QSARs for the toxicity of polychlorinated dibenzofurans through DFT-calculated descriptors of polarizabilities, hyperpolarizabilities and hyper-order electric moments.
DFT-B3LYP method with 6-31G(**) basis set was employed to fully optimize the electronic structures of 135 polychlorinated dibenzofurans and parent compound, namely dibenzofuran. It was demonstrated that polarizability anisotropy and mean polarizability could change sensitively and systematically with chlorine number and substitution pattern. And new quantitative structure-activity relationships (QSARs) focused on the binding affinities of aryl hydrocarbon receptor (AhR), aryl hydrocarbon hydroxylase (AHH) and 7-ethoxyresorufin O-deethylase (EROD) induction potencies of PCDFs were developed. It was concluded that polarizability anisotropy in conjunction with hyperpolarizabilties and hyper-order electric moments, e.g. octupole moments could well interpret the variation of toxicity of different congeners and dispersion interaction should be the leading form among various interactions. Although the terms of hyperpolarizabilities and hyper-order electric moments were not the same significant ones as polarizability anisotropy, the long-range interactions characterized by them should not be ignored in explaining the toxicity.
Gu
Chenggang
C
State Key Laboratory of Soil and Sustainable Agriculture, Nanjing Institute of Soil Science, Chinese Academy of Sciences, 71 East Beijing Road, Nanjing 210008, PR China.
Jiang
Xin
X
Ju
Xuehai
X
Yu
Guifen
G
Bian
Yongrong
Y
D000465:Algorithms; D016880:Anisotropy; D001572:Benzofurans / Q000737:chemistry* / Q000633:toxicity*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D019363:Cytochrome P-450 CYP1A1 / Q000096:biosynthesis; D003627:Data Interpretation, Statistical; D004563:Electrochemistry; D015233:Models, Statistical; D011108:Polymers / Q000737:chemistry* / Q000633:toxicity*; D021281:Quantitative Structure-Activity Relationship; D018336:Receptors, Aryl Hydrocarbon / Q000096:biosynthesis
D001572:Benzofurans; D011108:Polymers; D018336:Receptors, Aryl Hydrocarbon; C016068:polychlorodibenzofuran; D019363:Cytochrome P-450 CYP1A1