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  • 101.
    Tysklind, Mats
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Haglund, Peter
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    van Bavel, B
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Rappe, Christoffer
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Selection of polychlorinated biphenyls for use in quantitative structure-activity modelling1995Ingår i: SAR and QSAR in environmental research (Print), ISSN 1062-936X, E-ISSN 1029-046X, Vol. 4, nr 1, s. 11-19Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    By characterizing the 154 tetra- through heptachlorinated biphenyl (PCB) congeners with a multitude of physico-chemical descriptors, a model representing chemical similarities and differences is achieved. The multivariate characterization of the PCBs was based on 47 physico-chemical descriptor variables, which were summarised by using principal component analysis (PCA). By applying statistical design to the orthogonal scores from the PCA, a 24-factorial design was used to select a set of 16 congeners. In addition, four congeners were added to provide information about the interior region of the chemical domain of PCBs. This set of 20 structurally different congeners is suggested to be used in future quantitative structure-activity relationships (QSARs) for screening of the toxicological and biochemical effects of the PCBs.

  • 102.
    Tysklind, Mats
    et al.
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Harju, M
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Rattfelt, Jenny
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    A QSARs strategy - applications with focux on brominated flame reterdants2006Ingår i: Using chemistry in environmental and health risk assessment, US-AB Universitetsservice, Stockholm , 2006, s. 75-98Kapitel i bok, del av antologi (Refereegranskat)
  • 103. Van der Burght, A S A M
    et al.
    Tysklind, Mats
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Horbach, G J
    van den Berg, M
    Structure dependent induction of CYP1A by polychlorinated biphenyls in hepatocytes of male castrated pigs2000Ingår i: Chemosphere, Vol. 41, nr 10, s. 1697-1708Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Hepatocytes cultures prepared from castrated pig hepatocytes (Great YorkshirexDutch Landrace), as a model for human liver, were used to study the effect of twenty polychlorinated biphenyls (PCBs) on CYP1A activity, measured as the dealkylation of either ethoxyresorufin or methoxyresorufin. The selection of the PCBs was based on their differences in physico-chemical properties. The non-ortho and mono-ortho substituted PCBs were the most potent CYP1A inducers in pig hepatocytes. In addition, several multiple-ortho substituted congeners, with five or more chlorine atoms, were inducers of CYP1A activity as well. Their relative effect potencies (REP) were proximately 10,000 times lower than the most potent congener, 3,3',4,4',5 PeCB (PCB#126). Using partial least-squares (PLS) modeling, predictions of CYP1A activity could be made for all tetra to hepta substituted congeners. Several multiple-ortho substituted PCBs, which are highly abundant in the biotic and abiotic environment, have been found to induce CYP1A activity in pig hepatocytes. Because induction of CYP1A activity is used as biomarker for Ah-receptor mediated responses, it is suggested to include these congeners in future risk assessment.

  • 104.
    van Ede, Karin I.
    et al.
    Univ Utrecht, Inst Risk Assessment Sci, NL-3508 TD Utrecht, Netherlands.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Gaisch, Konrad P. J.
    Univ Utrecht, Inst Risk Assessment Sci, NL-3508 TD Utrecht, Netherlands.
    van den Berg, Martin
    Univ Utrecht, Inst Risk Assessment Sci, NL-3508 TD Utrecht, Netherlands.
    van Duursen, Majorie B. M.
    Univ Utrecht, Inst Risk Assessment Sci, NL-3508 TD Utrecht, Netherlands.
    Comparison of intake and systemic relative effect potencies of dioxin-like compounds in female rats after a single oral dose2014Ingår i: Archives of Toxicology, ISSN 0340-5761, E-ISSN 1432-0738, Vol. 88, nr 3, s. 637-646Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Risk assessment for mixtures of dioxin-like compounds uses the toxic equivalency factor (TEF) approach. Although current WHO-TEFs are mostly based on oral administration, they are commonly used to determine toxicity equivalencies (TEQs) in human blood or tissues. However, the use of "intake" TEFs to calculate systemic TEQs in for example human blood, has never been validated. In this study, intake and systemic relative effect potencies (REPs) for 1,2,3,7,8-pentachlorodibenzo-p-dioxin (PeCDD), 2,3,4,7,8-pentachlorodibenzofuran (4-PeCDF), 3,3',4,4',5-pentachlorobiphenyl (PCB-126), 2,3',4,4',5-pentachlorobiphenyl (PCB-118) and 2,3,3',4,4',5-hexachlorobiphenyl (PCB-156) were compared in rats. The effect potencies were calculated based on administered dose and liver, adipose or plasma concentrations in female Sprague-Dawley rats 3 days after a single oral dose, relative to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). Hepatic ethoxyresorufin-O-deethylase activity and gene expression of Cyp1a1, 1a2, 1b1 and aryl hydrocarbon receptor repressor in liver and peripheral blood lymphocytes were used as endpoints. Results show that plasma-based systemic REPs were generally within a half log range around the intake REPs for all congeners tested, except for 4-PeCDF. Together with our previously reported systemic REPs from a mouse study, these data do not warrant the use of systemic REPs as systemic TEFs for human risk assessment. However, further investigation for plasma-based systemic REPs for 4-PeCDF is desirable.

