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Volumn 23, Issue 5, 2010, Pages 946-954

QSAR modeling and prediction of the endocrine-disrupting potencies of brominated flame retardants

Author keywords

[No Author keywords available]

Indexed keywords

2,4,6 TRIBROMOPHENOL; AROMATIC HYDROCARBON RECEPTOR; BROMINATED FLAME RETARDANT; BROMINE; DIOXIN; ENDOCRINE DISRUPTOR; ESTROGEN RECEPTOR; FLAME RETARDANT; PROGESTERONE RECEPTOR; TETRABROMOBISPHENOL A; TETRABROMOBISPHENOL A BIS(2,3) DIBROMOPROPYL ETHER; UNCLASSIFIED DRUG;

EID: 77952353333     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx1000392     Document Type: Article
Times cited : (43)

References (48)
  • 1
    • 33745849215 scopus 로고    scopus 로고
    • Biomagnification of PBDEs and PCBs in food webs from the Baltic Sea and the northern Atlantic ocean
    • Burreau, S., Zebuhr, Y., Broman, D., and Ishaq, R. (2006) Biomagnification of PBDEs and PCBs in food webs from the Baltic Sea and the northern Atlantic ocean Sci. Total Environ. 366, 659-672
    • (2006) Sci. Total Environ. , vol.366 , pp. 659-672
    • Burreau, S.1    Zebuhr, Y.2    Broman, D.3    Ishaq, R.4
  • 3
    • 0242350966 scopus 로고    scopus 로고
    • A review on human exposure to brominated flame retardants- Particularly polybrominated diphenyl ethers
    • Sjödin, A., Patterson, D. G., and Bergman, (2003) A review on human exposure to brominated flame retardants- Particularly polybrominated diphenyl ethers Environ. Int. 29, 829-839
    • (2003) Environ. Int. , vol.29 , pp. 829-839
    • Sjödin, A.1    Patterson, D.G.2    Bergman, .3
  • 4
    • 0036223196 scopus 로고    scopus 로고
    • An overview of brominated flame retardants in the environment
    • de Wit, C. A. (2002) An overview of brominated flame retardants in the environment Chemosphere 46, 583-624
    • (2002) Chemosphere , vol.46 , pp. 583-624
    • De Wit, C.A.1
  • 5
    • 33744811426 scopus 로고    scopus 로고
    • Brominated flame retardant concentrations and trends in abiotic media
    • Hale, R. C., La Guardia, M. J., Harvey, E., Gaylor, M. O., and Mainor, T. M. (2006) Brominated flame retardant concentrations and trends in abiotic media Chemosphere 64, 181-186
    • (2006) Chemosphere , vol.64 , pp. 181-186
    • Hale, R.C.1    La Guardia, M.J.2    Harvey, E.3    Gaylor, M.O.4    Mainor, T.M.5
  • 6
    • 0242319569 scopus 로고    scopus 로고
    • Levels and trends of polybrominated diphenylethers and other brominated flame retardants in wildlife
    • Law, R. J., Alaee, M., Allchin, C. R., Boon, J. P., Lebeuf, M., Lepom, P., and Stern, G. A. (2003) Levels and trends of polybrominated diphenylethers and other brominated flame retardants in wildlife Environ. Int. 29, 757-770
    • (2003) Environ. Int. , vol.29 , pp. 757-770
    • Law, R.J.1    Alaee, M.2    Allchin, C.R.3    Boon, J.P.4    Lebeuf, M.5    Lepom, P.6    Stern, G.A.7
  • 8
    • 33750848245 scopus 로고    scopus 로고
    • Polybrominated diphenyl ethers: A case study for using biomonitoring data to address risk assessment questions
    • Birnbaum, L. S. and Cohen Hubal, E. A. (2006) Polybrominated diphenyl ethers: A case study for using biomonitoring data to address risk assessment questions Environ. Health Perspect. 114, 1770-1775
    • (2006) Environ. Health Perspect. , vol.114 , pp. 1770-1775
    • Birnbaum, L.S.1    Cohen Hubal, E.A.2
