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  • 1.
    Athanasiadou, Maria
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Athanassiadis, Ioannis
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Asplund, Lillemor
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Gas chromatography and mass spectrometry of methoxylated polybrominated diphenyl ethers (MeO-PBDEs).2006In: J Mass Spectrom, ISSN 1076-5174, Vol. 41, no 6, p. 790-801Article in journal (Other academic)
  • 2. Cantón, Rocío F
    et al.
    Scholten, Deborah E A
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    de Jong, Paul C
    van den Berg, Martin
    Inhibition of human placental aromatase activity by hydroxylated polybrominated diphenyl ethers (OH-PBDEs).2008In: Toxicol Appl Pharmacol, ISSN 0041-008X, Vol. 227, no 1, p. 68-75Article in journal (Refereed)
    Abstract [en]

    Polybrominated diphenyl ethers (PBDEs) are widely used as flame retardants in many different polymers, resins and substrates. Due to their widespread production and use, their high binding affinity to particles, and their lipophilic properties, several PBDE congeners can bioaccumulate in the environment. As a result, PBDEs and their hydroxylated metabolites (OH-PBDEs) have been detected in humans and various wildlife samples, such as birds, seals, and whales. Furthermore, certain OH-PBDEs and their methoxylated derivatives (MeO-PBDEs) are natural products in the marine environment. Recently, our laboratory focused on the possible effects on steroidogenesis of PBDEs and OH-PBDEs, e.g. in the human adrenocortical carcinoma (H295R) cell line indicating that some OH-PBDEs can significantly influence steroidogenic enzymes like CYP19 (aromatase) and CYP17. In the present study, human placental microsomes have been used to study the possible interaction of twenty two OH-PBDEs and MeO-PBDEs with aromatase, the enzyme that mediates the conversion of androgens into estrogens. All OH-PBDE derivates showed significant inhibition of placental aromatase activity with IC(50) values in the low micromolar range, while the MeO-PBDEs did not have any effect on this enzyme activity. Enzyme kinetics studies indicated that two OH-PBDEs, 5-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (5-OH-BDE47) and 6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (6-OH-BDE47), had a mixed-type inhibition of aromatase activity with apparent K(i)/K(i)' of 7.68/0,02 microM and 5.01/0.04 microM respectively. For comparison, some structurally related compounds, a dihydroxylated polybrominated biphenyl, which is a natural product (2,2'-dihyroxy-3,3',5,5'-tetrabromobiphenyl (2,2'-diOH-BB80)) and its non-bromo derivative were also included in the study. Again inhibition of aromatase activity could be measured, but their potency was significantly less than those observed for the OH-PBDEs. These results show that a wide range of OH-PBDEs have the potential to disturb steroidogenesis and indicate a potential mechanism of action of these brominated flame retardant derivatives as endocrine disruptors in humans and wildlife.

  • 3. Cantón, Rocío F
    et al.
    Scholten, Deborah E A
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    de Jong, Paul C
    van den Berg, Martin
    Inhibition of human placental aromatase activity by hydroxylated polybrominated diphenyl ethers (OH-PBDEs).2007In: Toxicol Appl Pharmacol, ISSN 0041-008XArticle in journal (Refereed)
    Abstract [en]

    Polybrominated diphenyl ethers (PBDEs) are widely used as flame retardants in many different polymers, resins and substrates. Due to their widespread production and use, their high binding affinity to particles, and their lipophilic properties, several PBDE congeners can bioaccumulate in the environment. As a result, PBDEs and their hydroxylated metabolites (OH-PBDEs) have been detected in humans and various wildlife samples, such as birds, seals, and whales. Furthermore, certain OH-PBDEs and their methoxylated derivatives (MeO-PBDEs) are natural products in the marine environment. Recently, our laboratory focused on the possible effects on steroidogenesis of PBDEs and OH-PBDEs, e.g. in the human adrenocortical carcinoma (H295R) cell line indicating that some OH-PBDEs can significantly influence steroidogenic enzymes like CYP19 (aromatase) and CYP17. In the present study, human placental microsomes have been used to study the possible interaction of twenty two OH-PBDEs and MeO-PBDEs with aromatase, the enzyme that mediates the conversion of androgens into estrogens. All OH-PBDE derivates showed significant inhibition of placental aromatase activity with IC(50) values in the low micromolar range, while the MeO-PBDEs did not have any effect on this enzyme activity. Enzyme kinetics studies indicated that two OH-PBDEs, 5-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (5-OH-BDE47) and 6-hydroxy-2,2',4,4'-tetrabromodiphenyl ether (6-OH-BDE47), had a mixed-type inhibition of aromatase activity with apparent K(i)/K(i)' of 7.68/0,02 muM and 5.01/0.04 muM respectively. For comparison, some structurally related compounds, a dihydroxylated polybrominated biphenyl, which is a natural product (2,2'-dihyroxy-3,3',5,5'-tetrabromobiphenyl (2,2'-diOH-BB80)) and its non-bromo derivative were also included in the study. Again inhibition of aromatase activity could be measured, but their potency was significantly less than those observed for the OH-PBDEs. These results show that a wide range of OH-PBDEs have the potential to disturb steroidogenesis and indicate a potential mechanism of action of these brominated flame retardant derivatives as endocrine disruptors in humans and wildlife

