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Occupational and Environmental Medicine Apr 2004Metabolites of pyrene and DNA adducts have been used as biomarkers of high level exposure to polycyclic aromatic hydrocarbons (PAHs). A systematic review was performed... (Review)
Review
Metabolites of pyrene and DNA adducts have been used as biomarkers of high level exposure to polycyclic aromatic hydrocarbons (PAHs). A systematic review was performed to evaluate whether these biomarkers are also valid markers of low level environmental exposure to PAHs. Thirty five studies were identified with more than 10 subjects that evaluated environmental air pollution to PAHs in relation to metabolites of PAHs, mainly hydroxypyrene (1-OHP), PAH-DNA adducts, or protein adducts. PAH metabolites and, to a less extent, PAH-DNA adducts correlated well at the group level with exposure to B(a)P even at low levels of air pollution. The use of these biomarkers should be more widely implemented in combination with more traditional techniques for the assessment of general population exposure to PAHs from ambient air pollution.
Topics: Air Pollutants; Biomarkers; DNA Adducts; Humans; Polycyclic Aromatic Hydrocarbons; Pyrenes
PubMed: 15031403
DOI: 10.1136/oem.2003.008375 -
Applied and Environmental Microbiology Jan 1996The degradation of three polycyclic aromatic hydrocarbons (PAH), pyrene (PYR), benz[a]anthracene (BAA), and benzo[a]pyrene (BaP), by Mycobacterium sp. strain RJGII-135...
The degradation of three polycyclic aromatic hydrocarbons (PAH), pyrene (PYR), benz[a]anthracene (BAA), and benzo[a]pyrene (BaP), by Mycobacterium sp. strain RJGII-135 was studied. The bacterium was isolated from an abandoned coal gasification site soil by analog enrichment techniques and found to mineralize [14C]PYR. Further degradation studies with PYR showed three metabolites formed by Mycobacterium sp. strain RJGII-135, including 4,5-phenanthrene-dicarboxylic acid not previously isolated, 4-phenanthrene-carboxylic acid, and 4,5-pyrene-dihydrodiol. At least two dihydrodiols, 5,6-BAA-dihydrodiol and 10,11-BAA-dihydrodiol, were confirmed by high-resolution mass spectral and fluorescence analyses as products of the biodegradation of BAA by Mycobacterium sp. strain RJGII-135. Additionally, a cleavage product of BAA was also isolated. Mass spectra and fluorescence data support two different routes for the degradation of BaP by Mycobacterium sp. strain RJGII-135. The 7,8-BaP-dihydrodiol and three cleavage products of BaP, including 4,5-chrysene-dicarboxylic acid and a dihydro-pyrene-carboxylic acid metabolite, have been isolated and identified as degradation products formed by Mycobacterium sp. strain RJGII-135. These latter results represent the first example of the isolation of BaP ring fission products formed by a bacterial isolate. We propose that while this bacterium appears to attack only one site of the PYR molecule, it is capable of degrading different sites of the BAA and BaP molecules, and although the sites of attack may be different, the ability of this bacterium to degrade these PAH is well supported. The proposed pathways for biodegradation of these compounds by this Mycobacterium sp. strain RJGII-135 support the dioxygenase enzymatic processes reported previously for other bacteria. Microorganisms like Mycobacterium sp. strain RJGII-135 will be invaluable in attaining the goal of remediation of sites containing mixtures of these PAH.
Topics: Benz(a)Anthracenes; Benzo(a)pyrene; Biodegradation, Environmental; Coal; Kinetics; Models, Chemical; Mycobacterium; Pyrenes; Soil Microbiology
PubMed: 8572690
DOI: 10.1128/aem.62.1.13-19.1996 -
Scientific Reports Jan 2024Pyrene is an extremely hazardous, carcinogenic polycyclic aromatic hydrocarbon (PAH). The plant-microbe interaction between Pseudomonas fragi DBC and Jatropha curcas was...