  • 10
    • 32044467384 scopus 로고    scopus 로고
    • Effects of developmental exposure to 2,2′,4,4′,5- pentabromodiphenyl ether (PBDE-99) on sex steroids, sexual development, and sexually dimorphic behavior in rats
    • Lilienthal, H., Hack, A., Roth-Harer, A., Grande, S. W., and Talsness, C. E. (2006) Effects of developmental exposure to 2,2′,4,4′,5- pentabromodiphenyl ether (PBDE-99) on sex steroids, sexual development, and sexually dimorphic behavior in rats Environ. Health Perspect. 114, 194-201
    • (2006) Environ. Health Perspect. , vol.114 , pp. 194-201
    • Lilienthal, H.1    Hack, A.2    Roth-Harer, A.3    Grande, S.W.4    Talsness, C.E.5
  • 13
    • 0035884494 scopus 로고    scopus 로고
    • Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah Receptor mediated pathway
    • Chen, G., Konstantinov, A. D., Chittim, B. G., Joyce, E. M., Bols, N. C., and Bunce, N. J. (2001) Synthesis of polybrominated diphenyl ethers and their capacity to induce CYP1A by the Ah Receptor mediated pathway Environ. Sci. Technol. 35, 3749-3756
    • (2001) Environ. Sci. Technol. , vol.35 , pp. 3749-3756
    • Chen, G.1    Konstantinov, A.D.2    Chittim, B.G.3    Joyce, E.M.4    Bols, N.C.5    Bunce, N.J.6
  • 15
    • 40349116028 scopus 로고    scopus 로고
    • Brominated flame retardants as possible endocrine disrupters
    • Darnerud, P. O. (2008) Brominated flame retardants as possible endocrine disrupters Int. J. Androl. 31, 152-160
    • (2008) Int. J. Androl. , vol.31 , pp. 152-160
    • Darnerud, P.O.1
  • 16
    • 0034994036 scopus 로고    scopus 로고
    • Effects of polybrominated diphenyl ethers (PBDEs) and polychlorinated biphenyls (PCBs) on thyroid hormone and vitamin A levels in rats and mice
    • Hallgren, S., Sinjari, T., Hakansson, H., and Darnerud, P. O. (2001) Effects of polybrominated diphenyl ethers (PBDEs) and polychlorinated biphenyls (PCBs) on thyroid hormone and vitamin A levels in rats and mice Arch. Toxicol. 75, 200-208
    • (2001) Arch. Toxicol. , vol.75 , pp. 200-208
    • Hallgren, S.1    Sinjari, T.2    Hakansson, H.3    Darnerud, P.O.4
  • 17
    • 77952395065 scopus 로고    scopus 로고
    • European Commission. Directive 2002/95/EC of the European Parliament and of the council of January 27, 2003 on the restriction of the use of certain hazardous substances in electrical and electronic equipment
    • European Commission. (2003) Directive 2002/95/EC of the European Parliament and of the council of January 27, 2003 on the restriction of the use of certain hazardous substances in electrical and electronic equipment. Off. J. Eur. Commun. L 37, 19.
    • (2003) Off. J. Eur. Commun. , vol.5037 , pp. 19
  • 18
    • 57849163560 scopus 로고    scopus 로고
    • Brominated flame retardants in the European chemicals policy of REACH-Regulation and determination in materials
    • Kemmlein, S., Herzke, D., and Law, R. J. (2009) Brominated flame retardants in the European chemicals policy of REACH-Regulation and determination in materials J. Chromatogr. A 1216, 320-333
    • (2009) J. Chromatogr. A , vol.1216 , pp. 320-333
    • Kemmlein, S.1    Herzke, D.2    Law, R.J.3
  • 19
    • 77952340930 scopus 로고    scopus 로고
    • REACH Regulation (EC) No. 1907/2006
    • REACH Regulation (EC) No. 1907/2006; http://eur-lex.europa.eu/LexUriServ/ site/en/oj/2006/l-396/l-39620061230en00010849.pdf.
