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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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(a) DPPH radical scavenging activity in the 60th minute; and (b) determination of hydroxyl radical scavenging activity, in vitro.
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f1-ijms-12-02822: (a) DPPH radical scavenging activity in the 60th minute; and (b) determination of hydroxyl radical scavenging activity, in vitro.

Mentions: Within the second test participants, 2–10c, the strong hydrogen donor ability has distinguished the 4c as the most powerful DPPH radical scavenger, regarding both test periods (IC50 values of 4.72 μg/mL and 3.54 μg/mL). The activity decreased in the raw 4c > 2c > 9c > 3c > 5c (Figure 1, a). The N-thiazole motif linked with favorable p-SO3H group (4c) as well as the presence of the additional OH group (2c, IC50 equal to 4.9 μg/mL and 6.97 μg/mL) increased the antiradical activity. The high 30 min activity of the 2c was not a surprise due to more look-a-like phenolic structure of the compound, related to increased number of the hydroxyl groups. The m-NO2 N-thiazole derivative (9c), reached full scavenging potential after 60 minutes test (IC50 = 4.79 μg/mL) thus overpowering the decreasing activity of 2c in the same period. Despite the favorable structure, 2c was the only compound that presented weaker potential after 60 min testing. The thiazole derivatives containing only N-tolyl (5c and 8c), N,N-diethyl (7c) and N-naphtyl residues, presented a total lack of activity.


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)

(a) DPPH radical scavenging activity in the 60th minute; and (b) determination of hydroxyl radical scavenging activity, in vitro.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

f1-ijms-12-02822: (a) DPPH radical scavenging activity in the 60th minute; and (b) determination of hydroxyl radical scavenging activity, in vitro.
Mentions: Within the second test participants, 2–10c, the strong hydrogen donor ability has distinguished the 4c as the most powerful DPPH radical scavenger, regarding both test periods (IC50 values of 4.72 μg/mL and 3.54 μg/mL). The activity decreased in the raw 4c > 2c > 9c > 3c > 5c (Figure 1, a). The N-thiazole motif linked with favorable p-SO3H group (4c) as well as the presence of the additional OH group (2c, IC50 equal to 4.9 μg/mL and 6.97 μg/mL) increased the antiradical activity. The high 30 min activity of the 2c was not a surprise due to more look-a-like phenolic structure of the compound, related to increased number of the hydroxyl groups. The m-NO2 N-thiazole derivative (9c), reached full scavenging potential after 60 minutes test (IC50 = 4.79 μg/mL) thus overpowering the decreasing activity of 2c in the same period. Despite the favorable structure, 2c was the only compound that presented weaker potential after 60 min testing. The thiazole derivatives containing only N-tolyl (5c and 8c), N,N-diethyl (7c) and N-naphtyl residues, presented a total lack of activity.

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