QSAR models for predicting toxicity of polychlorinated dibenzo-p-dioxins and dibenzofurans using quantum chemical descriptors

Bulletin of Environmental Contamination and Toxicology

Volumn 85, Issue 2, 2010, Pages 109-115

  Diao, Jianxiong ^a   Li, Yang ^a   Shi, Shuqiong ^b   Sun, Ye ^a   Sun, Ying ^a  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b BEIJING NORMAL UNIVERSITY   (China)

Author keywords

PCDD Fs; QSARs; Quantum chemical descriptors; Toxicity

Indexed keywords

ARYL HYDROCARBON RECEPTOR; BINDING AFFINITIES; BIOLOGICAL TOXICITY; MOLECULAR DESCRIPTORS; PARTIAL LEAST SQUARE REGRESSION; PCDD/FS; PM3 METHOD; POLYCHLORINATED DIBENZO-P-DIOXINS AND DIBENZOFURANS; PREDICTIVE CAPABILITIES; PREDICTOR VARIABLES; QSAR MODEL; QSARS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS; QUANTUM CHEMICAL DESCRIPTORS; SEMI-EMPIRICAL;

BINDING ENERGY; HYDROCARBONS; MOLECULAR GRAPHICS; TOXICITY;

INDICATORS (CHEMICAL);

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; AROMATIC HYDROCARBON RECEPTOR; BENZOFURAN DERIVATIVE; CHLORINATED DIBENZOFURANS; DRUG DERIVATIVE; POLYCHLORODIBENZO 4 DIOXIN; POLYCHLORODIBENZO-4-DIOXIN;

ANIMAL; ARTICLE; CELL CULTURE; CELL SURVIVAL; CHEMICAL MODEL; CHEMISTRY; DRUG EFFECT; LIVER CELL; METABOLISM; PREDICTION AND FORECASTING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM THEORY; RAT; SOIL POLLUTANT;

ANIMALS; BENZOFURANS; CELL SURVIVAL; CELLS, CULTURED; HEPATOCYTES; MODELS, CHEMICAL; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; RATS; RECEPTORS, ARYL HYDROCARBON; SOIL POLLUTANTS; TETRACHLORODIBENZODIOXIN;

EID: 77956094653     PISSN: 00074861     EISSN: 14320800     Source Type: Journal    
DOI: 10.1007/s00128-010-0065-2     Document Type: Article

References (29)

