Publication Details

Reference Category Journals
DOI / URL link
Title (Primary) Heterocyclic aromatic hydrocarbons show estrogenic activity upon metabolization in a recombinant transactivation assay
Author Brinkmann, M.; Maletz, S.; Krauss, M.; Bluhm, K.; Schiwy, S.; Kuckelkorn, J.; Tiehm, A.; Brack, W.; Hollert, H.;
Journal Environmental Science & Technology
Year 2014
Department WANA;
Volume 48
Issue 10
Language englisch;
POF III (all) T42;
UFZ wide themes RU3;
Abstract

Heterocyclic aromatic hydrocarbons (hetero-PAHs) are increasingly studied at contaminated sites; especially at former industrial facilities where coal tar-oil was handled, e.g., wood treatment plants, high concentrations of hetero-PAHs are frequently detected in groundwater plumes. In previous studies, fractions of groundwater with high estrogenic activity contained hetero-PAHs and their hydroxylated metabolites. To evaluate this preliminary evidence, selected hetero-PAHs were screened for their estrogenic activity in lyticase yeast estrogen screen (LYES) and ER CALUX. All tested substances were inactive in the LYES. Hetero-PAHs such as acridine, xanthene, indole, 2-methylbenzofuran, 2,3-dimethylbenzofuran, dibenzofuran, dibenzothiophene, quinoline, and 6-methylquinoline were positive in the ER CALUX, with estradiol equivalence factors (EEFs) from 2.85 × 10–7 to 3.18 × 10–5. The EEF values of these substances were comparable to those of other xenoestrogens (e.g., alkylphenols or bisphenol A) that are sometimes found in surface water. Chemical analyses revealed that T47Dluc cells could metabolize most of the substances. Among the metabolites (tentatively) identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS) were hydroxides and their keto tautomers, sulfates, sulfoxides, and N-oxides. Because of their high concentrations measured in groundwater, we conclude that hetero-PAHs and metabolites may be a potential risk and should be the subject of further research.

ID 14988
Persistent UFZ Identifier http://www.ufz.de/index.php?en=20939&ufzPublicationIdentifier=14988
Brinkmann, M., Maletz, S., Krauss, M., Bluhm, K., Schiwy, S., Kuckelkorn, J., Tiehm, A., Brack, W., Hollert, H. (2014):
Heterocyclic aromatic hydrocarbons show estrogenic activity upon metabolization in a recombinant transactivation assay
Environ. Sci. Technol. 48 (10), 5892 - 5901