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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...

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Autores principales: Mladenović, Milan, Mihailović, Mirjana, Bogojević, Desanka, Matić, Sanja, Nićiforović, Neda, Mihailović, Vladimir, Vuković, Nenad, Sukdolak, Slobodan, Solujić, Slavica
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International (MDPI) 2011
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.
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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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