Changes of biomarkers with oral exposure to benzo(a)pyrene, phenanthrene and pyrene in rats

PubMed Central

Kang, Hwan Goo; Cho, Myung Haing; Cho, Joon Hyoung

2007-01-01

Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental contaminants present in air and food. Among PAHs, benzo(a)pyrene(BaP), phenanthrene (PH) and pyrene (PY) are considered to be important for their toxicity or abundance. To investigate the changes of biomarkers after PAH exposure, rats were treated with BaP (150 µg/kg) alone or with PH (4,300 µg/kg) and PY (2,700 µg/kg) (BPP group) by oral gavage once per day for 30 days. 7-ethoxyresorufin-O-deethylase activity in liver microsomal fraction was increased in only BaP groups. The highest concentration (34.5 ng/g) of BaP, was found in muscle of rats treated with BaP alone at 20 days of treatment; it was 23.6 ng/g in BPP treated rats at 30 days of treatment. The highest PH concentration was 47.1 ng/g in muscle and 118.8 ng/g in fat, and for PY it was 29.7 ng/g in muscle and 219.9 ng/g in fat, in BPP groups. In urine, 114-161 ng/ml 3-OH-PH was found, while PH was 41-69 ng/ml during treatment. 201-263 ng/ml 1-OH-PY was found, while PH was 9-17 ng/ml in urine. The level of PY, PH and their metabolites in urine was rapidly decreased after withdrawal of treatment. This study suggest that 1-OH-PY in urine is a sensitive biomarker for PAHs; it was the most highly detected marker among the three PAHs and their metabolites evaluated during the exposure period and for 14 days after withdrawal. PMID:17993750

Biosorption and biodegradation of phenanthrene and pyrene in sterilized and unsterilized soil slurry systems stimulated by Phanerochaete chrysosporium.

PubMed

Chen, Baoliang; Ding, Jie

2012-08-30

To assess the "bioaccessible" pool of mycelia-bound polycyclic aromatic hydrocarbons (PAHs) and to quantify its biodegradation kinetics in soil, a soil-slurry system containing mycelial pellets of Phanerochaete chrysosporium as a separable biophase was set up. In sterilized and unsterilized soil-slurry, the distribution and dissipation of phenanthrene and pyrene in soil, fungal body of P. chrysosporium and water were independently quantified over the incubation periods. Biosorption and biodegradation contributions to bio-dissipation of dissolved- and sorbed-PAHs were identified. The biodegradation kinetics of PAHs by allochthonous P. chrysosporium and soil wild microorganisms was higher than those predicted by a coupled desorption-biodegradation model, suggesting both allochthonous and wild microorganisms could access sorbed-PAHs. The obvious hysteresis of PAHs in soil reduced their biodegradation, while the biosorbed-PAHs in P. chrysosporium body as an interim pool exhibited reversibly desorption and were almost exhausted via biodegradation. Both biosorption and direct biodegradation of PAHs in soil slurry were stimulated by allochthonous P. chrysosporium. After 90-day incubation, the respective biodegradation percentages for phenanthrene and pyrene were 63.8% and 51.9% in the unsterilized soil without allochthonous microorganisms, and then increased to 94.9% and 90.6% when amended with live P. chrysosporium. These indicate that allochthonous and wild microorganisms may synergistically attack sorbed-PAHs. Copyright © 2012 Elsevier B.V. All rights reserved.

Interactions among buffelgrass, phenanthrene and phenanthrene-degrading bacteria in gnotobiotic microcosms.

PubMed

Robert, Francoise M; Sun, Wenhao H; Toma, Marisa; Jones, Ryan K; Tang, Chung-Shih

2008-07-15

An experiment was undertaken in gnotobiotic microcosms to determine the role of buffelgrass (Cenchrus ciliaris) and a phenanthrene-degrading bacterium (strain PM600) in the degradation of phenanthrene. The Gram-negative bacterium was identified as a Sphingomonas sp. by 16S rRNA gene sequence analysis and as S. paucimobilis by biochemical tests (API 20 NE strips). Its yellow pigment corresponded to nostoxanthin and its cellular fatty acids were typical of the genus Sphingomonas. Moreover, it was devoid of lipopolysaccharides. Strain PM600 was tested for growth on mineral medium supplemented with No. 2 diesel, hexadecane, mineral oil, pristane, phenanthrene, and pyrene as single carbon sources. It was capable of utilizing phenanthrene only. In the gnotobiotic microcosms silica sand was either or not supplemented with 150 mg of phenanthrene kg(-1) sand, inoculated with strain PM600, and planted to sterile young seedlings of buffelgrass. After 28 days, 67% of the reduction of the phenanthrene concentration was assigned to degradation by the bacterium and ca. 20% to abiotic factors. No statistically significant effect of the young buffelgrass was found. In the absence of phenanthrene, the bacterial population significantly increased in the rhizosphere of buffelgrass. However, in the presence of buffelgrass and phenanthrene, the bacterial population preferentially responded to phenanthrene. The growth of buffelgrass was severely curtailed by phenanthrene in the absence of the bacterium. However, strain PM600 effectively protected buffelgrass against the phytotoxicity of phenanthrene.

Electrochemical synthesis, characterization and electrochromic properties of a copolymer based on 1,4-bis(2-thienyl)naphthalene and pyrene

NASA Astrophysics Data System (ADS)

Wang, Bin; Zhao, Jinsheng; Cui, Chuansheng; Wang, Min; Wang, Zhong; He, Qingpeng

2012-05-01

Electrochemical copolymerization of 1,4-bis(2-thienyl)naphthalene (BTN) with pyrene is carried out in acetonitrile (ACN) solution containing sodium perchlorate (NaClO4) as a supporting electrolyte. Characterizations of the resulting copolymer P(BTN-co-pyrene) are performed by cyclic voltammetry (CV), UV-vis spectroscopy, Fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM). The P(BTN-co-pyrene) film has distinct electrochromic properties and exhibits three different colors (yellowish green, green and blue) under various potentials. Maximum contrast (ΔT%) and response time of the copolymer film are measured as 37.8% and 1.71 s at 687 nm. An electrochromic device (ECD) based on P(BTN-co-pyrene) and poly(3,4-ethylenedioxythiophene) (PEDOT) is constructed and characterized. Neutral state of device shows green color while oxidized state reveals blue color. This ECD shows a maximum optical contrast (ΔT%) of 24.4% with a response time of 0.43 s at 635 nm. The coloration efficiency (CE) of the device is calculated to be 349 cm2 C-1 at 635 nm. In addition, the ECD also has satisfactory optical memories and redox stability.

Effect of Cosolutes on the Sorption of Phenanthrene onto Mineral Surface of River Sediments and Kaolinite

PubMed Central

2014-01-01

Sorption of phenanthrene onto the natural sediment with low organic carbon content (OC%), organic-free sediment, and kaolinite was investigated through isotherm experiments. Effects of cosolutes (pyrene, 4-n-nonyphenol (NP), and humic acid (HA)) on phenanthrene sorption were also studied by comparing apparent solid-water distribution coefficients (K d app) of phenanthrene. Two addition sequences, including “cosolute added prior to phenanthrene” and “cosolute and phenanthrene added simultaneously,” were adopted. The Freundlich model fits phenanthrene sorption on all 3 sorbents well. The sorption coefficients on these sorbents were similar, suggesting that mineral surface plays an important role in the sorption of hydrophobic organic contaminants on low OC% sediments. Cosolutes could affect phenanthrene sorption on the sorbents, which depended on their properties, concentrations, and addition sequences. Pyrene inhibited phenanthrene sorption. Sorbed NP inhibited phenanthrene sorption at low levels and promoted sorption at high levels. Similar to NP, effect of HA on phenanthrene sorption onto the natural sediment depended on its concentrations, whereas, for the organic-free sediment and kaolinite, preloading of HA at high levels led to an enhancement in phenanthrene K d app while no obvious effect was observed at low HA levels; dissolved HA could inhibit phenanthrene sorption on the two sorbents. PMID:25147865

MULTISUBSTRATE BIODEGRADATION KINETICS FOR BINARY AND COMPLEX MIXTURES OF POLYCYCLIC AROMATIC HYDROCARBONS

EPA Science Inventory

Biodegradation kinetics were studied for binary and complex mixtures of nine polycyclic aromatic hydrocarbons (PAHs): naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, 2-ethylnaphthalene, phenanthrene, anthracene, pyrene, fluorene and fluoranthene. Discrepancies between the ...

Heterologous Expression of Polycyclic Aromatic Hydrocarbon Ring-Hydroxylating Dioxygenase Genes from a Novel Pyrene-Degrading Betaproteobacterium

PubMed Central

Hu, Jing; Aitken, Michael D.