  • 4.
    Eriksson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Green, Nicholas
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Photochemical decomposition of fifteen polybrominated diphenyl ether congeners in methanol/water2004In: Environmental Science & Technology, ISSN 1520-5851, Vol. 38, no 11, p. 3119-3125Article in journal (Refereed)
    Abstract [en]

    Among all brominated flame retardants in use, the polybrominated diphenyl ethers (PBDEs) have been identified as being of particular environmental concern due to their global distribution and bioaccumulating properties, as observed in humans and wildlife worldwide. Still there is a need for more data on the basic characteristics of PBDEs to better understand and describe their environmental fate. Hence, the aim of this study was to investigate the photochemical degradation of PBDEs with different degrees of bromination. The photochemical degradation of 15 individual PBDEs substituted with 4−10 bromine atoms was studied in methanol/water (8:2) by UV light in the sunlight region. Nine of these were also studied in pure methanol, and four of the nine PBDEs were studied in tetrahydrofuran. The photochemical reaction rate decreased with decreasing number of bromine substituents in the molecule but also in some cases influenced by the PBDE substitution pattern. The reaction rate was dependent on the solvent in such a way that the reaction rate in a methanol/water solution was consistently around 1.7 times lower than in pure methanol and 2−3 times lower than in THF. The UV degradation half-life of decaBDE (T1/2 = 0.5 h) was more than 500 times shorter than the environmentally abundant congener 2,2‘,4,4‘-tetraBDE (T1/2 = 12 d) in methanol/water. The quantum yields in the methanol/water solution ranged from 0.1 to 0.3. The photochemical reaction of decaBDE is a consecutive debromination from ten- down to six-bromine-substituted PBDEs. Products with less than six bromines were tentatively identified as brominated dibenzofurans and traces of what was indicated as methoxylated brominated dibenzofurans.

  • 5. Houde, Magali
    et al.
    Pacepavicius, Grazina
    Darling, Colin
    Fair, Patricia A
    Alaee, Mehran
    Bossart, Gregory D
    Solomon, Keith R
    Letcher, Robert J
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Muir, Derek C G
    POLYBROMINATED DIPHENYL ETHERS AND THEIR HYDROXYLATED ANALOGS IN PLASMA OF BOTTLENOSE DOLPHINS (TURSIOPS TRUNCATUS) FROM THE UNITED STATES EAST COAST.2009In: Environmental Toxicology and Chemistry, ISSN 0730-7268, E-ISSN 1552-8618, Vol. 28, no 10, p. 2061-2068Article in journal (Refereed)
    Abstract [en]

