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Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones
Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151560/ https://www.ncbi.nlm.nih.gov/pubmed/28994740 http://dx.doi.org/10.3390/molecules22101685 |
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author | Polaquini, Carlos R. Torrezan, Guilherme S. Santos, Vanessa R. Nazaré, Ana C. Campos, Débora L. Almeida, Laíza A. Silva, Isabel C. Ferreira, Henrique Pavan, Fernando R. Duque, Cristiane Regasini, Luis O. |
author_facet | Polaquini, Carlos R. Torrezan, Guilherme S. Santos, Vanessa R. Nazaré, Ana C. Campos, Débora L. Almeida, Laíza A. Silva, Isabel C. Ferreira, Henrique Pavan, Fernando R. Duque, Cristiane Regasini, Luis O. |
author_sort | Polaquini, Carlos R. |
collection | PubMed |
description | Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal concentration) values of 77.9 to 312 µM against Staphylococcus aureus, Streptococcus mutans, and Streptococcus sanguinis. Compounds 2, 7, 10, and 18 presented potent effects against Mycobacterium tuberculosis (57.2 µM ≤ MIC ≤ 70.9 µM). Hydrophilic effects caused by substituents on ring B increased antibacterial activity against Gram-positive species. Thus, log P(o/w) were calculated by using high-performance liquid chromatography-photodiode array detection (HPLC-PDA) analyses, and cinnamylideneacetophenones presented values ranging from 2.5 to 4.1. In addition, the effects of 3 and 4 were evaluated on pulmonary cells, indicating their moderate toxicity (46.3 µM ≤ IC(50) ≤ 96.7 µM) when compared with doxorubicin. Bioactive compounds were subjected to in silico prediction of pharmacokinetic properties, and did not violate Lipinski’s and Veber’s rules, corroborating their potential bioavailability by an oral route. |
format | Online Article Text |
id | pubmed-6151560 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-61515602018-11-13 Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones Polaquini, Carlos R. Torrezan, Guilherme S. Santos, Vanessa R. Nazaré, Ana C. Campos, Débora L. Almeida, Laíza A. Silva, Isabel C. Ferreira, Henrique Pavan, Fernando R. Duque, Cristiane Regasini, Luis O. Molecules Article Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory concentration) and MBC (minimum bactericidal concentration) values of 77.9 to 312 µM against Staphylococcus aureus, Streptococcus mutans, and Streptococcus sanguinis. Compounds 2, 7, 10, and 18 presented potent effects against Mycobacterium tuberculosis (57.2 µM ≤ MIC ≤ 70.9 µM). Hydrophilic effects caused by substituents on ring B increased antibacterial activity against Gram-positive species. Thus, log P(o/w) were calculated by using high-performance liquid chromatography-photodiode array detection (HPLC-PDA) analyses, and cinnamylideneacetophenones presented values ranging from 2.5 to 4.1. In addition, the effects of 3 and 4 were evaluated on pulmonary cells, indicating their moderate toxicity (46.3 µM ≤ IC(50) ≤ 96.7 µM) when compared with doxorubicin. Bioactive compounds were subjected to in silico prediction of pharmacokinetic properties, and did not violate Lipinski’s and Veber’s rules, corroborating their potential bioavailability by an oral route. MDPI 2017-10-10 /pmc/articles/PMC6151560/ /pubmed/28994740 http://dx.doi.org/10.3390/molecules22101685 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Polaquini, Carlos R. Torrezan, Guilherme S. Santos, Vanessa R. Nazaré, Ana C. Campos, Débora L. Almeida, Laíza A. Silva, Isabel C. Ferreira, Henrique Pavan, Fernando R. Duque, Cristiane Regasini, Luis O. Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones |
title | Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones |
title_full | Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones |
title_fullStr | Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones |
title_full_unstemmed | Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones |
title_short | Antibacterial and Antitubercular Activities of Cinnamylideneacetophenones |
title_sort | antibacterial and antitubercular activities of cinnamylideneacetophenones |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6151560/ https://www.ncbi.nlm.nih.gov/pubmed/28994740 http://dx.doi.org/10.3390/molecules22101685 |
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