Recent advances in the analysis of TBBPA/TBBPS, TBBPA/TBBPS derivatives and their transformation products

Qu, Guangbo; Liu, Aifeng; Hu, Ligang; Liu, Sijin; Shi, Jianbo; Jiang, Guibin

doi:10.1016/j.trac.2016.06.021

Cited by 61 publications

(45 citation statements)

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“…[3 -15] The levels of TCBPA, TBBPA/S, and their derivatives and transformations are increasing year by year in the environment, which leads to potential environmental and human-health risks. [1,[16][17][18][19][20][21][22][23] For instance, they have been detected in umbilical-cord serum and in breast milk with concentrations up to 649.45 ng/g and 11 ng/g, respectively. [24,25] Evidence suggests that HFRs exhibit potential neurotoxicity, endocrine disruption effects on bio-organisms, and reproductive-development toxicity.…”

Section: Introductionmentioning

confidence: 99%

“…The degradation of TBBPA derivatives from bishydroxy substitution compounds to monohydroxy substitution compounds have been predicted by the University of Minnesota Pathway Prediction System (UM-PPS). [18] And the transformed compounds are of particular concern, because they may be more toxic to the environment and organisms. [44 -46] For instance, the debromination of tetrabromobisphenol A could yield partial TBBPA derivatives under specific conditions.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted‐Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant

Guo

Cao

et al. 2020

Chemistry & Biodiversity

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As an important branch of halogenated bisphenol compounds, the halogenated bisphenol monosubstitutedether compounds have received a lot of attention in environmental health science because of their toxicity and variability. In this study, a synthetic method for bisphenol monosubstituted-ether byproduct libraries was developed. By using the versatile and efficient method, tetrachlorobisphenol A, tetrabromobisphenol A, and tetrabromobisphenol S monosubstituted alkyl-ether compounds were accessed in 39-82 % yield. Subsequently, the cytotoxicity of 27 compounds were screened using three different cell lines (HepG2, mouse primary astrocytes and Chang liver cells). Compound 2,6-dibromo-4-[3,5-dibromo-4-(2-hydroxyethoxy)benzene-1sulfonyl]phenol was more toxic than other compounds in various cells, and the sensitivity of this compound to the normal hepatocytes and cancer cells was inconsistent. The compounds 2,6-dichloro-4-(2-{3,5-dichloro-4-[(prop-2-en-1-yl)oxy]phenyl}propan-2-yl)phenol and 2,6-dibromo-4-(2-{3,5-dibromo-4-[(prop-2-en-1-yl)oxy]-phenyl}propan-2-yl)phenol were the most toxic to HepG2 cells, and most of the other compounds inhibited cell proliferation. Moreover, typical compounds were also reproductive and developmental toxic to zebrafish embryos at different concentrations. The synthetic byproduct libraries could be used as pure standard compounds and applied in research on environmental behavior and the transformation of halogenated flame retardants.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted‐Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant

Guo

Cao

et al. 2020

Chemistry & Biodiversity

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“…Tetrabromobisphenol A (TBBPA) has been considered one of the most important brominated flame retardants (BFRs) in the world, accounting for 60% of the total global BFRs market (Covaci et al, 2009;Qu et al, 2016a). It has been estimated that approximately 150,000 tons of TBBPA were produced worldwide in 2006, and its production volume increases year by year (Covaci et al, 2011;Qu et al, 2016a).…”

Section: Introductionmentioning

confidence: 99%

“…It has been estimated that approximately 150,000 tons of TBBPA were produced worldwide in 2006, and its production volume increases year by year (Covaci et al, 2011;Qu et al, 2016a). According to data from the Bromine Science Environmental Forum, approximately 18% of the TBBPA produced was used in manufacturing derivatives (Liu et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

“…According to data from the Bromine Science Environmental Forum, approximately 18% of the TBBPA produced was used in manufacturing derivatives (Liu et al, 2017). The extensive use of these chemicals has led to their widespread occurrence in the environment: several derivatives of these substances have been found in water, sewage sludge, soils, and sediments, as well as in the herring gull eggs and marine animals (Letcher and Chu, 2010;Liu et al, 2016aLiu et al, , 2016bQu et al, 2016aQu et al, , 2011Qu et al, , 2013Shi et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