    Polybrominated diphenyl ethers (PBDEs) and hydroxylated-PBDEs (OH-PBDE) were determined in plasma of free-ranging bottlenose dolphins (Tursiops truncatus) from Charleston (CHS), South Carolina, and the Indian River Lagoon (IRL), Florida, US. Significantly lower sum (Sigma) of PBDE concentrations (sum of 12 congeners) were found in animals from the IRL [arithmetic mean: 5.454.63 ng/g wet weight (ww)] compared to CHS (3040 ng/g ww). BDE-47 was the predominant PBDE in dolphins from the IRL (50% of the SigmaPBDEs) and CHS (58%). SigmaPBDE concentrations in plasma of dolphins were negatively correlated with age at both locations. Fifteen and sixteen individual OH-PBDE congeners could be quantified in plasma of dolphins from IRL and CHS, respectively. Similar to SigmaPBDE, mean SigmaOH-PBDE concentrations were significantly higher in plasma of dolphins at CHS (1150708 pg/g ww) compared to IRL (624393 pg/g ww). The predominant congener at both locations was 6-OH-PBDE 47 (IRL: 384319 pg/g ww; CHS: 541344 pg/g ww) representing 61.5% of total SigmaOH-PBDE at IRL and 47.0% at CHS. Concentrations of SigmaOH-PBDEs were weakly negatively correlated with age in dolphins from both locations (P<0.05; IRL, R2=0.048; CHS, R2=0.021). In addition to the OH-PBDE congeners identified with technical standards, eight and four unidentified OH-PBDEs were detected and quantified respectively in animals from CHS (sum of unidentified OH-PBDEs=1.350.90 pg/g ww) and IRL (0.730.40 pg/g ww). Our results suggest that, unlike OH-PCBs, OH-PBDEs in bottlenose dolphins are minor products in plasma relative to SigmaPBDEs and a significant proportion may be a consequence of the dietary uptake of naturally produced methoxylated- and OH-PBDEs.

  • 6. Legradi, Jessica
    et al.
    Dahlberg, Anna-Karin
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Cenijn, Peter
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Asplund, Lillemor
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Legler, Juliette
    Disruption of oxidative phosphorylation (OXPHOS) by hydroxylated polybrominated diphenyl ethers (OH-PBDEs) present in the marine environment2014In: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 48, no 24, p. 14703-14711Article in journal (Refereed)
    Abstract [en]

    Hydroxylated polybrominated diphenyl ethers (OH-PBDEs) are of growing concern, as they have been detected in both humans and wildlife and have been shown to be toxic. Recent studies have indicated that OH-PBDEs can be more toxic than PBDEs, partly due to their ability to disrupt oxidative phosphorylation (OXPHOS), an essential process in energy metabolism. In this study, we determined the OXPHOS disruption potential of 18 OH-PBDE congeners reported in marine wildlife using two in vitro bioassays, namely the classic rat mitochondrial respiration assay, and a mitochrondrial membrane potential assay using zebrafish PAC2 cells. Single OH-PBDE congeners as well as mixtures were tested to study potential additive or synergistic effects. An environmental mixture composed of seven OH-PBDE congeners mimicking the concentrations reported in Baltic blue mussels were also studied. We report that all OH-PBDEs tested were able to disrupt OXPHOS via either protonophoric uncoupling and/or inhibition of the electron transport chain. Additionally we show that OH-PBDEs tested in combinations as found in the environment have the potential to disrupt OXPHOS. Importantly, mixtures of OH-PBDEs may show very strong synergistic effects, stressing the importance of further research on the in vivo impacts of these compounds in the environment

  • 7. Montano, Mauricio
    et al.
    Cocco, Emmanuelle
    Guignard, Cedric
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Hoffmann, Lucien
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Gutleb, Arno Christian
    Murk, Albertinka Jacoba
    New Approaches to Assess the Transthyretin Binding Capacity of Bioactivated Thyroid Hormone Disruptors2012In: Toxicological Sciences, ISSN 1096-6080, E-ISSN 1096-0929, Vol. 130, no 1, p. 94-105Article in journal (Refereed)
    Abstract [en]