Pyrene is an extremely hazardous, carcinogenic polycyclic aromatic hydrocarbon (PAH). The plant-microbe interaction between Pseudomonas fragi DBC and Jatropha curcas was employed for biodegradation of pyrene and their transcriptional responses were compared. The genome of P. fragi DBC had genes for PAH degrading enzymes i.e. dioxygenases and dehydrogenases, along with root colonization (trpD, trpG, trpE and trpF), chemotaxis (flhF and flgD), stress adaptation (gshA, nuoHBEKNMG), and detoxification (algU and yfc). The transcriptional expression of catA and yfc that respectively code for catabolic enzyme (catechol-1, 2-dioxygnase) and glutathione-s-transferase for detoxification functions were quantitatively measured by qPCR. The catA was expressed in presence of artificial root exudate with or without pyrene, and glucose confirming the non-selective approach of bacteria, as desired. Pyrene induced 100-fold increase of yfc expression than catA, while there was no expression of yfc in absence of pyrene. The transcriptome of plant roots, in presence of pyrene, with or without P. fragi DBC inoculation was analysed. The P. fragi DBC could upregulate the genes for plant growth, induced the systemic acquired resistance and also ameliorated the stress response in Jatropha roots.
Topics: Jatropha; Pseudomonas fragi; Rhizosphere; Pyrenes; Glutathione Transferase
PubMed: 38200308
DOI: 10.1038/s41598-024-51581-y -
International Journal of Environmental... Feb 2017The polycyclic aromatic hydrocarbon (PAH)-degrading strain Q8 was isolated from oilfield produced water. According to the analysis of a biochemical test, 16S rRNA gene,...
The polycyclic aromatic hydrocarbon (PAH)-degrading strain Q8 was isolated from oilfield produced water. According to the analysis of a biochemical test, 16S rRNA gene, house-keeping genes and DNA-DNA hybridization, strain Q8 was assigned to a novel species of the genus . The strain could not only grow in mineral salt medium (MM) and utilize naphthalene and pyrene as its sole carbon source, but also degraded mixed naphthalene, phenanthrene, anthracene and pyrene. The degradation ratio of these four PAHs reached 100%, 95.4%, 73.8% and 53.4% respectively after being degraded by Q8 for seven days. A comparative experiment found that the PAHs degradation efficiency of Q8 is higher than that of and , which have the capacities to remove PAHs. Fourier transform infrared spectra, saturate, aromatic, resin and asphaltene (SARA) and gas chromatography-mass spectrometry (GC-MS) analysis of crude oil degraded by Q8 were also studied. The results showed that Q8 could utilize -alkanes and PAHs in crude oil. The relative proportions of the naphthalene series, phenanthrene series, thiophene series, fluorene series, chrysene series, C21-triaromatic steroid, pyrene, and benz(a)pyrene were reduced after being degraded by Q8. sp. nov. Q8 had the capacity to remediate water and soil environments contaminated by PAHs or crude oil, and provided a feasible way for the bioremediation of PAHs and oil pollution.
Topics: Anthracenes; Biodegradation, Environmental; Gas Chromatography-Mass Spectrometry; Genes, rRNA; Gordonia Bacterium; Naphthalenes; Oil and Gas Fields; Petroleum Pollution; Phenanthrenes; Polycyclic Aromatic Hydrocarbons; Pyrenes; RNA, Ribosomal, 16S; Soil Pollutants; Water Pollutants
PubMed: 28241412
DOI: 10.3390/ijerph14020215 -
Environment International Aug 2019The bacterial community from estuarine sediment undertakes the bioremediation and energy transformation of anthropogenic pollutants especially polycyclic aromatic...
The bacterial community from estuarine sediment undertakes the bioremediation and energy transformation of anthropogenic pollutants especially polycyclic aromatic hydrocarbons (PAHs). However, information and studies on bacterial synergism and related metabolic profiles under the stress of PAHs are limited. In this study, sediments from estuarine were collected and co-incubated with a classical PAH, pyrene. The results showed that Alpha- and Gammaproteobacteria became abundant at the late domesticating phase with the dominant genus of ZD0117, the uncultivated bacteria affiliated into Gammaproteobacteria. Functional gene analysis based on metagenomic sequencing showed that quantitatively changes of genes directly related to the degradation of aromatic hydrocarbon coordinated with genes involved into various metabolic pathways such as acylglycerol degradation, nitrogen fixation, sulfate transport system, Arnon-Buchanan cycle, and Calvin cycle (P < 0.01 and |ρ| > 0.8). Fifty-six metagenome-assembled genomes (MAGs) were reconstructed, which were primarily composed by Alpha- and Gammaproteobacteria. Bacteria belonging to the phylum Proteobacteria were found to be abundant in MAGs and contained genes encoding for dehydrogenase, which are key enzymes for pyrene degradation. In addition, genomes of uncultivated bacteria were successfully reconstructed and were proven to carry genes of synergistically metabolizing pyrene. Based on analysis of typical MAGs, the metabolic pathways involved in syntrophic associations of a pyrene-degrading consortium were reconstructed. The results in this study could make us fully understand the metabolic patterns of pyrene-degrading consortium from the estuarine sediment and widen the scope of functional bacteria.