1. A Ashek C Lee H Park SJ Cho 2006 3D QSAR studies of dioxins and dioxin-like compounds using CoMFA and CoMSIA Chemosphere 65 521 529 10.1016/j.chemosphere.2006.01.010 1:CAS:528:DC%2BD28XosVOju7c%3D (Pubitemid 44223657)
2. S Bayen HK Lee JP Obbard 2007 Exposure and response of aquacultured oysters, Crassostrea gigas, to marine contaminants Environ Res 103 375 382 10.1016/j.envres.2006.06.012 1:CAS:528:DC%2BD2sXhvVymu7w%3D (Pubitemid 46217195)
3. B Bjorn H Krister 2000 Ecotoxicological risk assessment of environmental pollutants in the Arctic Toxicol Lett 112 111 118 10.1016/S0378-4274(99)00201-5 (Pubitemid 30138111)
4. JO Bustnes M Helberg K Strann JU Skaare 2006 Environmental pollutants in endangered vs. increasing subspecies of the lesser black-backed gull on the Norwegian Coast Environ Pollut 144 893 901 10.1016/j.envpol.2006.02.003 1:CAS:528:DC%2BD28XpslSlsbs%3D (Pubitemid 44344881)
5. JW Chen WJGM Peijnenburg X Quan S Chen D Martens K-W Schramm A Kettrup 2001 Is it possible to develop a QSPR model for direct photolysis half-lives of PAHs under irradiation of sunlight? Environ Pollut 114 137 143 10.1016/S0269-7491(00)00195-0 1:CAS:528:DC%2BD3MXkvVarsr0%3D (Pubitemid 32433351)
6. JW Chen X Quan Y Yan FL Yang WJGM Peijnenburg 2001 Quantitative structure-property relationship studies on direct photolysis of selected polycyclic aromatic hydrocarbons in atmospheric aerosol Chemosphere 42 263 270 10.1016/S0045-6535(00)00077-1 1:CAS:528:DC%2BD3cXovVWks74%3D
7. BV Cheney T Tolly 1979 Electronic factors affecting receptor binding of dibenzo-p-dioxins and dibenzofurans Int J Quantum Chem 16 87 110 10.1002/qua.560160113 1:CAS:528:DyaL3cXlsl2mtA%3D%3D
8. ENY Cheung JD McKinney 1989 Polybrominated naphthalene and diiodobenzene interactions with specific binding sites for 2,3,7,8-tetrachlorodibenzo-p-dioxin in rat liver cytosol Mol Toxicol 2 39 52 10.1002/jbt.2570040108 1:CAS:528:DyaK3cXhvFegsLw%3D (Pubitemid 20098297)
9. BW Clare 2006 QSAR of aromatic substances: toxicity of polychlorodibenzofurans J Mol Struct 763 205 213 1:CAS:528:DC%2BD28Xktlygtr4%3D
10. J Devillers N Marchand-Geneste JM Porcher 2006 SAR and QSAR modeling of endocrine disruptors SAR QSAR Environ Res 17 393 412 10.1080/10629360600884397 1:CAS:528:DC%2BD28XhtVCks7fK (Pubitemid 44277097)
11. JC Faucon R Bureau J Faisant F Briens S Rault 1999 Prediction of the fish acute toxicity from heterogeneous data coming from notification files Chemosphere 38 3261 3276 10.1016/S0045-6535(98)00558-X 1:CAS:528: DyaK1MXjtVartbc%3D (Pubitemid 29189024)
12. JY Hu T Aizawa 2003 Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals Water Res 37 1213 1222 10.1016/S0043-1354(02)00378-0 1:CAS:528:DC%2BD3sXht1Wgu70%3D (Pubitemid 36206468)
13. XY Huang L Lessner DO Carpenter 2006 Exposure to persistent organic pollutants and hypertensive disease Environ Res 102 101 106 10.1016/j.envres. 2005.12.011 1:CAS:528:DC%2BD28XntlWntLw%3D (Pubitemid 44080197)
14. IO Juranić BJ Drakulić SD Petrović DZ Mijin MV Stanković 2006 A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats Chemosphere 62 641 649 10.1016/j.chemosphere.2005.05. 005 (Pubitemid 41737397)
15. XX Long JF Niu 2007 Estimation of gas-phase reaction rate constants of alkylnaphthalenes with chlorine, hydroxyl and nitrate radicals Chemosphere 67 2028 2034 10.1016/j.chemosphere.2006.11.021 1:CAS:528:DC%2BD2sXjt1ShsL4%3D (Pubitemid 46412394)
16. G Miller S Sontum DG Crosby 1977 Electron-acceptor properties of chlorinated dibenzo-p-dioxins Environ Contam Toxicol 18 611 616 10.1007/BF01684008 1:CAS:528:DyaE1cXkslGitL8%3D (Pubitemid 8241461)
17. TI Netzeva TW Schultz 2005 QSARs for the aquatic toxicity of aromatic aldehydes from Tetrahymena data Chemosphere 61 1632 1643 10.1016/j.chemosphere. 2005.04.040 1:CAS:528:DC%2BD2MXht1OrsLbF (Pubitemid 41728194)
18. JF Niu G Yu 2004 Prediction of the ability of PAHs to be photocytotoxic to a cell line from the rainbow trout (Oncorhynchus mykiss) gill Bull Environ Contam Toxicol 73 659 665 1:CAS:528:DC%2BD2cXnvVyjsrY%3D (Pubitemid 39381910)
19. JF Niu JW Chen B Henkelmann X Quan FL Yang A Kettrup K-W Schramm 2003 Photodegradation of PCDD/Fs adsorbed on spruce (Picea abies (L.) Karst.) needles under sunlight irradiation Chemosphere 50 1217 1225 10.1016/S0045-6535(02) 00509-X 1:CAS:528:DC%2BD3sXlt1yhsA%3D%3D (Pubitemid 36188295)
20. JF Niu LP Huang JW Chen G Yu K-W Schramm 2005 Quantitative structure-property relationships on photolysis of PCDD/Fs adsorbed to spruce (Picea abies (L.) Karst.) needle surfaces under sunlight irradiation Chemosphere 58 917 924 10.1016/j.chemosphere.2004.09.051 1:CAS:528:DC%2BD2MXhvFymsA%3D%3D (Pubitemid 40091705)
21. JF Niu ZY Shen ZF Yang XX Long G Yu 2006 Quantitative structure-property relationships on photodegradation of polybrominated diphenyl ethers Chemosphere 64 658 665 10.1016/j.chemosphere.2005.10.051 1:CAS:528:DC%2BD28Xmt1Okt7c%3D (Pubitemid 43929059)
22. JF Niu XX Long SQ Shi 2007 Quantitative structure-activity relationships for prediction of the toxicity of hydroxylated and quinoid PCB metabolites J Mol Model 13 163 169 10.1007/s00894-006-0153-8 1:CAS:528:DC%2BD2sXnsFCksA%3D%3D (Pubitemid 44823964)
23. AB Okey 1990 Enzyme-induction in the cytochrome-p-450 system Pharmacol Ther 45 241 298 10.1016/0163-7258(90)90030-6 1:CAS:528:DyaK3cXntFKrsA%3D%3D (Pubitemid 20008908)
24. J Padmanabhan R Parthasarathi V Subramanian PK Chattaraj 2006 QSPR models for polychlorinated biphenyls: n-octanol/water partition coefficient Med Chem 14 1021 1028 10.1016/j.bmc.2005.09.017 1:CAS:528:DC%2BD28XhvFKkuw%3D%3D (Pubitemid 43059793)
25. PG Pearson 1986 Absolute electronegativity and hardness correlated with molecular orbital theory Proc Natl Acad Sci 83 8440 8441 10.1073/pnas.83.22.8440 1:CAS:528:DyaL2sXitlGjtg%3D%3D
26. A Poland E Glover AS Kende 1976 Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-para-dioxin by hepatic cytosol-evidence that binding species is receptor for induction of aryl-hydrocarbon hydroxylase J Biol Chem 251 4936 4946 1:CAS:528:DyaE28XlsFClu7o%3D
27. CL Waller JD McKinney 1992 Comparative molecular-field analysis of polyhalogenated dibenzo-p-dioxins, dibenzofurans, and biphenyls J Med Chem 35 3660 3666 10.1021/jm00098a010 1:CAS:528:DyaK38Xls1Gnsbk%3D
28. S Wold M Sjöström L Ericksson 2001 PLS-regression: a basic tool of chemometrics Chemomet Intell Lab Syst 58 109 130 10.1016/S0169-7439(01) 00155-1 1:CAS:528:DC%2BD3MXotF2mtLw%3D (Pubitemid 33033283)
29. ZY Zhang JF Niu X Zhi 2008 A QSAR model for predicting mutagenicity of nitronaphthalenes and methylnitronaphthalenes Bull Environ Contam Toxicol 81 498 502 10.1007/s00128-008-9540-4 1:CAS:528:DC%2BD1cXhtFert7nF