2012-01-01

A betaproteobacterium within the family Rhodocyclaceae previously identified as a pyrene degrader via stable-isotope probing (SIP) of contaminated soil (designated pyrene group 1 or PG1) was cultivated as the dominant member of a mixed bacterial culture. A metagenomic library was constructed, and the largest contigs were analyzed for genes associated with polycyclic aromatic hydrocarbon (PAH) metabolism. Eight pairs of genes with similarity to the α- and β-subunits of ring-hydroxylating dioxygenases (RHDs) associated with aerobic bacterial PAH degradation were identified and linked to PG1 through PCR analyses of a simplified enrichment culture. In tandem with a ferredoxin and reductase found in close proximity to one pair of RHD genes, six of the RHDs were cloned and expressed in Escherichia coli. Each cloned RHD was tested for activity against nine PAHs ranging in size from two to five rings. Despite differences in their predicted protein sequences, each of the six RHDs was capable of transforming phenanthrene and pyrene. Three RHDs could additionally transform naphthalene and fluorene, and these genotypes were also associated with the ability of the E. coli constructs to convert indole to indigo. Only one of the six cloned RHDs was capable of transforming anthracene and benz[a]anthracene. None of the tested RHDs were capable of significantly transforming fluoranthene, chrysene, or benzo[a]pyrene. PMID:22427500

Mechanism for Clastogenic Activity of Naphthalene

DOE Office of Scientific and Technical Information (OSTI.GOV)

Buchholz, Bruce A.

2016-06-24

Naphthalene incubations form DNA adducts in vitro in a dose dependent manner in both mouse and rat tissues. Rodent tissue incubations with naphthalene indicate that naphthalene forms as many DNA adducts as Benzo(a)pyrene, a known DNA binding carcinogen. The mouse airway has the greatest number of DNA adducts, corresponding to the higher metabolic activation of naphthalene in this location. Both rat tissues, the rat olfactory (tumor target) and the airways (non-tumor target), have similar levels of NA-DNA adducts, indicating that short term measures of initial adduct formation do not directly correlate with sites of tumor formation in the NTP bioassays.

Effects of inoculation of PAH-degrading bacteria and arbuscular mycorrhizal fungi on responses of ryegrass to phenanthrene and pyrene.

PubMed

Wu, Fuyong; Yu, Xiezhi; Wu, Shengchun; Wong, Minghung

2014-01-01

In order to investigate the effects of soil microorganisms on biochemical and physiological response of plants to PAHs, PAH-degrading bacteria (Acinetobacter sp.) and/or arbuscular mycorrhizal fungus (Glomus mosseae) were inoculated with ryegrass (Lolium multiflorum) under four different concentrations of phenanthrene and pyrene (0, 50 + 50, 100 + 100, 200 + 200 mg kg(-1)) in soils. Acinetobacter sp. played limited roles on the growth of ryegrass, chlorophyll content, water soluble carbohydrate content, malondialdehyde (MDA) content, activities of superoxide dismutase (SOD) and peroxidase (POD) in shoot. By contrast, G. mosseae significantly (P < 0.01) increased ryegrass growth, partially by improving the photosynthetic activity through increasing the chlorophyll content in shoot. G. mosseae also significantly decreased MDA content in shoot. However, G. mosseae significantly increased SOD activity in shoot, which seemed to be resulted from significantly higher pyrene concentrations in shoot. The present study suggested that AM fungi could reduce the damage of cell membranes caused by free radicals, which may be one of the mechanisms involved in mycorrhizal alleviation of plant stress under PAHs. The present study indicated that the dual inoculation was superior to single inoculation in remediating PAHs contaminated soils.

Contamination of agricultural lands by polycyclic aromatic hydrocarbons (Tver region, Russia)

NASA Astrophysics Data System (ADS)

Zhidkin, Andrey; Koshovskii, Timur; Gennadiev, Alexander

2016-04-01

It is important to study sources and concentrations of polycyclic aromatic hydrocarbons (PAHs) in the agriculture soils within areas without intensive contaminations. Our studied object was soil and snow cover in the taiga zone (Tver region, Russia). A total of 52 surface (0-30 cm) and 31 subsurface (30-50 cm) soil samples, and 13 snow samples were collected in 35 soil pits, located in forest, crop and layland soils. Studied concentrations of the following 11 individual compounds: two-ring compounds (diphenyl and naphthalene homologues); three-ring compounds (fluorene, phenanthrene, anthracene); four-ring compounds (chrysene, pyrene, tetraphene); five-ring compounds (perylene, benzo[a]pyrene); and six-ring compounds (benzo[ghi]perylene). Analyses made by specrtofluorometry method at the temperature of liquid nitrogen. The total concentrations of all PAHs in soil samples ranged from 9 to 770 ng*g-1 with a median of 96 ng*g-1. The sum of high molecular weight PAHs was significantly lower than the sum of low molecular weight PAHs in the studied soils. The phenanthrene concentration was highest and ranged from 1.2 to 720 ng*g-1 (medium 72 ng*g-1). Compared PAHs reserves in snow cover (μg*m-2) with the reserves in topsoil layer (μg*m-2 in the upper 30 cm). Low molecular weight PAHs (fluorene, phenanthrene, diphenyl, naphthalene) reserves in snow was less than 20% from the reserves in the soil surface layer. High molecular weight PAHs (benzo[a]pyrene, chrysene, perylene, pyrene and tetraphene) reserves in snow was about 50-70% from the reserves in soil surface layer. High molecular weight PAHs (benzo[ghi]perylene and anthracene) reserves in snow was more than in topsoil. PAHs vertical distribution in soil profiles was statistically examined. The total concentration of all PAHs decreased with depth in all studied forest soils. In the arable soils was no significant trend in domination of PAHs total concentrations in the plowing and subsoil layers. The ratio of topsoil

Degradation of some representative polycyclic aromatic hydrocarbons by the water-soluble protein extracts from Zea mays L. cv PR32-B10.

PubMed

Barone, Roberto; de Biasi, Margherita-Gabriella; Piccialli, Vincenzo; de Napoli, Lorenzo; Oliviero, Giorgia; Borbone, Nicola; Piccialli, Gennaro

2016-10-01

The ability of the water-soluble protein extracts from Zea mais L. cv. PR32-B10 to degrade some representative polycyclic aromatic hydrocarbons (PAHs), has been evaluated. Surface sterilized seeds of corn (Zea mais L. Pioneer cv. PR32-B10) were hydroponically cultivated in a growth chamber under no-stressful conditions. The water-soluble protein extracts isolated from maize tissues showed peroxidase, polyphenol oxidase and catalase activities. Incubation of the extracts with naphthalene, fluorene, phenanthrene and pyrene, led to formation of oxidized and/or degradation products. GC-MS and TLC monitoring of the processes showed that naphthalene, phenanthrene, fluorene and pyrene underwent 100%, 78%, 92% and 65% oxidative degradation, respectively, after 120 min. The chemical structure of the degradation products were determined by (1)H NMR and ESI-MS spectrometry. Copyright © 2016 Elsevier Ltd. All rights reserved.

Molecular modelling investigations on the possibility of phenanthrene dimers to be the primary nuclei of soot

NASA Astrophysics Data System (ADS)

Wei, Mingrui; Wu, Sheng; Li, Fan; Zhang, Dongju; Zhang, Tingting; Guo, Guanlun

2017-11-01

Pyrene dimerisation was successfully used to model the beginning of soot nucleation in some simulation models. However, the quantum mechanics (QM) calculations proved that the binding energy of a PAH dimer with three six-member rings was similar to that of a pyrene dimer. Meanwhile, the high concentration of phenanthrene at flame conditions indicated high probability of collisions among them. The small difference of the binding energy and high concentration indicated that PAHs structurally smaller than pyrene also could be involved in soot inception. Hence, binary collisions of phenanthrene were simulated to find out whether phenanthrene dimers can serve as soot primary nuclei or not by using non-equilibrium molecular dynamics (MD). Three temperatures, six collision orientations and 155 initial translational velocities (ITVs) were considered. The results indicated that the number of dimers with lifetime over 10 ps which can serve as soot nuclei decreased from 52 at 1000 K to 17 at 1600 K, and further to 6 at 2400 K, which means that low temperature was more favourable for phenanthrene to form soot nuclei. Meanwhile, no soot nuclei were formed at the high velocity region (HVR), compared to 43 and 9 at low and middle velocity regions (LVR and MVR), respectively, when temperature was 1000 K. Also, no soot nuclei were formed at HVR when the temperature was raised to 1600 K and 2400 K. This indicated that HVR was unfavourable for phenanthrene to form soot nuclei. The results computationally further illustrated that small PAHs such as phenanthrene could serve as soot primary nuclei, since they have similar mole fractions in some flames. This may be useful for future soot simulation models.

Energy transfer of highly vibrationally excited phenanthrene and diphenylacetylene.

