In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies.
2011
Authors:
Mladenović, MilanMihailović, Mirjana
Bogojević, Desanka
Matić, Sanja
Nićiforović, Neda
Mihailović, Vladimir
Vuković, Nenad
Sukdolak, Slobodan
Solujić, Slavica
Document Type:
Article (Published version)
Metadata
Show full item recordAbstract:
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.
Keywords:
4-hydroxycoumarins; Antioxidant activity in vitro; BDEs; DFT; Design; QSARSource:
International Journal of Molecular Sciences, 2011, 12, 5, 2822-2841Funding / projects:
- Preclinical investigation of bioactive substances (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-41010)
- Simultaneous Bioremediation and Soilification of Degraded Areas to Preserve Natural Resources of Biologically Active Substances, and Development and Production of Biomaterials and Dietetic Products (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-43004)
- Signaling molecules in diabetes: search for potential targets in intrinsic pathways for prediction and intervention in diabetes (RS-MESTD-Basic Research (BR or ON)-173020)
DOI: 10.3390/ijms12052822
ISSN: 1422-0067
PubMed: 21686153
WoS: 000290951800005
Scopus: 2-s2.0-79957795403
URI
http://www.scopus.com/inward/record.url?eid=2-s2.0-79957795403&partnerID=tZOtx3y1https://radar.ibiss.bg.ac.rs/handle/123456789/3207