  • 105.
    van Ede, Karin I.
    et al.
    Institute for Risk Assessment Sciences, Utrecht University, Utrecht, the Netherlands.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Gaisch, Konrad P. J.
    Institute for Risk Assessment Sciences, Utrecht University, Utrecht, the Netherlands.
    van den Berg, Martin
    Institute for Risk Assessment Sciences, Utrecht University, Utrecht, the Netherlands.
    van Duursen, Majorie B. M.
    Institute for Risk Assessment Sciences, Utrecht University, Utrecht, the Netherlands.
    Comparison of Intake and Systemic Relative Effect Potencies of Dioxin-like Compounds in Female Mice after a Single Oral Dose2013Ingår i: Journal of Environmental Health Perspectives, ISSN 0091-6765, E-ISSN 1552-9924, Vol. 121, nr 7, s. 847-853Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    BACKGROUND: Risk assessment for mixtures of polychlorinated dibenzo-p-dioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and polychlorinated biphenyls (PCBs) is performed using the toxic equivalency factor (TEF) approach. These TEF values are derived mainly from relative effect potencies (REPs) linking an administered dose to an in vivo toxic or biological effect, resulting in "intake" TEFs. At present, there is insufficient data available to conclude that intake TEFs are also applicable for systemic concentrations (e. g., blood and tissues). OBJECTIVE: We compared intake and systemic REPs of 1,2,3,7,8-pentachlorodibenzodioxin (PeCDD), 2,3,4,7,8-pentachlorodibenzofuran (4-PeCDF), 3,3', 4,4', 5-pentachlorobiphenyl (PCB-126), 2,3', 4,4', 5-pentachlorobiphenyl (PCB-118), and 2,3,3', 4,4', 5-hexachlorobiphenyl (PCB-156) in female C57BL/6 mice 3 days after a single oral dose. METHODS: We calculated intake REPs and systemic REPs based on administered dose and liver, adipose, or plasma concentrations relative to TCDD. Hepatic cytochrome P450 1Al-associated ethoxyresorufin-O-deethylase (EROD) activity and gene expression of Cyp1a1, 1a2 and 1b1 in the liver and peripheral blood lymphocytes (PBLs) were used as biological end points. RESULTS: We observed up to one order of magnitude difference between intake REPs and systemic REPs. Two different patterns were discerned. Compared with intake REPs, systemic REPs based on plasma or adipose levels were higher for PeCDD, 4-PeCDF, and PCB-126 but lower for the mono-ortho PCBs 118 and 156. CONCLUSIONS: Based on these mouse data, the comparison between intake REPs and systemic REPs reveals significant congener-specific differences that warrants the development of systemic TEFs to calculate toxic equivalents (TEQs) in blood and body tissues.

  • 106. van Ede, Karin I
    et al.
    Aylward, Lesa L
    Andersson, Patrik L
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    van den Berg, Martin
    van Duursen, Majorie BM
    Tissue distribution of dioxin-like compounds: potential impacts on systemic relative potency estimates2013Ingår i: Toxicology Letters, ISSN 0378-4274, E-ISSN 1879-3169, Vol. 220, nr 3, s. 294-302Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Relative effect potencies (REPs) for dioxins and dioxin-like compounds based on tissue concentration or internal dose ((systemic)REPs) can be considered of high relevance for human risk assessment. Within the EU-project SYSTEQ, (systemic)REPs for 1,2,3,7,8-pentachlorodibenzodioxin (PeCDD), 2,3,4,7,8,-pentachlorodibenzofuran (4-PeCDF), 3,3',4,4',5-pentachlorobiphenyl (PCB 126), 2,3',4,4',5-pentachlorobiphenyl (PCB 118) and 2,3,3',4,4',5-hexachlorobiphenyl (PCB 156) were calculated based on a plasma, adipose tissue or liver concentration in Sprague Dawley rats and C57bl/6 mice three days after a single oral dose. Compound-specific distribution as well as differences in accumulation and elimination can influence the tissue concentration and thereby the relative potency estimate of a congener. Here, we show that distribution patterns are generally similar for the tested congeners between the SYSTEQ dataset and other studies using either a single dose or subchronic dosing. Furthermore, the responding concentration for TCDD in single dose studies is comparable to the responding concentrations reported in subchronic studies. In contrast with data for laboratory rodents, available distribution data for humans in the general population display little or no hepatic sequestration. Because hepatic sequestration due to CYP1A2 protein binding may affect the amount of congener that is bioavailable for the AhR to produce hepatic responses, estimates of relative potencies between congeners with differing degrees of hepatic sequestration based on hepatic responses may be misleading for application to human risk assessment. Therefore, extra-hepatic concentration in blood serum/plasma or adipose tissue together with a biological extra-hepatic response might give a more accurate prediction of the relative potency of a congener for human responses under environmental conditions.