  • 20
    • 40849102532 scopus 로고    scopus 로고
    • Polybrominated diphenyl ethers (PBDEs) and bioaccumulative hydroxylated PBDE metabolites in young humans from Managua, Nicaragua
    • Athanasiadou, M., Cuadra, S. N., Marsh, G., Bergman, A., and Jakobsson, K. (2008) Polybrominated diphenyl ethers (PBDEs) and bioaccumulative hydroxylated PBDE metabolites in young humans from Managua, Nicaragua Environ. Health Perspect. 116, 400-408
    • (2008) Environ. Health Perspect. , vol.116 , pp. 400-408
    • Athanasiadou, M.1    Cuadra, S.N.2    Marsh, G.3    Bergman, A.4    Jakobsson, K.5
  • 21
    • 0343580450 scopus 로고    scopus 로고
    • Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota
    • Haglund, P. S., Zook, D. R., Buser, H. R., and Hu, J. W. (1997) Identification and quantification of polybrominated diphenyl ethers and methoxy-polybrominated diphenyl ethers in Baltic biota Environ. Sci. Technol. 31, 3281-3287
    • (1997) Environ. Sci. Technol. , vol.31 , pp. 3281-3287
    • Haglund, P.S.1    Zook, D.R.2    Buser, H.R.3    Hu, J.W.4
  • 22
    • 77952394592 scopus 로고    scopus 로고
    • CADASTER FP 7 PROJECT:; www.cadaster.eu
    • CADASTER FP 7 PROJECT: http://cordis.europa.eu/search/index.cfm- fuseaction=proj.document&PJ-LANG=EN&PJ-RCN=10374303; www.cadaster.eu.
  • 23
    • 0015417054 scopus 로고
    • Chance correlations in structure-activity studies using multiple regression analysis
    • Topliss, J. G. and Costello, R. J. (1972) Chance correlations in structure-activity studies using multiple regression analysis J. Med. Chem. 15, 1066-1068
    • (1972) J. Med. Chem. , vol.15 , pp. 1066-1068
    • Topliss, J.G.1    Costello, R.J.2
  • 24
    • 77952388627 scopus 로고    scopus 로고
    • OECD Quantitative Structure-Activity Relationships [(Q)SARs] Project Available online at
    • OECD Quantitative Structure-Activity Relationships [(Q)SARs] Project Available online at http://www.oecd.org/document/23/0,3343,fr-2649-34365- 33957015-1-1-1-1,00.html.
  • 25
    • 22044440858 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners
    • Wang, Y., Liu, H., Zhao, C., Liu, H., Cai, Z., and Jiang, G. (2005) Quantitative structure-activity relationship models for prediction of the toxicity of polybrominated diphenyl ether congeners Environ. Sci. Technol. 39, 4961-4966
    • (2005) Environ. Sci. Technol. , vol.39 , pp. 4961-4966
    • Wang, Y.1    Liu, H.2    Zhao, C.3    Liu, H.4    Cai, Z.5    Jiang, G.6
  • 26
    • 33745241632 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship for prediction of the toxicity of polybrominated diphenyl ether (PBDE) congeners
    • Wang, Y., Zhao, C., Ma, W., Liu, H., Wang, T., and Jiang, G. (2006) Quantitative structure-activity relationship for prediction of the toxicity of polybrominated diphenyl ether (PBDE) congeners Chemosphere 64, 515-524
    • (2006) Chemosphere , vol.64 , pp. 515-524
    • Wang, Y.1    Zhao, C.2    Ma, W.3    Liu, H.4    Wang, T.5    Jiang, G.6
  • 27
    • 33845241919 scopus 로고    scopus 로고
    • QSPR/QSAR models for prediction of the physicochemical properties and biological activity of polybrominated diphenyl ethers
    • Xu, H.-Y., Zou, J.-W., Yu, Q.-S., Wang, Y.-H., Zhang, J.-Y., and Jin, H.-X. (2007) QSPR/QSAR models for prediction of the physicochemical properties and biological activity of polybrominated diphenyl ethers Chemosphere 66, 1998-2010
    • (2007) Chemosphere , vol.66 , pp. 1998-2010
    • Xu, H.-Y.1    Zou, J.-W.2    Yu, Q.-S.3    Wang, Y.-H.4    Zhang, J.-Y.5    Jin, H.-X.6
  • 28
    • 34250681044 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship study on the Ah receptor binding affinities of polybrominated diphenyl ethers using a support vector machine
