QSPR/QSAR models for prediction of the physicochemical properties and biological activity of polybrominated diphenyl ethers

Xu, Hui; Zou, Jian‐Wei; Q, Yu; Wang, Yanhua; Zhang, Jianying; Jin, Haixiao

doi:10.1016/j.chemosphere.2006.07.072

Cited by 67 publications

(35 citation statements)

References 34 publications

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“…37 The diffusion coefficients of a family of quinones, nitroaromatics, ferrocenes, and aromatic hydrocarbons, which have molecular densities on the same order of magnitude, in acetonitrile, dimethyl sulfoxide, and dimethylformamide were also found to depend linearly on their molecular weights. 38,39 Based on the molecular volumes (0.18−0.34 nm 3 ) calculated from QSAR/QSPR, 40 PBDEs are expected to have roughly comparable molecular densities (2.38 ± 0.35 × 10 −3 nm −3 ). Thus, the linear dependence of the diffusion coefficients of PBDEs on molecular weights can be explained by a model derived from linearization of the rearrangement of the Stokes−Einstein equation, 38,39 which can also be used to predict the diffusion coefficients of other PBDEs.…”

Section: Environmental Science and Technologymentioning

confidence: 99%

Kinetics of Brominated Flame Retardant (BFR) Releases from Granules of Waste Plastics

Sun

Cheng

et al. 2016

Environ. Sci. Technol.

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Plastic components of e-waste contain high levels of brominated flame retardants (BFRs), whose releases cause environmental and human health concerns. This study characterized the release kinetics of polybrominated diphenyl ethers (PBDEs) from millimeter-sized granules processed from the plastic exteriors of two scrap computer displays at environmentally relevant temperatures. The release rate of a substitute of PBDEs, 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE), from the waste plastics, was reported for the first time. Deca-BDE was the most abundant PBDE congeners in both materials (87−89%), while BTBPE was also present at relatively high contents. The release kinetics of BFRs could be modeled as one-dimensional diffusion, while the temperature dependence of diffusion coefficients was well described by the Arrhenius equation. The diffusion coefficients of BFRs (at 30°C) in the plastic matrices were estimated to be in the range of 10 −27.16 to 10 −19.96 m 2 ·s −1 , with apparent activation energies between 88.4 and 154.2 kJ·mol −1 . The half-lives of BFR releases (i.e., 50% depletion) from the plastic granules ranged from thousands to tens of billions of years at ambient temperatures. These findings suggest that BFRs are released very slowly from the matrices of waste plastics through molecular diffusion, while their emissions can be significantly enhanced with wear-and-tear and pulverization.

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Section: Environmental Science and Technologymentioning

confidence: 99%

Kinetics of Brominated Flame Retardant (BFR) Releases from Granules of Waste Plastics

Sun

Cheng

et al. 2016

Environ. Sci. Technol.

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“…QSPR has been successfully applied in the partition property prediction of PBDEs. [21,22] However, a training set is needed to set up the relationships between the properties and structural descriptors.…”

Section: Introductionmentioning

confidence: 99%

RP-HPLC measurement and quantitative structure - property relationship analysis of the n-octanol - water partitioning coefficients of selected metabolites of polybrominated diphenyl ethers

Yu¹,

Yang²,

Gao³

et al. 2008

Environ. Chem.

