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  • 1.
    Bastos, Patricia Moreira
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Green, Nicholas
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    A standardized method for assessment of oxidative transformations of brominated phenols in water.2008In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 70, no 7, p. 1196-202Article in journal (Refereed)
  • 2.
    Christiansson, Anna
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Teclechiel, Daniel
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Identification and quantification of products formed via photolysis of decabromodiphenyl ether2009In: Environmental Science and Pollution Research, ISSN 0944-1344, E-ISSN 1614-7499, Vol. 16, no 3, p. 312-321Article in journal (Refereed)
    Abstract [en]

    BACKGROUND, AIM, AND SCOPE: Decabromodiphenyl ether (DecaBDE) is used as an additive flame retardant in polymers. It has become a ubiquitous environmental contaminant, particularly abundant in abiotic media, such as sediments, air, and dust, and also present in wildlife and in humans. The main DecaBDE constituent, perbrominated diphenyl ether (BDE-209), is susceptible to transformations as observed in experimental work. This work is aimed at identifying and assessing the relative amounts of products formed after UV irradiation of BDE-209. MATERIALS AND METHODS: BDE-209, dissolved in tetrahydrofuran (THF), methanol, or combinations of methanol/water, was exposed to UV light for 100 or 200 min. Samples were analyzed by gas chromatography/mass spectrometry (electron ionization) for polybrominated diphenyl ethers (PBDEs), dibenzofurans (PBDFs), methoxylated PBDEs, and phenolic PBDE products. RESULTS: The products formed were hexaBDEs to nonaBDEs, monoBDFs to pentaBDFs, and methoxylated tetraBDFs to pentaBDFs. The products found in the fraction containing halogenated phenols were assigned to be pentabromophenol, dihydroxytetrabromobenzene, dihydroxydibromodibenzofuran, dihydroxytribromodibenzofuran, and dihydroxytetrabromodibenzofuran. The PBDEs accounted for approximately 90% of the total amount of substances in each sample and the PBDFs for about 10%. DISCUSSION: BDE-209 is a source of PBDEs primarily present in OctaBDEs but also to some extent in PentaBDEs, both being commercial products now banned within the EU and in several states within the USA. It is notable that OH-PBDFs have not been identified or indicated in any of the photolysis studies performed to date. Formation of OH-PBDFs, however, may occur as pure radical reactions in the atmosphere. CONCLUSIONS: Photolysis of decaBDE yields a wide span of products, from nonaBDEs to hydroxylated bromobenzenes. It is evident that irradiation of decaBDE in water and methanol yields OH-PBDFs and MeO-PBDFs, respectively. BDE-202 (2,2',3,3',5,5',6,6'-octabromodiphenyl ether) is identified as a marker of BDE-209 photolysis. RECOMMENDATIONS AND PERSPECTIVES: BDE-209, the main constituent of DecaBDE, is primarily forming debrominated diphenyl ethers with higher persistence which are more bioaccumulative than the starting material when subjected to UV light. Hence, DecaBDE should be considered as a source of these PBDE congeners in the environment

  • 3. Degner, Amanda
    et al.
    Carlsson, Henrik
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.
    Karlsson, Isabella
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.
    Pujari, Suresh S.
    Tretyakova, Natalia Y.
    Törnqvist, Margareta
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.
    Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood2018In: Chemical Research in Toxicology, ISSN 0893-228X, E-ISSN 1520-5010, Vol. 31, no 12, p. 1305-1314Article in journal (Refereed)
    Abstract [en]

