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Molecules 2017, 22(11), 1532; doi:10.3390/molecules22111532

Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis

1
Department of Chemistry, Faculty of Sciences, Taibah University, P.O. Box 344, Al-Madinah Al-Munawarah 30002, Saudi Arabia
2
Laboratoire de Chimie et Electrochimie des Complexes Métalliques (LCECM) USTO-MB, Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, P.O. Box 1505, El M`nouar, Oran 31000, Algeria
3
Environment and Life Sciences Research Center, Kuwait Institute for Scientific Research, P.O. Box 24885, Safat 13109, Kuwait
4
Government Degree College Pulwama, University of Kashmir, Srinagar 192301, India
5
Department of Applied Sciences & Humanities, Faculty of Engineering & Technology, Jamia Millia Islamia, Central University, New Delhi 110025, India
*
Authors to whom correspondence should be addressed.
Received: 27 September 2017 / Accepted: 3 November 2017 / Published: 7 November 2017
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Abstract

A series of specific task ionic liquids (ILs) based on a pyridiniumhydrazone scaffold in combination with hexafluorophosphate (PF6), tetrafluoroboron (BF4) and/or trifluoroacetate (CF3COO) counter anion, were designed and characterized by IR, NMR and mass spectrometry. The reactions were conducted under both conventional and green ultrasound procedures. The antifungal potential of the synthesized compounds 225 was investigated against 40 strains of Candida (four standard and 36 clinical isolates). Minimum inhibitory concentrations (MIC90) of the synthesized compounds were in the range of 62.5–2000 μg/mL for both standard and oral Candida isolates. MIC90 results showed that the synthesized 1-(2-(4-chlorophenyl)-2-oxoethyl)-4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-pyridin-1-ium hexafluorophosphate (11) was found to be most effective, followed by 4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)-1-(2-(4-nitrophenyl)-2-oxoethyl)-pyridin-1-ium hexafluorophosphate (14) and 1-(2-ethoxy-2-oxoethyl)-4-(2-(4-fluorobenzylidene)hydrazinecarbonyl)pyridin-1-ium hexafluorophosphate (8). All the Candida isolates showed marked sensitivity towards the synthesized compounds. Ergosterol content was drastically reduced by more active synthesized compounds, and agreed well with MIC90 values. Confocal scanning laser microscopy (CLSM) results showed that the red colored fluorescent dye enters the test agent treated cells, which confirms cell wall and cell membrane damage. The microscopy results obtained suggested membrane-located targets for the action of these synthesized compounds. It appears that the test compounds might be interacting with ergosterol in the fungal cell membranes, decreasing the membrane ergosterol content and ultimately leading to membrane disruption as visible in confocal results. The present study indicates that these synthesized compounds show significant antifungal activity against Candida which forms the basis to carry out further in vivo experiments before their clinical use. View Full-Text
Keywords: ionic liquids; hydrazones; fluorine; ultrasound; Candida; fungal ergosterol; confocal microscopy ionic liquids; hydrazones; fluorine; ultrasound; Candida; fungal ergosterol; confocal microscopy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Rezki, N.; Al-Sodies, S.A.; Shreaz, S.; Shiekh, R.A.; Messali, M.; Raja, V.; Aouad, M.R. Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis. Molecules 2017, 22, 1532.

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