Author | Morais, Mayara Castro de | |
Author | Castillo, Yunierkis Perez | |
Author | Silva, Valdenizia Rodrigues | |
Author | Santos, Luciano de Souza | |
Author | Soares, Milena Botelho Pereira | |
Author | Bezerra, Daniel Pereira | |
Author | Castro, Ricardo Dias de | |
Author | Sousa, Damião Pergentino de | |
Access date | 2021-12-07T14:25:27Z | |
Available date | 2021-12-07T14:25:27Z | |
Document date | 2021 | |
Citation | MORAIS, Mayara Castro de et al. Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action. BioMed Research International, 2021. | pt_BR |
ISSN | 2314-6133 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/50202 | |
Sponsorship | 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. | pt_BR |
Language | eng | pt_BR |
Publisher | Hindawi | pt_BR |
Rights | open access | pt_BR |
Subject in Portuguese | Amidas | pt_BR |
Subject in Portuguese | Neoplasias | pt_BR |
Subject in Portuguese | Dicicloexilcarbodi-Imida | pt_BR |
Subject in Portuguese | Células | pt_BR |
Subject in Portuguese | Candida tropicalis | pt_BR |
Title | Cytotoxic and Antifungal Amides Derived from Ferulic Acid: Molecular Docking and Mechanism of Action | pt_BR |
Type | Article | pt_BR |
DOI | 10.1155/2021/3598000 | |
Abstract | 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. | pt_BR |
Affilliation | Federal University of Paraíba. Laboratory of Pharmaceutical Chemistry. Department of Pharmaceutical Sciences. João Pessoa, PB, Brazil. | pt_BR |
Affilliation | Universidad de Las Américas. Escuela de Ciencias Físicas y Matemáticas. Quito, Ecuador. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil. | pt_BR |
Affilliation | Federal University of Paraíba. Laboratory of Experimental Pharmacology and Cell Culture. Department of Clinical and Social Dentistry. Joao Pessoa, PB, Brazil. | pt_BR |
Affilliation | Federal University of Paraíba. Laboratory of Pharmaceutical Chemistry. Department of Pharmaceutial Sciences. João Pessoa, PB, Brazil. | pt_BR |
Subject | Amides | pt_BR |
Subject | Neoplasms | pt_BR |
Subject | Dicyclohexylcarbodiimide | pt_BR |
Subject | Cells | pt_BR |
Subject | Candida tropicalis | pt_BR |