    Humans are exposed to a wide range of electrophilic compounds present in our diet and environment or formed endogenously as part of normal physiological processes. These electrophiles can modify nucleophilic sites of proteins and DNA to form covalent adducts. Recently, powerful untargeted adductomic approaches have been developed for systematic screening of these adducts in human blood. Our earlier untargeted adductomics study detected 19 unknown adducts to N-terminal valine in hemoglobin (Hb) in human blood. We now describe a full characterization of one of these adducts, which corresponds to the addition of a 4-hydroxybenzyl (4-OHBn) group to N-terminal valine in Hb to form N(4-hydroxybenzyl)valine (4-OHBn-Val). The adduct structure was determined by comparison of its accurate mass, HPLC retention time, and MS/MS fragmentation to that of authentic standards prepared by chemical synthesis. Average 4-OHBn-Val adduct concentrations in 12 human blood samples were estimated to 380 +/- 160 pmol/g Hb. Two possible routes of 4-OHBnVal adduct formation are proposed using two different precursor electrophiles: 4-quinone methide (4-QM) and 4-hydroxybenzaldehyde (4-OHBA). We found that 4-QM reacts rapidly with valine to form the 4-OHBn-Val adduct; however, the quinone methide is unstable under physiological conditions due to hydrolysis. It was shown that 4-OHBA forms reversible Schiff base adducts with valine, which can be stabilized via reduction in blood generating the 4-OHBn-Val adduct. In addition, trace amounts of isomeric 2-hydroxybenzyl-valine (2-OHBn-Val) adducts were detected in 12 human blood samples (estimated mean adduct level, 5.0 +/- 1.4 pmol/g Hb). Further studies are needed to quantify the contributions from identified possible precursor electrophiles to the observed hydroxybenzyl adducts in humans.

  • 4.
    Eriksson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry.
    2,2’,6,6’-Tetrachloro-4,4’-propane-2,2-diyldiphenol, 2,2’,6-tribromo-4,4’-propane-2,2-diyldi phenol and 2,2’,6,6’-tetrabromo-4,4’-propane-2,2-diyldiphenol2001In: Acta crystallographica Section C, ISSN 0108-2701, Vol. 57, no 11, p. 1308-1312Article in journal (Refereed)
    Abstract [en]

    Three flame retardants with very similar molecular structures showing three different packing patterns have been studied. The crystal structure of 2,2',6,6'-tetrachloro-4,4'-propane-2,2-diyldiphenol, C15H12Cl4O2, can be described as a packing of sheets. The packing shows a very short intermolecular ClCl contact distance of 3.094  (2)  Å between pairs of molecules inside each sheet. The crystal structure of 2,2',6-tribromo-4,4'-propane-2,2-diyldiphenol, C15H13Br3O2, can be described as a packing of doubly stranded helical square tubes. These square helices are interconnected through BrBr contacts between different helices. Finally, a previously known structure, 2,2',6,6'-tetrabromo-4,4'-propane-2,2-diyldiphenol [Simonov, Cheban, Rotaru & Bels'skii (1986). Kristallografiya, 31, 397-399], C15H12Br4O2, which is the most commonly used flame retardant and which has twofold rotational symmetry, has been refined in the correct absolute configuration. The structure shows large differences from the chloro analogue with regard to packing, van der Waals distances and hydrogen-bond distances.

  • 5.
    Eriksson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry.
    Jakobsson, Eva
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry.
    Decabromodiphenyl ether1999In: Acta crystallographica Section C, ISSN 0108-2701, Vol. 55, no 12, p. 2169-2171Article in journal (Refereed)
    Abstract [en]

    Bis(pentabromophenyl) ether, C12Br100, shows strangedifferences in the endocyclic angles between the twodifferent rings, although they are both substituted inthe same manner. Several short van der Waals contact distances give clues to the anomalous endocyclic anglesand some hints to the formation of decompositionproducts. We suggest that the intermolecular Br...Brcontacts contribute to the distortions of the ring systems.Usually distortions of this kind would be explained fromhighly anisotropic TLS behaviour, but the data from thetitle compound do not show any conclusive TLS effects.

  • 6.
    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.

