Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives
The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution...
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doaj-9d59b99d475a4156b84c651aef05b0b02020-11-25T00:02:56ZengHindawi LimitedJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/34083153408315Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid DerivativesMarianna O. Araújo0Hilzeth L. Freire Pessoa1Andressa B. Lira2Yunierkis P. Castillo3Damião P. de Sousa4Postgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraíba, João Pessoa, PB, BrazilDepartment of Molecular Biology, Federal University of Paraíba, João Pessoa, PB, BrazilPostgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraíba, João Pessoa, PB, BrazilEscuela de Ciencias Físicas y Matemáticas, Universidad de Las Américas, Quito, EcuadorPostgraduate Program in Natural and Synthetic Bioactive Products, Federal University of Paraíba, João Pessoa, PB, BrazilThe present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed that five of the compounds present strong to optimum antibacterial effect. Of the sixteen ester derivatives evaluated, the products with alkyl side chains, as propyl caffeate (3), butyl caffeate (6), and pentyl caffeate (7), presented the best antibacterial activity with MIC values of around 0.20 μM against Escherichia coli and only butyl caffeate (6) showing the same MIC against Staphylococcus aureus. For products with aryl substituents, the best MIC results against the tested strain of Escherichia coli were 0.23 µM for (di-(4-chlorobenzyl)) caffeate (13) and 0.29 µM for diphenylmethyl caffeate (10) and all were less active against the Staphylococcus aureus strain. Preliminary quantitative structure-activity relationship (QSAR) analyses confirmed that certain structural characteristics, such as a median linear carbon chain and the presence of electron withdrawal substituents at the para position of the aromatic ring, help potentiate antibacterial activity.http://dx.doi.org/10.1155/2019/3408315 |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Marianna O. Araújo Hilzeth L. Freire Pessoa Andressa B. Lira Yunierkis P. Castillo Damião P. de Sousa |
spellingShingle |
Marianna O. Araújo Hilzeth L. Freire Pessoa Andressa B. Lira Yunierkis P. Castillo Damião P. de Sousa Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives Journal of Chemistry |
author_facet |
Marianna O. Araújo Hilzeth L. Freire Pessoa Andressa B. Lira Yunierkis P. Castillo Damião P. de Sousa |
author_sort |
Marianna O. Araújo |
title |
Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives |
title_short |
Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives |
title_full |
Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives |
title_fullStr |
Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives |
title_full_unstemmed |
Synthesis, Antibacterial Evaluation, and QSAR of Caffeic Acid Derivatives |
title_sort |
synthesis, antibacterial evaluation, and qsar of caffeic acid derivatives |
publisher |
Hindawi Limited |
series |
Journal of Chemistry |
issn |
2090-9063 2090-9071 |
publishDate |
2019-01-01 |
description |
The present study evaluates the antibacterial effects of a set of 16 synthesized caffeic acid ester derivatives against strains of Staphylococcus aureus and Escherichia coli, as well as discusses their structure-activity relationship (SAR). The antibacterial assays were performed using microdilution techniques in 96-well microplates to determine minimal inhibitory concentration (MIC). The results revealed that five of the compounds present strong to optimum antibacterial effect. Of the sixteen ester derivatives evaluated, the products with alkyl side chains, as propyl caffeate (3), butyl caffeate (6), and pentyl caffeate (7), presented the best antibacterial activity with MIC values of around 0.20 μM against Escherichia coli and only butyl caffeate (6) showing the same MIC against Staphylococcus aureus. For products with aryl substituents, the best MIC results against the tested strain of Escherichia coli were 0.23 µM for (di-(4-chlorobenzyl)) caffeate (13) and 0.29 µM for diphenylmethyl caffeate (10) and all were less active against the Staphylococcus aureus strain. Preliminary quantitative structure-activity relationship (QSAR) analyses confirmed that certain structural characteristics, such as a median linear carbon chain and the presence of electron withdrawal substituents at the para position of the aromatic ring, help potentiate antibacterial activity. |
url |
http://dx.doi.org/10.1155/2019/3408315 |
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