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Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action
Amides derived from ferulic acid have a wide spectrum of pharmacological activities, including antitumor and antifungal activity. In the present study, a series of ten amides were obtained by coupling reactions using the reagents (benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Hindawi
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8575619/ https://www.ncbi.nlm.nih.gov/pubmed/34761004 http://dx.doi.org/10.1155/2021/3598000 |
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author | de Morais, Mayara Castro Perez-Castillo, Yunierkis Silva, Valdenizia Rodrigues Santos, Luciano de Souza Soares, Milena Botelho Pereira Bezerra, Daniel Pereira de Castro, Ricardo Dias de Sousa, Damião Pergentino |
author_facet | de Morais, Mayara Castro Perez-Castillo, Yunierkis Silva, Valdenizia Rodrigues Santos, Luciano de Souza Soares, Milena Botelho Pereira Bezerra, Daniel Pereira de Castro, Ricardo Dias de Sousa, Damião Pergentino |
author_sort | de Morais, Mayara Castro |
collection | PubMed |
description | Amides derived from ferulic acid have a wide spectrum of pharmacological activities, including antitumor and antifungal activity. In the present study, a series of ten amides were obtained by coupling reactions using the reagents (benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (PyBOP) and N,N′-dicyclohexylcarbodiimide (DCC). All the compounds were identified on the basis of their IR, (1)H- and (13)C-NMR, HRMS data, and with yields ranging from 43.17% to 91.37%. The compounds were subjected to cytotoxic tests by the alamar blue technique and antifungal screening by the broth microdilution method to determine the minimum inhibitory concentration (MIC). The amides 10 and 11 displayed the best result in both biological evaluations, and compound 10 was the most potent and selective in HL-60 cancer cells, with no cytotoxicity on healthy cells. This amide had antifungal activity in all strains and had the lowest MIC against Candida albicans and Candida tropicalis. The possible mechanism of antifungal action occurs via the fungal cell wall. Molecular modeling suggested that compounds 10 and 11 interact with the enzymes GWT1 and GSC1, which are essential for the development of C. albicans. The findings of the present study demonstrated that compounds 10 and 11 may be used as a platform in drug development in the future. |
format | Online Article Text |
id | pubmed-8575619 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Hindawi |
record_format | MEDLINE/PubMed |
spelling | pubmed-85756192021-11-09 Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action de Morais, Mayara Castro Perez-Castillo, Yunierkis Silva, Valdenizia Rodrigues Santos, Luciano de Souza Soares, Milena Botelho Pereira Bezerra, Daniel Pereira de Castro, Ricardo Dias de Sousa, Damião Pergentino Biomed Res Int Research Article Amides derived from ferulic acid have a wide spectrum of pharmacological activities, including antitumor and antifungal activity. In the present study, a series of ten amides were obtained by coupling reactions using the reagents (benzotriazol-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate (PyBOP) and N,N′-dicyclohexylcarbodiimide (DCC). All the compounds were identified on the basis of their IR, (1)H- and (13)C-NMR, HRMS data, and with yields ranging from 43.17% to 91.37%. The compounds were subjected to cytotoxic tests by the alamar blue technique and antifungal screening by the broth microdilution method to determine the minimum inhibitory concentration (MIC). The amides 10 and 11 displayed the best result in both biological evaluations, and compound 10 was the most potent and selective in HL-60 cancer cells, with no cytotoxicity on healthy cells. This amide had antifungal activity in all strains and had the lowest MIC against Candida albicans and Candida tropicalis. The possible mechanism of antifungal action occurs via the fungal cell wall. Molecular modeling suggested that compounds 10 and 11 interact with the enzymes GWT1 and GSC1, which are essential for the development of C. albicans. The findings of the present study demonstrated that compounds 10 and 11 may be used as a platform in drug development in the future. Hindawi 2021-11-01 /pmc/articles/PMC8575619/ /pubmed/34761004 http://dx.doi.org/10.1155/2021/3598000 Text en Copyright © 2021 Mayara Castro de Morais et al. https://creativecommons.org/licenses/by/4.0/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. |
spellingShingle | Research Article de Morais, Mayara Castro Perez-Castillo, Yunierkis Silva, Valdenizia Rodrigues Santos, Luciano de Souza Soares, Milena Botelho Pereira Bezerra, Daniel Pereira de Castro, Ricardo Dias de Sousa, Damião Pergentino Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action |
title | Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action |
title_full | Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action |
title_fullStr | Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action |
title_full_unstemmed | Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action |
title_short | Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action |
title_sort | cytotoxic and antifungal amides derived from ferulic acid: molecular docking and mechanism of action |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8575619/ https://www.ncbi.nlm.nih.gov/pubmed/34761004 http://dx.doi.org/10.1155/2021/3598000 |
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