TY  - JOUR
AU  - Veselinović, Jovana
AU  - Veselinović, Aleksandar M.
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Nikolić, Goran M.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1586
AB  - A study on the structure-activity relationship of three hydroxy 4-phenyl coumarins, carried out by employing a series of different chemical cell-free tests is presented. Different assays involving one redox reaction with the oxidant (DPPH, ABTS, FRAP and CUPRAC) were employed. Further, the measurement of inhibition of oxidative degradation, such as lipid peroxidation, was used to define compound antioxidant activity. Our results confirm the good antioxidant activity of the 7,8-dihydroxy-4-phenyl coumarin and moderate antioxidant activity of 5,7-dihydroxy-4-phenyl coumarin. In this work, quantum chemical calculations based on density functional theory have been employed at B3LYP/6-311++G(d,p) level of theory to study the influence of number and position of hydroxyl groups in coumarin molecules on antioxidant activity. Calculated values for HOMO and LUMO energies, energy gap, stabilization energies and spin density distribution confirmed experimental results and were used for SAR definition. For determination of reaction mechanism in gas phase and selected solvents bond dissociation enthalpy, adiabatic ionization potential, proton dissociation enthalpy, proton affinity, electron transfer enthalpy and gas phase acidity have been calculated. Hydrogen Atom Transfer mechanism in vacuum and Single-Electron Transfer followed by the Proton Transfer mechanism in other studied systems are most probable free radical scavenging pathways. On the basis of these findings, these hydroxy 4-phenyl coumarins may be considered as potential therapeutic candidates for pathological conditions characterized by free radical overproduction.
PB  - Elsevier Ireland Ltd, Clare
T2  - Chemico-Biological Interactions
T1  - Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies
VL  - 214
SP  - 49
EP  - 56
DO  - 10.1016/j.cbi.2014.02.010
ER  - 

@article{
author = "Veselinović, Jovana and Veselinović, Aleksandar M. and Vitnik, Željko and Vitnik, Vesna and Nikolić, Goran M.",
year = "2014",
abstract = "A study on the structure-activity relationship of three hydroxy 4-phenyl coumarins, carried out by employing a series of different chemical cell-free tests is presented. Different assays involving one redox reaction with the oxidant (DPPH, ABTS, FRAP and CUPRAC) were employed. Further, the measurement of inhibition of oxidative degradation, such as lipid peroxidation, was used to define compound antioxidant activity. Our results confirm the good antioxidant activity of the 7,8-dihydroxy-4-phenyl coumarin and moderate antioxidant activity of 5,7-dihydroxy-4-phenyl coumarin. In this work, quantum chemical calculations based on density functional theory have been employed at B3LYP/6-311++G(d,p) level of theory to study the influence of number and position of hydroxyl groups in coumarin molecules on antioxidant activity. Calculated values for HOMO and LUMO energies, energy gap, stabilization energies and spin density distribution confirmed experimental results and were used for SAR definition. For determination of reaction mechanism in gas phase and selected solvents bond dissociation enthalpy, adiabatic ionization potential, proton dissociation enthalpy, proton affinity, electron transfer enthalpy and gas phase acidity have been calculated. Hydrogen Atom Transfer mechanism in vacuum and Single-Electron Transfer followed by the Proton Transfer mechanism in other studied systems are most probable free radical scavenging pathways. On the basis of these findings, these hydroxy 4-phenyl coumarins may be considered as potential therapeutic candidates for pathological conditions characterized by free radical overproduction.",
publisher = "Elsevier Ireland Ltd, Clare",
journal = "Chemico-Biological Interactions",
title = "Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies",
volume = "214",
pages = "49-56",
doi = "10.1016/j.cbi.2014.02.010"
}

Veselinović, J., Veselinović, A. M., Vitnik, Ž., Vitnik, V.,& Nikolić, G. M.. (2014). Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies. in Chemico-Biological Interactions
Elsevier Ireland Ltd, Clare., 214, 49-56.
https://doi.org/10.1016/j.cbi.2014.02.010

Veselinović J, Veselinović AM, Vitnik Ž, Vitnik V, Nikolić GM. Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies. in Chemico-Biological Interactions. 2014;214:49-56.
doi:10.1016/j.cbi.2014.02.010 .

Veselinović, Jovana, Veselinović, Aleksandar M., Vitnik, Željko, Vitnik, Vesna, Nikolić, Goran M., "Antioxidant properties of selected 4-phenyl hydroxycoumarins: Integrated in vitro and computational studies" in Chemico-Biological Interactions, 214 (2014):49-56,
https://doi.org/10.1016/j.cbi.2014.02.010 . .