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  • Halogenated 17β-estradiol surrogates: synthesis, estrogenic activity, and initial investigations of fate in soil/water systems.

    Author(s) : Casey, F. X. M.Shappell, N. W.Hakk, H.

    Author Affiliation : Dep. of Soil Science, School of Natural Resource Sciences, North Dakota State Univ., Fargo, ND 58108-6050, USA.

    Author Email : francis.casey@ndsu.edu

    Journal article : Journal of Environmental Quality 2017 Vol.46 No.4 pp.802-810

    Abstract : 17β-EstradiolestradiolSubject Category: Chemicals and Chemical Groups
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    (E2), a natural, endocrine-disrupting, steroid hormone, is excreted by all vertebrates and can enter the environmentenvironmentSubject Category: Miscellaneous
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    from domestic animal and wildlifewildlifeSubject Category: Organism Groups
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    wasteswastesSubject Category: Commodities and Products
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    . Multiple field studies using livestocklivestockSubject Category: Organism Groups
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    manures as E2 sources suggest significant background concentrations of E2 (e.g., wildlife sources, hydrolysishydrolysisSubject Category: Miscellaneous
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    of E2 conjugates, previous inputs). To accurately understand field fate and transport processestransport processesSubject Category: Miscellaneous
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    of E2, it is necessary to address the issue of background detections. In this study, two fluorinated and three brominated surrogate compounds of E2 were synthesized and compared to native E2 using soil/water batch experiments and for estrogenic activityactivitySubject Category: Miscellaneous
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    . Analytical difficulties presented by the two fluorinated congeners deemed these compounds to be unsuitable surrogates of E2, and further assessment was abandoned. However, the brominated congeners proved promising, with log(Koc) values that fell within the range previously reported for E2. Batch studies yielded similar relative aqueous concentrations and linear sorption isothermssorption isothermsSubject Category: Properties
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    across time for E2 and 2-bromo-17β-estradiol; however, the relative aqueous concentrations and linear sorption isotherms of 4-bromo-17β-estradiol and 2,4-dibromo-17β-estradiol were different from E2 but similar to one another. All three brominated congeners possessed estrogenic activity by E-Screen assay, albeit three orders of magnitude less than native E2, putatively due to steric interferenceinterferenceSubject Category: Miscellaneous
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    introduced by the large brominebromineSubject Category: Chemicals and Chemical Groups
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    atom on the phenolic ring, the group that mediates interaction with the estrogen receptor. The data suggest that 2-bromo-17β-estradiol may serve as a suitable surrogate for E2 in planned field scale tracer studies designed to distinguish between antecedent and de novo inputs.

    ISSN : 0047-2425

    DOI : 10.2134/jeq2017.02.0053

    Record Number : 20173323959

    Publisher : American Society of Agronomy

    Location of publication : Madison

    Country of publication : USA

    Language of text : English

    Indexing terms for this abstract:

    Descriptor(s) : activityactivitySubject Category: Miscellaneous
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    , animal manuresanimal manuresSubject Category: Miscellaneous
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    , assaysassaysSubject Category: Techniques, Methodologies and Equipment
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    , assessmentassessmentSubject Category: Techniques, Methodologies and Equipment
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    , brominebromineSubject Category: Chemicals and Chemical Groups
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    , disruptiondisruptionSubject Category: Miscellaneous
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    , domestic animalsdomestic animalsSubject Category: Organism Groups
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    , endocrine systemendocrine systemSubject Category: Anatomical and Morphological Structures
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    , environmentenvironmentSubject Category: Miscellaneous
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    , environmental assessmentenvironmental assessmentSubject Category: Techniques, Methodologies and Equipment
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    , estradiolestradiolSubject Category: Chemicals and Chemical Groups
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    , hydrolysishydrolysisSubject Category: Miscellaneous
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    , interactionsinteractionsSubject Category: Miscellaneous
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    , interferenceinterferenceSubject Category: Miscellaneous
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    , livestocklivestockSubject Category: Organism Groups
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    , manuresmanuresSubject Category: Miscellaneous
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    , oestrogenic propertiesoestrogenic propertiesSubject Category: Properties
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    , oestrogensoestrogensSubject Category: Chemicals and Chemical Groups
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    , soilsoilSubject Category: Miscellaneous
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    , soil watersoil waterSubject Category: Miscellaneous
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    , sorptionsorptionSubject Category: Natural Processes
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    , sorption isothermssorption isothermsSubject Category: Properties
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    , transport processestransport processesSubject Category: Miscellaneous
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    , wasteswastesSubject Category: Commodities and Products
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    , water supplywater supplySubject Category: Miscellaneous
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    , wild animalswild animalsSubject Category: Organism Groups
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    , wildlifewildlifeSubject Category: Organism Groups
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    Identifier(s) : estrogenic propertiesestrogenic propertiesSubject Category: Properties
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    , estrogensestrogensSubject Category: Chemicals and Chemical Groups
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    , isotherms, oestradiol, soil moisture, soil transport processes, transport processes in soil systems, water supplies