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The Science of the Total Environment Apr 2023Polycyclic aromatic hydrocarbons (PAHs) are generated by incomplete combustion of organic matter. They have health effects in multiple organs and can cause lung, skin,...
Polycyclic aromatic hydrocarbons (PAHs) are generated by incomplete combustion of organic matter. They have health effects in multiple organs and can cause lung, skin, and bladder cancers in humans. Although data regarding their toxicity is available, information on the absorption, distribution, metabolism, and excretion of PAHs in humans is very limited. In the present study, deuterium-labeled naphthalene (Nap), fluorene (Flu), phenanthrene (Phe), and pyrene (Pyr) were orally administered as a single dose (0.02-0.04 mg/kg) to eight healthy adults. Both serum and urine samples were monitored for 72 h after the exposure. Parent compounds and PAH metabolites (monohydroxy-PAHs; OH-PAHs) were measured by headspace-solid phase microextraction coupled with gas chromatography-mass spectrometry and high-performance liquid chromatography-tandem mass spectrometry, respectively. Based on the time-concentration profiles in serum and urine, non-compartmental analysis was performed, and two-compartment models were constructed and validated for each PAH. Subsequently, all of the parent compounds were rapidly absorbed (T: 0.25 to 1.50 h) after oral administration and excreted in urine with a biological half-life (T) of 1.01 to 2.99 h. The fractional urinary excretion (F) of OH-PAHs ranged from 0.07 % to 11.3 %; their T values ranged from 3.4 to 11.0 h. The two-compartment models successfully described the toxicokinetic characteristics of each PAH and its metabolites. F and the two-compartment models could be useful tools for exposure simulation or dose-reconstruction of PAHs. The results of this study will provide useful information for interpreting biomonitoring data of PAHs.
Topics: Adult; Humans; Toxicokinetics; Pyrenes; Polycyclic Aromatic Hydrocarbons; Phenanthrenes; Naphthalenes; Fluorenes; Biomarkers; Environmental Monitoring
PubMed: 36716884
DOI: 10.1016/j.scitotenv.2023.161899 -
Molecules (Basel, Switzerland) Jan 2022Microbial degradation is a useful tool for inhibiting or preventing polycyclic aromatic hydrocarbons (PAHs) widely distributed in marine environment after oil spill...
Microbial degradation is a useful tool for inhibiting or preventing polycyclic aromatic hydrocarbons (PAHs) widely distributed in marine environment after oil spill accidents. This study aimed to evaluate the potential and diversity of bacteria Bacillus sp. PAH-2 on Benzo (a) anthracene (BaA), Pyrene (Pyr), and Benzo (a) pyrene (BaP), their composite system, aromatic components system, and crude oil. The seven-day degradation rates against BaA, Pyr, and BaP were 20.6%, 12.83%, and 17.49%, respectively. Further degradation study of aromatic components demonstrated PAH-2 had a high degradation rate of substances with poor stability of molecular structure. In addition, the degradation of PAHs in crude oil suggested PAH-2 not only made good use of PAHs in such a more complex structure of pollutants but the saturated hydrocarbons in the crude oil also showed a good application potential.
Topics: Bacillus; Bacteria; Benzo(a)pyrene; Biodegradation, Environmental; Environmental Restoration and Remediation; Petroleum; Petroleum Pollution; Polycyclic Aromatic Hydrocarbons; Pyrenes; Seawater
PubMed: 35163953
DOI: 10.3390/molecules27030687 -
Biodegradation Dec 2022Bioaugmentation effectively enhances microbial bioremediation of hazardous polycyclic aromatic hydrocarbons (PAHs) from contaminated environments. While screening for...
