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 (...

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Autores principales:	Mayara Castro de Morais, Yunierkis Perez-Castillo, Valdenizia Rodrigues Silva, Luciano de Souza Santos, Milena Botelho Pereira Soares, Daniel Pereira Bezerra, Ricardo Dias de Castro, Damião Pergentino de Sousa
Formato:	article
Lenguaje:	EN
Publicado:	Hindawi Limited 2021
Materias:	Medicine R
Acceso en línea:	https://doaj.org/article/cd2490ad924146c698479f151f21c282
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spelling	oai:doaj.org-article:cd2490ad924146c698479f151f21c2822021-11-15T01:18:57ZCytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action2314-614110.1155/2021/3598000https://doaj.org/article/cd2490ad924146c698479f151f21c2822021-01-01T00:00:00Zhttp://dx.doi.org/10.1155/2021/3598000https://doaj.org/toc/2314-6141Amides 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, 1H- and 13C-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.Mayara Castro de MoraisYunierkis Perez-CastilloValdenizia Rodrigues SilvaLuciano de Souza SantosMilena Botelho Pereira SoaresDaniel Pereira BezerraRicardo Dias de CastroDamião Pergentino de SousaHindawi LimitedarticleMedicineRENBioMed Research International, Vol 2021 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R
spellingShingle	Medicine R Mayara Castro de Morais Yunierkis Perez-Castillo Valdenizia Rodrigues Silva Luciano de Souza Santos Milena Botelho Pereira Soares Daniel Pereira Bezerra Ricardo Dias de Castro Damião Pergentino de Sousa Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action
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, 1H- and 13C-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	article
author	Mayara Castro de Morais Yunierkis Perez-Castillo Valdenizia Rodrigues Silva Luciano de Souza Santos Milena Botelho Pereira Soares Daniel Pereira Bezerra Ricardo Dias de Castro Damião Pergentino de Sousa
author_facet	Mayara Castro de Morais Yunierkis Perez-Castillo Valdenizia Rodrigues Silva Luciano de Souza Santos Milena Botelho Pereira Soares Daniel Pereira Bezerra Ricardo Dias de Castro Damião Pergentino de Sousa
author_sort	Mayara Castro de Morais
title	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_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_sort	cytotoxic and antifungal amides derived from ferulic acid: molecular docking and mechanism of action
publisher	Hindawi Limited
publishDate	2021
url	https://doaj.org/article/cd2490ad924146c698479f151f21c282
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Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action

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