Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis
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 conducte...
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MDPI AG
2017-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/22/11/1532 |
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| author | Nadjet Rezki Salsabeel A. Al-Sodies Sheikh Shreaz Rayees Ahmad Shiekh Mouslim Messali Vaseem Raja Mohamed R. Aouad |
| author_facet | Nadjet Rezki Salsabeel A. Al-Sodies Sheikh Shreaz Rayees Ahmad Shiekh Mouslim Messali Vaseem Raja Mohamed R. Aouad |
| author_sort | Nadjet Rezki |
| collection | DOAJ |
| description | 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 2–25 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. |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-24T05:20:19Z |
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| spelling | doaj.art-d5da5d009d084dbf9365200b00e7e6582022-12-21T17:13:28ZengMDPI AGMolecules1420-30492017-11-012211153210.3390/molecules22111532molecules22111532Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol BiosynthesisNadjet Rezki0Salsabeel A. Al-Sodies1Sheikh Shreaz2Rayees Ahmad Shiekh3Mouslim Messali4Vaseem Raja5Mohamed R. Aouad6Department of Chemistry, Faculty of Sciences, Taibah University, P.O. Box 344, Al-Madinah Al-Munawarah 30002, Saudi ArabiaDepartment of Chemistry, Faculty of Sciences, Taibah University, P.O. Box 344, Al-Madinah Al-Munawarah 30002, Saudi ArabiaEnvironment and Life Sciences Research Center, Kuwait Institute for Scientific Research, P.O. Box 24885, Safat 13109, KuwaitDepartment of Chemistry, Faculty of Sciences, Taibah University, P.O. Box 344, Al-Madinah Al-Munawarah 30002, Saudi ArabiaDepartment of Chemistry, Faculty of Sciences, Taibah University, P.O. Box 344, Al-Madinah Al-Munawarah 30002, Saudi ArabiaDepartment of Applied Sciences & Humanities, Faculty of Engineering & Technology, Jamia Millia Islamia, Central University, New Delhi 110025, IndiaDepartment of Chemistry, Faculty of Sciences, Taibah University, P.O. Box 344, Al-Madinah Al-Munawarah 30002, Saudi ArabiaA 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 2–25 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.https://www.mdpi.com/1420-3049/22/11/1532ionic liquidshydrazonesfluorineultrasoundCandidafungal ergosterolconfocal microscopy |
| spellingShingle | Nadjet Rezki Salsabeel A. Al-Sodies Sheikh Shreaz Rayees Ahmad Shiekh Mouslim Messali Vaseem Raja Mohamed R. Aouad 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 ionic liquids hydrazones fluorine ultrasound Candida fungal ergosterol confocal microscopy |
| title | Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis |
| title_full | Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis |
| title_fullStr | Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis |
| title_full_unstemmed | Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis |
| title_short | Green Ultrasound versus Conventional Synthesis and Characterization of Specific Task Pyridinium Ionic Liquid Hydrazones Tethering Fluorinated Counter Anions: Novel Inhibitors of Fungal Ergosterol Biosynthesis |
| title_sort | green ultrasound versus conventional synthesis and characterization of specific task pyridinium ionic liquid hydrazones tethering fluorinated counter anions novel inhibitors of fungal ergosterol biosynthesis |
| topic | ionic liquids hydrazones fluorine ultrasound Candida fungal ergosterol confocal microscopy |
| url | https://www.mdpi.com/1420-3049/22/11/1532 |
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