    (C) 2013 Elsevier Ireland Ltd. All rights reserved.

  • 107. Viluksela, Matti
    et al.
    Heikkinen, Paivi
    van der Ven, Leo T. M.
    Rendel, Filip
    Roos, Robert
    Esteban, Javier
    Korkalainen, Merja
    Lensu, Sanna
    Miettinen, Hanna M.
    Savolainen, Kari
    Sankari, Satu
    Lilienthal, Hellmuth
    Adamsson, Annika
    Toppari, Jorma
    Herlin, Maria
    Finnila, Mikko
    Tuukkanen, Juha
    Leslie, Heather A.
    Hamers, Timo
    Hamscher, Gerd
    Al-Anati, Lauy
    Stenius, Ulla
    Dervola, Kine-Susann
    Bogen, Inger-Lise
    Fonnum, Frode
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Schrenk, Dieter
    Halldin, Krister
    Håkansson, Helen
    Toxicological Profile of Ultrapure 2,2 ',3,4,4 ',5,5 '-Heptachlorbiphenyl (PCB 180) in Adult Rats2014Ingår i: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 9, nr 8, s. e104639-Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    PCB 180 is a persistent non-dioxin-like polychlorinated biphenyl (NDL-PCB) abundantly present in food and the environment. Risk characterization of NDL-PCBs is confounded by the presence of highly potent dioxin-like impurities. We used ultrapure PCB 180 to characterize its toxicity profile in a 28-day repeat dose toxicity study in young adult rats extended to cover endocrine and behavioral effects. Using a loading dose/maintenance dose regimen, groups of 5 males and 5 females were given total doses of 0, 3, 10, 30, 100, 300, 1000 or 1700 mg PCB 180/kg body weight by gavage. Dose-responses were analyzed using benchmark dose modeling based on dose and adipose tissue PCB concentrations. Body weight gain was retarded at 1700 mg/kg during loading dosing, but recovered thereafter. The most sensitive endpoint of toxicity that was used for risk characterization was altered open field behavior in females; i.e. increased activity and distance moved in the inner zone of an open field suggesting altered emotional responses to unfamiliar environment and impaired behavioral inhibition. Other dose-dependent changes included decreased serum thyroid hormones with associated histopathological changes, altered tissue retinoid levels, decreased hematocrit and hemoglobin, decreased follicle stimulating hormone and luteinizing hormone levels in males and increased expression of DNA damage markers in liver of females. Dose-dependent hypertrophy of zona fasciculata cells was observed in adrenals suggesting activation of cortex. There were gender differences in sensitivity and toxicity profiles were partly different in males and females. PCB 180 adipose tissue concentrations were clearly above the general human population levels, but close to the levels in highly exposed populations. The results demonstrate a distinct toxicological profile of PCB 180 with lack of dioxin-like properties required for assignment of WHO toxic equivalency factor. However, PCB 180 shares several toxicological targets with dioxin-like compounds emphasizing the potential for interactions.

  • 108. Voiea, Ø A
    et al.
    Tysklind, Mats
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Fonnum, F
    Activation of Respiratory Burst in Human Granulocytes by Polychlorinated Biphenyls: A Structure–Activity Study2000Ingår i: Toxicology and Applied Pharmacology, Vol. 167, nr 2, s. 118-24Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The respiratory burst in human granulocytes activated by 33 different congeners of polychlorinated biphenyls (PCBs) was measured as luminol-amplified chemoluminescence. The selection of 20 (training set) compounds was based on multivariate chemical characterization, laying the groundwork for covering the whole chemical series of tetra- through hepta-chlorinated PCBs. In addition 6 congeners were used as a validation set, and 7 were mono- to tri-chlorinated congeners representing low-chlorinated compounds not covered by the training set. Only ortho-substituted biphenyls activate respiratory burst. There is a correlation between activated respiratory burst and the total surface area of congeners up to 230 × 10−20 m2. Congeners of larger size show a reduced activity. There is also a correlation between respiratory burst activity and the number of ortho-substituents. Furthermore, there is also a correlation with parameters that describe absolute hardness of the molecule and respiratory burst activity. Congeners with a 2,4,6-substitution on one biphenyl ring are optimal activators. In conclusion, all three factors, size, rotation, and electronic properties, which are not independent of each other, are important for the activity of the PCBs.