  • 7. Eriksson, Johan
    et al.
    Karlsson, Mikael
    Reuter, Marta
    Stockholm University, Faculty of Social Sciences, Department of Political Science.
    Technocracy, Politicization and Non-involvement: Politics of Expertise in the European Regulation of Chemicals2010In: Review of Policy Research, ISSN 1541-132X, E-ISSN 1541-1338, Vol. 27, no 2, p. 167-185Article in journal (Refereed)
    Abstract [en]

    This article addresses the relationship between scientific expertise and policy in European chemicals regulation. We argue that the role of scientific expertise in the European regulation of chemicals varies across decision-making levels, countries, and stages of the policy process. Our case study of the role of scientific expertise in the regulation of brominated flame retardants illustrates considerably different manifestations of this interconnected process across regulatory arenas, even though this case concerns a single group of substances. On the European Union level, we find a mix of technocracy and politicization; in Sweden, a clear-cut politicization; and in Poland, noninvolvement. Such differences can be explained by a combination of factors, in particular frame dominance, and mobilization of advocacy coalitions. [ABSTRACT FROM AUTHOR] Copyright of Review of Policy Research is the property of Wiley-Blackwell and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.

  • 8.
    Eriksson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Marsh, G
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Å
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry.
    3,4,5,6-Tetrabromo phenyl-2,3,4,5,6-pentabromo phenyl ether, C12HBr9O, 2,4,5,6-tetrabromo phenyl-2,3,4,5,6-pentabromo phenyl ether, C12HBr9O and 2,3,5,6-tetrabromo phenyl-2,3,4,5,6-pentabromo phenyl ether, C12HBr9O2004Manuscript (preprint) (Other (popular science, discussion, etc.))
  • 9.
    Eriksson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Rahm, Sara
    Stockholm University, Stockholm Resilience Centre, Interdisciplinary Environmental Research (CTM). Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Green, Nicholas
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Jakobsson, Eva
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Photochemical transformations of tetrabromobisphenol A and related phenols in water2004In: Chemosphere, ISSN 0045-6535, Vol. 54, no 1, p. 117-126Article in journal (Refereed)
    Abstract [en]

    romobisphenolA (TBBPA), tribromobisphenol A (TriBBPA), tetrachlorobisphenol A (TCBPA), 2,4-dichlorophenolat various pHs as well as 2-chlorophenol, 2-bromophenol, 3,4-dichlorophenol and bisphenol A at pH 11. The absorbancespectra of the compounds and the emission spectra of the light-source were determined and used to calculatedisappearance quantum yields of the photochemical reactions that were taking place. No major differences between thedisappearance quantum yields of TBBPA and TCBPA were observed at pH 10, while the disappearance quantum yieldof TriBBPA was approximately two times higher. The rate of decomposition of TBBPA was six times higher at pH 8than at pH 6. Identification of the degradation products of TBBPA and TriBBPA, by GC–MS analysis and bycomparison to synthesised reference compounds, indicated that TBBPA and TriBBPA decompose via differentmechanisms. Three isopropylphenol derivatives; 4-isopropyl-2,6-dibromophenol, 4-isopropylene-2,6-dibromophenoland 4-(2-hydroxyisopropyl)-2,6-dibromophenol, were identified as major degradation products of TBBPA while themajor degradation product of TriBBPA was tentatively identified as 2-(2,4-cyclopentadienyl)-2-(3,5-dibromo-4-hydroxyphenyl)propane.

  • 10.
    Fång, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Widmalm, Göran
    Department of Organic Chemistry.
    Separation and NMR characterisation of Hexabromocyclododecane (HBCDD)2007In: Svensk-norsk miljökjemisk vintermöte: Dr. Holms Hotell, Geilo, 2007, p. 34-Conference paper (Other academic)
  • 11.
    Granelli, Lisa
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Athanasiadou, Maria
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Reductive debromination of nonabrominated diphenyl ethers by sodium borohydride and identification of octabrominated diphenyl ether products2011In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 82, no 6, p. 839-846Article in journal (Refereed)
    Abstract [en]