PubMed

Hsu, Hsu Chen; Tsai, Ming-Tsang; Dyakov, Yuri; Ni, Chi-Kung

2011-05-14

The energy transfer between Kr atoms and highly vibrationally excited, rotationally cold phenanthrene and diphenylacetylene in the triplet state was investigated using crossed-beam/time-of-flight mass spectrometer/time-sliced velocity map ion imaging techniques. Compared to the energy transfer between naphthalene and Kr, energy transfer between phenanthrene and Kr shows a larger cross-section for vibrational to translational (V → T) energy transfer, a smaller cross-section for translational to vibrational and rotational (T → VR) energy transfer, and more energy transferred from vibration to translation. These differences are further enlarged in the comparison between naphthalene and diphenylacetylene. In addition, less complex formation and significant increases in the large V → T energy transfer probabilities, termed supercollisions in diphenylacetylene and Kr collisions were observed. The differences in the energy transfer between these highly vibrationally excited molecules are attributed to the low-frequency vibrational modes, especially those vibrations with rotation-like wide-angle motions.

Enhanced polyaromatic hydrocarbon degradation by adapted cultures of actinomycete strains.

PubMed

Bourguignon, Natalia; Isaac, Paula; Alvarez, Héctor; Amoroso, María J; Ferrero, Marcela A

2014-12-01

Fifteen actinomycete strains were evaluated for their potential use in removal of polycyclic aromatic hydrocarbons (PAH). Their capability to degrade of naphthalene, phenanthrene, and pyrene was tested in minimal medium (MM) and MM with glucose as another substrate. Degradation of naphthalene in MM was observed in all isolates at different rates, reaching maximum values near to 76% in some strains of Streptomyces, Rhodococcus sp. 016 and Amycolatopsis tucumanensis DSM 45259. Maximum values of degradation of phenanthrene in MM occurred in cultures of A. tucumanensis DSM 45259 (36.2%) and Streptomyces sp. A12 (20%), while the degradation of pyrene in MM was poor and only significant with Streptomyces sp. A12 (4.3%). Because of the poor performance when growing on phenanthrene and pyrene alone, Rhodococcus sp. 20, Rhodococcus sp. 016, A. tucumanensis DSM 45259, Streptomyces sp. A2, and Streptomyces sp. A12 were challenged to an adaptation schedule of successive cultures on a fresh solid medium supplemented with PAHs, decreasing concentration of glucose in each step. As a result, an enhanced degradation of PAHs by adapted strains was observed in the presence of glucose as co-substrate, without degradation of phenanthrene and pyrene in MM while an increase to up to 50% of degradation was seen with these strains in glucose amended media. An internal fragment of the catA gene, which codes for catechol 1,2-dioxygenase, was amplified from both Rhodococcus strains, showing the potential for degradation of aromatic compounds via salycilate. These results allow us to propose the usefulness of these actinomycete strains for PAH bioremediation in the environment. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Functional Categorization of Transcriptome in the Species Symphysodon aequifasciatus Pellegrin 1904 (Perciformes: Cichlidae) Exposed to Benzo[a]pyrene and Phenanthrene

PubMed Central

Lemgruber, Renato de Souza Pinto; Marshall, Nislanha Ana dos Anjos; Ghelfi, Andrea; Fagundes, Daniel Barros; Val, Adalberto Luis

2013-01-01

This study aims to evaluate the transcriptome alterations, through cDNA libraries, associated with the combined effects of two PAHs, benzo[a]pyrene (0.5 µg/L) and phenanthrene (50 µg/L), present in crude oil, on specimens of Symphysodon aequifasciatus (discus fish) after 48 h of exposure. The cDNA libraries were constructed according to the SOLiD™ SAGE™ protocol for sequencing in the SOLiD v.3 Plus sequencer. The results were analyzed by bioinformatics and differentially expressed genes were categorized using the gene ontology program. The functional categories (terms) found in the gene ontology and the gene network generated using STRING software were used to predict the adverse effects of benzo[a]pyrene and phenanthrene in the liver. In the present study, 27,127 genes (compared to Danio rerio database) were identified. Considering only those genes with a p-value less than or equal to 0.05 and greater than or equal to two-fold change in expression across libraries, we found 804 genes, 438 down-regulated (54%) and 366 up-regulated (46%), in the experimental group compared to the control. Out of this total, 327 genes were successfully categorized, 174 down-regulated and 153 up-regulated, using gene ontology. Using String, the gene network was composed by 199 nodes, 124 of them resulting in 274 interactions. The results showed that even an acute exposure of 48 h caused metabolic change in response to environmental contaminants, resulting in changes of cell integrity, in oxidation-reduction processes, in the immune response and disturbances of intracellular signaling of discus fish. Also the gene network has showed no central interplay cluster, exhibiting instead interconnected clusters interactions and connected sub-networks. These findings highlight that even an acute sublethal exposure of PAHs can cause metabolism changes that may affect survival of discus. Our findings using SOLiD coupled with SAGE-method resulted in a powerful and reliable means for gene

Removal Capacities of Polycyclic Aromatic Hydrocarbons (PAHs) by a Newly Isolated Strain from Oilfield Produced Water

PubMed Central

Qi, Yi-Bin; Wang, Chen-Yu; Lv, Cheng-Yuan; Lun, Zeng-Min; Zheng, Cheng-Gang

2017-01-01

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 Gordonia. 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 Gordonia alkaliphila and Gordonia paraffinivorans, 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 n-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. Gordonia 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. PMID:28241412

Analysis of Particulate and Chemical Residue Resulting from Exposure to Burning and Abrading Composite Materials

DTIC Science & Technology

2013-05-31

21 Figure 15. Example of a Possible Foreign Object Observed in a Small Number of Slides. This Object May Be a Hair, Thread, or Plant Material that...h)anthracene Fluoranthene Fluorene Indeno(1,2,3-cd)pyrene Naphthalene Phenanthrene Pyrene 16 Distribution A. Approved for public release...material during sampling. These were subject to particle analysis as described above in order to estimate the coverage ratio and particle density of

Evaluation of sewage sludge and slow pyrolyzed sewage sludge-derived biochar for adsorption of phenanthrene and pyrene.

PubMed

Zielińska, Anna; Oleszczuk, Patryk

2015-09-01

The present study investigated the sorption of phenanthrene (PHE) and pyrene (PYR) by sewage sludges and sewage sludge-derived biochars. The organic carbon normalized distribution coefficient (log K(OC) for C(w) = 0.01 S(w)) for the sewage sludges ranged from 5.62 L kg(-1) to 5.64 L kg(-1) for PHE and from 5.72 L kg(-1) to 5.75 L kg(-1) for PYR. The conversion of sewage sludges into biochar significantly increased their sorption capacity. The value of log K(OC) for the biochars ranged from 5.54 L kg(-1) to 6.23 L kg(-1) for PHE and from 5.95 L kg(-1) to 6.52 L kg(-1) for PYR depending on temperature of pyrolysis. The dominant process was monolayer adsorption in the micropores and/or multilayer surface adsorption (in the mesopores), which was indicated by the significant correlations between log K(OC) and surface properties of biochars. PYR was sorbed better on the tested materials than PHE. Copyright © 2015 Elsevier Ltd. All rights reserved.

Attenuation of phenanthrene and pyrene adsorption by sewage sludge-derived biochar in biochar-amended soils.

PubMed

Zielińska, Anna; Oleszczuk, Patryk

2016-11-01

The aim of this study was to evaluate the effect of soils on the sorption of phenanthrene (PHE) and pyrene (PYR) by sewage sludge-derived biochars (SS-derived biochars). The SS-derived biochars were added to soils with varying properties as well as with a different degree and source of polycyclic aromatic hydrocarbons (PAHs) contamination. The biochars (BCs) were produced from sewage sludge during pyrolysis at temperatures of 500 °C (BC500) and 700 °C (BC700). The addition of biochars to the soils (5 %, w/w) increased the sorption of PHE from 8.3 to 20.3 % and PYR from 14.5 to 31.7 % by amended soil. BC700 biochar was characterized by better sorption capacity than BC500 biochar. Nevertheless, the presence of soil reduces the effectiveness of biochars in binding the compounds studied. The sorption capacity of the biochars decreased several times after they had been mixed with the soil compared to pure biochars. The study found dissolved organic carbon (DOC) and clay minerals present in the soils to have a significant effect on reducing the efficiency of PHE and PYR sorption by biochar. A greater impact of fouling was observed in the case of BC500 biochar characterized by lower porosity than BC700 biochar.

Carboxylation as an initial reaction in the anaerobic metabolism of naphthalene and phenanthrene by sulfidogenic consortia.

