In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.
2011
Autori:
Mladenović, MilanMihailović, Mirjana
Bogojević, Desanka
Matić, Sanja
Nićiforović, Neda
Mihailović, Vladimir
Vuković, Nenad
Sukdolak, Slobodan
Solujić, Slavica
Tip dokumenta:
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt:
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.
Ključne reči:
4-hydroxycoumarins; Antioxidant activity in vitro; BDEs; DFT; Design; QSARIzvor:
International Journal of Molecular Sciences, 2011, 12, 5, 2822-2841Finansiranje / projekti:
- Preklinička ispitivanja bioaktivnih supstanci (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41010)
- Simultana bioremedijacija i soilifikacija degradiranih prostora, za očuvanje prirodnih resursa biološki aktivnih supstanci i razvoj i proizvodnju biomaterijala i dijetetskih proizvoda (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-43004)
- Signalni molekuli u dijabetesu: identifikacija potencijalnih bioloških markera uključenih u modifikaciju i integraciju signalnih puteva u cilju predikcije i intervencije u dijabetesu (RS-MESTD-Basic Research (BR or ON)-173020)
DOI: 10.3390/ijms12052822
ISSN: 1422-0067
PubMed: 21686153