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Density Functional Study of Relationship Between Structure and Carcinogenicity/Mutagenicity of Heterocyclic Aromatic Amines


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Density Functional Study of Relationship Between Structure and Carcinogenicity/Mutagenicity of Heterocyclic Aromatic Amines
HU Chen-yaoWANG TaoJU Xue-haiZENG Xiu-lin
School of Chemical Engineering,NUST,Nanjing 210094,China
heterocyclic aromatic amines carcinogenicity mutagenicity quantitative structure-activity relationship density functional theory
Based on the metabolic mechanisms of the heterocyclic aromatic amines(HCAs)in the organism,the DFT-B3LYP quantum chemistry calculations are performed on 19 HCAs with carcinogenicity and mutagenicity in the gaseous state or the water solvent,and the relationships between the structures and the carcinogenicity/mutagenicity are established.Results show that the carcinogenicity for 9 HCAs is related with their frontier orbital gap ΔEgap,neutral,the energy of highest occupied-molecular orbital EHOMO and the number of fused rings linked to the amine group n.The related coefficient r is 0.969,and the F factor is 25.47(larger than the corresponding critical value F* *0.01).The mutagenicity of 19 HACs in the water solvent is related to their molecular dipole moment μ,the frontier orbital gap of the Ar-NH+ΔEgap,ion and its square and the fused ring number.The r is 0.912 and F is 17.3(larger than F* *0.01).


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Last Update: 2012-10-12