    Polychlorinated biphenyls (PCBs) and polybrominated diphenyl-ethers (PBDEs) are metabolized into hydroxylated metabolites (OH-PCBs/PBDEs), which can disrupt the thyroid hormone homeostasis. Binding of these metabolites to transport proteins such as transthyretin (TTR) is an important mechanism of their toxicity. Several methods to quantify the competitive thyroxine (T-4) displacement potency of pure metabolites exist. However, quantification of the potency of in vitro metabolized PCBs and PBDEs has drawbacks related to the coextraction of compounds disturbing the T-4-TTR competitive binding assay. This study identifies and quantifies the major coextractants namely cholesterol, saturated and nonsaturated fatty acids (SFA and NSFA) at levels above 20 nmol per mg equivalent protein following various extraction methods. Their TTR binding potency was analyzed in a downscaled, nonradioactive fluorescence displacement assay. At concentration factors needed for TTR competitive binding, at least 10M of these coextracts is present, whereas individual SFA and NSFA disturb the assay from 0.3M. The effectiveness of the in vitro metabolism and extraction of the model compounds CB 77 and BDE 47 was chemically quantified with a newly developed chromatographic method analyzing silylated derivatives of the OH-metabolites and coextractants. A new method to selectively extract metabolites and limit coextraction of disturbing compounds to less than 5 nmol per mg equivalent protein is presented. It is now possible to make a dose-response curve up to 50% inhibition with bioactivated CB 77 and BDE 47. The toxic potencies of bioactivated persistent organic pollutants (POPs) should be taken into account to prevent serious underestimation of their hazard and risk.

  • 8.
    Rydén, Andreas
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Synthesis of polybrominated diphenyl ethers via unsymmetrical diaryliodonium triflatesManuscript (preprint) (Other academic)
    Abstract [en]

    Polybrominated diphenyl ethers (PBDEs) are ubiquitous environmental pollutants due to theirpersistent character and extensive use as additive flame retardants. In order to assess theirbiological effects, fate, environmental concentrations and other parameters related to riskassessment, authentic PBDE congers are needed for research purposes. In the present work anew general method for the preparation of individual PBDE congeners is presented. Themethodology used is based on recent advances in unsymmetrical diaryliodonium saltsynthesis as well as advances in O-arylation of phenols with these types of salts. Accordingly,three brominated diphenyliodonium triflates were prepared i.e. phenyl(2,4,5-tribromophenyl)iodonium triflate, phenyl(2,4,6-tribromophenyl)iodonium triflate andphenyl(2,3,4,6-tetrabromophenyl)iodonium triflate from 1,2,4-tribromo-5-iodobenzene, 1,3,5-tribromo-2-iodobenzene and 1,2,3,5-tetrabromo-4-iodobenzene, respectively. Yields indiaryliodonium salt syntheses ranged from 69-96%. These salts were further used to O-arylatevarious brominated phenols giving individual tetra- to octa-BDE congeners in yields rangingfrom 64-98%. The O-arylation method used was given after a minor optimisation study, regarding reaction time and temperature, which is reported herein. In addition, this O-arylationmethod was also used with two brominated methoxyphenols in the syntheses of twomethoxylated PBDEs.

  • 9.
    Rydén, Andreas
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Nestor, Gustav
    Jakobsson, Kristina
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Synthesis and tentative identification of novel polybrominated diphenyl ether metabolites in human blood2012In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 88, no 10, p. 1227-1234Article in journal (Refereed)
    Abstract [en]

    Hydroxylated polybrominated diphenyl ethers (OH-PDBEs) are exogenous, bioactive compounds that originate, to a large extent, from anthropogenic activities, although they are also naturally produced in the environment. In the present study nine new authentic OH-PBDE reference standards and their corresponding methyl ether derivatives (MeO-PBDEs) were synthesised and characterised by NMR spectroscopy and mass spectrometry. Seven of the authentic reference standards prepared were thereafter tentatively identified in a pooled human blood sample. The tentatively identified OH-PBDEs were 3-hydroxy-2,2',4,4',6-pentabromodiphenyl ether, 3'-hydroxy-2,2',4,4',6-pentabromodiphenyl ether, 3-hydroxy-2,2',4,4',5-pentabromodiphenyl ether, 3-hydroxy-2,2',4,4',5,6'-hexabromodiphenyl ether. 3'-hydroxy-2,2',4,4',5,6'-hexabromodiphenyl ether, 3-hydroxy-2,2',4,4',5,5'-hexabromodiphenyl ether and 4-hydroxy-2,2',3,4',5,5',6-heptabromodiphenyl ether. An additional seven OH-PBDEs were tentatively identified in the pooled human blood sample, of which one OH-PBDE, 4'-hydroxy-2,2',4,5,5'-pentabromodiphenyl ether, has not been identified in human blood before. The identification was performed using gas chromatography-mass spectrometry (GC-MS) recording the bromine ions m/z 79, 81. The tentative identification was supported by the peaks relative retention times (RRTs) compared to authentic references on two GC columns of different polarities for the hexa-, and heptabrominated OH-PBDEs, and three different GC columns for the pentabrominated OH-PBDEs. The OH-PBDE congeners most likely originate from human metabolism of a flame retardant, i.e. polybrominated diphenyl ethers (PBDEs), due to the relatively high concentrations of PBDEs in the same human blood sample and the fact that these PBDEs could form the tentatively identified OH-PBDEs via metabolic direct hydroxylation or via 1,2-shift.

