DFT study on the bromination pattern dependence of electronic properties and their validity in quantitative structure-activity relationships of polybrominated diphenyl ethers

SAR and QSAR in Environmental Research

Volumn 20, Issue 3-4, 2009, Pages 287-307

  Gu, C G ^a,b   Ju, X H ^c   Jiang, X ^b   Wang, F ^b   Yang, S G ^a   Sun, C ^a  

^a NANJING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

DFT; Polarisability; Polarisability anisotropy; Polybrominated diphenyl ethers; QSAR; Quadrupole moment

Indexed keywords

ANISOTROPY; COMPUTATION THEORY; COMPUTATIONAL CHEMISTRY; DISPERSIONS; ELECTRONIC PROPERTIES; ETHERS; ORGANIC POLLUTANTS; POLARIZATION; QUANTUM CHEMISTRY; TOXICITY;

DENSITY FUNCTIONAL THEORY STUDIES; DENSITY-FUNCTIONAL-THEORY; PATTERN DEPENDENCE; POLARISABILITIES; POLARISABILITY ANISOTROPY; POLYBROMINATED DIPHENYLETHERS; QUADRUPOLE MOMENTS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTUM CHEMICAL COMPUTATIONS;

DENSITY FUNCTIONAL THEORY;

DIPHENYL ETHER DERIVATIVE;

ARTICLE; CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL MODEL;

HALOGENATED DIPHENYL ETHERS; MODELS, STATISTICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67949103700     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629360902949468     Document Type: Article

References (54)

