2-2--4-5--tetrabromodiphenyl-ether and 2-2--4-4--tetrabromodiphenyl-ether

PBDEs occur in a range of commonly consumed foods but there is very little current information on occurrence in dietary supplements such as cod liver oil or cod livers used as food. This study retrospectively investigated a number of these products, sourced from the Baltic Sea and North Atlantic, historically dating from 1972 to 2017. For the sum of 17 measured PBDEs (ΣPBDE), the concentrations ranged from 9.9 to 415 ng g

Topics: Animals; Baltic States; Environmental Exposure; Environmental Monitoring; Flame Retardants; Gadus morhua; Halogenated Diphenyl Ethers; Humans; Iceland; Liver; Norway; Polybrominated Biphenyls; Retrospective Studies; Water Pollutants, Chemical

A combination of previous studies and the present study indicated species-specific debromination of polybromodiphenyl ethers (PBDEs) in teleost fish. Three situations of debromination were found, namely rapid debromination represented by debromination of BDE 99 to BDE 47 observed in common carp, tilapia, crucian carp, and oscar fish; slow debromination represented by debromination of BDE 99 to BDE 49 observed in the abovementioned fish and rainbow trout, salmon, and snakehead; and no or minor debromination observed in catfish. The results of experiments on cofactors, inhibitors, and substrate competitors indicated that activities of outer ring deiodinase of 3, 3', 5'-triiodothyronine (type I deiodinase), which cannot be inhibited by 6-propyl-2-thiouracil, were responsible for the rapid debromination, and the outer ring deiodinase of thyroxine (type II deiodinase) regulated the slow debromination. The debromination of BDE 99 to BDE 49 was more common, but occurred at a much lower rate (approximately 100 times lower) than the debromination of BDE 99 to BDE 47. This was because the activity of type II deiodinase was nearly two orders of magnitude lower than that of type I deiodinase in the fish species studied. Further studies on debromination of PBDEs and properties of deiodinase in more species are needed to confirm the hypothesis.

Topics: Animals; Carps; Catfishes; Fishes; Halogenated Diphenyl Ethers; Inactivation, Metabolic; Iodide Peroxidase; Oncorhynchus mykiss; Salmon; Species Specificity; Water Pollutants, Chemical

The occurrence of polybrominated diphenyl ethers (PBDEs), hexabromocyclododecanes (HBCDs), tetrabromobisphenol A (TBBPA) and other phenolic brominated flame retardants (BFRs) in Irish foodstuffs has been assessed. A total of 53 food samples including eggs, milk, fish, fat and offal were tested. Eighty-one percent of the samples contained at least one measurable PBDE congener. The most abundant and frequently occurring congeners were BDE-47, BDE-49, BDE-99, BDE-100 and BDE-209 with the highest concentrations found in fish, fat and eggs. Summed concentrations for the measured PBDEs ranged from 0.02 μg/kg to 1.37 μg/kg whole weight. At least one HBCD stereoisomer was found in twenty-six percent of the samples with α-HBCD being the most frequently detected. The highest concentrations were found in fat and oily fish samples. TBBPA was only detected in one farmed salmon sample at 0.01 μg/kg. Bromophenol residues were found in fourteen out of the 53 samples, specifically in eggs and fish, with concentrations ranging from 0.28 to 0.98 μg/kg whole weight. These data contribute to the EU-wide EFSA risk assessment on these contaminants that is currently underway.

Topics: Animals; Dietary Exposure; Eggs; Environmental Monitoring; Environmental Pollutants; Fishes; Flame Retardants; Food Contamination; Halogenated Diphenyl Ethers; Humans; Hydrocarbons, Brominated; Polybrominated Biphenyls; Polychlorinated Biphenyls