  • 10.
    Teclechiel, Daniel
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Christiansson, Anna
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Synthesis of Octabrominated Diphenyl Ethers from Aminodiphenyl Ethers2007In: Environ. Sci. Technol., ISSN 0013-936X, Vol. 41, no 21, p. 7459-7463Article in journal (Refereed)
    Abstract [en]

    Polybrominated diphenyl ethers (PBDEs) are additive brominated flame retardants (BFRs), which have become widespread pollutants in abiotic and biotic environments including man. Tetra- to hexaBDEs and decaBDE are the most common environmental PBDE contaminants. Congeners of octabromodiphenyl ethers (octaBDEs) originate from used industrial OctaBDE mixtures and from transformation products of the high-volume industrial BFR mixture "DecaBDE", which most exclusively consists of perbrominated diphenyl ether (BDE-209). The objective of the present work was to develop methods for the synthesis of authentic octaBDE congeners in order to make them available as standards for analytical, toxicological, and stability studies, as well as studies concerning physical-chemical properties. The syntheses of six octaBDEs, 2,2',3,3',4,4',5,5'-octabromodiphenyl ether (BDE-194), 2,2',3,3',4,4',5,6'-octabromodiphenyl ether (BDE-196), 2,2',3,3',4,5,5',6-octabromodiphenyl ether (BDE-198), 2,2',3,3',4,5',6,6'-octabromodiphenyl ether (BDE-201), 2,2',3,3',5,5',6,6'-octabromodiphenyl ether (BDE-202), and 2,2',3,4,4',5,6,6'-octabromdipheny ether (BDE-204), are described, of which BDE-204 was prepared via two different pathways. Syntheses of BDE-198, BDE-201, BDE-202, and BDE-204 are based on octabromination of mono- or diaminodiphenyl ethers followed by diazotization and reduction of the amino group(s). BDE-194 and BDE-196 were prepared by bromination of 3,3',4,4',5,5'-hexabromodiphenyl ether (BDE-169) and 2,3,3',4,4',5',6-heptabromodiphenyl ether (BDE-191), respectively, and BDE-169 and BDE-191 were prepared from 4,4'-diaminodiphenyl ether and 3,4'-diamiodiphenyl ether, respectively. The synthesized PBDE congeners are described by 1H NMR, 13C NMR, electron ionization mass spectra, and their melting points.

  • 11.
    Teclechiel, Daniel
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Sundström, Maria
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Improved synthesis of polybrominated diphenyl ethers via iodonium salt coupling2007In: Organohalogen Compounds: Brominated flameretardants II (Environment and fate), 2007, p. 2724-2727Conference paper (Refereed)
  • 12. Teuten, Emma L.
    et al.
    Johnson, Carl G.
    Mandalakis, Manolis
    Asplund, Lillemor
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Gustafsson, Örjan
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Unger, Maria
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Reddy, Christopher M.
    Spectral characterization of two bioaccumulated methoxylated polybrominated diphenyl ethers2006In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 62, no 2, p. 197-203Article in journal (Refereed)
    Abstract [en]

    Two methoxylated polybrominated diphenyl ethers (MeO-PBDEs) were isolated from a True’s beaked whale (Mesoplodon mirus) and identified by NMR (1H, 1H–1H and 1H–13C) and high resolution mass spectrometry as 2-(2′,4′-dibromophenoxy)-3,5-dibromoanisole (6-MeO-BDE47) and 2-(2′,4′-dibromophenoxy)-4,6-dibromoanisole (2′-MeO-BDE68). Previously the structures of these bioaccumulated compounds have been determined by comparison of their mass spectra and gas chromatographic (GC) retention times with those of authentic standards. While this method is accepted and generally successful, NMR of the isolated compounds allows us to definitively identify the congeners. Our characterizations are consistent with those made for MeO-PBDEs in other organisms, identified by chromatographic methods.