PubMed Central

Zhang, X; Young, L Y

1997-01-01

The anaerobic biodegradation of naphthalene (NAP) and phenanthrene (PHE) was investigated by using sediment collected from the Arthur Kill in New York/New Jersey harbor. The initial cultures were composed of 10% sediment and 90% mineral medium containing 20 mM sulfate. Complete loss of NAP and PHE (150 to 200 muM) was observed after 150 days of incubation. Upon refeeding, NAP and PHE were utilized within 14 days. The utilization of both compounds was inhibited in the presence of 20 mM molybdate. [14C]NAP and [14C]PHE were mineralized to 14CO2. The activities could be maintained and propagated by subculturing in mineral medium. In the presence of halogenated analogs, 2-naphthoate was detected in NAP-utilizing enrichments. The mass spectrum of the derivatized 2-napththoate from the enrichment supplemented with both [13C]bicarbonate and NAP indicates the incorporation of 13CO2 into NAP. In the PHE-utilizing enrichment, a metabolite was detected by both high-pressure liquid chromatography and gas chromatography-mass spectrometry analyses. The molecular ion and fragmentation pattern of its mass spectrum indicate that it was phenanthrenecarboxylic acid. The results obtained with [13C] bicarbonate indicate that 13CO2 was incorporated into PHE. It appears, therefore, that carboxylation is an initial key reaction for the anaerobic metabolism and NAP and PHE. To our knowledge, this is the first report providing evidence for intermediates of PAH degradation under anaerobic conditions. PMID:9471963

Characterization of a Microbial Consortium for the Bioremoval of Polycyclic Aromatic Hydrocarbons (PAHs) in Water

PubMed Central

Blanco-Enríquez, Esmeralda G.; Zavala-Díaz de la Serna, Francisco Javier; Peralta-Pérez, María del Rosario; Ballinas-Casarrubias, Lourdes; Salmerón, Iván; Rubio-Arias, Héctor; Rocha-Gutiérrez, Beatriz A.

2018-01-01

Pollution of freshwater ecosystems from polycyclic aromatic hydrocarbons (PAHs) is a global concern. The US Environmental Protection Agency (EPA) has included the PAHs pyrene, phenanthrene, and naphthalene among the 16 priority compounds of special concern for their toxicological effects. The aim of this study was to adapt and characterize a microbial consortium from ore waste with the potential to remove these three PAHs from water. This microbial consortium was exposed to the target PAHs at levels of 5, 10, 20, 50, and 100 mg L−1 for 14 days. PAH bioremoval was measured using the analytical technique of solid phase microextraction, followed by gas chromatography mass spectrometry (SPME-GC/MS). The results revealed that up to 90% of the target PAHs can be removed from water after 14 days at a concentration level of 100 mg L−1. The predominant group of microorganisms identified at the phylum taxonomic level were the Proteobacteria, while the Actinobacteria were the predominant subgroup. The removal of phenanthrene, naphthalene, and pyrene predominantly occurred in specimens of genera Stenotrophomonas, Williamsia, and Chitinophagaceae, respectively. This study demonstrates that the use of specific microorganisms is an alternative method of reducing PAH levels in water. PMID:29757264

Infrared Spectroscopy of Polycyclic Aromatic Hydrocarbon Cations. 3; The Members

NASA Technical Reports Server (NTRS)

Hudgins, D. M.; Allamandola, L. J.; Wittebon, Fred C. (Technical Monitor)

1994-01-01

In spite of the fact that the infrared spectroscopic properties of only a few isolated ionized polycyclic aromatic hydrocarbons (PAHs) are known, gaseous, ionized PAHs are thought to be responsible for a very common family of infrared interstellar emission bands. In order to provide a data base to test this hypothesis and, if borne out, to use this emission band family as a probe of many different interstellar environments, we are carrying out a thorough study of the infrared spectroscopic properties of neutral and ionized PAHs in argon matrices. Here we present the near and mid-infrared spectra of the cations of the five most thermodynamically favored PAHs up to coronene: phenanthrene, pyrene, benzo[e]pyrene, benzo[ghilperylene, and coronene. The properties of naphthalene, the first member of the series, are given elsewhere. The spectra of perdeuterated phenanthrene and pyrene are also reported. For those molecules which have been previously studied (pyrene, d(10)-pyrene, and coronene), band positions and relative intensities are in agreement. In all cases we report additional features. Absolute integrated absorbance values are given for the phenanthrene, perdeutero-phenanthrene, pyrene, benzo[ghi]perylene, and coronene cations. With the exception of coronene,the cation bands corresponding to the CC modes are typically 2-5 times more intense than those of the CH out-of-plane bending vibrations. For the cations the CC stretching and CH in-plane bending modes give rise to bands which are an order of magnitude stronger than for the neutral species, and the CH out-of-plane bends produce bands which are 5-20 times weaker than in the neutral species. This behavior is similar to that found in most other PAH cations studied to date. The astronomical implications of these PAH cation spectra are also discussed.

Biodegradation of phenanthrene in bioaugmented microcosm by consortium ASP developed from coastal sediment of Alang-Sosiya ship breaking yard.

PubMed

Patel, Vilas; Patel, Janki; Madamwar, Datta

2013-09-15

A phenanthrene-degrading bacterial consortium (ASP) was developed using sediment from the Alang-Sosiya shipbreaking yard at Gujarat, India. 16S rRNA gene-based molecular analyses revealed that the bacterial consortium consisted of six bacterial strains: Bacillus sp. ASP1, Pseudomonas sp. ASP2, Stenotrophomonas maltophilia strain ASP3, Staphylococcus sp. ASP4, Geobacillus sp. ASP5 and Alcaligenes sp. ASP6. The consortium was able to degrade 300 ppm of phenanthrene and 1000 ppm of naphthalene within 120 h and 48 h, respectively. Tween 80 showed a positive effect on phenanthrene degradation. The consortium was able to consume maximum phenanthrene at the rate of 46 mg/h/l and degrade phenanthrene in the presence of other petroleum hydrocarbons. A microcosm study was conducted to test the consortium's bioremediation potential. Phenanthrene degradation increased from 61% to 94% in sediment bioaugmented with the consortium. Simultaneously, bacterial counts and dehydrogenase activities also increased in the bioaugmented sediment. These results suggest that microbial consortium bioaugmentation may be a promising technology for bioremediation. Copyright © 2013 Elsevier Ltd. All rights reserved.

The anharmonic quartic force field infrared spectra of five non-linear polycyclic aromatic hydrocarbons: Benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene

NASA Astrophysics Data System (ADS)

Mackie, Cameron J.; Candian, Alessandra; Huang, Xinchuan; Maltseva, Elena; Petrignani, Annemieke; Oomens, Jos; Mattioda, Andrew L.; Buma, Wybren Jan; Lee, Timothy J.; Tielens, Alexander G. G. M.

2016-08-01

The study of interstellar polycyclic aromatic hydrocarbons (PAHs) relies heavily on theoretically predicted infrared spectra. Most earlier studies use scaled harmonic frequencies for band positions and the double harmonic approximation for intensities. However, recent high-resolution gas-phase experimental spectroscopic studies have shown that the harmonic approximation is not sufficient to reproduce experimental results. In our previous work, we presented the anharmonic theoretical spectra of three linear PAHs, showing the importance of including anharmonicities into the theoretical calculations. In this paper, we continue this work by extending the study to include five non-linear PAHs (benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene), thereby allowing us to make a full assessment of how edge structure, symmetry, and size influence the effects of anharmonicities. The theoretical anharmonic spectra are compared to spectra obtained under matrix isolation low-temperature conditions, low-resolution, high-temperature gas-phase conditions, and high-resolution, low-temperature gas-phase conditions. Overall, excellent agreement is observed between the theoretical and experimental spectra although the experimental spectra show subtle but significant differences.

The anharmonic quartic force field infrared spectra of five non-linear polycyclic aromatic hydrocarbons: Benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene.

PubMed

Mackie, Cameron J; Candian, Alessandra; Huang, Xinchuan; Maltseva, Elena; Petrignani, Annemieke; Oomens, Jos; Mattioda, Andrew L; Buma, Wybren Jan; Lee, Timothy J; Tielens, Alexander G G M

2016-08-28

The study of interstellar polycyclic aromatic hydrocarbons (PAHs) relies heavily on theoretically predicted infrared spectra. Most earlier studies use scaled harmonic frequencies for band positions and the double harmonic approximation for intensities. However, recent high-resolution gas-phase experimental spectroscopic studies have shown that the harmonic approximation is not sufficient to reproduce experimental results. In our previous work, we presented the anharmonic theoretical spectra of three linear PAHs, showing the importance of including anharmonicities into the theoretical calculations. In this paper, we continue this work by extending the study to include five non-linear PAHs (benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene), thereby allowing us to make a full assessment of how edge structure, symmetry, and size influence the effects of anharmonicities. The theoretical anharmonic spectra are compared to spectra obtained under matrix isolation low-temperature conditions, low-resolution, high-temperature gas-phase conditions, and high-resolution, low-temperature gas-phase conditions. Overall, excellent agreement is observed between the theoretical and experimental spectra although the experimental spectra show subtle but significant differences.

