杂环芳胺结构与致癌性和致突性的密度泛函研究

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

根据杂环芳胺(HCAs)在生物体内的代谢特征,用DFT-B3LYP方法分别进行了19种杂环芳胺类致癌/致突化合物在气相和水溶剂下的量子化学计算,获得了其结构与致癌性和致突性的相关关系。结果表明:9种HCAs的致癌性与分子的前线轨道能量之差ΔEgap,neutral、最高占有轨道能量EHOMO及与氨基相连的稠环数n有较好的线性关系,相关系数r为0.969,F检验因子为25.47(大于其F0*.*01临界值)。对19种致突性HCAs在水溶剂化条件下的计算表明:分子偶极矩μ和Ar-NH+离子前线轨道能级差ΔEgap,ion及其平方与致突性密切相关,r为0.912,F为17.3(大于其F0*.*01临界值)。

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 F0.01^＊＊）.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 F0.01^＊＊）.