Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity
Isougenol is a phytoconstituent found in several essential oils. Since many natural products are potent antimicrobials, the synthesis of hybrid molecules—combining the chemical skeleton of the phytochemical with synthetic groups—can generate substances with enhanced biological activity. Based on thi...
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MDPI AG
2020-10-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/13/10/291 |
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| author | Daianne Medeiros José Oliveira-Júnior Jefferson Nóbrega Laísa Cordeiro Jeane Jardim Helivaldo Souza Gracielle Silva Petrônio Athayde-Filho José Barbosa-Filho Luciana Scotti Edeltrudes Lima |
| author_facet | Daianne Medeiros José Oliveira-Júnior Jefferson Nóbrega Laísa Cordeiro Jeane Jardim Helivaldo Souza Gracielle Silva Petrônio Athayde-Filho José Barbosa-Filho Luciana Scotti Edeltrudes Lima |
| author_sort | Daianne Medeiros |
| collection | DOAJ |
| description | Isougenol is a phytoconstituent found in several essential oils. Since many natural products are potent antimicrobials, the synthesis of hybrid molecules—combining the chemical skeleton of the phytochemical with synthetic groups—can generate substances with enhanced biological activity. Based on this, the objective of this study was to evaluate the antifungal activity of isoeugenol and hybrid acetamides against <i>Candida albicans</i> isolated from the oral cavity. The methodologies used were the determination of minimum inhibitory concentration (MIC), minimum fungicidal concentration (MFC), action on fungal micromorphology, interaction test with nystatin by the checkerboard method and molecular docking study with important enzymes in the maintenance of fungal viability. The synthetic molecules did not demonstrate significant antifungal activity in vitro. The isoeugenol MIC and MFC varied between 128 and 256 µg/mL, being the phytoconstituent able to interfere in the formation of blastoconid and chlamydoconid structures, important in the pathogenic process of the species. The molecular docking study revealed that isoeugenol is a potential inhibitor of the enzymes 14-α-demethylase and delta-14-sterol reductase, interfering in the fungal cell membrane biosynthesis. Thus, this research provides clearer expectations for future pharmacological studies with isoeugenol and derived molecules, aiming at its therapeutic application against infections caused by <i>Candida</i> spp. |
| first_indexed | 2024-03-10T15:50:58Z |
| format | Article |
| id | doaj.art-b4bb064f4b3649d3a01654bf0d87027d |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-10T15:50:58Z |
| publishDate | 2020-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-b4bb064f4b3649d3a01654bf0d87027d2023-11-20T16:01:58ZengMDPI AGPharmaceuticals1424-82472020-10-01131029110.3390/ph13100291Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral CavityDaianne Medeiros0José Oliveira-Júnior1Jefferson Nóbrega2Laísa Cordeiro3Jeane Jardim4Helivaldo Souza5Gracielle Silva6Petrônio Athayde-Filho7José Barbosa-Filho8Luciana Scotti9Edeltrudes Lima10Department of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilDepartment of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilDepartment of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilDepartment of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilChemistry Department, Exact and Natural Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, BrazilChemistry Department, Exact and Natural Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, BrazilChemistry Department, Exact and Natural Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, BrazilChemistry Department, Exact and Natural Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, BrazilDepartment of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilDepartment of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilDepartment of Pharmaceutical Science, Health Sciences Center, Federal University of Paraíba, 58033-455 João Pessoa, Paraíba, BrazilIsougenol is a phytoconstituent found in several essential oils. Since many natural products are potent antimicrobials, the synthesis of hybrid molecules—combining the chemical skeleton of the phytochemical with synthetic groups—can generate substances with enhanced biological activity. Based on this, the objective of this study was to evaluate the antifungal activity of isoeugenol and hybrid acetamides against <i>Candida albicans</i> isolated from the oral cavity. The methodologies used were the determination of minimum inhibitory concentration (MIC), minimum fungicidal concentration (MFC), action on fungal micromorphology, interaction test with nystatin by the checkerboard method and molecular docking study with important enzymes in the maintenance of fungal viability. The synthetic molecules did not demonstrate significant antifungal activity in vitro. The isoeugenol MIC and MFC varied between 128 and 256 µg/mL, being the phytoconstituent able to interfere in the formation of blastoconid and chlamydoconid structures, important in the pathogenic process of the species. The molecular docking study revealed that isoeugenol is a potential inhibitor of the enzymes 14-α-demethylase and delta-14-sterol reductase, interfering in the fungal cell membrane biosynthesis. Thus, this research provides clearer expectations for future pharmacological studies with isoeugenol and derived molecules, aiming at its therapeutic application against infections caused by <i>Candida</i> spp.https://www.mdpi.com/1424-8247/13/10/291<i>Candida albicans</i>isoeugenolcheckerboard methodmolecular dockingantifungal activityoral candidiasis |
| spellingShingle | Daianne Medeiros José Oliveira-Júnior Jefferson Nóbrega Laísa Cordeiro Jeane Jardim Helivaldo Souza Gracielle Silva Petrônio Athayde-Filho José Barbosa-Filho Luciana Scotti Edeltrudes Lima Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity Pharmaceuticals <i>Candida albicans</i> isoeugenol checkerboard method molecular docking antifungal activity oral candidiasis |
| title | Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity |
| title_full | Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity |
| title_fullStr | Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity |
| title_full_unstemmed | Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity |
| title_short | Isoeugenol and Hybrid Acetamides against <i>Candida albicans</i> Isolated from the Oral Cavity |
| title_sort | isoeugenol and hybrid acetamides against i candida albicans i isolated from the oral cavity |
| topic | <i>Candida albicans</i> isoeugenol checkerboard method molecular docking antifungal activity oral candidiasis |
| url | https://www.mdpi.com/1424-8247/13/10/291 |
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