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.
Keywords: Polycyclic aromatic hydrocarbons, aromatic amines, quantum-chemical calculations, mutagenic/carcinogenic metabolites, DNA covalent adducts, carbocations
Current Medicinal Chemistry
Title: Quantum Chemical Studies on Ultimate Carcinogenic Metabolites from Polycyclic Aromatic Hydrocarbons
Volume: 15 Issue: 28
Author(s): Gabriela L. Borosky
Affiliation:
- Unidad de Matematica y Fisica, INFIQC, Facultad de Ciencias Quimicas, Universidad Nacional de Cordoba, Ciudad Universitaria, Cordoba 5000, Argentina.,Argentina
Keywords: Polycyclic aromatic hydrocarbons, aromatic amines, quantum-chemical calculations, mutagenic/carcinogenic metabolites, DNA covalent adducts, carbocations
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.
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Cite this article as:
Borosky L. Gabriela, Quantum Chemical Studies on Ultimate Carcinogenic Metabolites from Polycyclic Aromatic Hydrocarbons, Current Medicinal Chemistry 2008; 15(28) . https://dx.doi.org/10.2174/092986708786848686
DOI https://dx.doi.org/10.2174/092986708786848686 |
Print ISSN 0929-8673 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-533X |

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