Potential Metabolic Activation of a Representative C2-Alkylated Polycyclic Aromatic Hydrocarbon 6-Ethylchrysene Associated with the Deepwater Horizon Oil Spill in Human Hepatoma (HepG2) Cells
| العنوان: | Potential Metabolic Activation of a Representative C2-Alkylated Polycyclic Aromatic Hydrocarbon 6-Ethylchrysene Associated with the Deepwater Horizon Oil Spill in Human Hepatoma (HepG2) Cells |
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| المؤلفون: | Ian A. Blair, Trevor M. Penning, Suhong Zhang, Clementina Mesaros, Meng Huang |
| المصدر: | Chemical Research in Toxicology |
| بيانات النشر: | American Chemical Society, 2016. |
| سنة النشر: | 2016 |
| مصطلحات موضوعية: | inorganic chemicals, 0301 basic medicine, Ethylchrysene, Polycyclic aromatic hydrocarbon, 010501 environmental sciences, Alkylation, Toxicology, Catechol O-Methyltransferase, 01 natural sciences, Article, Chrysenes, 03 medical and health sciences, Food chain, Cytochrome P-450 Enzyme System, Tumor Cells, Cultured, Organic chemistry, Humans, Petroleum Pollution, 0105 earth and related environmental sciences, chemistry.chemical_classification, integumentary system, Molecular Structure, organic chemicals, General Medicine, Metabolism, Hep G2 Cells, Alkaline Phosphatase, 030104 developmental biology, chemistry, Environmental chemistry, Hepg2 cells, Deepwater horizon, Oil spill, Sulfotransferases |
| الوصف: | Exposure to polycyclic aromatic hydrocarbons (PAHs) is the major human health hazard associated with the Deepwater Horizon oil spill. C2-Chrysenes are representative PAHs present in crude oil and could contaminate the food chain. We describe the metabolism of a C2-chrysene regioisomer, 6-ethylchrysene (6-EC), in human HepG2 cells. The structures of the metabolites were identified by HPLC-UV-fluorescence detection and LC-MS/MS. 6-EC-tetraol isomers were identified as signature metabolites of the diol-epoxide pathway. O-Monomethyl-O-monosulfonated-6-EC-catechol, its monohydroxy products, and N-acetyl-l-cysteine(NAC)-6-EC-ortho-quinone were discovered as signature metabolites of the ortho-quinone pathway. Potential dual metabolic activation of 6-EC involving the formation of bis-electrophiles, i.e., a mono-diol-epoxide and a mono-ortho-quinone within the same structure, bis-diol-epoxides, and bis-ortho-quinones was observed as well. The identification of 6-EC-tetraol, O-monomethyl-O-monosulfonated-6-EC-catechol, its monohydroxy products, and NAC-6-EC-ortho-quinone supports potential metabolic activation of 6-EC by P450 and AKR enzymes followed by metabolic detoxification of the ortho-quinone through interception of its redox cycling capability by catechol-O-methyltransferase and sulfotransferase enzymes. The tetraols and catechol conjugates could be used as biomarkers of human exposure to 6-EC resulting from oil spills. |
| اللغة: | English |
| تدمد: | 1520-5010 0893-228X |
| الوصول الحر: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ee61599fec0b3e7b14c0adc3054efb12Test http://europepmc.org/articles/PMC4916485Test |
| حقوق: | OPEN |
| رقم الانضمام: | edsair.doi.dedup.....ee61599fec0b3e7b14c0adc3054efb12 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 15205010 0893228X |
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