  • 109.
    Weidemann, Eva
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Bidleman, Terry
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Boman, Christoffer
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Institutionen för tillämpad fysik och elektronik.
    Carlin, Danielle J.
    Collina, Elena
    Cormier, Stephania A.
    Gouveia-Figueira, Sandra C.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Gullett, Brian K.
    Johansson, Christer
    Lucas, Donald
    Lundin, Lisa
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Lundstedt, Staffan
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Marklund, Stellan
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Nording, Malin L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Ortuno, Nuria
    Sallam, Asmaa A.
    Schmidt, Florian M.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Institutionen för tillämpad fysik och elektronik.
    Jansson, Stina
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    14th congress of combustion by-products and their health effects-origin, fate, and health effects of combustion-related air pollutants in the coming era of bio-based energy sources2016Ingår i: Environmental science and pollution research international, ISSN 0944-1344, E-ISSN 1614-7499, Vol. 23, nr 8, s. 8141-8159Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The 14th International Congress on Combustion By-Products and Their Health Effects was held in UmeAyen, Sweden from June 14th to 17th, 2015. The Congress, mainly sponsored by the National Institute of Environmental Health Sciences Superfund Research Program and the Swedish Research Council for Environment, Agricultural Sciences and Spatial Planning, focused on the "Origin, fate and health effects of combustion-related air pollutants in the coming era of bio-based energy sources". The international delegates included academic and government researchers, engineers, scientists, policymakers and representatives of industrial partners. The Congress provided a unique forum for the discussion of scientific advances in this research area since it addressed in combination the health-related issues and the environmental implications of combustion by-products. The scientific outcomes of the Congress included the consensus opinions that: (a) there is a correlation between human exposure to particulate matter and increased cardiac and respiratory morbidity and mortality; (b) because currently available data does not support the assessment of differences in health outcomes between biomass smoke and other particulates in outdoor air, the potential human health and environmental impacts of emerging air-pollution sources must be addressed. Assessment will require the development of new approaches to characterize combustion emissions through advanced sampling and analytical methods. The Congress also concluded the need for better and more sustainable e-waste management and improved policies, usage and disposal methods for materials containing flame retardants.

  • 110. Weiss, Jana M
    et al.
    Andersson, Patrik L
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Lamoree, Marja H
    Leonards, Pim E G
    van Leeuwen, Stefan P J
    Hamers, Timo
    Competitive Binding of Poly- and Perfluorinated Compounds to the Thyroid Hormone Transport Protein Transthyretin2009Ingår i: Toxicological sciences : an official journal of the Society of Toxicology, ISSN 1096-0929, Vol. 109, nr 2, s. 206-16Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Due to their unique surfactant properties, poly- and perfluorinated compounds (PFCs) have been extensively used, and can be found all over the environment.. Concern about their environmental fate and toxicological properties have initiated several research projects. In the present study, we investigated if PFCs can compete with thyroxin (T4, i.e. the transport form of thyroid hormone) for binding to the human thyroid hormone transport protein transthyretin (TTR). Such competitive capacity may lead to decreased thyroid hormone levels as previously reported for animals exposed to PFCs.

    Twenty four PFCs, together with six structurally similar natural fatty acids, were tested for binding capacity in a radioligand binding assay. The binding potency decreased in the order: PFHxS>PFOS/PFOA>PFHpA>L-PFOSi>PFNA, with TTR binding potencies 12.5-50 times lower than the natural ligand thyroxine (T4). Some lower molecular weight compounds with structural similarity to these PFCs were >100 times less potent than T4.

    Simple descriptors based on the two dimensional molecular structures of the compounds were used to visualize the chemical variation and to model the structure-activity relationship for the competitive potencies of the TTR-binding compounds. The models indicated the dependence on molecular size and functional group(s), but demanded a more detailed description of the chemical properties and data for validation and further QSAR development.

    Competitive binding of PFCs to TTR as observed for human TTR in the present study, may explain altered thyroid hormone levels described for PFC-exposed rats and monkeys. Median human blood levels of the most potent TTR-binding PFCs are 1-2 orders of magnitude lower than IC50-values determined in the present study. In addition, this study contributes to the understanding of the bioaccumulation of PFCs in man and possibly in other wildlife species.

  • 111. Weiss, Jana M.
    et al.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Zhang, Jin
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Simon, Eszter
    Leonards, Pim E. G.
    Hamers, Timo
    Lamoree, Marja H.
    Tracing thyroid hormone-disrupting compounds: database compilation and structure-activity evaluation for an effect-directed analysis of sediment2015Ingår i: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 407, nr 19, s. 5625-5634Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A variety of anthropogenic compounds has been found to be capable of disrupting the endocrine systems of organisms, in laboratory studies as well as in wildlife. The most widely described endpoint is estrogenicity, but other hormonal disturbances, e.g., thyroid hormone disruption, are gaining more and more attention. Here, we present a review and chemical characterization, using principal component analysis, of organic compounds that have been tested for their capacity to bind competitively to the thyroid hormone transport protein transthyretin (TTR). The database contains 250 individual compounds and technical mixtures, of which 144 compounds are defined as TTR binders. Almost one third of these compounds (n = 52) were even more potent than the natural hormone thyroxine (T-4). The database was used as a tool to assist in the identification of thyroid hormone-disrupting compounds (THDCs) in an effect-directed analysis (EDA) study of a sediment sample. Two compounds could be confirmed to contribute to the detected TTR-binding potency in the sediment sample, i.e., triclosan and nonylphenol technical mixture. They constituted less than 1 % of the TTR-binding potency of the unfractionated extract. The low rate of explained activity may be attributed to the challenges related to identification of unknown contaminants in combination with the limited knowledge about THDCs in general. This study demonstrates the need for databases containing compound-specific toxicological properties. In the framework of EDA, such a database could be used to assist in the identification and confirmation of causative compounds focusing on thyroid hormone disruption.

