title: A quantum chemical based toxicity study of estimated reduction potential and hydrophobicity in series of nitroaromatic compounds.
abstract: Nitroaromatic compounds and the products of their degradation are toxic to bacteria, cells and animals. Various studies have been carried out to better understand the mechanism of toxicity of aromatic nitrocompounds and their relationship to humans and the environment. Recent data relate cytotoxicity of nitroaromatic compounds to their single- or two-electron enzymatic reduction. However, mechanisms of animal toxicity could be more complex. This work investigates the estimated reduction and oxidation potentials of 34 nitroaromatic compounds using quantum chemical approaches. All geometries were optimized with density functional theory (DFT) using the solvation model based on density (SMD) and polarizable continuum model (PCM) solvent model protocols. Quantitative structure-activity/property (QSAR/QSPR) models were developed using descriptors obtained from quantum chemical optimizations as well as the DRAGON software program. The QSAR/QSPR equations developed consist of two to four descriptors. Correlations have been identified between electron affinity (ELUMO) and hydrophobicity (log P).
authors.affiliation: a Interdisciplinary Center for Nanotoxicity, Jackson State University , Jackson , USA.
authors.forename: A
authors.initials: A
authors.lastname: Gooch
authors.affiliation: a Interdisciplinary Center for Nanotoxicity, Jackson State University , Jackson , USA.
authors.forename: N
authors.initials: N
authors.lastname: Sizochenko
authors.affiliation: a Interdisciplinary Center for Nanotoxicity, Jackson State University , Jackson , USA.|b Department of Organic Chemistry , Oles Honchar Dnipropetrovsk National University , Dnipropetrovsk , Ukraine.
authors.forename: L
authors.initials: L
authors.lastname: Sviatenko
authors.affiliation: a Interdisciplinary Center for Nanotoxicity, Jackson State University , Jackson , USA.|c HX5 , Vicksburg , USA.
authors.forename: L
authors.initials: L
authors.lastname: Gorb
authors.affiliation: a Interdisciplinary Center for Nanotoxicity, Jackson State University , Jackson , USA.
authors.forename: J
authors.initials: J
authors.lastname: Leszczynski
mesh_terms: D000818:Animals; D003198:Computer Simulation; D006801:Humans; D006841:Hydrocarbons, Aromatic / Q000737:chemistry* / Q000633:toxicity*; D057927:Hydrophobic and Hydrophilic Interactions; D015233:Models, Statistical; D009574:Nitro Compounds / Q000737:chemistry* / Q000633:toxicity*; D010084:Oxidation-Reduction; D021281:Quantitative Structure-Activity Relationship
chemical_list: D006841:Hydrocarbons, Aromatic; D009574:Nitro Compounds
keywords: LUMO energy; QSAR; hydrophobicity; nitroaromatic; reduction potential; toxicity