title: Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
abstract: The applicability of the newly developed RM1 and PM6 methods implemented in the semiempirical quantum chemistry mopac2009 software package in modeling free radical scavenging activity of flavonoids was examined. Bond dissociation enthalpy (BDE) of OH groups could be calculated much faster than with DFT method but with similar quality. Despite the known shortcomings of the Trolox equivalent antioxidant capacity (TEAC) assay, we show that taking into account the hydrogen atom transfer (HAT) mechanism of free radical scavenging of flavonoids encoded by minimal BDE values (BDE(min)) and the number of OH groups (nOH), as well as experimental data, reasonable QSAR models could be developed. For TEAC values of 38 flavonoids measured by the ABTS free radical, a model based on BDE(min) and nOH was developed, having very good statistical parameters (r=0.983, r(cv)=0.976). The applicability of this model to three different data sets of flavonoids and reliability of TEAC values measured in distinct laboratories were discussed. Finally, a reasonably good model of experimental vitamin C equivalent antioxidant capacity (VCEAC) of 36 flavonoids was obtained (r=0.954, r(cv)=0.947), involving BDE(min) and nOH as descriptors. Additionally, all presented models have comparable fit and cross-validated statistical parameters, as well as significant regression coefficients.
authors: Faculty of Agriculture, The Josip Juraj Strossmayer University, PO Box 719, HR-31107 Osijek, Croatia. damic@pfos.hr
authors: Dragan
authors: D
authors: Amić
authors: Bono
authors: B
authors: Lucić
mesh_terms: D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000494:pharmacology; D008954:Models, Biological; D021281:Quantitative Structure-Activity Relationship; D011789:Quantum Theory; D012984:Software; D013816:Thermodynamics
chemical_list: D005419:Flavonoids; D016166:Free Radical Scavengers