  • 112. Westerlund, L
    et al.
    Billsson, K
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Tysklind, Mats
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Olsson, PE
    Early life-stage mortality in zebrafish (Danio rerio) following maternal exposure to polychlorinated biphenyls and estrogen2000Ingår i: Environmental Toxicology and Chemistry, ISSN 0730-7268, Vol. 19, nr 6, s. 1582-8Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    In the present study, specific polychlorinated biphenyl (PCB) congeners were examined far embryo and early life stage mortality in zebrafish (Danio rerio). A set of eight PCBs and two hydroxylated PCBs and 17 beta-estradiol were tested. Of the compounds tested, 4'-OH-PCB30 (hydroxylated polychlorinated biphenyl) and PCB 104 were found to be highly toxic to embryos following maternal exposure and transfer to the oocyte. It was also observed that 17 beta-estradiol exposure resulted in a high incidence of embryo mortality. Analysis of estrogen receptor levels during embryonic development showed increased mRNA (ribonucleic acid) levels from the 1K stage to 50% epiboly. Following injection of the different compounds, the estrogen receptor mRNA levels were also analyzed in adult male fish to determine if there was a correlation between embryo mortality and estrogenicity of the studied PCBs. The two PCBs that were highly embryo toxic were observed to be estrogenic.

  • 113.
    Wiberg, Karin
    et al.
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Berg, H
    Olsson, P-E
    Haglund, Peter
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    The fate of chiral organochlorine compounds and selected metabolites in intraperitoneally exposed Arctic char (Salvelinus alpinus)2006Konferensbidrag (Övrigt vetenskapligt)
    Abstract [en]

    Abstract to 1st Network Conference, POPs 29 and 30 March, Birmingham, U.K. 2006, oral presentation

  • 114.
    Wiberg, Karin
    et al.
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Patrik
    Matematik och matematisk statistik.
    Berg, Håkan
    Olsson, Per-Erik
    Haglund, Peter
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    The fate of chiral organochlorine compounds and selected metabolites in intraperitoneally exposed arctic char (Salvelinus alpinus).2006Ingår i: Environmental Toxicology & Chemistry, ISSN 0730-7268, Vol. 25, nr 6, s. 1465-73Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The fate of chiral organochlorine compounds (OCs) and selected metabolites in exposed Arctic char (Salvelinus alpinus) was investigated. The contaminants alpha-hexachlorocyclohexane (alpha-HCH), cis-chlordane, 13C4-heptachlor, o,p'-DDT, and the atropisomeric chlorinated biphenyls (CBs) 95, 132, 136, 149, and 174 were solved in peanut oil and injected into the peritoneal cavity. The exposed fish were sampled three times during a five-week period, and the OC residues and detected metabolites (heptachlorexo-epoxide) were quantified in muscle and liver tissues by chiral and achiral gas chromatography-mass spectrometry and gas chromatography-electron-capture detection. Peak concentrations were reached after one to two weeks, and thereafter, the levels declined. At the end of the experiment, liver concentrations had decreased 76 to 92% relative to peak concentrations, whereas muscle concentrations showed a moderate decline (5-38%), with the exception of alpha-HCH (91%). Hydrophobicity and steric hindrance were shown to influence the assimilation process, and a significant linear relationship between the product of the steric hindrance coefficients and the inverse of the octanol-water partition coefficients (Kow) versus peak concentration was found for the CBs (r2 = 0.86, p = 0.02). The assimilation of the contaminants into muscle and liver tissues generally resulted in racemic mixtures, whereas elimination was enantioselective for alpha-HCH, cis-chlordane, o,p'-DDT, CB-132, and CB-136. The chiral heptachlor metabolite 13C4-heptachlor-exo-epoxide was formed in the fish. The enantiomeric composition of the formed metabolite indicated racemic formation, whereas the elimination process appeared to be enantioselective.