Bioaugmentation effectively enhances microbial bioremediation of hazardous polycyclic aromatic hydrocarbons (PAHs) from contaminated environments. While screening for pyrene-degrading bacteria from a former manufactured gas plant soil (MGPS), the mixed enrichment culture was found to be more efficient in PAHs biodegradation than the culturable pure strains. Interestingly, analysis of 16S rRNA sequences revealed that the culture was dominated by a previously uncultured member of the family Rhizobiaceae. The culture utilized C1 and other methylotrophic substrates, including dimethylformamide (DMF), which was used as a solvent for supplementing the culture medium with PAHs. In the liquid medium, the culture rapidly degraded phenanthrene, pyrene, and the carcinogenic benzo(a)pyrene (BaP), when provided as the sole carbon source or with DMF as a co-substrate. The efficiency of the culture in the bioremediation of PAHs from the MGPS and a laboratory waste soil (LWS) was evaluated in bench-scale slurry systems. After 28 days, 80% of Σ16 PAHs were efficiently removed from the inoculated MGPS. Notably, the bioaugmentation achieved 90% removal of four-ringed and 60% of highly recalcitrant five- and six-ringed PAHs from the MGPS. Likewise, almost all phenanthrene, pyrene, and 65% BaP were removed from the bioaugmented LWS. This study highlights the application of the methylotrophic enrichment culture dominated by an uncultured bacterium for the efficient bioremediation of PAHs.
Topics: Biodegradation, Environmental; Polycyclic Aromatic Hydrocarbons; RNA, Ribosomal, 16S; Soil Pollutants; Soil Microbiology; Benzo(a)pyrene; Dimethylformamide; Soil; Pyrenes; Phenanthrenes; Bacteria; Carbon; Solvents
PubMed: 35976498
DOI: 10.1007/s10532-022-09996-9 -
International Journal of Environmental... Jun 2007Polycyclic aromatic hydrocarbons (PAHs) are widespread genotoxic environmental pollutants and potentially pose a health risk to humans. Although the biological and...
Polycyclic aromatic hydrocarbons (PAHs) are widespread genotoxic environmental pollutants and potentially pose a health risk to humans. Although the biological and toxicological activities, including metabolism, mutagenicity and carcinogenicity of PAHs have been thoroughly studied, their phototoxicity and photo-induced biological activities have not been well examined. In this research, we studied the photoirradiation of isomeric methylbenzo[a]pyrene (MBaP) and methylbenzo[e]pyrene (MBeP) by UVA light in the presence of a lipid, methyl linoleate, and evaluated the potential of these compounds to induce lipid peroxidation. The compounds chosen for study included BaP, 3-MBaP, 4-MBaP, 6-MBaP, 7-MBaP, 10-MBaP, BeP, 4-MBeP, and 9-MBeP. The results indicate that upon photoirradiation by UVA at 7 and 21 J/cm2, these compounds induced lipid peroxidation. The levels of the induced lipid peroxidation were similar among BaP and the isomeric MBaPs, and among the BeP and MBePs, with the BaP group higher than the BeP group. There was also a co-relation between the UV A light dose and the level of lipid peroxidation induced. Lipid peroxide formation was inhibited by NaN3 (singlet oxygen and free radical scavenger) and was enhanced by the presence of deuterium oxide (D2O) (extends singlet oxygen lifetime). These results suggest that photoirradiation of MBaPs and MBePs by UVA light generates reactive oxygen species (ROS), which induce lipid peroxidation.
Topics: Benzo(a)pyrene; Benzopyrenes; Free Radical Scavengers; Humans; Lipid Peroxidation; Lipid Peroxides; Phototherapy; Polycyclic Aromatic Hydrocarbons; Pyrenes; Reactive Oxygen Species; Singlet Oxygen; Superoxides; Ultraviolet Rays
PubMed: 17617679
DOI: 10.3390/ijerph2007040010 -
Biophysical Journal Sep 2016A54145 is a lipopeptide antibiotic related to daptomycin that permeabilizes bacterial cell membranes. Its action requires both calcium and phosphatidylglycerol in the...
A54145 is a lipopeptide antibiotic related to daptomycin that permeabilizes bacterial cell membranes. Its action requires both calcium and phosphatidylglycerol in the target membrane, and it is accompanied by the formation of membrane-associated oligomers. We here probed the interaction of A54145 with model membranes composed of dimyristoylphosphatidylcholine and dimyristoylphosphatidylglycerol, using the steady-state and time-resolved fluorescence of a pyrene-labeled derivative (Py-A54145). In solution, the labeled peptide was found to exist as a monomer. Its membrane interaction occurred in two stages that could be clearly distinguished by varying the calcium concentration. In the first stage, which was observed between 0.15 and 1 mM calcium, Py-A54145 bound to the membrane, as indicated by a strong increase in pyrene monomer emission. At the same calcium concentration, excimer emission increased also, suggesting that Py-A54145 had oligomerized. A global analysis of the time-resolved pyrene monomer and excimer fluorescence confirmed that Py-A54145 forms oligomers quantitatively and concomitantly with membrane binding. When calcium was raised beyond 1 mM, a distinct second transition was observed that may correspond to a doubling of the number of oligomer subunits. The collective findings confirm and extend our understanding of the action mode of A54145 and daptomycin.