    • Zheng, G., Xiao, M., and Lu, X. (2007) Quantitative structure-activity relationship study on the Ah receptor binding affinities of polybrominated diphenyl ethers using a support vector machine QSAR Comb. Sci. 26, 536-541
    • (2007) QSAR Comb. Sci. , vol.26 , pp. 536-541
    • Zheng, G.1    Xiao, M.2    Lu, X.3
  • 29
    • 34247515897 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship modeling on in vitro endocrine effects and metabolic stability involving 26 selected brominated flame retardants
    • Harju, M., Hamers, T., Kamstra, J. H., Sonneveld, E., Boon, J. P., Tysklind, M., and Andersson, P. L. (2007) Quantitative structure-activity relationship modeling on in vitro endocrine effects and metabolic stability involving 26 selected brominated flame retardants Environ. Toxicol. Chem. 26, 816-826
    • (2007) Environ. Toxicol. Chem. , vol.26 , pp. 816-826
    • Harju, M.1    Hamers, T.2    Kamstra, J.H.3    Sonneveld, E.4    Boon, J.P.5    Tysklind, M.6    Andersson, P.L.7
  • 30
    • 41949131790 scopus 로고    scopus 로고
    • Biotransformation of brominated flame retardants into potentially endocrine-disrupting metabolites, with special attention to 2,2′,4, 4′-tetrabromodiphenyl ether (BDE-47)
    • Hamers, T., Kamstra, J. H., Sonneveld, E., Murk, A. J., Visser, T. J., Van Velzen, M. J. M., Brouwer, A., and Bergman, A. (2008) Biotransformation of brominated flame retardants into potentially endocrine-disrupting metabolites, with special attention to 2,2′,4,4′-tetrabromodiphenyl ether (BDE-47) Mol. Nutr. Food Res. 52, 284-298
    • (2008) Mol. Nutr. Food Res. , vol.52 , pp. 284-298
    • Hamers, T.1    Kamstra, J.H.2    Sonneveld, E.3    Murk, A.J.4    Visser, T.J.5    Van Velzen, M.J.M.6    Brouwer, A.7    Bergman, A.8
  • 32
    • 72149125979 scopus 로고    scopus 로고
    • Hypercube, Inc., Hypercube, Inc., Florida
    • Hypercube, Inc. (2000) HYPERCHEM 7.03 for Windows, Hypercube, Inc., Florida.
    • (2000) HYPERCHEM 7.03 for Windows
  • 35
    • 0033557262 scopus 로고    scopus 로고
    • The K correlation index: Theory development and its application in chemometrics
    • Todeschini, R., Maiocchi, A., and Consonni, V. (1999) The K correlation index: Theory development and its application in chemometrics Chemom. Intell. Lab. 46, 13-29
    • (1999) Chemom. Intell. Lab. , vol.46 , pp. 13-29
    • Todeschini, R.1    Maiocchi, A.2    Consonni, V.3
  • 36
    • 0038724207 scopus 로고    scopus 로고
    • The importance of being Earnest: Validation is the absolute essential for successful application and interpretation of QSPR models
    • Tropsha, A., Gramatica, P., and Gombar, V. K. (2003) The importance of being Earnest: Validation is the absolute essential for successful application and interpretation of QSPR models QSAR Comb. Sci. 22, 69-77
    • (2003) QSAR Comb. Sci. , vol.22 , pp. 69-77
    • Tropsha, A.1    Gramatica, P.2    Gombar, V.K.3
  • 37
    • 34250628103 scopus 로고    scopus 로고
    • Principles of QSAR models validation: Internal and external
    • Gramatica, P. (2007) Principles of QSAR models validation: Internal and external QSAR Comb. Sci. 26, 694-701
    • (2007) QSAR Comb. Sci. , vol.26 , pp. 694-701
    • Gramatica, P.1
  • 38
    • 68149182282 scopus 로고    scopus 로고
    • Comments on the definition of the Q2 parameter for QSAR validation
    • Consonni, V., Ballabio, D., and Todeschini, R. (2009) Comments on the definition of the Q2 parameter for QSAR validation J. Chem. Inf. Model. 49, 1669-1678
    • (2009) J. Chem. Inf. Model. , vol.49 , pp. 1669-1678
    • Consonni, V.1    Ballabio, D.2    Todeschini, R.3
  • 40
    • 0001219854 scopus 로고    scopus 로고
    • Deriving the 3D structure of organic molecules from their infrared spectra