  • 115. Wigestrand, Mattis B.
    et al.
    Stenberg, Mia
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Waalas, S Ivar
    Fonnum, Frode
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Non-dioxin-like PCBs inhibit [3H]WIN-35,428 binding to dopamine active transporter:  a structure activity relationship study2013Ingår i: Naunyn-Schmiedeberg's Archives of Pharmacology, ISSN 0028-1298, E-ISSN 1432-1912Artikel i tidskrift (Övrigt vetenskapligt)
  • 116.
    Zhang, Jin
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Begum, Afshan
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Brännström, Kristoffer
    Umeå universitet, Medicinska fakulteten, Institutionen för medicinsk kemi och biofysik.
    Grundström, Christin
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Iakovleva, Irina
    Umeå universitet, Medicinska fakulteten, Institutionen för medicinsk kemi och biofysik.
    Olofsson, Anders
    Umeå universitet, Medicinska fakulteten, Institutionen för medicinsk kemi och biofysik.
    Sauer-Eriksson, A. Elisabeth
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Structure-based Virtual Screening Protocol for in silico Identification of Potential Thyroid Disrupting Chemicals Targeting Transthyretin2016Ingår i: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 50, nr 21, s. 11984-11993Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Thyroid disruption by xenobiotics is associated with a broad spectrum of severe adverse outcomes. One possible molecular target of thyroid hormone disrupting chemicals (THDCs) is transthyretin (TTR), a thyroid hormone transporter in vertebrates. To better understand the interactions between TTR and THDCs, we determined the crystallographic structures of human TTR in complex with perfluorooctanesulfonic acid (PFOS), perfluorooctanoic acid (PFOA), and 2,2',4,4'-tetrahydroxybenzophenone (BP2). The molecular interactions between the ligands and TTR were further characterized using molecular dynamics simulations. A structure-based virtual screening (VS) protocol was developed with the intention of providing an efficient tool for the discovery of novel TTR-binders from the Tox21 inventory. Among the 192 predicted binders, 12 representatives were selected, and their TTR binding affinities were studied with isothermal titration calorimetry, of which seven compounds had binding affinities between 0.26 and 100 mu M. To elucidate structural details in their binding to TTR, crystal structures were determined of TTR in complex with four of the identified compounds including 2,6-dinitro-p-cresol, bisphenol S, clonixin, and triclopyr. The compounds were found to bind in the TTR hormone binding sites as predicted. Our results show that the developed VS protocol is able to successfully identify potential THDCs, and we suggest that it can be used to propose THDCs for future toxicological evaluations.

  • 117.
    Zhang, Jin
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Grundström, Christin
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Brännström, Kristoffer
    Umeå universitet, Medicinska fakulteten, Institutionen för medicinsk kemi och biofysik.
    Iakovleva, Irina
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Lindberg, Mikael J.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Olofsson, Anders
    Umeå universitet, Medicinska fakulteten, Institutionen för medicinsk kemi och biofysik.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Sauer-Eriksson, A. Elisabeth
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Interspecies variation between fish and human transthyretins in their binding of thyroid-disrupting chemicals2018Ingår i: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 52, nr 20, s. 11865-11874Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Thyroid-disrupting chemicals (TDCs) are xenobiotics that can interfere with the endocrine system and cause adverse effects in organisms and their offspring. TDCs affect both the thyroid gland and regulatory enzymes associated with thyroid hormone homeostasis. Transthyretin (TTR) is found in the serum and cerebrospinal fluid of vertebrates, where it transports thyroid hormones. Here, we explored the interspecies variation in TDC binding to human and fish TTR (exemplified by Gilthead seabream (Sparus aurata)). The in vitro binding experiments showed that TDCs bind with equal or weaker affinity to seabream TTR than to the human TTR, in particular, the polar TDCs (>500-fold lower affinity). Crystal structures of the seabream TTR TDC complexes revealed that all TDCs bound at the thyroid binding sites. However, amino acid substitution of Ser117 in human TTR to Thr117 in seabream prevented polar TDCs from binding deep in the hormone binding cavity, which explains their low affinity to seabream TTR Molecular dynamics and in silico alanine scanning simulation also suggested that the protein backbone of seabream TTR is more rigid than the human one and that Thr117 provides fewer electrostatic contributions than Ser117 to ligand binding. This provides an explanation for the weaker affinities of the ligands that rely on electrostatic interactions with Thr117. The lower affinities of TDCs to fish TTR, in particular the polar ones, could potentially lead to milder thyroid-related effects in fish.