The reductive aromatization of naphthalene diimide: a versatile platform for 2,7-diazapyrenes.

PubMed

Nakazato, Takumi; Kamatsuka, Takuto; Inoue, Junichi; Sakurai, Tsuneaki; Seki, Shu; Shinokubo, Hiroshi; Miyake, Yoshihiro

2018-05-17

The reductive aromatization of naphthalene diimide provides tetrapivaloxy-2,7-diazapyrene, which serves as a versatile platform toward peripherally substituted 2,7-diazapyrenes. Time-resolved microwave conductivity measurements demonstrated that the intrinsic electron mobility of 2,7-diazapyrene is significantly higher than that of the corresponding pyrene.

Sediments from stormwater drainage system as sorbents of organic and inorganic pollutants

NASA Astrophysics Data System (ADS)

Sałata, Aleksandra; Dąbek, Lidia

2017-11-01

The study presents the results of tests aimed at determining variations in concentrations of polycyclic aromatic hydrocarbons (naphthalene, acenaphthylene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenzo[a, h]anthracene, benzo[g, h, i]perylene and indeno[1, 2, 3-c, d]pyrene) and heavy metals (copper, cadmium, chromium, nickel, lead and zinc) in the sediments from the stormwater sewer system. Results of this study were then compared to Polish regulations and established ecological screening values to determine their potential risk to environment. The results suggest that stormwater sediments are moderately contaminated with PAHs and heavy metals according to domestic regulations and highly contaminated according to ecological benchmarks.

Influence of the presence of PAHs and coal tar on naphthalene sorption in soils

NASA Astrophysics Data System (ADS)

Bayard, Rémy; Barna, Ligia; Mahjoub, Borhane; Gourdon, Rémy

2000-11-01

The mobility of the most water-soluble polynuclear aromatic hydrocarbons (PAHs) such as naphthalene in contaminated soils from manufactured gas plant (MGP) sites or other similar sites is influenced not only by the naturally occurring soil organic matter (SOM) but also, and in many cases mostly, by the nature and concentration of coal tar xenobiotic organic matter (XOM) and other PAH molecules present in the medium under various physical states. The objective of the present study was to quantify the effects of these factors using batch experiments, in order to simulate naphthalene transport in soil-tar-water systems using column experiments. Naphthalene sorption was studied in the presence of (i) solid coal tar particles, (ii) phenanthrene supplied as pure crystals, in the aqueous solution or already sorbed onto the soil, (iii) fluoranthene as pure crystals, and (iv) an aqueous solution of organic molecules extracted from a liquid tar. All experiments were conducted under abiotic conditions using short naphthalene/sorbent contact times of 24-60 h. Although these tests do not reflect true equilibrium conditions which usually take more time to establish, they were used to segregate relatively rapid sorption phenomena ("pseudo equilibrium") from slow sorption and other aging phenomena. For longer contact times, published data have shown that experimental biases due to progressive changes in the characteristics of the soil and the solution may drastically modify the affinity of the solutes for the soil. Slow diffusion in the microporosity and in dense organic phases may also become significant over the long term, along with some irreversible aging phenomena which have not been addressed in this work. Results showed that PAHs had no effect on naphthalene sorption when present in the aqueous solution or as pure crystals, due to their low solubility in water. Adsorbed phenanthrene was found to reduce naphthalene adsorption only when present at relatively high

Agarose-chitosan-C18 film micro-solid phase extraction combined with high performance liquid chromatography for the determination of phenanthrene and pyrene in chrysanthemum tea samples.

PubMed

Ng, Nyuk Ting; Sanagi, Mohd Marsin; Wan Ibrahim, Wan Nazihah; Wan Ibrahim, Wan Aini

2017-05-01

Agarose-chitosan-immobilized octadecylsilyl-silica (C 18 ) film micro-solid phase extraction (μSPE) was developed and applied for the determination of phenanthrene (PHE) and pyrene (PYR) in chrysanthemum tea samples using high performance liquid chromatography-ultraviolet detection (HPLC-UV). The film of blended agarose and chitosan allows good dispersion of C 18 , prevents the leaching of C 18 during application and enhances the film mechanical stability. Important μSPE parameters were optimized including amount of sorbent loading, extraction time, desorption solvent and desorption time. The matrix match calibration curves showed good linearity (r⩾0.994) over a concentration range of 1-500ppb. Under the optimized conditions, the proposed method showed good limits of detection (0.549-0.673ppb), good analyte recoveries (100.8-105.99%) and good reproducibilities (RSDs⩽13.53%, n=3) with preconcentration factors of 4 and 72 for PHE and PYR, respectively. Copyright © 2016 Elsevier Ltd. All rights reserved.

Impact of bacterial activity on turnover of insoluble hydrophobic substrates (phenanthrene and pyrene)-Model simulations for prediction of bioremediation success.

PubMed

Rein, Arno; Adam, Iris K U; Miltner, Anja; Brumme, Katja; Kästner, Matthias; Trapp, Stefan

2016-04-05

Many attempts for bioremediation of polycyclic aromatic hydrocarbon (PAH) contaminated sites failed in the past, but the reasons for this failure are not well understood. Here we apply and improve a model for integrated assessment of mass transfer, biodegradation and residual concentrations for predicting the success of remediation actions. First, we provide growth parameters for Mycobacterium rutilum and Mycobacterium pallens growing on phenanthrene (PHE) or pyrene (PYR) degraded the PAH completely at all investigated concentrations. Maximum metabolic rates vmax and growth rates μ were similar for the substrates PHE and PYR and for both strains. The investigated Mycobacterium species were not superior in PHE degradation to strains investigated earlier with this method. Real-world degradation scenario simulations including diffusive flux to the microbial cells indicate: that (i) bioaugmentation only has a small, short-lived effect; (ii) Increasing sorption shifts the remaining PAH to the adsorbed/sequestered PAH pool; (iii) mobilizing by solvents or surfactants resulted in a significant decrease of the sequestered PAH, and (iv) co-metabolization e.g. by compost addition can contribute significantly to the reduction of PAH, because active biomass is maintained at a high level by the compost. The model therefore is a valuable contribution to the assessment of potential remediation action at PAH-polluted sites. Copyright © 2015 Elsevier B.V. All rights reserved.

Naphthalene degradation by bacterial consortium (DV-AL) developed from Alang-Sosiya ship breaking yard, Gujarat, India.

PubMed

Patel, Vilas; Jain, Siddharth; Madamwar, Datta

2012-03-01

Naphthalene degrading bacterial consortium (DV-AL) was developed by enrichment culture technique from sediment collected from the Alang-Sosiya ship breaking yard, Gujarat, India. The 16S rRNA gene based molecular analyzes revealed that the bacterial consortium (DV-AL) consisted of four strains namely, Achromobacter sp. BAB239, Pseudomonas sp. DV-AL2, Enterobacter sp. BAB240 and Pseudomonas sp. BAB241. Consortium DV-AL was able to degrade 1000 ppm of naphthalene in Bushnell Haas medium (BHM) containing peptone (0.1%) as co-substrate with an initial pH of 8.0 at 37°C under shaking conditions (150 rpm) within 24h. Maximum growth rate and naphthalene degradation rate were found to be 0.0389 h(-1) and 80 mg h(-1), respectively. Consortium DV-AL was able to utilize other aromatic and aliphatic hydrocarbons such as benzene, phenol, carbazole, petroleum oil, diesel fuel, and phenanthrene and 2-methyl naphthalene as sole carbon source. Consortium DV-AL was also efficient to degrade naphthalene in the presence of other pollutants such as petroleum hydrocarbons and heavy metals. Copyright © 2011 Elsevier Ltd. All rights reserved.