1. WHO: Environmental Health Criteria 162. Brominated diphenyl ethers, International Programme on Chemical Safety, World Health Organisation, Geneva, Switzerland, 1994.
2. R. Renner, What fate for brominated fire retardants?, Environ. Sci. Technol. 34 (2000), pp. 223A-226A.
3. C.A. De Wit, An overview of brominated flame retardants in the environment, Chemosphere 42 (2002), pp. 583-624.
4. I. Watanabe and S. Sakai, Environmental release and behavior of brominated flame retardants, Environ. Int. 29 (2003), pp. 665-682.
5. A.K. Peters, J.T. Sanderson, A. Bergman, and M. van den Berg, Antagonism of TCDD-induced ethoxyresorufin-O-deethylation activity by polybrominated diphenyl ethers (PBDEs) in primary cynomolgus monkey (Macaca fascicularis) hepatocytes, Toxicol. Lett. 164 (2006), pp. 123-132.
6. J.M. Luross, M. Alaee, D.B. Sergeant, D.M. Whittle, and K.R. Solomon, Spatial and temporal distribution of polybrominated diphenyl ethers in lake trout from the great lakes, Organohalogen Compd. 47 (2000), pp. 73-76.
7. M.G. Ikonomou, M. Fischer, T. He, R.F. Addison, and T. Smith, Congener patterns, spatial and temporal trends of polybrominated diphenyl ethers in biota samples from the Canadian west coast and the Northwest Territories, Organohalogen Compd. 47 (2000), pp. 77-80.
8. M.G. Ikonomou, S. Rayne, and R.F. Addison, Exponential increases of the brominated flame retardant polybrominated diphenyl ethers in the Canadian Arctic from 1981, Environ. Sci. Technol. 36 (2002), pp. 1886-1892.
9. U. Sellström, A. Kierkegaard, C.A. de Wit, and B. Jansson, Polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from a Swedish river, Environ. Toxicol. Chem. 17 (1998), pp. 1065-1072.
10. C.R. Allchin, R.J. Law, and S. Morris, Polybrominated diphenylethers in sediments and biota and downstream of potential sources in the UK, Environ. Pollut 105 (1999), pp. 197-207.
11. A. Covaci, A. Gheorghe, S. Voorspoels, J. Maervoet, E. Steen Redeker, R. Blust, and P. Schepens, Polybrominated diphenyl ethers, polychlorinated biphenyls and organochlorine pesticides in sediment cores from the Western Scheldt river (Belgium): analytical aspects and depth profiles, Environ. Int. 31 (2005), pp. 367-375.
12. D. Meironyte ́, A. Bergman, and K. Nore ́n Analysis of polybrominated diphenyl ethers in human milk, Organohalogen Comp. 35 (1998), pp. 387-390.
13. K. Nore ́n and D. Meironyte ́, Certain organochlorine and organobromine contaminants in Swedish human milk in perspective of past 20, Chemosphere 40 (2000), pp. 1111-1123.
14. E. Klasson-Wehler, L. Hovander, A. Bergman, New organohalogens in human plasmaidentification and quantification, Organohalogen Comp. 33 (1997), pp. 420-425.
15. A. Sjö din, L. Hagmar, E. Klasson-Wehler, K. Kronholm-Diab, E. Jakobsson, and A. Bergman, Polybrominated diphenyl ethers (PBDEs) in blood from Swedish workers, Environ. Health Perspect. 107 (1999), pp. 643-648.
16. P.S. Haglund, D.R. Zook, H.-R. Buser, and J. Hu, Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota, Environ. Sci. Technol. 31 (1997), pp. 3281-3287.
17. I.A.T.M. Meerts, J.J. van Zanden, E.A.C. Luijks, I. van Leeuwen-Bol, G. Marsh, E. Jakobsson, A Bergman, and A. Brouwer, Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro, Toxicol. Sci. 56 (2000), pp. 95-104.
18. J. Bezares-Cruz, C.T. Jafvert, and I. Hua, Solar photodecomposition of decabromodiphenyl ether: products and quantum yield, Environ. Sci. Technol. 38 (2004), pp. 4149-4156.
19. Y.S. Keum and Q.X. Li, Reductive debromination of polybrominated diphenyl ethers by zerovalent iron, Environ. Sci. Technol. 39 (2005), pp. 2280-2286.
20. T. Zhou, M.M. Taylor, M.J. DeVito, and K.M. Crofton, Developmental exposure to brominated diphenyl ethers results in thyroid hormone disruption, Toxicol. Sci. 66 (2002), pp. 105-116.
21. I. Branchi, F. Capone, E. Alleva, and L.G. Costa, Polybrominated diphenyl ethers: neurobehavioral effects following developmental exposure, Neurotoxicol. 24 (2003), pp. 449-462.
22. P.O. Darnerud, Toxic effects of brominated flame retardants in man and in wildlife, Environ. Int. 29 (2003), pp. 841-853.
23. P.O. Darnerud, Brominated flame retardants as possible endocrine disrupters, Int. J. Androl. 31 (2008), pp. 152-160.
24. L. Von Meyerinck, B. Hufnagel, A. Schmoldt, and H.F. Benthe, Induction of rat liver microsomal cytochrome P-450 by pentabromo diphenyl ether bromakal 70 and half-lives of its components in adipose tissue, Toxicology 61 (1990), pp. 259-274.
25. A.B. Okey, D.S. Riddick, and P.A. Harper, The Ah receptor: mediator of the toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and related compounds, Toxicol. Lett. 70 (1994), pp. 1-22.
26. I.A.T.M. Meerts, E.A.C. Luijks, G. Marsh, E. Jakobsson, A Bergman, and A. BrouwerPolybrominated diphenyl ethers (PBDEs) as Ah-receptor agonists and antagonists, Organohalogen Compd. 35 (1998), pp. 147-150.
27. P.A. Behnisch, K. Hosoe, and S.I. Sakai, Brominated dioxin-like compounds: in vitro assessment in comparison to classical dioxin-like compounds and other polyaromatic compounds, Environ. Int. 29 (2003), pp. 861-877.
28. G. Chen, A.D. Konstantinov, B.G. Chittim, E.M. Joyce, N.C. Bols, and N.J. Bunce, Synthesis of polybrominated dipheryl ethers and their capacity to induce CYP1A by the Ah receptor mediated pathway, Environ. Sci. Technol. 35 (2001), pp. 3749-3756.
