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Heterocyclic aromatic hydrocarbons show estrogenic activity upon metabolization in a recombinant transactivation assay
- Source :
- Environmental sciencetechnology. 48(10)
- Publication Year :
- 2014
-
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.
- Subjects :
- Transcriptional Activation
Bisphenol A
Quantitative Structure-Activity Relationship
chemistry.chemical_compound
Tandem Mass Spectrometry
Cell Line, Tumor
Confidence Intervals
Environmental Chemistry
Bioassay
Organic chemistry
Humans
Polycyclic Aromatic Hydrocarbons
Xanthene
Indole test
Recombination, Genetic
Quinoline
Water
Estrogens
General Chemistry
Dibenzofuran
chemistry
Receptors, Estrogen
Dibenzothiophene
Acridine
Biological Assay
Chromatography, Liquid
Subjects
Details
- ISSN :
- 15205851
- Volume :
- 48
- Issue :
- 10
- Database :
- OpenAIRE
- Journal :
- Environmental sciencetechnology
- Accession number :
- edsair.doi.dedup.....d53b8804760055aacc40b7447dbf9850