Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action

Detalhes bibliográficos
Autor(a) principal: Morais, Mayara Castro de
Data de Publicação: 2021
Outros Autores: Castillo, Yunierkis Perez, Silva, Valdenizia Rodrigues, Santos, Luciano de Souza, Soares, Milena Botelho Pereira, Bezerra, Daniel Pereira, Castro, Ricardo Dias de, Sousa, Damião Pergentino de
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/50202
Resumo: Brazilian agencies: National Council for Scientific and Technological Development (CNPq) and Coordination for the Improvement of Higher Education Personnel (CAPES). The authors would like to thank the Multi-User Characterization and Analysis Laboratory (LMCA-UFPB), for the analysis of the nuclear magnetic resonance spectroscopic samples, and the Northeast Strategic Technologies Center (CETENE-UFPE) and the staff Julia Campos, for the high-resolution mass spectroscopic analyzes.
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spelling Morais, Mayara Castro deCastillo, Yunierkis PerezSilva, Valdenizia RodriguesSantos, Luciano de SouzaSoares, Milena Botelho PereiraBezerra, Daniel PereiraCastro, Ricardo Dias deSousa, Damião Pergentino de2021-12-07T14:25:27Z2021-12-07T14:25:27Z2021MORAIS, Mayara Castro de et al. Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action. BioMed Research International, 2021.2314-6133https://www.arca.fiocruz.br/handle/icict/5020210.1155/2021/3598000Brazilian agencies: National Council for Scientific and Technological Development (CNPq) and Coordination for the Improvement of Higher Education Personnel (CAPES). The authors would like to thank the Multi-User Characterization and Analysis Laboratory (LMCA-UFPB), for the analysis of the nuclear magnetic resonance spectroscopic samples, and the Northeast Strategic Technologies Center (CETENE-UFPE) and the staff Julia Campos, for the high-resolution mass spectroscopic analyzes.Federal University of Paraíba. Laboratory of Pharmaceutical Chemistry. Department of Pharmaceutical Sciences. João Pessoa, PB, Brazil.Universidad de Las Américas. Escuela de Ciencias Físicas y Matemáticas. Quito, Ecuador.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Federal University of Paraíba. Laboratory of Experimental Pharmacology and Cell Culture. Department of Clinical and Social Dentistry. Joao Pessoa, PB, Brazil.Federal University of Paraíba. Laboratory of Pharmaceutical Chemistry. Department of Pharmaceutial Sciences. João Pessoa, PB, Brazil.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.engHindawiAmidasNeoplasiasDicicloexilcarbodi-ImidaCélulasCandida tropicalisAmidesNeoplasmsDicyclohexylcarbodiimideCellsCandida tropicalisCytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Actioninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-83097https://www.arca.fiocruz.br/bitstream/icict/50202/1/license.txt36b51ef91c52b5338d9d29ba0cc807bcMD51ORIGINALMorais, Mayara Castro de Cytotoxic....pdfMorais, Mayara Castro de 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dc.title.pt_BR.fl_str_mv 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
spellingShingle Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action
Morais, Mayara Castro de
Amidas
Neoplasias
Dicicloexilcarbodi-Imida
Células
Candida tropicalis
Amides
Neoplasms
Dicyclohexylcarbodiimide
Cells
Candida tropicalis
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
author Morais, Mayara Castro de
author_facet Morais, Mayara Castro de
Castillo, Yunierkis Perez
Silva, Valdenizia Rodrigues
Santos, Luciano de Souza
Soares, Milena Botelho Pereira
Bezerra, Daniel Pereira
Castro, Ricardo Dias de
Sousa, Damião Pergentino de
author_role author
author2 Castillo, Yunierkis Perez
Silva, Valdenizia Rodrigues
Santos, Luciano de Souza
Soares, Milena Botelho Pereira
Bezerra, Daniel Pereira
Castro, Ricardo Dias de
Sousa, Damião Pergentino de
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Morais, Mayara Castro de
Castillo, Yunierkis Perez
Silva, Valdenizia Rodrigues
Santos, Luciano de Souza
Soares, Milena Botelho Pereira
Bezerra, Daniel Pereira
Castro, Ricardo Dias de
Sousa, Damião Pergentino de
dc.subject.other.pt_BR.fl_str_mv Amidas
Neoplasias
Dicicloexilcarbodi-Imida
Células
Candida tropicalis
topic Amidas
Neoplasias
Dicicloexilcarbodi-Imida
Células
Candida tropicalis
Amides
Neoplasms
Dicyclohexylcarbodiimide
Cells
Candida tropicalis
dc.subject.en.pt_BR.fl_str_mv Amides
Neoplasms
Dicyclohexylcarbodiimide
Cells
Candida tropicalis
description Brazilian agencies: National Council for Scientific and Technological Development (CNPq) and Coordination for the Improvement of Higher Education Personnel (CAPES). The authors would like to thank the Multi-User Characterization and Analysis Laboratory (LMCA-UFPB), for the analysis of the nuclear magnetic resonance spectroscopic samples, and the Northeast Strategic Technologies Center (CETENE-UFPE) and the staff Julia Campos, for the high-resolution mass spectroscopic analyzes.
publishDate 2021
dc.date.accessioned.fl_str_mv 2021-12-07T14:25:27Z
dc.date.available.fl_str_mv 2021-12-07T14:25:27Z
dc.date.issued.fl_str_mv 2021
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv MORAIS, Mayara Castro de et al. Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action. BioMed Research International, 2021.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/50202
dc.identifier.issn.pt_BR.fl_str_mv 2314-6133
dc.identifier.doi.none.fl_str_mv 10.1155/2021/3598000
identifier_str_mv MORAIS, Mayara Castro de et al. Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action. BioMed Research International, 2021.
2314-6133
10.1155/2021/3598000
url https://www.arca.fiocruz.br/handle/icict/50202
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Hindawi
publisher.none.fl_str_mv Hindawi
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
instname_str Fundação Oswaldo Cruz (FIOCRUZ)
instacron_str FIOCRUZ
institution FIOCRUZ
reponame_str Repositório Institucional da FIOCRUZ (ARCA)
collection Repositório Institucional da FIOCRUZ (ARCA)
bitstream.url.fl_str_mv https://www.arca.fiocruz.br/bitstream/icict/50202/1/license.txt
https://www.arca.fiocruz.br/bitstream/icict/50202/2/Morais%2c%20Mayara%20Castro%20de%20Cytotoxic....pdf
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repository.name.fl_str_mv Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)
repository.mail.fl_str_mv repositorio.arca@fiocruz.br
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