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Sensitive immunoassay for simultaneous determination of tetrabromobisphenol A bis(2-hydroxyethyl) ether and tetrabromobisphenol A mono(hydroxyethyl) ether: An effective and reliable strategy to estimate the typical tetrabromobisphenol A derivative and byproduct in aquatic environments

Zhang

Zhu

Huang

et al. 2017

Environmental Pollution

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a b s t r a c tTetrabromobisphenol A bis(2-hydroxyethyl) ether (TBBPA DHEE), as one of the TBBPA derivatives, is frequently applied as a flame retardant. To date, however, little evidence has been gathered regarding its environmental behavior and fate. This is mainly attributed to the lack of an analytical approach available to measure it. Mass spectrometry cannot determine levels of TBBPA DHEE. LC-MS could not ionize TBBPA DHEE to yield enough fragments, while GC-MS could not be applied for the analysis either, due to the thermal degradation of TBBPA DHEE. We here designed a novel hapten, then conjugated it with a carrier protein and produced a type of polyclonal antibody capable of recognizing TBBPA DHEE. Based on this approach, a sensitive and high-throughput indirect competitive enzyme-linked immunosorbent assay (ELISA) was established. The respective detection limit (LOD, based on 90% B/B 0 ) and IC 50 calculated from the standard curve were 0.702 and 9.868 ng/mL for TBBPA DHEE. And the established method showed good tolerance to various matrix interferents. Using our ELISA, we measured the concentrations of these substances from environmental water samples with no pretreatment other than filtration. We found the presence of TBBPA DHEE in environmental water samples collected in Jiangsu province, and the detected concentrations ranging from 1.5 to 7.7 ng/mL. Our proposed method here could be applied to completely and systematically investigate TBBPA DHEE and TBBPA MHEE concentrations in environmental samples.

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Application of Dispersive Liquid–Liquid Microextraction Followed by High‐Performance Liquid Chromatography/Tandem Mass Spectrometry Analysis to Determine Tetrabromobisphenol A in Complex Matrices

Macêdo

Bernegossi

Sabatini

et al. 2020

Enviro Toxic and Chemistry

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An accurate and sensitive ultrasound-dispersive liquid-liquid microextraction technique followed by highperformance liquid chromatography separation coupled with electrospray ionization tandem mass spectrometry detection method to determine the presence of tetrabromobisphenol A (TBBPA) in complex environmental matrices is proposed. The miniaturized procedure was used to extract and quantify the analyte in domestic sewage, anaerobic sludge, and the aquatic test organism species Daphnia magna and Chironomus sancticaroli, which are standardized organisms for ecotoxicity bioassays. Limits of detection of 2 ng L −1 (domestic sewage), 2 ng g −1 (anaerobic sludge), 0.25 ng g −1 (D. magna), and 5 ng g −1 (C. tentans) were obtained. The presence of TBBPA was determined in domestic sewage and anaerobic sludge from an anaerobic batch bioreactor at a concentration of 0.2 ± 0.03 μg L −1 and 507 ± 79 ng g −1 , respectively. In D. magna and C. sancticaroli exposed to TBBPA in an acute toxicity bioassay, the micropollutant accumulated at 3.74 and 8.87 μg g −1 , respectively. The proposed method is a simple and cost-effective tool to determine TBBPA environmental occurrence and biomagnification potential compared with conventional extraction methods. To the best of our knowledge, this is the first liquid-liquid miniaturized extraction method to be applied to D. magna and C. sancticaroli.

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Recent advances in the analysis of TBBPA/TBBPS, TBBPA/TBBPS derivatives and their transformation products

Cited by 61 publications

References 61 publications

Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted‐Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant

Synthesis and Toxicity of Halogenated Bisphenol Monosubstituted‐Ethers: Establishing a Library for Potential Environmental Transformation Products of Emerging Contaminant

Sensitive immunoassay for simultaneous determination of tetrabromobisphenol A bis(2-hydroxyethyl) ether and tetrabromobisphenol A mono(hydroxyethyl) ether: An effective and reliable strategy to estimate the typical tetrabromobisphenol A derivative and byproduct in aquatic environments

Application of Dispersive Liquid–Liquid Microextraction Followed by High‐Performance Liquid Chromatography/Tandem Mass Spectrometry Analysis to Determine Tetrabromobisphenol A in Complex Matrices

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