title: Quantum chemical studies on ultimate carcinogenic metabolites from polycyclic aromatic hydrocarbons.
abstract: Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants well known as mutagenic/carcinogenic agents. This review will discuss recent theoretical studies regarding the stability and reactivity of ultimate carcinogenic metabolites from PAHs, focusing on their diol epoxide and amine derivatives. Geometrical and electronic features will be analyzed in order to obtain structure-activity relationships. Charge delocalization modes (positive charge density distribution), substituent effects, and conformational aspects will be considered. Computed properties will be compared with the available biological activity data. Correlations between experimental mutagenic potencies reported in the literature and calculated reaction energies and electronic properties will be shown. Heteroaromatic compounds (aza-PAHs, thia-PAHs, and heteroaromatic amines) will also be examined. To model the important step of covalent adduct formation, calculation of the adducts resulting from bond formation between some of these electrophilic intermediates and nucleotide bases (guanine, cytosine) will be described.
authors.affiliation: Unidad de Matemática y Física, INFIQC, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, Córdoba 5000, Argentina. gborosky@fcq.unc.edu.ar
authors.forename: Gabriela L
authors.initials: GL
authors.lastname: Borosky
mesh_terms: D000588:Amines / Q000737:chemistry; D000818:Animals; D002273:Carcinogens / Q000737:chemistry; D018736:DNA Adducts / Q000737:chemistry; D004785:Environmental Pollutants; D004852:Epoxy Compounds / Q000737:chemistry; D006801:Humans; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D008968:Molecular Conformation; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry*; D011789:Quantum Theory; D012984:Software; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D000588:Amines; D002273:Carcinogens; D018736:DNA Adducts; D004785:Environmental Pollutants; D004852:Epoxy Compounds; D011084:Polycyclic Aromatic Hydrocarbons; D012997:Solvents