Topics: Bacteria; Biodegradation, Environmental; Environmental Pollutants; Geologic Sediments; Metagenomics; Pyrenes; Soil Microbiology; Water Microbiology
PubMed: 31150973
DOI: 10.1016/j.envint.2019.05.028 -
Biochemical Pharmacology Dec 2018In its classical genomic mode of action, the aryl hydrocarbon receptor (AhR) acts as a ligand activated transcription factor regulating expression of target genes such...
In its classical genomic mode of action, the aryl hydrocarbon receptor (AhR) acts as a ligand activated transcription factor regulating expression of target genes such as CYP1A1 and CYP1B1. Some ligands may also trigger more rapid nongenomic responses through AhR, including calcium signaling (Ca). In the present study we observed that pyrene induced a relatively rapid increase in intracellular Ca-concentrations ([Ca]) in human microvascular endothelial cells (HMEC-1) and human embryonic kidney cells (HEK293) that was attenuated by AhR-inhibitor treatment and/or transient AhR knockdown by RNAi. In silico molecular docking based on homology models, suggested that pyrene is not able to bind to the human AhR in the agonist conformation. Instead, pyrene docked in the antagonist conformation of the AhR PAS-B binding pocket, although the interaction differed from antagonists such as GNF-351 and CH223191. Accordingly, pyrene did not induce CYP1A1 or CYP1B1, but suppressed CYP1-expression by benzo[a]pyrene (B[a]P) in HMEC-1 cells, confirming that pyrene act as an antagonist of AhR-induced gene expression. Use of pharmacological inhibitors and Ca-free medium indicated that the pyrene-induced AhR nongenomic [Ca] increase was initiated by Ca-release from intracellular stores followed by a later phase of extracellular Ca-influx, consistent with store operated calcium entry (SOCE). These effects was accompanied by an AhR-dependent reduction in ordered membrane lipid domains, as determined by di-4-ANEPPDHQ staining. Addition of cholesterol inhibited both the pyrene-induced [Ca]-increase and alterations in membrane lipid order. In conclusion, we propose that pyrene binds to AhR, act as an antagonist of the canonical genomic AhR/Arnt/CYP1-pathway, reduces ordered membrane lipid domains, and activates AhR nongenomic Ca-signaling from intracellular stores.
Topics: Azo Compounds; Basic Helix-Loop-Helix Transcription Factors; Binding Sites; Calcium Signaling; Endothelial Cells; HEK293 Cells; Humans; Indoles; Molecular Docking Simulation; Protein Structure, Secondary; Purines; Pyrazoles; Pyrenes; Receptors, Aryl Hydrocarbon
PubMed: 30248327
DOI: 10.1016/j.bcp.2018.09.023 -
International Journal of Molecular... Feb 2019The adsorption of three typical polycyclic aromatic hydrocarbons (PAHs), naphthalene, phenanthrene, and pyrene with different ring numbers, on a common mesoporous...
The adsorption of three typical polycyclic aromatic hydrocarbons (PAHs), naphthalene, phenanthrene, and pyrene with different ring numbers, on a common mesoporous material (MCM-41) was simulated based on a well-validated model. The adsorption equilibriums (isotherms), states (angle distributions and density profiles), and interactions (radial distribution functions) of three PAHs within the mesopores were studied in detail. The results show that the simulated isotherms agreed with previous experimental results. Each of the PAHs with flat molecules showed an adsorption configuration that was parallel to the surface of the pore, in the following order according to the degree of arrangement: pyrene (Pyr) > phenanthrene (Phe) > naphthalene (Nap). In terms of the interaction forces, there were no hydrogen bonds or other strong polar forces between the PAHs and MCM-41, and the O⁻H bond on the adsorbent surface had a unique angle in relation to the PAH molecular plane. The polarities of different H atoms on the PAHs were roughly the same, while those of the C atoms on the PAHs decreased from the molecular centers to the edges. The increasing area of the π-electron plane on the PAHs with the increasing ring number could lead to stronger adsorption interactions, and thus a shorter distance between the adsorbate and the adsorbent.
Topics: Adsorption; Computer Simulation; Models, Molecular; Naphthalenes; Phenanthrenes; Pyrenes; Silicon Dioxide
PubMed: 30717495
DOI: 10.3390/ijms20030665 -
Anais Da Academia Brasileira de Ciencias 2022The inappropriate disposal of toxic compounds generated by industrial activity has considerably impacted the environment. Microbial communities inhabiting contaminated...