  • 118.
    Zhang, Jin
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Kamstra, Jorke H.
    Ghorbanzadeh, Mehdi
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Weiss, Jana M.
    Hamers, Timo
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    In Silico Approach To Identify Potential Thyroid Hormone Disruptors among Currently Known Dust Contaminants and Their Metabolites2015Ingår i: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 49, nr 16, s. 10099-10107Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Thyroid hormone disrupting chemicals (THDCs) interfere with the thyroid hormone system and may induce multiple severe physiological disorders. Indoor dust ingestion is a major route of THDCs exposure in humans, and one of the molecular targets of these chemicals is the hormone transporter transthyretin (TTR). To virtually screen indoor dust contaminants and their metabolites for THDCs targeting TTR, we developed a quantitative structure activity relationship (QSAR) classification model. The QSAR model was applied to an in-house database including 485 organic dust contaminants reported from literature data and their 433 in silico derived metabolites. The model predicted 37 (7.6%) dust contaminants and 230 (53.1%) metabolites as potential TTR binders. Four new THDCs were identified after testing 23 selected parent dust contaminants in a radio-ligand TTR binding assay; 2,2',4,4'-tetrahydroxybenzophenone, perfluoroheptanesulfonic acid, 3,5,6-trichloro-2-pyridinol, and 2,4,5-trichlorophenoxyacetic acid. These chemicals competitively bind to TTR with 50% inhibition (IC50) values at or below 10 mu M. Molecular docking studies suggested that these THDCs interacted similarly with TTR via the residue Ser117A, but their binding poses were dissimilar to the endogenous ligand T4. This study identified new THDCs using an in silico approach in combination with bioassay testing and highlighted the importance of metabolic activation for TTR binding.

  • 119.
    Zhang, Jin
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Li, Yaozong
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Gupta, Arun A.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Nam, Kwangho
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Identification and Molecular Interaction Studies of Thyroid Hormone Receptor Disruptors among Household Dust Contaminants2016Ingår i: Chemical Research in Toxicology, ISSN 0893-228X, E-ISSN 1520-5010, Vol. 29, nr 8, s. 1345-1354Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Thyroid hormone disrupting chemicals (THDCs), often found abundantly in the environment, interfere with normal thyroid hormone signaling and induce physiological malfunctions, possibly by affecting thyroid hormone receptors (THRs). Indoor dust ingestion is a significant human exposure route of THDCs, raising serious concerns for human health. Here, we developed a virtual screening protocol based on an ensemble of X-ray crystallographic structures of human THRβ1 and the generalized Born solvation model to identify potential THDCs targeting the human THRβ1 isoform. The protocol was applied to virtually screen an in-house indoor dust contaminant inventory, yielding 31 dust contaminants as potential THRβ1 binders. Five predicted binders and one negative control were tested using isothermal titration calorimetry, of which four, i.e., 2,4,5-trichlorophenoxyacetic acid (2,4,5-T), bisphenol A (3-chloro-2-hydroxypropyl) (2,3-dihydroxypropyl) ether (BADGE-HCl-H2O), 2,2',4,4'-tetrahydroxybenzophenone (BP2), and 2,4-dichlorophenoxyacetic acid (2,4-D), were identified as THRβ1 binders with binding affinities ranging between 60 μM and 460 μM. Molecular dynamics (MD) simulations were employed to examine potential binding modes of these binders and provided a rationale for explaining their specific recognition by THRβ1. The combination of in vitro binding affinity measurements and MD simulations allowed identification of four new potential THR-targeting THDCs that have been found in household dust. We suggest using the developed structure-based virtual screening protocol to identify and prioritize testing of potential THDCs.

  • 120. Zhang, Wen
    et al.
    Gago-Ferrero, Pablo
    Gao, Qiuju
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Ahrens, Lutz
    Blum, Kristin M.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Rostvall, Ande
    Björlenius, Berndt
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Wiberg, Karin
    Haglund, Peter
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Renman, Gunno
    Evaluation of five filter media in column experiment on the removal of selected organic micropollutants and phosphorus from household wastewater2019Ingår i: Journal of Environmental Management, ISSN 0301-4797, E-ISSN 1095-8630, Vol. 246, s. 920-928Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A bench-scale column experiment was performed to study the removal of 31 selected organic micropollutants (MPs) and phosphorus by lignite, xyloid lignite (Xylit), granular activated carbon (GAC), Polonite (R) and sand over a period of 12 weeks. In total 29 out of the 31 MPs showed removal efficiency > 90% by GAC with an average removal of 97 +/- 6%. Xylit and lignite were less efficient with an average removal of 80 +/- 28% and 68 +/- 29%, respectively. The removal efficiency was found to be impacted by the characterization of the sorbents and physicochemical properties of the compounds, as well as the interaction between the sorbents and compounds. For instance, Xylit and lignite performed well for relatively hydrophobic (log octanol/water partition coefficient (K-ow) >= 3) MPs, while the removal efficiency of moderately hydrophilic, highly hydrophilic and negatively charged MPs were lower. The organic sorbents were found to have more functional groups at their surfaces, which might explain the higher adsorption of MPs to these sorbents. The removal of several MPs improved after four weeks in sand, Xylit, GAC and lignite which may be related to increased biological activity and biofilm development. GAC and sand had limited ability to remove phosphorus (12 +/- 27% and 14 +/- 2%, respectively), while the calcium-silicate material Polonite (R) precipitated phosphorus efficiently and increased the total phosphorus removal from 12% to 96% after the GAC filter.

