QSARs for the toxicity of polychlorinated dibenzofurans through DFT-calculated descriptors of polarizabilities, hyperpolarizabilities and hyper-order electric moments

Chemosphere

Volumn 67, Issue 7, 2007, Pages 1325-1334

  Gu, Chenggang ^a   Jiang, Xin ^a   Ju, Xuehai ^b   Yu, Guifen ^a   Bian, Yongrong ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Binding affinities; DFT B3LYP; Induction potencies; PCDFs; Polarizability anisotropy; QSAR

Indexed keywords

ANISOTROPY; OPTIMIZATION; PROBABILITY DENSITY FUNCTION; TOXIC MATERIALS; TOXICITY;

BINDING AFFINITIES; INDUCTION POTENCIES; POLARIZABILITY ANISOTROPY; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS (QSAR);

AROMATIC COMPOUNDS;

AROMATIC HYDROCARBON RECEPTOR; ETHOXYRESORUFIN DEETHYLASE; POLYCHLORINATED DIBENZOFURAN; UNSPECIFIC MONOOXYGENASE;

ANISOTROPY; AROMATIC COMPOUNDS; OPTIMIZATION; PROBABILITY DENSITY FUNCTION; TOXIC MATERIALS; TOXICITY;

ANISOTROPY; CHEMICAL BINDING; CHLORINE; DIBENZOFURAN; ELECTRIC FIELD; MOLECULAR ANALYSIS; PCDF; TOXICITY;

ANIMAL TISSUE; ANISOTROPY; ARTICLE; BINDING AFFINITY; CHEMICAL ANALYSIS; DENSITY FUNCTIONAL THEORY; HYPERPOLARIZATION; NONHUMAN; POLARIZATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT;

EID: 33846870355     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2006.10.057     Document Type: Article

References (35)