A Novel Phenanthrene Dioxygenase from Nocardioides sp. Strain KP7: Expression in Escherichia coli

PubMed Central

Saito, Atsushi; Iwabuchi, Tokuro; Harayama, Shigeaki

2000-01-01

Nocardioides sp. strain KP7 grows on phenanthrene but not on naphthalene. This organism degrades phenanthrene via 1-hydroxy-2-naphthoate, o-phthalate, and protocatechuate. The genes responsible for the degradation of phenanthrene to o-phthalate (phd) were found by Southern hybridization to reside on the chromosome. A 10.6-kb DNA fragment containing eight phd genes was cloned and sequenced. The phdA, phdB, phdC, and phdD genes, which encode the α and β subunits of the oxygenase component, a ferredoxin, and a ferredoxin reductase, respectively, of phenanthrene dioxygenase were identified. The gene cluster, phdAB, was located 8.3 kb downstream of the previously characterized phdK gene, which encodes 2-carboxybenzaldehyde dehydrogenase. The phdCD gene cluster was located 2.9 kb downstream of the phdB gene. PhdA and PhdB exhibited moderate (less than 60%) sequence identity to the α and β subunits of other ring-hydroxylating dioxygenases. The PhdC sequence showed features of a [3Fe-4S] or [4Fe-4S] type of ferredoxin, not of the [2Fe-2S] type of ferredoxin that has been found in most of the reported ring-hydroxylating dioxygenases. PhdD also showed moderate (less than 40%) sequence identity to known reductases. The phdABCD genes were expressed poorly in Escherichia coli, even when placed under the control of strong promoters. The introduction of a Shine-Dalgarno sequence upstream of each initiation codon of the phdABCD genes improved their expression in E. coli. E. coli cells carrying phdBCD or phdACD exhibited no phenanthrene-degrading activity, and those carrying phdABD or phdABC exhibited phenanthrene-degrading activity which was significantly less than that in cells carrying the phdABCD genes. It was thus concluded that all of the phdABCD genes are necessary for the efficient expression of phenanthrene-degrading activity. The genetic organization of the phd genes, the phylogenetically diverged positions of these genes, and an unusual type of ferredoxin component

The polycyclic aromatic hydrocarbons benzo[a]pyrene and phenanthrene inhibit intestinal lipase activity in rainbow trout (Oncorhynchus mykiss).

PubMed

de Gelder, Stefan; Sæle, Øystein; de Veen, Bas T H; Vos, Joëlle; Flik, Gert; Berntssen, Marc H G; Klaren, Peter H M

2017-08-01

Elevated levels of polycyclic aromatic hydrocarbons (PAHs) are detected in aquafeeds where fish oils are (partially) replaced by vegetable oils. The highly lipophilic PAHs solubilize readily in oil droplets and micelles in the intestinal lumen that can affect enzymatic lipid digestion by altering lipase activity. We therefore investigated the effect of two PAHs, benzo[a]pyrene (BaP) and phenanthrene (PHE), on bile salt-activated lipase (BAL) activity in desalted luminal extracts of the proximal intestine of rainbow trout (Oncorhynchus mykiss) using the triacylglycerides rapeseed oil and fish oil as substrates. The hydrolysis of rapeseed oil and fish oil measured at a calculated substrate concentration of 2.2mM, increased linearly up to 30min at 15°C. Substrate dependency under initial velocity conditions was described by simple Michaelis-Menten kinetics with a K m value of 1.2mM for rapeseed and fish oil. Rapeseed oil hydrolysis was inhibited by 1nM BaP and 10nM PHE. The hydrolysis of fish oil was only inhibited by 10μM BaP. The in vitro lipase activity data were corroborated by TLC/HPLC analysis of the reaction products, showing that in the presence of BaP and PHE, 46-80% less free fatty acids (FFA) were hydrolysed from rapeseed and fish oil triacylglycerides. The presence of low concentrations of BaP and PHE decreased rapeseed oil hydrolysis by BAL whereas fish oil hydrolysis was not affected. The replacement of fish oil by rapeseed oil in aquafeeds introduces PAHs that could affect lipid digestion. Copyright © 2017 Elsevier Inc. All rights reserved.

Bacterial Degradation of Aromatic Compounds

PubMed Central

Seo, Jong-Su; Keum, Young-Soo; Li, Qing X.

2009-01-01

Aromatic compounds are among the most prevalent and persistent pollutants in the environment. Petroleum-contaminated soil and sediment commonly contain a mixture of polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatics. Aromatics derived from industrial activities often have functional groups such as alkyls, halogens and nitro groups. Biodegradation is a major mechanism of removal of organic pollutants from a contaminated site. This review focuses on bacterial degradation pathways of selected aromatic compounds. Catabolic pathways of naphthalene, fluorene, phenanthrene, fluoranthene, pyrene, and benzo[a]pyrene are described in detail. Bacterial catabolism of the heterocycles dibenzofuran, carbazole, dibenzothiophene, and dibenzodioxin is discussed. Bacterial catabolism of alkylated PAHs is summarized, followed by a brief discussion of proteomics and metabolomics as powerful tools for elucidation of biodegradation mechanisms. PMID:19440284

Products from the incomplete metabolism of pyrene by polycyclic aromatic hydrocarbon-degrading bacteria

DOE Office of Scientific and Technical Information (OSTI.GOV)

Kazunga, C.; Aitken, M.D.

Pyrene is a regulated pollutant at sites contaminated with polycyclic aromatic hydrocarbons (PAH). It is mineralized by some bacteria but is also transformed to nonmineral products by a variety of other PAH-degrading bacteria. The authors examined the formation of such products by four bacterial strains and identified and further characterized the most apparently significant of these metabolites. Pseudomonas stutzeri strain P16 and Bacillus cereus strain P21 transformed pyrene primarily to cis-4,5-dihydro-4,5-dihydroxypyrene (PYRdHD), the first intermediate in the known pathway for aerobic bacterial mineralization of pyrene. Sphingomonas yanoikuyae strain R1 transformed pyrene to PYRdHD and pyrene-4,5-dione (PYRQ). Both strain R1 andmore » Pseudomonas saccharophila strain P15 transform PYRdHD to PYRQ nearly stoichiometrically, suggesting that PYRQ is formed by oxidation of PYRdHD to 4,5-dihydroxypyrene and subsequent autoxidation of this metabolite. A pyrene-mineralizing organism, Mycobacterium strain PYR-1, also transforms PYRdHD to PYRQ at high initial concentrations of PYRdHD. However, strain PYR-1 is able to use both PYRdHD and PYRQ as growth substrates. PYRdHD strongly inhibited phenanthrene degradation by strains P15 and R1 but had only a minor effect on strains P16 and P21. At their aqueous saturation concentrations, both PYRdHD and PYRQ severely inhibited benzo[a]pyrene mineralization by strains P15 and R1. Collectively, these findings suggest that products derived from pyrene transformation have the potential to accumulate in PAH-contaminated systems and that such products can significantly influence the removal of other PAH. However, these products may be susceptible to subsequent degradation by organisms able to metabolize pyrene more extensively if such organisms are present in the system.« less

Association of atmospheric concentrations of polycyclic aromatic hydrocarbons with their urinary metabolites in children and adolescents.

PubMed

Poursafa, Parinaz; Amin, Mohammad Mehdi; Hajizadeh, Yaghoub; Mansourian, Marjan; Pourzamani, Hamidreza; Ebrahim, Karim; Sadeghian, Babak; Kelishadi, Roya

2017-07-01

This study aims to determine the atmospheric concentrations of particulate matter 2.5 (PM 2.5 )-bounded polycyclic aromatic hydrocarbons (PAHs) and their association with their urinary metabolites in children and adolescents. This study was conducted from October 2014 to March 2016 in Isfahan, Iran. We measured 16 species of PAHs bounded to PM 2.5 by gas chromatography mass spectrometry (GC/MS) from 7 parts of the city. Moreover, PAH urinary metabolites were measured in 186 children and adolescents, randomly selected from households. Urinary metabolites consisted of 1-hydroxy naphthalene (1-naphthol), 2-hydroxy naphthalene (2-naphthol), 9-hydroxy phenanthrene (9-phenanthrol), and 1-hydroxy pyrene using GC/MS. Considering the short half-lives of PAHs, we measured the metabolites twice with 4 to 6 months of time interval. We found that the ambient concentrations of PAHs were significantly associated with their urinary metabolites. 1-hydroxy naphthalene and 2-hydroxy naphthalene concentrations showed an increase of 1.049 (95% CI: 1.030, 1.069) and 1.047 (95% CI: 1.025, 1.066) for each unit increase (1 ng/m 3 ) in ambient naphthalene. Similarly, 1-hydroxy pyrene showed an increase of 1.009 (95% CI: 1.006-1.011) for each unit increase (1 ng/m 3 ) in ambient pyrene concentration after adjustment for body mass index, physical activity level, urinary creatinine, age, and sex. The association of urinary 9-hydroxyphenanthrene and ambient phenantherene was significant in the crude model; however after adjustment for the abovementioned covariates, it was no more significant. We found significant correlations between exposure to ambient PM 2.5 -bounded PAHs and their urinary excretion. Considering the adverse health effects of PAHs in the pediatric age group, biomonitoring of PAHs should be underscored; preventive measures need to be intensified.

PAH composition of Water Based Drilling Mud and drill cuttings in the offshore region, east coast of India.