  • 13. Ueno, Daisuke
    et al.
    Darling, Colin
    Alaee, Mehran
    Pacepavicius, Grazina
    Teixeira, Camilla
    Campbell, Linda
    Letcher, Robert James
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Muir, Derek
    Hydroxylated polybrominated diphenyl ethers (OH-PBDEs) in the abiotic environment: surface water and precipitation from Ontario, Canada.2008In: Environ Sci Technol, ISSN 0013-936X, Vol. 42, no 5, p. 1657-64Article in journal (Refereed)
    Abstract [en]

    Hydroxylated polybrominated diphenyl ethers (OH-PBDEs) have been identified as metabolites of PBDEs, and also as compounds of natural origin in the marine environment; however, there has only been very limited study of their presence in the abiotic environment. In the present study, OH-PBDEs were determined in samples of surface water and precipitation (rain and snow) collected from sites in Ontario, Canada. OH-PBDEs were detected in all the samples analyzed, although half of the observed peaks did not correspond to any of the 18 authentic standards available. Fluxes of sigmaOH-PBDEs ranged from 3.5 to 190 pg/m2 in snow and from 15 to 170 pg/m2/day in rain, and those were higher at three of the southern Ontario locations relative to a single northern remote site. Concentrations of sigmaOH-PBDEs ranged from 2.2 to 70 pg/L in water and from < 1 to 420 pg/g in particulate organic carbon (POC), and higher values were found near sewage treatment plant (STP) outfalls in Lake Ontario. Partition coefficients (log K(oc)) for OH-PBDEs ranged from 4.0 to 5.1. The results in this study suggest that OH-PBDEs are ubiquitous in the abiotic environment and most likely are produced through reaction of PBDEs with atmospheric OH radicals. As well, they may be present in surface waters near STPs due to oxidation of PBDEs and inflows from metabolism by humans and animals.

  • 14.
    Unger, Maria
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Asplund, Lillemor
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Gustafsson, Örjan
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Characaterization of an abundant and novel methyl- and methoxy-substituted brominated diphenyl ether isolated from whale blubber2010In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 79, no 4, p. 408-413Article in journal (Refereed)
    Abstract [en]

    A previously unidentified yet abundant substituted polybrominated diphenyl ether (PBDE) was isolated from a northern bottlenose whale (Hyperoodon ampullatus) found dead in the Skagerrak, North Sea. A combination of gas chromatography, high and low resolution mass spectrometry and nuclear magnetic resonance spectroscopy (NMR) (1H, 1H–1H and 1H–13C) after isolation with preparative capillary gas chromatography (PCGC) lead to the identification of the unknown substance as 6-MeO-5-Me-2,2′,3,4′-tetrabromo diphenyl ether (6-MeO-5-Me-BDE42). To our knowledge this is only the second time PCGC has been used to isolate individual organohalogen compounds present in trace amounts for identification with NMR. The concentration of this novel bioaccumulated compound was estimated to be about 100 ng g−1 lipid, which was 2.5 times higher compared with the most abundant MeO-PBDE congeners.

  • 15. van Boxtel, Antonius L
    et al.
    Kamstra, Jorke H
    Cenijn, Peter H
    Pieterse, Bart
    Wagner, J Marijke
    Antink, Maartje
    Krab, Klaas
    van der Burg, Bart
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Brouwer, Abraham
    Legler, Juliette
    Microarray analysis reveals a mechanism of phenolic polybrominated diphenylether toxicity in zebrafish.2008In: Environ Sci Technol, ISSN 0013-936X, Vol. 42, no 5, p. 1773-9Article in journal (Other academic)
    Abstract [en]

