.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol.144, pp.255-261, 2018 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 144
  • Publication Date: 2018
  • Doi Number: 10.1016/j.ejmech.2017.12.020
  • Journal Name: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.255-261
  • Keywords: Triazole, Oxadiazole, Anticandidal, Apoptosis, Cytotoxicity, 1,3,4-OXADIAZOLE ANALOGS, ANTIMICROBIAL ACTIVITY, BIOLOGICAL-ACTIVITY, ANTITUMOR-ACTIVITY, AMPHOTERICIN-B, CELL-DEATH, AGENTS, YEAST, DERIVATIVES, ALBICANS
  • Anadolu University Affiliated: Yes

Abstract

In search of potent and safe antifungal agents, herein, we report the synthesis, characterization and biological activities of triazole-oxadiazole compounds. The structural verification of the molecules was carried out by H-1 NMR, C-13 NMR and mass spectral data. The in vitro antifungal and apoptotic activity were investigated against C. albicans, C. parapsilosis, C. krusei and C. glabrata. The compounds namely N-(4-nitrophenyl)-2-[(5-(2-((4-methyl-4H-1,2,4-triazol-3-yl)thio)ethyl)-1,3,4-oxadiazol-2-yl)thio]acetamide (4e) and N-(6-fluorobenzothiazol-2-yl)-2-[(5-(2-((4-methyl-4H-1,2,4-triazol-3-yl)thio)ethyl)-1,3,4-oxadiazol-2-yl)thio]acetamide (4i) were detected as the most potent compounds against C. albicans and C. glabrata (MIC90 = 62.5 mu g/mL). According to studies on their mechanism of action, it was confirmed that compound 4i has apoptotic effect on four Candida via Annexin V-PI with flow cytometry. The MTT assay revealed that all compounds were determined to be non-toxic against healthy cells in the tested concentrations. (C) 2017 Elsevier Masson SAS. All rights reserved.