PubMed

Jagwani, Devaanshi; Kulkarni, Atul; Shukla, Parth; Ramteke, Dilip S; Juneja, Harjeet D

2011-11-01

As a consequence of offshore drilling, used Water Based Drilling Muds (WBMs) are typically disposed off, by discharging into the sea; such a disposal does not fully eliminate the environmental hazards. Hence, in this study, 2, 3, 4 and 5 ringed polycyclic aromatic hydrocarbons (PAHs i.e. naphthalene, fluorene, phenanthrene, fluoranthene, chrysene and benzo (a) pyrene) were determined from the WBMs and associated drill cuttings obtained from varying depths(viz. 150, 300 and 600 m) from three offshore wells present in East coast of India. In both WBMs and drill cuttings, concentration of naphthalene was maximum i.e. 81.59 ± 2.73 and 39.87 ± 2.40 mg/kg respectively, while benzo (a) pyrene was minimum i.e. 0.19 ± 0.07 and 0.12 ± 0.03 mg/kg respectively. The WBMs contained significantly (p < 0.05) higher PAH concentration than drill cuttings. The individual PAH concentration significantly (p < 0.01) increased with increasing depth in each well.

Characterization of Cultures Enriched from Acidic Polycyclic Aromatic Hydrocarbon-Contaminated Soil for Growth on Pyrene at Low pH▿

PubMed Central

Uyttebroek, Maarten; Vermeir, Steven; Wattiau, Pierre; Ryngaert, Annemie; Springael, Dirk

2007-01-01

Two polycyclic aromatic hydrocarbon (PAH)-contaminated soils of pH 2 were successfully used as inoculum to enrich cultures growing on phenanthrene and pyrene at different pHs, including pH 3. Selected pyrene-utilizing cultures obtained at pH 3, pH 5, and pH 7 were further characterized. All showed rapid [14C]pyrene mineralization at pH 3 and pH 5 and grew on pyrene at pH values ranging from 2 to 6. Eubacterial and mycobacterial 16S rRNA gene denaturing gradient gel electrophoresis fingerprinting and sequencing indicated that the cultures were dominated by a single bacterium closely related to Mycobacterium montefiorense, belonging to the slow-growing Mycobacterium sp. In contrast, a culture enriched on pyrene at pH 7 from a slightly alkaline soil sampled at the same site was dominated by Pseudomonas putida and a fast-growing Mycobacterium sp. The M. montefiorense-related species dominating the pyrene-utilizing cultures enriched from the acidic soils was also the dominant Mycobacterium species in the acidic soils. Our data indicate that a slow-growing Mycobacterium species is involved in PAH degradation in that culture and show that bacteria able to degrade high-molecular-weight PAHs at low pH are present in acidic PAH-contaminated soil. PMID:17369339

Dissipation of phenanthrene and pyrene at the aerobic-anaerobic soil interface: differentiation induced by the rhizosphere of PAH-tolerant and PAH-sensitive rice (Oryza sativa L.) cultivars.

PubMed

He, Yan; Xia, Wen; Li, Xinfeng; Lin, Jiajiang; Wu, Jianjun; Xu, Jianming

2015-03-01

A pot experiment was conducted to reveal the removal of two polycyclic aromatic hydrocarbons (PAHs) (phenanthrene, PHE, and pyrene, PYR) during rice cultivation in a paddy field. The rhizosphere effect on facilitating dissipation of PAHs varied simultaneously as a function of soil properties, PAH types, cultivation time, and genotypes within rice cultivars, with differences performed for PYR but not PHE. Changes in soil PLFA profiles evidenced that the growth of rice roots modified the dominant species within rhizosphere microbial communities and induced a selective enrichment of Gram-negative aerobic bacteria capable of degrading, thereby resulting in the differentiated dissipation of PYR. While the insignificant differences in PHE dissipation might be attributed to its higher solubility and availability under flooded condition that concealed the differences in improvement of bioavailability for microorganisms between rhizosphere and non-rhizosphere, and between both soils and both rice cultivars. Our findings illustrate that the removal of PAHs in paddy soils was more complex relative to those in dryland soils. This was possibly due to the specialty of rice roots for oxygen secretion that provides development of redox heterogeneous microbial habitats at root-soil interface under flooded condition.

Comparison of polycyclic aromatic hydrocarbons level between suspended solid and sediment samples of Pengkalan Chepa River, Kelantan state, Malaysia

NASA Astrophysics Data System (ADS)

Muslim, Noor Zuhartini Md; Babaheidari, Seyedreza Hashemi; Zakaria, Mohamad Pauzi

2015-09-01

Sixteen type of common Polycyclic Aromatic Hydrocarbons (PAHs) which consist of naphthalene, acenaphthene, acenaphthylene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, benzo[ghi]-perylene, indeno[1,2,3-cd]-pyrene and dibenz[a,h]-anthracene in suspended solid and sediment samples of Pengkalan Chepa River, Kelantan state, Malaysia were investigated. The analysis samples were taken from six different sites of Pengkalan Chepa River during sunny day. The samples were subjected to a series of pre-treatment before the level of PAHs can be determined. A Gas Chromatography-Mass Spectrometry (GC-MS) was the prime method for the analysis of PAHs level. A total of 16 PAHs concentration in suspended solid of the whole Pengkalan Chepa River was found to be 2144.6 ng/g dry weights. This concentration was about eight times more than 16 PAHs concentration in sediment which found to be 266.5 ng/g dry weights.

A Survey of 42 Semi-Volatile Organic Contaminants in Groundwater along the Grand Canal from Hangzhou to Beijing, East China.

PubMed

Li, Xiaojie; Rao, Zhu; Yang, Zhipeng; Guo, Xiaochen; Huang, Yi; Zhang, Jing; Guo, Feng; Liu, Chen

2015-12-18

The status of organic pollution in groundwater in eastern China along the Grand Canal from Hangzhou to Beijing was evaluated. Forty-two semi-volatile organic contaminants were analyzed, including 16 polycyclic aromatic hydrocarbons (PAHs), seven polychlorinated biphenyls (PCBs), 12 organochlorine pesticides (OCPs) and seven organophosphorus pesticides (OPPs). Among the detected contaminants, PAHs were the most widespread compounds. One PCB and six OCPs were detected in the groundwater samples, but none of the target OPPs was detected. The total concentration of the 16 PAHs ranged from 0.21 to 1006 ng/L, among which phenanthrene (271 ng/L) and fluoranthene (233 ng/L) were present at very high concentrations and naphthalene (32 positive detections in 50 samples) and fluorene (28 detections in 50 samples) were the most frequently detected. Benzo[a]pyrene equivalents indicated a high environmental risk related to PAHs in a few groundwater samples. To identify the possible sources of PAHs, three concentration ratios, low molecular weight PAHs/high molecular weight PAHs, anthracene/(anthracene + phenanthrene) and fluoranthene/(fluoranthene + pyrene), were determined, that indicated that the PAHs mainly originated from mixed sources: pyrolytic and petrogenic sources with different ratios at different sites.

A Survey of 42 Semi-Volatile Organic Contaminants in Groundwater along the Grand Canal from Hangzhou to Beijing, East China

PubMed Central

Li, Xiaojie; Rao, Zhu; Yang, Zhipeng; Guo, Xiaochen; Huang, Yi; Zhang, Jing; Guo, Feng; Liu, Chen

2015-01-01

The status of organic pollution in groundwater in eastern China along the Grand Canal from Hangzhou to Beijing was evaluated. Forty-two semi-volatile organic contaminants were analyzed, including 16 polycyclic aromatic hydrocarbons (PAHs), seven polychlorinated biphenyls (PCBs), 12 organochlorine pesticides (OCPs) and seven organophosphorus pesticides (OPPs). Among the detected contaminants, PAHs were the most widespread compounds. One PCB and six OCPs were detected in the groundwater samples, but none of the target OPPs was detected. The total concentration of the 16 PAHs ranged from 0.21 to 1006 ng/L, among which phenanthrene (271 ng/L) and fluoranthene (233 ng/L) were present at very high concentrations and naphthalene (32 positive detections in 50 samples) and fluorene (28 detections in 50 samples) were the most frequently detected. Benzo[a]pyrene equivalents indicated a high environmental risk related to PAHs in a few groundwater samples. To identify the possible sources of PAHs, three concentration ratios, low molecular weight PAHs/high molecular weight PAHs, anthracene/(anthracene + phenanthrene) and fluoranthene/(fluoranthene + pyrene), were determined, that indicated that the PAHs mainly originated from mixed sources: pyrolytic and petrogenic sources with different ratios at different sites. PMID:26694442

High Voltage Electrochemiluminescence (ECL) as a New Method for Detection of PAH During Screening for PAH-Degrading Microbial Consortia.