1. Arulmozhiraja S., and Morita M. Structure-activity relationships for the toxicity of polychlorinated dibenzofurans: approach through density functional theory-based descriptors. Chem. Res. Toxicol. 17 (2004) 348-356
2. Asatryan R.S., Mailyan N.S., Khachatryan L., and Dellinger B. Electronic elasticity-toxicity relationships for polychlorinated dibenzo-p-dioxin congeners. Chemosphere 48 (2002) 227-236
3. Bandiera S., Sawyer T.W., Campbell M.A., Fujita T., and Safe S. Competitive binding to the cytosolic 2,3,7,8-TCDD receptor; effects of structure on the affinities of substituted halogenated biphenyls-a QSAR analysis. Biochem. Pharmacol. 32 (1983) 3803-3813
4. Bandiera S., Sawyer T., Romkes M., Zmudzka B., Safe L., Mason G., Keys B., and Safe S. Polychlorinated dibenzofurans (PCDFs): effects of structure on binding to the 2,3,7,8-TCDD cytosolic receptor protein, AHH induction and toxicity. Toxicology 32 (1984) 131-144
5. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98 (1993) 5648-5652
6. Chattaraj P.K., Maiti B., and Sarkar U. Philicity: a unified treatment of chemical reactivity and selectivity. J. Phys. Chem. A 107 (2003) 4973-4975
7. Denomme M.A., Homonko K., Fujita T., Sawyer T., and Safe S. Substituted polychlorinated dibenzofuran receptor binding affinities and aryl hydrocarbon hydroxylase induction potencies - a QSAR analysis. Chem.-Biol. Interact. 57 (1986) 175-187
8. 2 from vibration-rotation-tunneling spectra. J. Chem. Phys. 103 (1995) 933-949
9. Flannery M.R., Vrinceanu D., and Ostrovsky V.N. Long-range interaction between polar Rydberg atoms. J. Phys. B: At. Mol. Opt. 38 (2005) S279-S293
10. Fraschini E., Bonati L., and Pitea D. Molecular polarizability as a tool for understanding the binding properties of polychlorinated dibenzo-p-dioxins: definition of a reliable computational procedure. J. Phys. Chem. 100 (1996) 10564-10569
11. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision B.03 (2003), Gaussian Inc., Pittsburgh, PA
12. Hirokawa S., Imasaka T., and Imasaka T. Chlorine substitution pattern, molecular electronic properties, and the nature of the ligand-receptor interaction: quantitative property-activity relationships of polychlorinated dibenzofurans. Chem. Res. Toxicol. 18 (2005) 232-238
13. Kafafi S.A., Afeefy H.Y., Said H.K., and Hakimi J.M. A new structure-activity model for Ah receptor binding. polychlorinated dibenzo-p-dioxins and dibenzofurans. Chem. Res. Toxicol. 5 (1992) 856-862
14. Kafafi S.A., Afeefy H.Y., Said H.K., and Kafafi A.G. Relationship between aryl hydrocarbon receptor binding, induction of aryl hydroxylase and 7-ethoxyresorufin O-deethylase enzymes, and toxic activities of aromatic xenobiotics in animals. A new model. Chem. Res. Toxicol. 6 (1993) 328-334
15. Lee C., Yang W., and Parr R.G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37 (1988) 785-789
16. Mason G., Sawyer T., Keys B., Bandiera S., Romkes M., Piskorska-Pliszczynska J., Zmudzka B., and Safe S. Ploychlorinated dibenzofurans (PCDFs): correlation between in vivo and in vitro structure-activity relationships. Toxicology 37 (1985) 1-12
17. McKinney J.D., Gottschalk K.E., and Penerson L. The polarizability of planar aromatic systems. An application to polychlorinated biphenyl (PCB's), dioxins and polyaromatic hydrocarbons. J. Mol. Struct. (Theochem) 105 (1983) 427-438
18. McKinney J.D., Darden T., Lyerly M.A., and Pederson L.G. PCB and related compound binding to the Ah receptor(s). Theoretical model based on molecular parameters and molecular mechanics. Quant. Struct.-Act. Relat. 4 (1985) 166-172
19. Mekenyan O.G., Veith G.D., Call D.J., and Ankley G.T. A QSAR evaluation of Ah receptor binding of halogenated aromatic xenobiotics. Environ. Health Persp. 104 (1996) 1302-1310
20. Mhin B.J., Lee J.E., and Choi W. Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxins: chlorination pattern and molecular quadrupole moment. J. Am. Chem. Soc. 124 (2002) 144-148
21. Parr R.G., and Yang W. Density Functional Theory of Atoms and Molecules (1989), Oxford University Press, Oxford
22. Parr R.G., Szentpály L.V., and Liu S. Electrophilicity index. J. Am. Chem. Soc. 121 (1999) 1922-1924
23. Pearson R.G. Absolute electronegativity and hardness correlated with molecular orbital theory. P. Natl. Acad. Sci. USA 83 (1986) 8440-8441
24. Poland A., and Knutson J.C. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. Annu. Rev. Pharmacol. 22 (1982) 517-554
25. Poso A., Tuppurainen K., Ruuskanen J., and Gynther J. Binding of some dioxins and dibenzofurans to the Ah receptor. A QSAR model based on comparative molecular field analysis (CoMFA). J. Mol. Struct. (Theochem) 282 (1993) 259-264
26. Safe S.H. Comparative toxicology and mechanism of action of polychlorinated dibenzo-p-dioxins and dibenzofurans. Annu. Rev. Pharmacol. 26 (1986) 371-399
27. Safe S. Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins(PCDDs), dibenzofurans (PCDFs), and related compounds: environmental and mechanistic consideration which support the development of toxic equivalency factors (TEFs). Crit. Rev. Toxicol. 21 (1990) 51-88
28. Sarkar U., Padmanabhan J., Parthasarathi R., Subramanian V., and Chattaraj P.K. Toxicity analysis of polychlorinated dibenzofurans through global and local electrophilicities. J. Mol. Struct. (Theochem) 758 (2006) 119-125
29. Seminario J.M., and Politzer P. Modern Density Functional Theory: A Tool for Chemistry (1995), Elsevier, Amsterdam
30. So S.S., and Karplus M. Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural network. 2. Applications. J. Med. Chem. 40 (1997) 4360-4371
31. Tuppurainen K., and Ruuskanen J. Electronic eigenvalue (EEVA): a new QSAR/QSPR descriptor for electronic substituent effects based on molecular orbital energies. A QSAR approach to the Ah recepor binding affinity of polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs). Chemosphere 41 (2000) 843-848
32. Wagener M., Sadowski J., and Gasteiger J. Autocorrelation of molecular surface properties for modeling Corticosteroid Binding Globulin and cytosolic Ah receptor activity by neural networks. J. Am. Chem. Soc. 117 (1995) 7769-7775
33. Waller C.L., and McKinney J.D. Comparative molecular field analysis of polyhalogenated dibenzo-p-dioxins, dibenzofurans, and biphenyls. J. Med. Chem. 35 (1992) 3660-3666
34. Waller C.L., and McKinney J.D. Three-dimensional quantitative-activity relationships of dioxins and dioxin-like compounds: model validation and Ah receptor characterization. Chem. Res. Toxicol. 8 (1995) 847-858
35. Wold S. Cross-validation estimation of the number of components in factor and principal components analysis. Technometrics 24 (1978) 397-405