    Polybrominated diphenylethers (PBDEs) are ubiquitous in the environment, with the lower brominated congener 2,2',4,4'-tetrabromodiphenylether (BDE47) among the most prevalent. The phenolic PBDE, 6-hydroxy-BDE47 (6-OH-BDE47) is both an important metabolite formed by in vivo metabolism of BDE47 and a natural product produced by marine organisms such as algae. Although this compound has been detected in humans and wildlife, including fish, virtually nothing is known of its in vivo toxicity. Here we report that 6-OH-BDE47 is acutely toxic in developing and adult zebrafish at concentrations in the nanomolar (nM) range. To identify possible mechanisms of toxicity, we used microarray analysis as a diagnostic tool. Zebrafish embryonic fibroblast (PAC2) cells were exposed to 6-OH-BDE47, BDE47, and the methoxylated metabolite 6-MeO-BDE47. These experiments revealed that 6-OH-BDE47 alters the expression of genes involved in proton transport and carbohydrate metabolism. These findings, combined with the acute toxicity, suggested that 6-OH-BDE47 causes disruption of oxidative phosphorylation (OXPHOS).Therefore, we further investigated the effect of 6-OH-BDE47 on OXPHOS in zebrafish mitochondria. Results show unequivocally that this compound is a potent uncoupler of OXPHOS and is an inhibitor of complex II of the electron transport chain. This study provides the first evidence of the in vivo toxicity and an important potential mechanism of toxicity of an environmentally relevant phenolic PBDE of both anthropogenic and natural origin. The results of this study emphasize the need for further investigation on the presence and toxicity of this class of polybrominated compounds.

  • 16. Vetter, Walter
    et al.
    Turek, Claudia
    Marsh, Göran
    Stockholm University.
    Gaus, Caroline
    Identification and quantification of new polybrominated dimethoxybiphenyls (PBDMBS) in marine mammals from Australia2008In: Organohalogen compounds: Chiral xenobiotics and natural halogenated compounds, 2008, p. 2388-2391Conference paper (Other academic)
  • 17. Vetter, Walter
    et al.
    Turek, Claudia
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Gaus, Caroline
    Identification and quantification of new polybrominated dimethoxybiphenyls (PBDMBs) in marine mammals from Australia.2008In: Chemosphere, ISSN 0045-6535, Vol. 73, no 4, p. 580-6Article in journal (Refereed)
    Abstract [en]

    Marine mammals from Queensland, Australia, are bioaccumulating elevated concentrations of a range of polybrominated natural products. In this study, we detected three new polybrominated dimethoxybiphenyls (PBDMBs) in the blubber of selected marine mammal samples which were identified as 2,6'-dimethoxy-3,3',5-tribromobiphenyl (2,6'-diMeO-BB 36), 2,2'-dimethoxy-3,3'-dibromobiphenyl (2,2'-diMeO-BB 36), and 6,6'-dimethoxy-3,3'-dibromobiphenyl (6,6'-diMeO-BB 11). These three PBDMBs are structurally related to the known natural product 2,2'-dimethoxy-3,3',5,5'-tetrabromobiphenyl (2,2'-diMeO-BB 80). In the first part of this study, 2,2'-diMeO-BB 80 was photochemically debrominated under UV irradiation. This resulted in seven of eight possible mono- to triBDMBs as debromination products. In the second part of this study, the structure of all PBDMBs debromination products was investigated. This was supported by synthesis of two diBDMB and one triBDMB via bromination and subsequent methylation of 2,2'-biphenyldiol. Structures of the remaining PBDMBs were tentatively assigned by considering the retention times, mass spectra and amounts formed during UV irradiation of 2,2'-diMeO-BB 80 . In the third part of this study, blubber of marine mammals from Australia was analysed for PBDMBs using gas chromatography in combination with electron ionization mass spectrometry (GC/EI-MS) in the selected ion monitoring mode. In these samples, 2,2'-diMeO-BB 80 was found at concentrations of 200-1800ngg(-1) lipid weight (lw). The latter represents the highest concentration reported for this compound in environmental samples. 6,6'-diMeO BB 11, 2,2'-diMeO BB 36, and 2,6'-diMeO BB 36 were present at approximately 7ngg(-1) lipids, or 0.43-1.5% of diMeO-BB 80. No further PBDMBs were detected in the samples. The di- and triBDMBs identified in marine mammal blubber have not been reported as natural products. They may represent either new natural products or transformation products of 2,2'-diMeO-BB 80.

  • 18. Vetter, Walter
    et al.
    Turek, Claudia
    Marsh, Göran
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Gaus, Caroline
    Identification and quantification of new polybrominated dimethoxybiphenyls (PBDMBS) in marine mammals from Australia2008In: Organohalogen compounds: Chiral xenobiotics and natural halogenated compounds, 2008, p. 658-661Conference paper (Other academic)
1 - 18 of 18
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