ArticleChemical research in toxicology2012
In vitro metabolism of the brominated flame retardants 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate (TBPH) in human and rat tissues.
Article in Chemical research in toxicology, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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35 citing papers in PubMed, 91 citations in OpenAlex.
- SPME-based investigation of thapsigargin-induced alterations in the volatilome of human melanoma cells.Analytical and bioanalytical chemistry · 2026Article
- Update of the risk assessment on emerging and novel brominated flame retardants in food.EFSA journal. European Food Safety Authority · 2026Article
- A modified QuEChERS method coupled with GC-MS/MS for the rapid and simultaneous analysis of polybrominated diphenyl ethers and novel brominated flame retardant residues in animal-derived foods.Food chemistry: X · 2025Article
- Children's exposure to brominated flame retardants in the home: The TESIE study.Environmental pollution (Barking, Essex : 1987) · 2024Article
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- Impacts of Gestational FireMaster 550 Exposure on the Neonatal Cortex Are Sex Specific and Largely Attributable to the Organophosphate Esters.Neuroendocrinology · 2023Article
- A review of the success and challenges in characterizing human dermal exposure to flame retardants.Archives of toxicology · 2021Review
- A review on the analytical procedures of halogenated flame retardants by gas chromatography coupled with single quadrupole mass spectrometry and their levels in human samples.Environmental pollution (Barking, Essex : 1987) · 2021Review
- Bioaccumulation of Bis-(2-ethylhexyl)-3,4,5,6-tetrabromophthalate and Mono-(2-ethylhexyl)-3,4,5,6-tetrabromophthalate by Lumbriculus variegatus.Archives of environmental contamination and toxicology · 2021Article
- Mechanisms of action, chemical characteristics, and model systems of obesogens.BMC biomedical engineering · 2020Review
- Quantification of 16 urinary biomarkers of exposure to flame retardants, plasticizers, and organophosphate insecticides for biomonitoring studies.Chemosphere · 2019Article
- Characterization of the Fundulus heteroclitus embryo transcriptional response and development of a gene expression-based fingerprint of exposure for the alternative flame retardant, TBPH (bis (2-ethylhexyl)-tetrabromophthalate).Environmental pollution (Barking, Essex : 1987) · 2019Article
- Flame retardant exposure assessment: findings from a behavioral intervention study.Journal of exposure science & environmental epidemiology · 2019Article
- Bioaccumulation and effects of dietary exposure to the alternative flame retardant, bis(2-ethylhexyl) tetrabromophthalate (TBPH), in the Atlantic killifish, Fundulus heteroclitus.Environmental toxicology and chemistry · 2018Article
- Exposure to organophosphate flame retardant chemicals in the U.S. general population: Data from the 2013-2014 National Health and Nutrition Examination Survey.Environment international · 2018Article
- Associations between flame retardant applications in furniture foam, house dust levels, and residents' serum levels.Environment international · 2017Article
- Sex Specific Placental Accumulation and Behavioral Effects of Developmental Firemaster 550 Exposure in Wistar Rats.Scientific reports · 2017Article
- Disposition of the emerging brominated flame retardant, bis(2-ethylhexyl) tetrabromophthalate, in female Sprague Dawley rats: effects of dose, route and repeated administration.Xenobiotica; the fate of foreign compounds in biological systems · 2017Article
- Quantification of three chlorinated dialkyl phosphates, diphenyl phosphate, 2,3,4,5-tetrabromobenzoic acid, and four other organophosphates in human urine by solid phase extraction-high performance liquid chromatography-tandem mass spectrometry.Analytical and bioanalytical chemistry · 2017Article
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3 authors at 1 institution in 1 country.
Funding
Abstract
Due to the phaseout of polybrominated diphenyl ether (PBDE) flame retardants, new chemicals, such as 2-ethylhexyl-2,3,4,5-tetrabromobenzoate (TBB) and bis(2-ethylhexyl) 2,3,4,5-tetrabromophthalate (TBPH), have been used as replacements in some commercial flame retardant mixtures. Both chemicals have been detected in indoor dust at concentrations approaching the concentrations of PBDEs; however, little is known about their fate, metabolism, or toxicity. The goal of this study was to investigate the potential metabolism of these two brominated flame retardants in human and rat tissues by conducting in vitro experiments with liver and intestinal subcellular fractions. In all the experiments, TBB was consistently metabolized to 2,3,4,5-tetrabromobenzoic acid (TBBA) via cleavage of the 2-ethylhexyl chain without requiring any added cofactors. TBBA was also formed in purified porcine carboxylesterase but at a much faster rate of 6.29 ± 0.58 nmol min(-1) mg protein(-1). The estimated K(m) and V(max) values for TBB metabolism in human microsomes were 11.1 ± 3.9 μM and 0.644 ± 0.144 nmol min(-1) mg protein(-1), respectively. A similar K(m) of 9.3 ± 2.2 μM was calculated for porcine carboxylesterase, indicating similar enzyme specificity. While the rapid formation of TBBA may reduce the bioaccumulation potential of TBB in mammals and may be useful as a biomarker of TBB exposure, the toxicity of this brominated benzoic acid is unknown and may be a concern based on its structural similarity to other toxic pollutants. In contrast to TBB, no metabolites of TBPH were detected in human or rat subcellular fractions. However, a metabolic product of TBPH, mono(2-ethylhexyl) tetrabromophthalate (TBMEHP), was formed in purified porcine carboxylesterase at an approximate rate of 1.08 pmol min(-1) mg protein(-1). No phase II metabolites of TBBA or TBMEHP were observed. More research is needed to understand the in vivo toxicokinetics and health effects of these compounds given their current ubiquitous presence in most US households and the resulting probability of chronic exposure, particularly to young children.
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