In the present study, we investigated the oxidative biotransformation of 2,2',4,4'-tetrabromodiphenyl ether (BDE-47) and 2,2',4,4',5-pentabromodiphenyl ether (BDE-99) by liver microsomes from wild lesser snow geese (Chen caerulescens caerulescens) and domesticated Japanese quail (Coturnix japonica). Formation of hydroxy-metabolites was analyzed using an ultra-high performance liquid chromatography-tandem mass spectrometry-based method. Incubation of BDE-47 with avian liver microsomes produced sixteen hydroxy-metabolites, eight of which were identified using authentic standards. The major metabolites formed by liver microsomes from individual lesser snow geese were 4-hydroxy-2,2',3,4'-tetrabromodiphenyl ether (4-OH-BDE-42), 3-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (3-OH-BDE-47), and 4'-hydroxy-2,2',4,5'-tetrabromodiphenyl ether (4'-OH-BDE-49). By comparison, 4-OH-BDE-42 and 4'-OH-BDE-49, but not 3-OH-BDE-47, were major metabolites of Japanese quail liver microsomes. Unidentified metabolites included monohydroxy- and dihydroxy-tetrabromodiphenyl ethers. Incubation of BDE-99 with avian liver microsomes produced seventeen hydroxy-metabolites, twelve of which were identified using authentic standards. The major metabolites formed by lesser snow goose liver microsomes were 2,4,5-tribromophenol, 3-OH-BDE-47, 4'-OH-BDE-49, 4-hydroxy-2,2',3,4',5-pentabromodiphenyl ether (4-OH-BDE-90), and 5'-hydroxy-2,2',4,4',5-pentabromodiphenyl ether (5'-OH-BDE-99). By comparison, the major metabolites produced by liver microsomes from Japanese quail included 6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (6-OH-BDE-47) and 2-hydroxy-2',3,4,4',5-pentabromodiphenyl ether (2-OH-BDE-123), but not 3-OH-BDE-47. Unidentified metabolites consisted of monohydroxy-pentabromodiphenyl ethers, monohydroxy-tetrabromodiphenyl ethers and dihydroxy-tetrabromodiphenyl ethers. Another difference between the two species was that formation rates of BDE-47 and BDE-99 metabolites were greater with liver microsomes from male than female Japanese quail, but a sex difference was not observed with lesser snow geese.

Topics: Animals; Biotransformation; Coturnix; Environmental Pollutants; Geese; Halogenated Diphenyl Ethers; Male; Microsomes, Liver; Oxidation-Reduction; Polybrominated Biphenyls

Polybrominated diphenyl ethers (PBDEs) are widespread environmental contaminants associated with adverse neurodevelopmental outcomes in children and preclinical models; however, the mechanisms by which PBDEs cause developmental neurotoxicity remain speculative. The structural similarity between PBDEs and nondioxin-like (NDL) polychlorinated biphenyls (PCBs) suggests shared toxicological properties. Consistent with this, both NDL PCBs and PBDEs have been shown to stabilize ryanodine receptors (RyRs) in the open configuration. NDL PCB effects on RyR activity are causally linked to increased dendritic arborization, but whether PBDEs similarly enhance dendritic growth is not known. In this study, we quantified the effects of individual PBDE congeners on not only dendritic but also axonal growth since both are regulated by RyR-dependent mechanisms, and both are critical determinants of neuronal connectivity. Neuronal-glial co-cultures dissociated from the neonatal rat hippocampus were exposed to BDE-47 or BDE-49 in the culture medium. At concentrations ranging from 20 pM to 2 µM, neither PBDE congener altered dendritic arborization. In contrast, at concentrations ≥ 200 pM, both congeners delayed neuronal polarization resulting in significant inhibition of axonal outgrowth during the first few days in vitro. The axon inhibitory effects of these PBDE congeners occurred independent of cytotoxicity, and were blocked by pharmacological antagonism of RyR or siRNA knockdown of RyR2. These results demonstrate that the molecular and cellular mechanisms by which PBDEs interfere with neurodevelopment overlap with but are distinct from those of NDL PCBs, and suggest that altered patterns of neuronal connectivity may contribute to the developmental neurotoxicity of PBDEs.

Topics: Animals; Animals, Newborn; Calcium Signaling; Cell Survival; Coculture Techniques; Dose-Response Relationship, Drug; Female; Halogenated Diphenyl Ethers; Hippocampus; Male; Neuroglia; Neuronal Outgrowth; Neurons; Primary Cell Culture; Rats, Sprague-Dawley; Ryanodine Receptor Calcium Release Channel

