Alkylated phenanthrene distributions in black rockfish (Sebastes schlegelii) and biotransformation into hydroxylated metabolites after intragastric administration

Ndabambi, Mlamuli; Kim, Ki Yong; Jung, Jee-Hyun; Yim, Un Hyuk; Oh, Jeong‐Eun

doi:10.1016/j.scitotenv.2020.143160

Cited by 3 publications

(3 citation statements)

References 55 publications

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“…In the case of alkyl-substituted phenanthrenes, the predominant metabolites with the incubation of human and rat liver microsomes were alcohols, such as 3-hydroxymethylphenanthrene and 9-hydroxymethylphenanthrene for 3-methylphenanthrene and 9-methylphenanthrene, respectively . Similarly, in studies using rat S9 incubations and human HepG2 cells, hydroxymethylphenanthrenes were identified as the primary metabolites of 1-methyl-, 2-methyl, 3-methyl-, 4-methyl-, 9-methylphenanthrene, and 9-ethylphenanthrene. , In another recent in vivo study, researchers identified four monohydroxylated metabolites of 3,6-dimethylphenanthrene and six monohydroxylated metabolites of 3-methylphenanthrene through tandem mass spectrometry analysis of fish bile . For pyrene congeners such as 1-methylpyrene and 1-ethylpyrene, side-chain oxidation was also identified as the primary metabolic pathway.…”

Section: Biotransformation Routes Of Pah Derivatives and Potential Ex...mentioning

confidence: 94%

A Systematic Review of Polycyclic Aromatic Hydrocarbon Derivatives: Occurrences, Levels, Biotransformation, Exposure Biomarkers, and Toxicity

Peng,

Dong,

et al. 2023

Environ. Sci. Technol.

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Polycyclic aromatic hydrocarbon (PAH) derivatives constitute a significant class of emerging contaminants that have been ubiquitously detected in diverse environmental matrixes, with some even exhibiting higher toxicities than their corresponding parent PAHs. To date, compared with parent PAHs, fewer systematic summaries and reanalyses are available for PAH derivatives with great environmental concerns. This review summarizes the current knowledge on the chemical species, levels, biotransformation patterns, chemical analytical methods, internal exposure routes with representative biomarkers, and toxicity of PAH derivatives, primarily focusing on nitrated PAHs (NPAHs), oxygenated PAHs (OPAHs), halogenated PAHs (XPAHs), and alkylated PAHs (APAHs). A collection of 188 compounds from four categories, 44 NPAHs, 36 OPAHs, 56 APAHs, and 52 XPAHs, has been compiled from 114 studies that documented the environmental presence of PAH derivatives. These compounds exhibited weighted average air concentrations that varied from a lower limit of 0.019 pg/m3 to a higher threshold of 4060 pg/m3. Different analytical methods utilizing comprehensive two-dimensional gas chromatography coupled with high-resolution time-of-flight mass spectrometry (GC × GC-TOF-MS), gas chromatography coupled to time-of-flight mass spectrometry (GC-TOF-MS), comprehensive two-dimensional gas chromatography coupled to quadrupole mass spectrometry (GC × GC-QQQ-MS), and Fourier-transform ion cyclotron resonance mass spectrometry (FT-ICR MS), that adopted untargeted strategies for the identification of PAH derivatives are also reviewed here. Additionally, an in-depth analysis of biotransformation patterns for each category is provided, including the likelihood of specific biotransformation reaction types. For the toxicity, we primarily summarized key metabolic activation pathways, which could result in the formation of reactive metabolites capable of covalently bonding with DNA and tissue proteins, and potential health outcomes such as carcinogenicity and genotoxicity, oxidative stress, inflammation and immunotoxicity, and developmental toxicity that might be mediated by the aryl hydrocarbon receptor (AhR). Finally, we pinpoint research challenges and emphasize the need for further studies on identifying PAH derivatives, tracking external exposure levels, evaluating internal exposure levels and associated toxicity, clarifying exposure routes, and considering mixture exposure effects. This review aims to provide a broad understanding of PAH derivatives’ identification, environmental occurrence, human exposure, biotransformation, and toxicity, offering a valuable reference for guiding future research in this underexplored area.

