| Autor: |
Vasić J; Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia., Dimić D; Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia., Antonijević M; Institute for Information Technologies Kragujevac, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia., Avdović EH; Institute for Information Technologies Kragujevac, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia., Milenković D; Institute for Information Technologies Kragujevac, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia., Nakarada Đ; Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia., Dimitrić Marković J; Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia., Molnar M; Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, Josip Juraj Strossmayer University of Osijek, Franje Kuhača 18, 31000 Osijek, Croatia., Lončarić M; Department of Applied Chemistry and Ecology, Faculty of Food Technology Osijek, Josip Juraj Strossmayer University of Osijek, Franje Kuhača 18, 31000 Osijek, Croatia., Bešlo D; Department of Agroecology and Environmental Protection, Faculty of Agrobiotechnical Sciences Osijek, Josip Juraj Strossmayer University of Osijek, Vladimir Prelog 1, 31000 Osijek, Croatia., Marković Z; Institute for Information Technologies Kragujevac, University of Kragujevac, Jovana Cvijica bb, 34000 Kragujevac, Serbia. |
| Abstrakt: |
Coumarin derivatives are a class of compounds with pronounced biological activities that depend primarily on the present substituents. Four 3-methoxycarbonylcoumarin derivatives with substituents of different electron-donating/electron-withdrawing abilities (Br, NO 2 , OH, and OMe) were investigated structurally by NMR, IR, and UV-VIS spectroscopies and density functional theory methods. The appropriate level of theory (B3LYP-D3BJ/6-311++G(d,p) was selected after comparing similar compounds' experimental and theoretical structural parameters. The natural bond orbital and quantum theory of atoms in molecules were employed to investigate the intramolecular interactions governing stability. The electronic effects of substituents mostly affected the aromatic ring that the substituents are directly attached to. The antioxidant properties were investigated by electron paramagnetic resonance spectroscopy towards HO • , and the percentages of reduction were between 13% ( 6-Br ) and 23% ( 6-OMe ). The protein binding properties towards transport proteins were assessed by spectrofluorimetry, molecular docking, and molecular dynamics (MD). The experimentally determined binding energies were well reproduced by molecular docking, showing that the spontaneity of ibuprofen binding was comparable to the investigated compounds. The flexibility of HSA in MD simulations depended on the substituents. These results proved the importance of electronic effects for the protein binding affinities and antioxidant properties of coumarin derivatives. |