Topics: Anti-Bacterial Agents; Bacillus subtilis; Calcium; Cations, Divalent; Daptomycin; Dimerization; Dimyristoylphosphatidylcholine; Fluorescent Dyes; Lipoproteins; Liposomes; Models, Theoretical; Molecular Structure; Phosphatidylglycerols; Pyrenes; Solutions; Spectrum Analysis; Water
PubMed: 27653485
DOI: 10.1016/j.bpj.2016.07.018 -
Journal of Oleo Science 2015According to the conventional Gibbs adsorption model, which is a common assumption about the molecular concentration at surfaces, the adsorbed film of soluble... (Review)
Review
According to the conventional Gibbs adsorption model, which is a common assumption about the molecular concentration at surfaces, the adsorbed film of soluble amphiphiles is located at the air/solution interface just like Langmuir monolayer which is illustrated in many physical chemistry text books on "Colloid and Interface Science". According to many proofs of the experimental results here, the newer idea for the surface adsorption is confirmed and explained, which is quite different from the conventional Gibbs surface excess model at the air/solution interface.
Topics: Adsorption; Air; Ethylene Glycol; Models, Theoretical; Pyrenes; Solubility; Solutions; Spectrometry, Fluorescence; Surface Properties; Surface-Active Agents; Thermogravimetry; Unilamellar Liposomes; Volatilization; Water
PubMed: 25742921
DOI: 10.5650/jos.ess14213 -
Molecules (Basel, Switzerland) Feb 2021Selective recognition of nucleotides with synthetic receptors is an emerging direction to solve a series of nucleic acid-related challenges in biochemistry. Towards this...
Selective recognition of nucleotides with synthetic receptors is an emerging direction to solve a series of nucleic acid-related challenges in biochemistry. Towards this goal, a new aza-cyclophane with two different dyes, naphthalimide and pyrene, connected through a triamine linker has been synthesized and studied for the ability to bind and detect nucleoside triphosphates in an aqueous solution. The receptor shows Foerster resonance energy transfer (FRET) in fluorescence spectra upon excitation in DMSO, which is diminished dramatically in the presence of water. According to binding studies, the receptor has a preference to bind ATP (adenosine triphosphate) and CTP (cytidine triphosphate) with a "turn-on" fluorescence response. Two separate emission bands of dyes allow one to detect nucleotides in a ratiometric manner in a broad concentration range of 10-10 M. Spectroscopic measurements and quantum chemical calculations suggest the formation of receptor-nucleotide complexes, which are stabilized by dispersion interactions between a nucleobase and dyes, while hydrogen bonding interactions of nucleobases with the amine linkers are responsible for selectivity.
Topics: Adenosine Triphosphate; Ethers, Cyclic; Fluorescent Dyes; Hydrogen Bonding; Molecular Structure; Naphthalimides; Nucleotides; Piperidines; Pyrenes; Solutions; Spectrometry, Fluorescence; Water
PubMed: 33673272
DOI: 10.3390/molecules26040980 -
Journal of Applied Microbiology Jun 2010This study aimed to isolate and identify potential polycyclic aromatic hydrocarbon (PAH)-degrading and/or metal-tolerant fungi from PAH-contaminated and...
AIMS
This study aimed to isolate and identify potential polycyclic aromatic hydrocarbon (PAH)-degrading and/or metal-tolerant fungi from PAH-contaminated and metal-contaminated soils.
METHODS AND RESULTS
Pyrene-degrading fungi were isolated from contaminated soil and tested for metal (Cu, Zn and Pb) compound solubilization and metal accumulation. Three strains of Fusarium solani and one of Hypocrea lixii were able to degrade more than 60% of initial supplied pyrene (100 mg l(-1)) after 2 weeks. The isolates were grown on toxic metal (Cu, Pb and Zn)-containing media: all isolates accumulated Cu in their mycelia to values ranging from c. 5.9 to 10.4 mmol per kg dry weight biomass. The isolates were also able to accumulate Zn (c. 3.7-7.2 mmol per kg dry weight biomass) from zinc phosphate-amended media. None of the isolates accumulated Pb.