This study evaluated decabromodiphenyl ether (BDE-209) anaerobic debromination and bacterial community changes in mangrove sediment. BDE-209 debromination rates were enhanced with zerovalent iron compared to without zerovalent iron in the sediment. BDE-209 debromination rates in microcosms constructed with sediments collected in autumn were higher than in microcosms constructed with sediments collected in spring and were higher at the Bali sampling site than the Guandu sampling site. The intermediate products resulting from the reductive debromination of BDE-209 in sediment were nona-BDE (BDE-206, BDE-207), octa-BDEs (BDE-196, BDE-197), hepta-BDEs (BDE-183, BDE-184, BDE-191), hexa-BDEs (BDE-137, BDE-138, BDE-154, BDE-157), penta-BDEs (BDE-85, BDE-99, BDE-100, BDE-126), tetra-BDEs (BDE-47, BDE-49, BDE-66, BDE-77), tri-BDEs (BDE-17, BDE-28), and di-BDEs (BDE-15). Fifty bacterial genera associated with BDE-209 debromination were identified. Overall, 12 of the 50 bacterial genera were reported to be involved in dehalogenation of aromatic compounds. These bacteria have high potential to be BDE-209 debromination bacteria. Different combinations of bacterial community composition exhibit different abilities for BDE-209 anaerobic debromination.

Topics: Bacteria; Biodegradation, Environmental; Halogenated Diphenyl Ethers; Polybrominated Biphenyls; Wetlands

Polar bears are at the top of the Arctic marine food chain and are subject to exposure and bioaccumulation of environmental chemicals of concern such as polybrominated diphenyl ethers (PBDEs), which were widely used as flame retardants. The aim of the present study was to evaluate the in vitro oxidative metabolism of 2,2',4,4'-tetrabrominated diphenyl ether (BDE-47) and 2,2',4,4',5-pentabrominated diphenyl ether (BDE-99) by polar bear liver microsomes. The identification and quantification of the hydroxy-brominated diphenyl ethers formed were assessed using an ultra-high performance liquid chromatography-tandem mass spectrometry-based method. Incubation of BDE-47 with archived individual liver microsomes, prepared from fifteen polar bears from northern Canada, produced a total of eleven hydroxylated metabolites, eight of which were identified using authentic standards. The major metabolites were 4'-hydroxy-2,2',4,5'-tetrabromodiphenyl ether and 5'-hydroxy-2,2',4,4'-tetrabromodiphenyl ether. Incubation of BDE-99 with polar bear liver microsomes produced a total of eleven hydroxylated metabolites, seven of which were identified using authentic standards. The major metabolites were 2,4,5-tribromophenol and 4-hydroxy-2,2',3,4',5-pentabromodiphenyl ether. Among the CYP specific antibodies tested, anti-rat CYP2B was found to be the most active in inhibiting the formation of hydroxylated metabolites of both BDE-47 and BDE-99, indicating that CYP2B was the major CYP enzyme involved in the oxidative biotransformation of these two congeners. Our study shows that polar bears are capable of forming multiple hydroxylated metabolites of BDE-47 and BDE-99 in vitro and demonstrates the role of CYP2B in the biotransformation and possibly in the toxicity of BDE-47 and BDE-99 in polar bears.

Topics: Animals; Biotransformation; Canada; Chromatography, Liquid; Flame Retardants; Halogenated Diphenyl Ethers; Hydroxylation; In Vitro Techniques; Liver; Male; Microsomes, Liver; Rats; Ursidae

Trophic transfer of polybrominated diphenyl ethers (PBDEs) in aquatic ecosystems is an important criterion for assessing their environmental risk. This study analyzed 13 PBDEs in marine organisms collected from coastal area of Bohai Bay, China. The concentrations of total PBDEs (Σ13PBDEs) ranged from 12 ± 1.1 ng/g wet weight (ww) to 230 ± 54 ng/g ww depending on species. BDE-47 was the predominant compound, with a mean abundance of 20.21 ± 12.97% of total PBDEs. Stable isotopic ratios of carbon (δ(13)C) and nitrogen (δ(15)N) were analyzed to determine the food web structure and trophic level respectively. Trophic magnification factors (TMFs) of PBDEs were assessed as the slope of lipid equivalent concentrations regressed against trophic levels. Significant positive relationships were found for Σ13PBDEs and eight PBDE congeners (BDE-28, BDE-47, BDE-49, BDE-66, BDE-85, BDE-99, BDE-100 and BDE-154). Monte-Carlo simulations showed that the probabilities of TMF >1 were 100% for Σ13PBDEs, BDE-47, BDE-85, BDE-99 and BDE-100, 99% for DE-28, BDE-49, BDE-66 and BDE-154, 94% for BDE-153, and 35% for BDE-17.

Topics: Animals; Aquatic Organisms; Bays; Body Burden; Carbon Isotopes; China; Food Chain; Halogenated Diphenyl Ethers; Nitrogen Isotopes; Polybrominated Biphenyls; Water Pollutants, Chemical