title: Importance of hydrogen bonding and aromaticity indices in QSAR modeling of the antioxidative capacity of selected (poly)phenolic antioxidants.
abstract: The quantitative structure-activity relationship (QSAR) models for predicting antioxidative capacity of 21 structurally similar natural and synthetic phenolic antioxidants was considered. The one-, two- and three-descriptor QSAR models were developed. For this purpose the literature data on the vitamin C equivalent antioxidative capacity (VCEAC) values were used as experimental descriptor of antioxidative capacity. Some thermodynamic and aromaticity properties, as well as the natural bond analysis (NBO) based quantities aimed at measuring the strength of intramolecular hydrogen bonds, were used as independent variables. It was examined whether a combination of these variables can yield a mathematical function that is in good correlation with the VCEAC values. It was shown that a combination of a certain thermodynamic descriptor (related to the single proton loss electron transfer mechanism) with the NBO-based quantities results in several two-descriptor models with the correlation coefficient greater than 0.950. Thus, a significant influence of internal hydrogen bonds on the antioxidative capacity of the studied molecules was confirmed. The best correlation with the VCEAC values was achieved within a three-descriptor QSAR model. This model was obtained by including a magnetic aromaticity index. It was found that aromaticity has only secondary effects on the antioxidative capacity.
authors.affiliation: Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300 Novi Pazar, Serbia. Electronic address: sjeremic@np.ac.rs.
authors.forename: Svetlana
authors.initials: S
authors.lastname: Jeremić
authors.affiliation: Faculty of Science, University of Kragujevac, 12 Radoja Domanovića, P.O. Box 60, 34000 Kragujevac, Serbia.
authors.forename: Slavko
authors.initials: S
authors.lastname: Radenković
authors.affiliation: Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300 Novi Pazar, Serbia.
authors.forename: Miloš
authors.initials: M
authors.lastname: Filipović
authors.affiliation: Faculty of Science, University of Kragujevac, 12 Radoja Domanovića, P.O. Box 60, 34000 Kragujevac, Serbia.
authors.forename: Marija
authors.initials: M
authors.lastname: Antić
authors.affiliation: Department of Biology, Josip Juraj Strossmayer University of Osijek, Cara Hadrijana 8a, 31000 Osijek, Croatia.
authors.forename: Ana
authors.initials: A
authors.lastname: Amić
authors.affiliation: Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300 Novi Pazar, Serbia.
authors.forename: Zoran
authors.initials: Z
authors.lastname: Marković
mesh_terms: D000975:Antioxidants / Q000737:chemistry* / Q000494:pharmacology*; D001205:Ascorbic Acid / Q000378:metabolism; D006860:Hydrogen Bonding; D010084:Oxidation-Reduction; D059808:Polyphenols / Q000737:chemistry* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D013816:Thermodynamics
chemical_list: D000975:Antioxidants; D059808:Polyphenols; D001205:Ascorbic Acid
keywords: Antioxidative activity; Hydrogen bond energy; Phenolic compounds; QSAR; Thermodynamic parameters