CONCLUSIONS
These fungal isolates appear to show promise for use in bioremediation of pyrene or related xenobiotics and removal of copper and zinc from wastes contaminated singly or in combination with these substances.
SIGNIFICANCE AND IMPACT OF THE STUDY
Microbial responses to mixed organic and inorganic pollution are seldom considered: this research highlights the abilities of certain fungal strains to interact with both xenobiotics and toxic metals and is relevant to other studies on natural attenuation and bioremediation of polluted sites.
Topics: Biodegradation, Environmental; Copper; Fusarium; Gasoline; Hypocrea; Polycyclic Aromatic Hydrocarbons; Pyrenes; Soil; Soil Microbiology; Soil Pollutants; Zinc
PubMed: 19922595
DOI: 10.1111/j.1365-2672.2009.04613.x -
Biochimica Et Biophysica Acta.... Jan 2021The push-pull solvatochromic pyrene derivatives PA and PK have been applied to the study of model membrane vesicles, cells and purified human serum lipoproteins, using...
The push-pull solvatochromic pyrene derivatives PA and PK have been applied to the study of model membrane vesicles, cells and purified human serum lipoproteins, using both confocal fluorescence microscopy and fluorescence spectroscopy. These polarity-sensitive probes provide information similar to that obtained by Laurdan or Prodan, i.e. mainly lipid order in biomembranes, but they have the essential advantage of being excitable by a standard 405 nm laser light, bypassing the use of multiphoton excitation. In addition, they are brighter and much more photostable than those dimethylamino naphthalene derivatives. Our results with model membrane spectroscopy (multilamellar vesicles) and with microscopy (giant unilamellar vesicles) showed the capacity of PA and PK to report differently on liquid-disordered, liquid-ordered and gel phase bilayers. Moreover, a ratiometric parameter, the Red/Blue Intensity Ratio (RBIR) could be used for inter-domain, inter-vesicle and even inter-technique comparison, and the appropriate microscopy-spectroscopy conversion coefficients could be estimated. In studies at the cellular level, PA probe stained almost exclusively the plasma membrane of red blood cells, revealing its high degree of lipid order. Using Chinese Hamster Ovary cells PA was shown to be an excellent probe for the detection of cytoplasmic lipid droplets, superior to Nile Red in that PA provides simultaneously a detailed information of membrane order in the whole cell, in which the lipid droplets appear with a very good contrast. Moreover, spectrofluorometric data of PA-stained serum lipoproteins indicated an essentially identical value of RBIR for lipid droplets and for high-density lipoproteins.
Topics: Animals; CHO Cells; Cricetulus; Erythrocyte Membrane; Fluorescent Dyes; Humans; Lipid Droplets; Lipoproteins; Microscopy, Fluorescence; Pyrenes; Staining and Labeling
PubMed: 32898535
DOI: 10.1016/j.bbamem.2020.183470 -
Chembiochem : a European Journal of... Mar 2012Two pyrene-modified UNA monomers were synthesized and incorporated into 21-mer DNA oligonucleotides. Melting temperatures and thermodynamic properties of the modified...
Two pyrene-modified UNA monomers were synthesized and incorporated into 21-mer DNA oligonucleotides. Melting temperatures and thermodynamic properties of the modified duplexes were measured, and the fluorescence properties of single strands and duplexes containing one or more pyrene-UNA modifications were studied. It was found that incorporation of pyrene-UNA monomers increased duplex stability relative to UNA monomers, and thermodynamic studies revealed significant mismatch discriminative capabilities of the pyrene-UNA modified oligonucleotides. Furthermore, the steady-state fluorescence emission intensities of pyrene-UNA modified oligonucleotides were increased upon hybridization to DNA, which to the best of our knowledge is unprecedented for an acyclic pyrene modification in DNA. Interestingly, pyrene excimer emission was observed for single-stranded oligonucleotides containing three pyrene-UNA modifications, whereas this excimer emission disappeared after hybridization to DNA. In view of both the pyrene monomer and the excimer fluorescence emission, the triply modified oligonucleotides show intriguing properties relating to the development of new DNA/RNA detection tools.
Topics: Fluorescence; Molecular Structure; Nucleic Acids; Pyrenes; Stereoisomerism; Thermodynamics
PubMed: 22315188
DOI: 10.1002/cbic.201100689