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In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.

Mladenović M, Mihailović M, Bogojević D, Matić S, Nićiforović N, Mihailović V, Vuković N, Sukdolak S, Solujić S - Int J Mol Sci (2011)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Faculty of Science, P.O. Box 60, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia; E-Mails: nneda@kg.ac.rs (N.N.); vladam@kg.ac.rs (V.M.); nvukovic@kg.ac.rs (N.V.); duda@kg.ac.rs (S.S.); ssolujic@kg.ac.rs (S.S.).

ABSTRACT
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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Related in: MedlinePlus

Plot of observed vs. calculated biological values of the training set compounds obtained from (a) Equation (2); (b) Equation (3); (c) Equation (4); (d) Equation (5).
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f3-ijms-12-02822: Plot of observed vs. calculated biological values of the training set compounds obtained from (a) Equation (2); (b) Equation (3); (c) Equation (4); (d) Equation (5).

Mentions: QSAR studies were administrated to the antioxidant activity as a tool to describe and explain the activity of the tested coumarin derivatives. The results of the in vitro testing and the concentrations of the test compounds that reduce 50% of the initial free radical concentration were used for the QSAR study. Logarithmic values of the biological activity were used for the generation of the QSAR equations with relevant molecular descriptors (Figure 3). From the equations, we ascertained the possible mechanisms by which our coumarins occur as antioxidants.


In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.

Mladenović M, Mihailović M, Bogojević D, Matić S, Nićiforović N, Mihailović V, Vuković N, Sukdolak S, Solujić S - Int J Mol Sci (2011)

Plot of observed vs. calculated biological values of the training set compounds obtained from (a) Equation (2); (b) Equation (3); (c) Equation (4); (d) Equation (5).
© Copyright Policy - open-access
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC3116159&req=5

f3-ijms-12-02822: Plot of observed vs. calculated biological values of the training set compounds obtained from (a) Equation (2); (b) Equation (3); (c) Equation (4); (d) Equation (5).
Mentions: QSAR studies were administrated to the antioxidant activity as a tool to describe and explain the activity of the tested coumarin derivatives. The results of the in vitro testing and the concentrations of the test compounds that reduce 50% of the initial free radical concentration were used for the QSAR study. Logarithmic values of the biological activity were used for the generation of the QSAR equations with relevant molecular descriptors (Figure 3). From the equations, we ascertained the possible mechanisms by which our coumarins occur as antioxidants.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Faculty of Science, P.O. Box 60, University of Kragujevac, Radoja Domanovića 12, 34000 Kragujevac, Serbia; E-Mails: nneda@kg.ac.rs (N.N.); vladam@kg.ac.rs (V.M.); nvukovic@kg.ac.rs (N.V.); duda@kg.ac.rs (S.S.); ssolujic@kg.ac.rs (S.S.).

ABSTRACT
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.

Show MeSH
Related in: MedlinePlus