    A method was developed to study reductive transformation of highly brominated diphenyl ethers (BDEs). The method development is a part of a broader project where it will be used to determine the susceptibility of environmental pollutants to reductive conditions, in an attempt to create a scheme for determination of chemical’s persistence. This paper focuses on identification of octabrominated diphenyl ether transformation products from reductive debromination of the three nonabrominated diphenyl congeners (nonaBDE), BDE-206, -207 and -208. Sodium borohydride was used to explore the reductive debromination of the nonaBDEs. The transformation products were collected at two time-points and identified products were quantified by GC–MS. The reduction of the nonaBDEs lead primarily to debrominated products, mainly octaBDEs. The three nonabrominated DEs gave isomer-related transformation product patterns. BDE-207 and BDE-208 showed a propensity for ortho-debromination in the initial reaction step, while no discrimination between initial debromination positions was seen for BDE-206. All three nonabrominated DEs displayed a preferred initial debromination on the fully brominated DE ring.

  • 12.
    Granelli, Lisa
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Photolysis of four novel brominated flame retardantsManuscript (preprint) (Other academic)
  • 13.
    Granelli, Lisa
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Eriksson, Johan
    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).
    Sodium borohydride reduction of individual polybrominated diphenyl ethers2012In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 86, no 10, p. 1008-1012Article in journal (Refereed)
    Abstract [en]

    Many chemicals in use today lack appropriate documentation on their environmental properties, fate, and effects. To counteract this lack of documentation it is vital to thoroughly investigate a compound's fate in the environment before it comes into use. The present study is describing a novel method for assessing the reduction potential of polybrominated diphenyl ethers (PBDEs), as a part of a project aimed to create an experimental model for determination of chemical persistence. The reductive transformation of 15 PBDE congeners using sodium borohydride was determined. Pseudo-first-order reaction rate constants of the transformations were determined by monitoring the disappearance of the investigated congeners. The reductions lead primarily to formation of lower brominated PBDEs. Each PBDE congener was tested in a total of ten replicates which showed a relative standard deviation of 31% or less. The deca-BDE, BDE-209 was approximately 3 times as prone to reductive transformation as BDE-207. The three nonaBDEs, BDE-206, BDE-207, and BDE-208, showed similar reductive potential. The reactivity of the tested octaBDEs was quite variable, from 5% to 24% of the reactivity of BDE-209 for BDE-196 and BDE-198, respectively. The heptaBDEs studied were in the range of the less reactive octaBDEs, except for BDE-181 which was as high as 13% of the reactivity of BDE-209. The results presented give a method for measuring the propensity of PBDEs, and possibly similar compounds, to undergo reductions. They indicate a potential route to a vital piece of information in the assessment of environmental persistence of chemicals.

  • 14.
    Granelli, Lisa
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Sodium borohydride reduction of individual polybrominated diphenyl ethersManuscript (preprint) (Other academic)
  • 15.
    Hedenbrant, Ulla
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Haglund, Johanna
    Alsberg, Tomas
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Törnqvist, Margareta
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Development of a method for determination of serum albumin adducts of benzo(a)pyrene by LC/ESI-MS2008Conference paper (Other academic)
  • 16. Heimstad, Eldbjørg Sofie
    et al.
    Moreira Bastos, Patricia
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Harju, Mikael
    Quantitative structure-Photodegradation relationships of polybrominated diphenyl ethers, phenoxyphenols and selected organochlorines2009In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 77, no 7, p. 914-921Article in journal (Refereed)
    Abstract [en]

    Among other developments, the technological revolution has lead to introduction of new chemicals to better serve in instruments and materials. The consequences of the extensive increase in use of new chemicals can be detected in the environment world wide, i.e. in wildlife and humans. To ensure this problem to be minimised in the future, new chemicals need to be subjected to predictive assessments before commercialised. To facilitate screening, qualitative structure-activity relationships, quantitative structure-activity relationships may be applied to describe reactivity of chemicals. Physico-chemical properties of chemicals such as partition coefficients and half-lives for the various environmental compartments are essential input data in multimedia environmental fate models. In this study we examine how structural characteristics can quantitatively describe laboratory determined photolytic half-lives of halogenated compounds of different classes, such as polybrominated diphenyl ethers (PBDEs), hydroxylated brominated diphenyl ethers (OH-PBDEs), and other organohalogens. A total of 30 chemicals with experimentally measured half-lives are used. Results reveal that the most important descriptors for describing the half-lives of the brominated compounds are the energy gap (GAP-1) between HOMO-1 and LUMO, the lowest partial charge on a halogen atom (Qhal-), topological polar surface area (TPSA), the atom with highest radical superdelocalizability (Rad-super+) and LUMO density (LUMO+).