29. J. Hu, L. Eriksson, A Bergman, E. Kolehmainen, J. Knuutinen, R. Suontamo, and X. Wei Molecular orbital studies on brominated dipheryl ethers. Part I-conformational properties, Chemosphere 59 (2005), pp. 1033-1041.
30. J. Hu, L. Eriksson, A Bergman, E. Jakobsson, E. Kolehmainen, J. Knuutinen, R. Suontamo, and X. Wei, Molecular orbital studies on brominated dipheryl ethers. Part II-reactivity and quantitative structure-activity (property) relationships, Chemosphere 59 (2005), pp. 1043-1057.
31. X. Zeng, P.K. Freeman, Y.V. Vasil'ev, V.G. Voinov, S.L. Simonich, and D.F. Barofsky, Theoretical calculation of thermodynamic properties of polybrominated dipheryl ethers, J. Chem. Eng. Data 50 (2005), pp. 1548-1556.
32. M. Grabda, S. Oleszek-Kudlak, E. Shibata, and T. Nakamura, Gas phase thermodynamic properties of PBDEs, PBBs, PBPs, HBCD and TBBPA predicted using DFT method, J. Mol. Struct. (THEOCHEM) 822 (2007), pp. 38-44.
33. Y.Y. Zhao, F.M. Tao, and E.Y. Zeng, Theoretical study on the chemical properties of polybrominated diphenyl ethers, Chemosphere 70 (2008), pp. 901-907.
34. M. Harju, P.L. Andersson, P. Haglund, and M. Tysklind, Multivariate physicochemical characterisation and quantitative structure-property relationship modeling of polybrominated diphenyl ethers, Chemosphere 47 (2002), pp. 375-384.
35. Y. Wang, C. Zhao, W. Ma, H. Liu, T. Wang, and G. Jiang, Quantitative structure-activity relationship for prediction of the toxicity of polybrominated diphenyl ether (PBDE) congeners, Chemosphere 64 (2006), pp. 515-524.
36. E. Fraschini, L. Bonati, and D. Pitea, Molecular polarisability as a tool for understanding the binding properties of polychlorinated dibenzo-p-dioxins: definition of a reliable computational procedure, J. Phys. Chem. 100 (1996), pp. 10564-10569.
37. S. Hirokawa, T. Imasaka, and T. Imasaka, 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), pp. 232-238.
38. C.G. Gu, X. Jiang, X.H. Ju, G.F. Yu, and Y.R. Bian, QSARs for the toxicity of polychlorinated dibenzofurans through DFT-calculated descriptors of polarisabilities, hyperpolarisabilities and hyper-order electric moments, Chemosphere 67 (2007), pp. 1325-1334.
39. B.J. Mhin, J.E. Lee, and W. Choi, Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxins: chlorination pattern and molecular quadrupole moment, J. Am. Chem. Soc. 124 (2002), pp. 144-148.
40. J. Chao, M.A. Desando, D.L. Gourlay, D.E. Orr, and S. Walker, Eyring activation barriers for the anomalous dielectric relaxations of diphenyl ether-type molecules, J. Phys. Chem. 88 (1984), pp. 711-716.
41. B. Uno, T. Iwanoto, and N. Okumura, Importance of substituent intramolecular chargetransfer effect on the molecular conformation of diphenyl ethers, J. Org. Chem. 63 (1998), pp. 9794-9800.
42. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart, Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model, J. Am. Chem. Soc. 107 (1985), pp. 3902-3909.
43. J.J.P. Stewart, Optimisation of parameters for semiempirical methods I. Method, J. Comput. Chem. 10 (1989), pp. 209-220.
44. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven Jr, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson,. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian .B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, .J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, .K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortis, Q. Cui, A.G. Baboul, Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, .L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople, Gaussian 03, Revision B.03, Gaussian Inc., Pittsburgh PA, 2003.
45. S.C. Basak, B.D. Gute, and G.D. Grunwald, Characterisation of the molecular similarity of chemicals using topological invariants, Adv. Mol. Sim. 2 (1998), pp. 171-185.
46. M.C. Bagchia, B.C. Maitib, and S. Bose, QSAR of anti tuberculosis drugs of INH type using graphical invariants, J. Mol. Struct. (THEOCHEM) 679 (2004), pp. 179-186.
47. R. Todeschini and P. Gramatica, 3D-modelling and prediction by WHIM descriptors: Part 5. Theory development and chemical meaning of WHIM descriptors, Quant. Struct.-Acta. Relat. 16 (1997), pp. 113-119.
48. R. Todeschini and P. Gramatica, 3D-modelling and prediction by WHIM descriptors: Part 6. Application of WHIM descriptors in QSAR studies, Quant. Struct.-Acta. Relat. 16 (1997), pp. 120-125.
49. R. Todeschini and P. Gramatica, New 3D molecular descriptors: the WHIM theory and QSAR applications, Perspect. Drug Discov. 9-11 (1998), pp. 355-380.
50. J.D. McKinney, A. Richard, C. Waller, M.C. Newman, and F. Gerberick, The practice of structure activity relationships (SAR) in toxicology, Toxicol. Sci. 56 (2000), pp. 8-17.
51. S. Wold, Cross-validation estimation of the number of components in factor and principal components analysis, Technometrics 24 (1978), pp. 397-405.
52. P. Geladi, Notes on the history and nature of partial least squares (PLS) modeling, J. Chemom. 2 (1988), pp. 231-246.
53. Y. Wang, H. Liu, C. Zhao, H. Liu, Z. Cai, and G. Jiang, Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners, Environ. Sci. Technol. 39 (2005), pp. 4961-4966.
54. B.V. Cheney, Structural factors affecting aryl hydrocarbon hydroxylase induction by dibenzopdioxins and dibenzofrurans, Int. J. Quantum Chem. 21 (1982), pp. 445-463.