The inappropriate disposal of toxic compounds generated by industrial activity has considerably impacted the environment. Microbial communities inhabiting contaminated sites may represent ecological alternatives for the decontamination of environments. The present work aimed to search the potential of fungi isolated from wastewater treatment plant of a textile industry for bioremediation processes. Twenty-three fungi previously isolated from textile effluent were evaluated for their abilities to degrade pollutants using heavy metal and hydrocarbon tolerance assays. One isolate was subjected to pyrene degradation due its ability to tolerate hydrocarbon. The majority of isolates were resistant to at least two metals tested, i.e. chrome, copper, lead and aluminum. Isolates Penicillium sp. ITF 2, Penicillium rubens ITF 4, Penicillium sp. ITF 12 and ITF 20 (not identified) showed tolerance to tested heavy metals in all concentrations. ITF 12 and ITF 20 were able to tolerate benzene, toluene and hexane, separately. ITF 12 was able to degrade 24.9% of pyrene after 5 days of cultivation. The results encourage future studies to optimize the tolerance and degradation assay using the isolates that showed the best results, as well as studies on the treatment of environments contaminated with heavy metals and hydrocarbons, including industrial textile effluents.
Topics: Biodegradation, Environmental; Fungi; Metals, Heavy; Pyrenes; Textiles
PubMed: 35674605
DOI: 10.1590/0001-3765202220201020 -
The Journal of Veterinary Medical... Oct 2015Pyrene (PY) is a polycyclic aromatic hydrocarbon (PAH) that is often used as a biomarker for human and wildlife exposure to PAHs. As the metabolites of PAHs, similar to...
Pyrene (PY) is a polycyclic aromatic hydrocarbon (PAH) that is often used as a biomarker for human and wildlife exposure to PAHs. As the metabolites of PAHs, similar to their parent compounds, pose public health risks, it is necessary to study their characteristics and tissue-specific distribution. The present study was performed to experimentally characterize PY metabolites and analyze the tissue-specific distribution of the conjugated metabolites after oral administration of PY to rats. PY metabolites, such as pyrenediol-disulfate (PYdiol-diS), pyrenediol-sulfate (PYdiol-S), pyrene-1-sulfate (PYOS), pyrene-1-glucuronide (PYOG) and 1-hydroxypyrene (PYOH), were detected in rat urine. Although glucuronide conjugate was the predominant metabolite, the metabolite composition varied among tissues. Interestingly, the proportion of PYOH was high in the large intestine. Furthermore, PYOH was the only PY metabolite detected in feces.
Topics: Animals; Brain; Digestive System; Environmental Pollutants; Feces; Kidney; Lung; Male; Myocardium; Pyrenes; Rats; Rats, Wistar; Testis; Tissue Distribution
PubMed: 26028020
DOI: 10.1292/jvms.14-0632 -
International Journal of Molecular... Apr 2023Nucleocapsid protein (N protein) is an appropriate target for early determination of viral antigen-based severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). We...
Nucleocapsid protein (N protein) is an appropriate target for early determination of viral antigen-based severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). We have found that β-cyclodextrin polymer (β-CDP) has shown a significant fluorescence enhancement effect for fluorophore pyrene via host-guest interaction. Herein, we developed a sensitive and selective N protein-sensing method that combined the host-guest interaction fluorescence enhancement strategy with high recognition of aptamer. The DNA aptamer of N protein modified with pyrene at its 3' terminal was designed as the sensing probe. The added exonuclease I (Exo I) could digest the probe, and the obtained free pyrene as a guest could easily enter into the hydrophobic cavity of host β-CDP, thus inducing outstanding luminescent enhancement. While in the presence of N protein, the probe could combine with it to form a complex owing to the high affinity between the aptamer and the target, which prevented the digestion of Exo I. The steric hindrance of the complex prevented pyrene from entering the cavity of β-CDP, resulting in a tiny fluorescence change. N protein has been selectively analyzed with a low detection limit (11.27 nM) through the detection of the fluorescence intensity. Moreover, the sensing of spiked N protein from human serum and throat swabs samples of three volunteers has been achieved. These results indicated that our proposed method has broad application prospects for early diagnosis of coronavirus disease 2019.
Topics: Humans; Polymers; SARS-CoV-2; Fluorescence; COVID-19; Pyrenes
PubMed: 37108336
DOI: 10.3390/ijms24087174