  • 17.
    Moreira Bastos, Patricia
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Vidarson, Jenny
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Oxidative transformation of polybrominated diphenyl ether congeners (PBDEs) and of hydroxylated PBDEs (OH-PBDEs)2008In: Environmental Science and Pollution Research, ISSN 0944-1344, E-ISSN 1614-7499, Vol. 15, no 7, p. 606-613Article in journal (Refereed)
    Abstract [en]

    BACKGROUND, AIM, AND SCOPE: The historical and widespread use of polybrominated diphenyl ethers (PBDEs) as flame retardants in consumer products worldwide has caused PBDEs to now be regarded as pervasive environmental contaminants. Most recently, hydroxylated PBDEs (OH-PBDEs) and methoxylated PBDEs (MeO-PBDEs) have emerged as environmentally relevant due to reports of their natural production and metabolism. An important parameter for assessing the environmental impact of a chemical substance is persistence. By formulating the concept that persistence is the result of the substance's physicochemical properties and chemical reactivity, Green and Bergman have proposed a new methodology to determine the inherent persistence of a chemical. If persistence could be predicted by straightforward methods, substances with this quality could be screened out before large-scale production/manufacturing begins. To provide data to implement this concept, we have developed new methodologies to study chemical transformations through photolysis; hydrolysis, substitution, and elimination; and via oxidation. This study has focused on adapting an oxidative reaction method to be applicable to non-water soluble organic pollutants. MATERIALS AND METHODS: PBDEs and one MeO-PBDE were dissolved in tetrahydrofuran/methanol and then diluted in alkaline water. The OH-PBDEs were dissolved in alkaline water prior to reaction. The oxidation degradation reaction was performed at 50 degrees C using potassium permanganate as described elsewhere. The pH was maintained at 7.6 with disodium hydrogen phosphate and barium hydrogen phosphate, the latter also serving as a trapping agent for manganate ions. The oxidation reactions were monitored by high-performance liquid chromatography and reaction rates were calculated. RESULTS: The OH-PBDEs have very fast oxidative transformation rates compared to the PBDEs. The reaction rates seem to be primarily dependent on substitution pattern of the pi-electron-donating bromine substituents and of bromine content. There are indications that further reactions of OH-PBDEs, e.g., methylation to the MeO-PBDEs, decrease the oxidation rates, and thereby generate more persistent substances. DISCUSSION: The resistance of PBDEs to oxidation, a major degradation pathway in air, should be further investigated, since these compounds do undergo long range transport. With slight modifications, the original method has been adapted to include a larger variety of chemical substances, and preliminary data are now available on the oxidative transformation rates for PBDEs and of OH-PBDEs. CONCLUSIONS: The original oxidation degradation method can now include non-water soluble compounds. This modification, using low concentrations of test chemicals, allows us to measure oxidative transformation rates, for some of the lower brominated DEs, data that can be used to assess their persistence in future model calculations. Oxidative transformation rates for PBDEs are slow compared to those for the OH-PBDEs. This suggests that OH-PBDEs, when released into the environment, undergo faster oxidative metabolism and excretion than the PBDEs. RECOMMENDATIONS AND PERSPECTIVES: To evaluate the modified method, more degradation reactions with non-water soluble compounds should be investigated. Recent studies show that OH-PBDEs are present in rats and in humans and, because of their activity as endocrine disruptors, determining their subsequent environmental fate is of importance. The resistance of PBDEs to oxidative degradation should be acknowledged as of possible future concern. Several other compound classes (such as polychlorinated biphenyls (PCBs), hydroxylated polychlorinated biphenyls (OH-PCBs), and pharmaceuticals) need to be subjected to this screening method to increase the database of transformation rates that can be used with this model.