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Section: Biotransformation Routes Of Pah Derivatives and Potential Ex...mentioning

confidence: 94%

A Systematic Review of Polycyclic Aromatic Hydrocarbon Derivatives: Occurrences, Levels, Biotransformation, Exposure Biomarkers, and Toxicity

Peng,

Dong,

et al. 2023

Environ. Sci. Technol.

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“…There was research reported that the proportion of parent PAHs in animal samples was higher than that in the sediments where the samples were collected, while the proportion of methylated derivatives became lower, suggesting that the preferential metabolism of methylated PAHs or the preferential absorption of parent PAHs . Another study on the distribution of APAHs in black rockfish found the opposite result to that predicted by the octanol/water partition coefficient; that is, under the same dosage, the concentration of 3-methylphenanthrene in the liver and blood was about an order of magnitude higher than the concentration of 3,6-dimethylphenanthrene . This can also be speculated to be affected by metabolic rate.…”

Section: Tissue Distribution Of Pahs and The Derivatives In Vivomentioning

confidence: 94%

“…131 Another study on the distribution of APAHs in black rockfish found the opposite result to that predicted by the octanol/water partition coefficient; that is, under the same dosage, the concentration of 3-methylphenanthrene in the liver and blood was about an order of magnitude higher than the concentration of 3,6-dimethylphenanthrene. 132 This can also be speculated to be affected by metabolic rate.…”

Section: Lipid Content Of Organsmentioning

confidence: 99%

Influence of Exposure Pathways on Tissue Distribution and Health Impact of Polycyclic Aromatic Hydrocarbon Derivatives

et al. 2023

Environ. Health

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The oxygen (OPAHs), nitro (NPAHs), hydroxyl (OH-PAHs), and alkylated (APAHs) derivatives of polycyclic aromatic hydrocarbon (PAHs) are ubiquitous pollutants in the environment. The concentrations of NPAHs, OPAHs, OH-PAHs, and APAHs are lower than that of PAHs in the environment, but the carcinogenic abilities of the derivatives are usually 10 to 1,000-fold higher than that of parent PAHs. There are three main pathways for the exposure of polycyclic aromatic compounds to humans, including inhalation, direct contact, and ingestion. After exposure by inhalation, they are mainly distributed in the lungs, affecting lung function and causing inflammation, asthma, etc. Due to the digestive system’s strong capacity for metabolism, intake of PAHs and the derivatives is primarily distributed in the digestive system and metabolized there. And it may lead to dysplasia of these organs and even to cancer. The skin is the primary site of direct contact with PAH derivatives. PAH derivatives can enter the bloodstream through all three contact pathways, thereby accumulating in various organs. This study aimed to summarize the influence of exposure pathways on tissue distribution and the health impact of PAH derivatives to provide references for future research and evaluation on public health.

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Assessment of PAH pollution in mediterranean lakes and health implications for fish and consumers, case study: Manzala Lake, Egypt

Khedr,

Ahmed,

Salaah

et al. 2024

Water Cycle

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Alkylated phenanthrene distributions in black rockfish (Sebastes schlegelii) and biotransformation into hydroxylated metabolites after intragastric administration

Cited by 3 publications

References 55 publications

A Systematic Review of Polycyclic Aromatic Hydrocarbon Derivatives: Occurrences, Levels, Biotransformation, Exposure Biomarkers, and Toxicity

A Systematic Review of Polycyclic Aromatic Hydrocarbon Derivatives: Occurrences, Levels, Biotransformation, Exposure Biomarkers, and Toxicity

Influence of Exposure Pathways on Tissue Distribution and Health Impact of Polycyclic Aromatic Hydrocarbon Derivatives

Assessment of PAH pollution in mediterranean lakes and health implications for fish and consumers, case study: Manzala Lake, Egypt

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