  • 121.
    Zheng, Ziye
    et al.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Peters, Gregory M.
    Arp, Hans Peter H.
    Andersson, Patrik L.
    Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
    Combining in Silico Tools with Multicriteria Analysis for Alternatives Assessment of Hazardous Chemicals: A Case Study of Decabromodiphenyl Ether Alternatives2019Ingår i: Environmental Science and Technology, ISSN 0013-936X, E-ISSN 1520-5851, Vol. 53, nr 11, s. 6341-6351Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Alternatives assessment is applied for minimizing the risk of unintentionally replacing a hazardous chemical with another hazardous chemical. Central challenges are the diversity of properties to consider and the lack of high-quality experimental data. To address this, a novel alternatives assessment procedure was developed based on in silico data and multicriteria decision analysis (MCDA) methods. As a case study, 16 alternatives to the flame retardant decabromodiphenyl ether were considered. The hazard properties included persistence (P), bioaccumulation potential (B), toxicities (T), and mobility in water (M). Databases were consulted and 2866 experimental data points were collected for the target chemicals; however, these were mostly replicate data points for some hazard criteria for a subset of alternatives. Therefore, in silico data and three MCDA strategies were tested including heat mapping, multiattribute utility theory (MAUT), and Elimination Et Choix Traduisant la REalite (ELECTRE III). The heat map clearly showed that none of the target chemicals are hazard-free, whereas MAUT and ELECTRE III agreed on ranking the "least worst" choices. This study identified several challenges and the complexity in the alternatives assessment processes motivating more case studies combining in silico and MCDA approaches.

  • 122. Åkerblom, N
    et al.
    Olsson, K
    Berg, A H
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Tysklind, Mats
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Förlin, L
    Norrgren, L
    Impact of Polychlorinated Naphthalenes (PCNs) in Juvenile Baltic Salmon, Salmo salar: Evaluation of Estrogenic Effects, Development, and CYP1A Induction2000Ingår i: Archives of Environmental Contamination and Toxicology, ISSN 0090-4341 (Print) 1432-0703 (Online), Vol. 38, nr 2, s. 225-33Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Juvenile Baltic salmon, Salmo salar, were fed commercial salmon food contaminated with different concentrations of polychlorinated naphthalenes (PCNs; 0.1, 1, 2, or 10 μg PCN/g food). Among other effects, possible estrogenic impact caused by PCNs were evaluated. Fish were therefore fed a diet contaminated with 17β-estradiol (E2; 0.94 or 9.4 μg E2/g food), as a positive control. After 8, 13, 17, and 41 weeks, sampling took place. Growth, liver somatic index (LSI), EROD activity, and vitellogenin content in blood plasma were measured along with morphological studies of gonads and chemical analyses to determine the effects caused by PCNs. Exposure to PCNs did not seem to have any effects on body weight gain, since the group fed the high dose followed the growth in the control group during the entirely experimental period. After 41 weeks of exposure the groups fed 2 and 10 μg PCN/g food had significantly lower LSIs compared with the control, indicating liver toxic effects of PCNs. Furthermore, a dose-dependent induction of EROD activity was found. At week 41, the control group had an activity of 4.9 ± 4.8 pmol/mg prot/min, whereas it was between 69 ± 21 and 720 ± 370 pmol/mg prot/min in the exposed groups, respectively. Examination of gonadal morphology showed that PCNs also had negative effects on ovaries in Baltic salmon, including delayed development. The distribution between females and males, gonadal morphology, and vitellogenin content in blood plasma did, however, indicate that PCNs are not capable of causing effects similar to E2 or xenoestrogens. Exposure to both of the concentrations of E2 resulted in decreased body weight gain, increased LSI, and feminization of the gonads. E2 did, however, not induce any EROD activity.

  • 123.
    Öberg, Lars
    et al.
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Barbro
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Haglund, Peter
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Johansson, M
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Karlsson, S
    Lundstedt, Staffan
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Lövgren, Lars
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Marklund, Ann
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Nording, Malin
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Wiberg, Karin
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Undergraduate Education in Environmental Chemistry at Umeå University, Sweden2004Ingår i: SETAC 4th World Congress/25th Annual Meeting in North America, 14-18 November, Portland OR, USA, 2004Konferensbidrag (Övrigt vetenskapligt)
    Abstract [en]

    Abstract to the Fourth SETAC World Congress, oral presentation.

  • 124. Öberg, M
    et al.
    Andersson, Patrik
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Johansson, N
    Tysklind, Mats
    Umeå universitet, Teknisk-naturvetenskaplig fakultet, Kemi.
    Hâkansson, H
    Multivariate modelling of polychlorinated biphenyl-induced CYP1A activity in the MH1C1 rat hepatoma cell line2001Ingår i: ATLA Alternatives to Laboratory Animals, Vol. 29, nr 3, s. 291-5Artikel, forskningsöversikt (Övrig (populärvetenskap, debatt, mm))
123 101 - 124 av 124
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