  • 18. Pohl, Johannes
    et al.
    Golovko, Oksana
    Carlsson, Gunnar
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.
    Glynn, Anders
    Örn, Stefan
    Weiss, Jana
    Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.
    Carbamazepine Ozonation Byproducts: Toxicity in Zebrafish (Danio rerio) Embryos and Chemical Stability2020In: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 54, no 5, p. 2913-2921Article in journal (Refereed)
    Abstract [en]

    Carbamazepine (CBZ) is an anticonvulsant medication with highly persistent properties in the aquatic environment, where it has the potential to affect nontarget biota. Because CBZ and many other pharmaceuticals are not readily removed in conventional sewage treatment plants (STP), additional STP effluent treatment technologies are being evaluated and implemented. Whole effluent ozonation is a prospective method to remove pharmaceuticals such as CBZ, yet knowledge on the toxicity of CBZ ozonation byproducts (OBPs) is lacking. This study presents, for the first time, in vivo individual and mixture toxicity of four putative OBPs, that is, carbamazepine 10,11-epoxide, 10,11-Dihydrocarbamazepine, 1-(2-benzaldehyde)-4-hydro-(1H,3H)-quinazoline-2-one (BQM), and 1-(2-benzaldehyde)-(1H,3H)-quinazoline-2,4-dione (BQD) in developing zebrafish (Danio rerio) embryos. BQM and BQD were isolated from the ozonated solution as they were not commercially available. The study confirmed that the OBP mixture caused embryotoxic responses comparable to that of ozonated CBZ. Individual compound embryotoxicity assessment further revealed that BQM and BQD were the drivers of embryotoxicity. OBP chemical stability in ozonated CBZ water solution during 2 week dark storage at 22 degrees C was also assessed. The OBP concentrations remained over time, except for BQD which decreased by 94%. Meanwhile, ozonated CBZ persistently induced embryotoxicity over 2 week storage, potentially illustrating environmental concern.

  • 19. Qiu, Yanling
    et al.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Granelli, Lisa
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Environmental Chemistry.
    An improved method for assessing relative nucleophilic substitution reactivities of polychlorinated benzenes2009In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 75, no 1, p. 78-82Article in journal (Refereed)
    Abstract [en]

    An existing substitution reaction method was improved as part of a system to measure the persistency of selected chemicals in the environment by evaluating their chemical reactivity. Hexachlorobenzene (HCB), pentachlorobenzene, 1,2,4,5-tetrachlorobenzene and 1,2,4-trichlorobenzene were selected as model compounds. Sodium methoxide in methanol was used as a nucleophile and found to be stable for at least 35 days after preparation. The substitution reaction system was modified so that nitrogen protection was not necessary to avoid oxidation and hydrolysis effects, which led to improved results. The reactivity of polychlorinated benzenes (PCBz), which substituted chlorine for methoxide according to a second-order rate constant, increased as the number of chlorine atoms on the benzene ring increased. HCB was selected as a standard for the k2 calculations of the substitution reactions. A normalized k2 (kN) was calculated as kN = kPCBz/kHCB. GC–MS analysis confirmed that the reactions were pure nucleophilic aromatic substitutions without side reactions.