    • Hemmer, M. C., Steinhauer, V., and Gasteiger, J. (1999) Deriving the 3D structure of organic molecules from their infrared spectra Vib. Spectrosc. 19, 151-164
    • (1999) Vib. Spectrosc. , vol.19 , pp. 151-164
    • Hemmer, M.C.1    Steinhauer, V.2    Gasteiger, J.3
  • 41
    • 0030934104 scopus 로고    scopus 로고
    • 3D-modelling and prediction by WHIM descriptors. Part 5. Theory development and chemical meaning of the WHIM descriptors
    • Todeschini, R. and Gramatica, P. (1997) 3D-modelling and prediction by WHIM descriptors. Part 5. Theory development and chemical meaning of the WHIM descriptors Quant. Struct. Act. Relat. 16, 113-119
    • (1997) Quant. Struct. Act. Relat. , vol.16 , pp. 113-119
    • Todeschini, R.A.G.P.1
  • 42
    • 0000224701 scopus 로고    scopus 로고
    • The coding of the three-dimensional structure of molecules by molecular transforms and its application to structure spectra correlations and studies of biological activity
    • Schuur, J. H., Selzer, P., and Gasteiger, J. (1996) The coding of the three-dimensional structure of molecules by molecular transforms and its application to structure spectra correlations and studies of biological activity J. Chem. Inf. Comput. Sci. 36, 334-344
    • (1996) J. Chem. Inf. Comput. Sci. , vol.36 , pp. 334-344
    • Schuur, J.H.1    Selzer, P.2    Gasteiger, J.3
  • 43
    • 0000960565 scopus 로고
    • The contiguity ratio and statistical mapping
    • Geary, R. C. (1954) The contiguity ratio and statistical mapping Incorp. Statist. 5, 115-145
    • (1954) Incorp. Statist. , vol.5 , pp. 115-145
    • Geary, R.C.1
  • 44
    • 76549254593 scopus 로고
    • Notes on continuous stochastic phenomena
    • Moran, P. A. P. (1950) Notes on continuous stochastic phenomena Biometrika 37, 17-23
    • (1950) Biometrika , vol.37 , pp. 17-23
    • Moran, P.A.P.1
  • 45
    • 0004315104 scopus 로고    scopus 로고
    • (Mannhold, R., Kubinyi, H., and Timmerman, H., Eds.), Wiley-VCH, Weinheim
    • Todeschini, R. and Consonni, V. (2000) In Handbook of Molecular Descriptors (Mannhold, R., Kubinyi, H., and Timmerman, H., Eds.) Vol. 11, Wiley-VCH, Weinheim.
    • (2000) Handbook of Molecular Descriptors , vol.11
    • Todeschini, R.1    Consonni, V.2
  • 46
    • 0036963632 scopus 로고    scopus 로고
    • Potent inhibition of estrogen sulfotransferase by hydroxylated metabolites of polyhalogenated aromatic hydrocarbons reveals alternative mechanism for estrogenic activity of endocrine disrupters
    • Kester, M. H. A., Bulduk, S., Van Toor, H., Tibboel, D., Meinl, W., Glatt, H., Falany, C. N., Coughtrie, M. W. H., Schuur, A. G., Brouwer, A., and Visser, T. J. (2002) Potent inhibition of estrogen sulfotransferase by hydroxylated metabolites of polyhalogenated aromatic hydrocarbons reveals alternative mechanism for estrogenic activity of endocrine disrupters J. Clin. Endocrinol. Metab. 87, 1142-1150
    • (2002) J. Clin. Endocrinol. Metab. , vol.87 , pp. 1142-1150
    • Kester, M.H.A.1    Bulduk, S.2    Van Toor, H.3    Tibboel, D.4    Meinl, W.5    Glatt, H.6    Falany, C.N.7    Coughtrie, M.W.H.8    Schuur, A.G.9    Brouwer, A.10    Visser, T.J.11
  • 47
    • 77952326585 scopus 로고    scopus 로고
    • Current state of knowledge and monitoring requirements- Emerging "new" brominated flame retardants in flame retarded products and the environment (TA-2462/2009)
    • Norwegian Pollution Control Authority. Current state of knowledge and monitoring requirements- Emerging "new" brominated flame retardants in flame retarded products and the environment (TA-2462/2009); http://www.sft.no/publikasjoner/2462/ta2462.pdf.
    • Norwegian Pollution Control Authority


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