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Environmental context. Polybrominated diphenyl ethers (PBDEs) are ubiquitous environmental contaminants and numerous studies have demonstrated a marked increase in the levels of PBDEs in human biological tissues and fluids, especially breast milk. How PBDEs are transported through the environment, taken up by biota, transported across membranes, and metabolised depends strongly on such fundamental properties as lipophilicity (log K OW ). However, very little data on log K OW exist for PBDEs. In the present paper, the authors determine PBDE metabolites' log K OW using reversed-phase high performance liquid chromatography, as recommended by the Organisation for Economic Co-operation and Development and US Environmental Protection Agency, along with quantitative structure-property relationships.Abstract. n-Octanol-water partitioning coefficient (log K OW ) values of selected hydroxylated and methoxylated polybrominated diphenyl ether metabolites were measured for the first time by reversed-phase high performance liquid chromatography (RP-HPLC) using a C18 stationary phase with a water/methanol mixture as a mobile phase. The retention parameters, log k w (extrapolated retention indices) and k (gradient retention indices) were calibrated to log K OW by a set of calibration standards. For the PBDE metabolites investigated, extrapolated retention indices from isocratic elution seem to be more reliable and their RP-HPLC-derived log K OW values were found to range from 4.63 to 7.67. Some commonly available software, including ClogP, KowWin, AclogP, MlogP, AlogP, MilogP, and XlogP, was used to estimate the log K OW values of the analytes. Significant correlations were obtained between the RP-HPLC-derived log K OW and the software-computed log K OW , with squared correlation coefficients (R 2 ) ranging from 0.793 to 0.922, but the difference between them was also significant. Then a quantitative structure-property relationship model based on topological descriptors was established and showed good reliability and predictive power for the estimation of RP-HPLC-derived log K OW values of PBDE metabolites. It was applied to estimate the log K OW values of some PBDE metabolites that are commercially available or have appeared in the literature. Lastly, factor analysis was carried out using the theoretical linear salvation/free-energy relationships, which indicated the average polarisability (α) and the most negative atomic partial Mulliken charge in the molecule (q − ) were the most important parameters affecting their partition between n-octanol and water, supporting the factorisation of log K OW in bulk and electronic terms.

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“…Unidentified PBDEs can be presumptively identified by comparing relative retention time and order with those reported in the retention studies of non-BDEs including BDE207 and BDE208 [9,23], and octa-BDEs [24][25][26][27]. For BDE209 quantitative analysis, the method detection limit (MDL) was 0.01 µg$L -1 and the method recovery was greater than 80%.…”

Section: Methodsmentioning

confidence: 99%

Removing polybrominated diphenyl ethers in pure water using Fe/Pd bimetallic nanoparticles

Zhang

Lü

et al. 2015

Front. Environ. Sci. Eng.

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Polybrominated diphenyl ethers (PBDEs) have been widely used as fire-retardants. Due to their high production volume, widespread usage, and environmental persistence, PBDEs have become ubiquitous contaminants in various environments.Nanoscale zero-valent iron (ZVI) is an effective reductant for many halogenated organic compounds. To enhance the degradation efficiency, ZVI/ Palladium bimetallic nanoparticles (nZVI/Pd) were synthesized in this study to degrade decabromodiphenyl ether (BDE209) in water. Approximately 90% of BDE209 was rapidly removed by nZVI/Pd within 80 min, whereas about 25% of BDE209 was removed by nZVI. Degradation of BDE209 by nZVI/Pd fits pseudo-first-order kinetics. An increase in pH led to sharply decrease the rate of BDE209 degradation. The degradation rate constant in the treatment with initial pH at 9.0 was more than 6.8 Â higher than that under pH 5.0. The degradation intermediates of BDE209 by nZVI/Pd were identified and the degradation pathways were hypothesized. Results from this study suggest that nZVI/Pd may be an effective tool for treating polybrominated diphenyl ethers (PBDEs) in water.

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QSPR/QSAR models for prediction of the physicochemical properties and biological activity of polybrominated diphenyl ethers

Cited by 67 publications

References 34 publications

Kinetics of Brominated Flame Retardant (BFR) Releases from Granules of Waste Plastics

Kinetics of Brominated Flame Retardant (BFR) Releases from Granules of Waste Plastics

RP-HPLC measurement and quantitative structure - property relationship analysis of the n-octanol - water partitioning coefficients of selected metabolites of polybrominated diphenyl ethers

Removing polybrominated diphenyl ethers in pure water using Fe/Pd bimetallic nanoparticles

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