  • 20.
    Sundström, Maria
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Bogdanska, Jasna
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Pham, Hung V.
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Athanasios, Vlastaras
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Nobel, Stefan
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    McAlees, Alan
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    DePierre, Joseph W.
    Stockholm University, Faculty of Science, Department of Biochemistry and Biophysics.
    Bergman, Åke
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Radiosynthesis of perfluorooctanesulfonate (PFOS) and perfluorobutanesulfonate (PFBS), including solubility, partition and adhesion studies2012In: Chemosphere, ISSN 0045-6535, E-ISSN 1879-1298, Vol. 87, no 8, p. 865-871Article in journal (Refereed)
    Abstract [en]

    Here, we describe for the first time the synthesis of [S-35] PFOS and [S-35] PFBS with sulfur-35 enriched sulfur dioxide as the radiolabelled reagent, resulting in 2.5 and 2.3 mCi of product, respectively. Basic information concerning the physicochemical properties of perfluorooctanesulfonate (PFOS), perfluorobutanesulfonate (PFBS) and perfluorooctanoic acid (PFOA) are still limited. Hence, we utilized these radiolabelled perfluoroalkanesulfonates (PFSAs), as well as carbon-14 labelled perfluorooctanoic acid a, ([C-14] PFOA) to determine some basic characteristics of physiological and experimental significance. The solubility of PFOS in buffered aqueous solutions at pH 7.4 was found to be severely reduced in the presence of potassium and sodium ions, which, however, did not reduce the solubility of PFOA or PFBS. PFOS was found to adhere to a small extent to polypropylene and polystyrene, whereas no such adhesion of PFOA or PFBS was detected. The extents of adhesion of PFOS and PFOA to glass were found to be 20% and 10%, respectively. For the first time, the partition coefficients for PFOS, PFBS and PFOA between n-octanol and water were determined experimentally, to be -0.7, -0.3, and 1.4, respectively, reflecting the difference in the amphiphilic natures of these molecules.

  • 21. Svanfelt, Jesper
    et al.
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Environmental Chemistry.
    Kronberg, Leif
    Photochemical transformation of the thyroid hormone levothyroxine in aqueous solution2011In: Environmental Science and Pollution Research, ISSN 0944-1344, E-ISSN 1614-7499, Vol. 18, no 6, p. 871-876Article in journal (Refereed)
    Abstract [en]

    Purpose The direct aqueous photolysis of the thyroid hormone levothyroxine (T(4)) has been studied. Methods and Result One of the major photoproducts, i.e., 4-[4-(2-amino-2-carboxy-ethyl)-2,6-diiodo-phenoxy]-penta-2,4-dienoic acid (P1), was isolated by liquid chromatography and structurally assigned by mass spectrometric (MS) and nuclear magnetic resonance spectroscopic methods. The identity of a second major product, i.e., 3,5-diiodo-l-thyrosine (P3), was confirmed through access to a commercially available standard. Furthermore, the structures of three additional transformation products are proposed on the basis of data obtained by high-resolution MS analyses. UV absorption spectra were determined for T(4) and the two photoproducts P1 and P3. Disappearance quantum yields were calculated for T(4) (I center dot = 0.014 at pH 12) and P3 (I center dot = 0.024 at pH 12 and I center dot = 0.010 at pH 8.5), whereas the compound P1 was found to be stable under the studied conditions (T(1/2) = 600 min). Conclusion The results indicate that solar UV light may have a significant impact on the fate of T(4) in the aquatic environment.

  • 22.
    Vryonidis, Efstathios
    et al.
    Stockholm University, Faculty of Science, Department of Environmental Science.
    Karlsson, Isabella
    Stockholm University, Faculty of Science, Department of Environmental Science.
    Aasa, Jenny
    Carlsson, Henrik
    Motwani, Hitesh Vijay
    Stockholm University, Faculty of Science, Department of Environmental Science.
    Pedersen, Marie
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Environmental Science.
    Törnqvist, Margareta
    Stockholm University, Faculty of Science, Department of Environmental Science.
    Pathways to Identify Electrophiles In Vivo Using Hemoglobin Adducts: Hydroxypropanoic Acid Valine Adduct and Its Possible Precursors2022In: Chemical Research in Toxicology, ISSN 0893-228X, E-ISSN 1520-5010, Vol. 35, no 12, p. 2227-2240Article in journal (Refereed)
    Abstract [en]

