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In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies
The series of fifteen synthesized 4-hydroxycoumarin derivatives was subjected to antioxidant activity evaluation in vitro, through total antioxidant capacity, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl radical, lipid peroxide scavenging and chelating activity. The highest activity was detected...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Molecular Diversity Preservation International (MDPI)
2011
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3116159/ https://www.ncbi.nlm.nih.gov/pubmed/21686153 http://dx.doi.org/10.3390/ijms12052822 |
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author | Mladenović, Milan Mihailović, Mirjana Bogojević, Desanka Matić, Sanja Nićiforović, Neda Mihailović, Vladimir Vuković, Nenad Sukdolak, Slobodan Solujić, Slavica |
author_facet | Mladenović, Milan Mihailović, Mirjana Bogojević, Desanka Matić, Sanja Nićiforović, Neda Mihailović, Vladimir Vuković, Nenad Sukdolak, Slobodan Solujić, Slavica |
author_sort | Mladenović, Milan |
collection | PubMed |
description | The series of fifteen synthesized 4-hydroxycoumarin derivatives was subjected to antioxidant activity evaluation in vitro, through total antioxidant capacity, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl radical, lipid peroxide scavenging and chelating activity. The highest activity was detected during the radicals scavenging, with 2b, 6b, 2c, and 4c noticed as the most active. The antioxidant activity was further quantified by the quantitative structure-activity relationships (QSAR) studies. For this purpose, the structures were optimized using Paramethric Method 6 (PM6) semi-empirical and Density Functional Theory (DFT) B3LYP methods. Bond dissociation enthalpies of coumarin 4-OH, Natural Bond Orbital (NBO) gained hybridization of the oxygen, acidity of the hydrogen atom and various molecular descriptors obtained, were correlated with biological activity, after which we designed 20 new antioxidant structures, using the most favorable structural motifs, with much improved predicted activity in vitro. |
format | Online Article Text |
id | pubmed-3116159 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | Molecular Diversity Preservation International (MDPI) |
record_format | MEDLINE/PubMed |
spelling | pubmed-31161592011-06-16 In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies Mladenović, Milan Mihailović, Mirjana Bogojević, Desanka Matić, Sanja Nićiforović, Neda Mihailović, Vladimir Vuković, Nenad Sukdolak, Slobodan Solujić, Slavica Int J Mol Sci Article The series of fifteen synthesized 4-hydroxycoumarin derivatives was subjected to antioxidant activity evaluation in vitro, through total antioxidant capacity, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl radical, lipid peroxide scavenging and chelating activity. The highest activity was detected during the radicals scavenging, with 2b, 6b, 2c, and 4c noticed as the most active. The antioxidant activity was further quantified by the quantitative structure-activity relationships (QSAR) studies. For this purpose, the structures were optimized using Paramethric Method 6 (PM6) semi-empirical and Density Functional Theory (DFT) B3LYP methods. Bond dissociation enthalpies of coumarin 4-OH, Natural Bond Orbital (NBO) gained hybridization of the oxygen, acidity of the hydrogen atom and various molecular descriptors obtained, were correlated with biological activity, after which we designed 20 new antioxidant structures, using the most favorable structural motifs, with much improved predicted activity in vitro. Molecular Diversity Preservation International (MDPI) 2011-04-29 /pmc/articles/PMC3116159/ /pubmed/21686153 http://dx.doi.org/10.3390/ijms12052822 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0 This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Mladenović, Milan Mihailović, Mirjana Bogojević, Desanka Matić, Sanja Nićiforović, Neda Mihailović, Vladimir Vuković, Nenad Sukdolak, Slobodan Solujić, Slavica In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies |
title | In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies |
title_full | In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies |
title_fullStr | In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies |
title_full_unstemmed | In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies |
title_short | In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies |
title_sort | in vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives—sar, qsar and dft studies |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3116159/ https://www.ncbi.nlm.nih.gov/pubmed/21686153 http://dx.doi.org/10.3390/ijms12052822 |
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