    Analytical methods and tools for the characterization of the human exposome by untargeted mass spectrometry approaches are advancing rapidly. Adductomics methods have been developed for untargeted screening of short-lived electrophiles, in the form of adducts to proteins or DNA, in vivo. The identification of an adduct and its precursor electrophile in the blood is more complex than that of stable chemicals. The present work aims to illustrate procedures for the identification of an adduct to N-terminal valine in hemoglobin detected with adductomics, and pathways for the tracing of its precursor and possible exposure sources. Identification of the adduct proceeded via preparation and characterization of standards of adduct analytes. Possible precursor(s) and exposure sources were investigated by measurements in blood of adduct formation by precursors in vitro and adduct levels in vivo. The adduct was identified as hydroxypropanoic acid valine (HPA-Val) by verification with a synthesized reference. The HPA-Val was measured together with other adducts (from acrylamide, glycidamide, glycidol, and acrylic acid) in human blood (n = 51, schoolchildren). The HPA-Val levels ranged between 6 and 76 pmol/g hemoglobin. The analysis of reference samples from humans and rodents showed that the HPA-Val adduct was observed in all studied samples. No correlation of the HPA-Val level with the other studied adducts was observed in humans, nor was an increase in tobacco smokers observed. A small increase was observed in rodents exposed to glycidol. The formation of the HPA-Val adduct upon incubation of blood with glycidic acid (an epoxide) was shown. The relatively high adduct levels observed in vivo in relation to the measured reactivity of the epoxide, and the fact that the epoxide is not described as naturally occurring, suggest that glycidic acid is not the only precursor of the HPA-Val adduct identified in vivo. Another endogenous electrophile is suspected to contribute to the in vivo HPA-Val adduct level. 

  • 23.
    Westberg, Emelie
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Hedebrant, Ulla
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Haglund, Johanna
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Alsberg, Tomas
    Stockholm University, Faculty of Science, Department of Applied Environmental Science (ITM).
    Eriksson, Johan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Seidel, Albrecht
    Törnqvist, Margareta
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Conditions for sample preparation and quantitative HPLC/MS-MS analysis of bulky adducts to serum albumin with diolepoxides of polycyclic aromatic hydrocarbons as models2014In: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 406, no 5, p. 1519-1530Article in journal (Refereed)
    Abstract [en]

    Stable adducts to serum albumin (SA) from electrophilic and genotoxic compounds/metabolites can be used as biomarkers for quantification of the corresponding in vivo dose. In the present study, conditions for specific analysis of stable adducts to SA formed from carcinogenic polycyclic aromatic hydrocarbons (PAH) were evaluated in order to achieve a sensitive and reproducible quantitative method. Bulky adducts from diolepoxides (DE) of PAH, primarily DE of benzo[a]pyrene (BPDE) and also DE of dibenzo[a,l]pyrene (DBPDE) and dibenzo[a,h]anthracene (DBADE), were used as model compounds. The alkylated peptides obtained after enzymatic hydrolysis of human SA modified with the different PAHDE were principally PAHDE-His-Pro, PAHDE-His-Pro-Tyr and PAHDE-Lys. Alkaline hydrolysis under optimised conditions gave the BPDE-His as the single analyte of alkylated His, but also indicated degradation of this adduct. It was not possible to obtain the BPDE-His as one analyte from BPDE-alkylated SA through modifications of the enzymatic hydrolysis. The BPDE-His adduct was shown to be stable during the weak acidic conditions used in the isolation of SA. Enrichment by HPLC or SPE, but not butanol extraction, gave good recovery, using Protein LoBind tubes. A simple internal standard (IS) approach using SA modified with other PAHDE as IS was shown to be applicable. A robust analytical procedure based on digestion with pronase, enrichment by HPLC or SPE, and analysis with HPLC/MS-MS electrospray ionisation was achieved. A good reproducibility (coefficient of variation (CV) 11 %) was obtained, and the achieved limit of detection for the studied PAHDE, using standard instrumentation, was approximately 1 fmol adduct/mg SA analysing extract from 5 mg SA.

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