PubMed

Staninska, Justyna; Szczepaniak, Zuzanna; Staninski, Krzysztof; Czarny, Jakub; Piotrowska-Cyplik, Agnieszka; Nowak, Jacek; Marecik, Roman; Chrzanowski, Łukasz; Cyplik, Paweł

The search for new bacterial consortia capable of removing PAH from the environment is associated with the need to employ novel, simple, and economically efficient detection methods. A fluorimetric method (FL) as well as high voltage electrochemiluminescence (ECL) on a modified surface of an aluminum electrode were used in order to determine the changes in the concentrations of PAH in the studied aqueous solutions. The ECL signal (the spectrum and emission intensity for a given wavelength) was determined with the use of an apparatus operating in single photon counting mode. The dependency of ECL and FL intensity on the concentration of naphthalene, phenanthrene, and pyrene was linear in the studied concentration range. The biodegradation kinetics of the particular PAH compounds was determined on the basis of the obtained spectroscopic determinations. It has been established that the half-life of naphthalene, phenanthrene, and pyrene at initial concentrations of 50 mg/l (beyond the solubility limit) reached 41, 75, and 130 h, accordingly. Additionally, the possibility of using ECL for rapid determination of the soluble fraction of PAH directly in the aqueous medium has been confirmed. Metagenomic analysis of the gene encoding 16S rRNA was conducted on the basis of V4 hypervariable region of the 16S rRNA gene and allowed to identify 198 species of bacteria that create the S4consortium. The consortium was dominated by Gammaproteobacteria (78.82 %), Flavobacteria (9.25 %), Betaproteobacteria (7.68 %), Sphingobacteria (3.76 %), Alphaproteobacteria (0.42 %), Clostridia (0.04 %), and Bacilli (0.03 %).

Oxidation kinetics of polycyclic aromatic hydrocarbons by permanganate.

PubMed

Forsey, Steven P; Thomson, Neil R; Barker, James F

2010-04-01

The reactivity of permanganate towards polycyclic aromatics hydrocarbons (PAHs) is well known but little kinetic information is available. This study investigated the oxidation kinetics of a selected group of coal tar creosote compounds and alkylbenzenes in water using permanganate, and the correlation between compound reactivity and physical/chemical properties. The oxidation of naphthalene, phenanthrene, chrysene, 1-methylnaphthalene, 2-methylnaphthalene, acenaphthene, fluorene, carbazole isopropylbenzene, ethylbenzene and methylbenzene closely followed pseudo first-order reaction kinetics. The oxidation of pyrene was initially very rapid and did not follow pseudo first-order kinetics at early times. Fluoranthene was only partially oxidized and the oxidation of anthracene was too fast to be captured. Biphenyl, dibenzofuran, benzene and tert-butylbenzene were non-reactive under the study conditions. The oxidation rate was shown to increase with increasing number of polycyclic rings because less energy is required to overcome the aromatic character of a polycyclic ring than is required for benzene. Thus the rate of oxidation increased in the series naphthalene. The rate of side chain reactivity is controlled by the C-H bond strength. For the alkyl substituted benzenes an excellent correlation was observed between the reaction rate coefficients and bond dissociation energies, but for the substituted PAHs the relationship was poor. A trend was found between the reaction rate coefficients and the calculated heats of complexation indicating that significant ring oxidation occurred in addition to side chain oxidation. Clar's aromatic sextet theory was used to predict the relative stability of arenes towards ring oxidation by permanganate. 2010 Elsevier Ltd. All rights reserved.

Effects of biochars on the bioaccessibility of phenanthrene/pyrene/zinc/lead and microbial community structure in a soil under aerobic and anaerobic conditions.

PubMed

Ni, Ni; Shi, Renyong; Liu, Zongtang; Bian, Yongrong; Wang, Fang; Song, Yang; Jiang, Xin

2018-01-01

The immobilization of co-contaminants of organic and inorganic pollutants by biochar is an efficient remediation strategy. However, the effect of biochar amendments on the bioaccessibility of the co-contaminants in dry versus flooded soils has rarely been compared. In batch experiments, bamboo-derived biochar (BB) had a higher sorption capacity for phenanthrene (Phe)/pyrene (Pyr)/zinc (Zn) than corn straw-derived biochar (CB), while CB had a higher sorption capacity for lead (Pb) than BB. After 150days of incubation, the amendments of 2% CB, 0.5% BB and 2% BB effectively suppressed the dissipation and reduced the bioaccessibility of Phe/Pyr by 15.65%/18.02%, 17.07%/18.31% and 25.43%/27.11%, respectively, in the aerobic soils. This effectiveness was more significant than that in the anaerobic soils. The accessible Zn/Pb concentrations were also significantly lower in the aerobic soils than in the anaerobic soils, regardless of treatments. The Gram-negative bacterial biomass and the Shannon-Weaver index in the aerobic soil amended with 2% CB were the highest. The soil microbial community structure was jointly affected by changes in the bioaccessibility of the co-contaminants and the soil physiochemical properties caused by biochar amendments under the two conditions. Therefore, dry land farming may be more reliable than paddy soil cultivation at reducing the bioaccessibility of Phe/Pyr/Zn/Pb and enhancing the soil microbial diversity in the short term. Copyright © 2017. Published by Elsevier B.V.

Emission of polycyclic aromatic hydrocarbons from diesel engine in a bus station, Londrina, Brazil

NASA Astrophysics Data System (ADS)

Tavares, Moacir; Pinto, Jurandir P.; Souza, Alexandre L.; Scarmínio, Ieda S.; Cristina Solci, Maria

2004-09-01

The concentrations of vapor phase polycyclic aromatic hydrocarbons (PAHs) were measured at the Central Bus Station of Londrina, where only diesel-powered vehicles circulate. The samples were collected within a period of 24 h for 14 consecutive days in January 2002. The semi-volatile PAHs were collected using a cartridge packed with XAD-2 resin, extracted under sonication and subsequently analyzed by gas chromatograph equipped with the flame ionization and mass spectrometer detectors (GC-FID and GC/MS). Ten PAH compounds were found (naphthalene, acenapthylene, acenapthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benzo(a)anthracene and chrysene). The average concentrations ranged from 1.4±0.3 ng m-3 for benzo(a)anthracene to 348.0±32.7 ng m-3 for phenanthrene. The species that presented higher concentration were phenanthrene (348.0±32.7 ng m-3), fluorene (140.2±17.3 ng m-3) and naphthalene (97.7±10.3 ng m-3). The PAHs with two and three rings were responsible by 90.2% of the total concentration among 10 PAHs. The concentrations of PAHs were lower on Sunday in comparison with the workdays, due to the reduction of bus traffic in the station. Correlations and principal component analysis with Varimax rotation were used to estimate the local PAH emission source profile originating from the diesel exhaust. The ratio PHEN/FLU of 2.5 calculated from the results is suggested as indication from diesel combustion exhaust.

Sample preparation of sewage sludge and soil samples for the determination of polycyclic aromatic hydrocarbons based on one-pot microwave-assisted saponification and extraction.

PubMed

Pena, M Teresa; Pensado, Luis; Casais, M Carmen; Mejuto, M Carmen; Cela, Rafael

2007-04-01

A microwave-assisted sample preparation (MASP) procedure was developed for the analysis of polycyclic aromatic hydrocarbons (PAHs) in sewage sludge and soil samples. The procedure involved the simultaneous microwave-assisted extraction of PAHs with n-hexane and the hydrolysis of samples with methanolic potassium hydroxide. Because of the complex nature of the samples, the extracts were submitted to further cleaning with silica and Florisil solid-phase extraction cartridges connected in series. Naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, dibenz[a,h]anthracene, benzo[g,h,i]perylene, and indeno[1,2,3-cd]pyrene, were considered in the study. Quantification limits obtained for all of these compounds (between 0.4 and 14.8 microg kg(-1) dry mass) were well below of the limits recommended in the USA and EU. Overall recovery values ranged from 60 to 100%, with most losses being due to evaporation in the solvent exchange stages of the procedure, although excellent extraction recoveries were obtained. Validation of the accuracy was carried out with BCR-088 (sewage sludge) and BCR-524 (contaminated industrial soil) reference materials.

Remarkably constant PAH concentrations in Swiss soils over the last 30 years.

PubMed

Gubler, Andreas; Wächter, Daniel; Blum, Franziska; Bucheli, Thomas D

2015-10-01

Although polycyclic aromatic hydrocarbons (PAH) are of concern due to their carcinogenic, mutagenic, and teratogenic properties and their ubiquitous occurrence in environmental compartments, only few studies assessed the temporal evolutions of PAH contents of soils over extended time periods. The Swiss Soil Monitoring Network NABO runs long-term monitoring sites resampled every five years since the 1980s. In the present study, soil (0-20 cm) samples collected from 1985 through 2013 at 25 selected monitoring sites were analysed for the 16 priority PAH according to the U.S. EPA and five PAH marker substances. We observed divergent trends for light PAH, such as naphthalene and phenanthrene, compared with heavy PAH, such as benzo[a]pyrene and benzo[ghi]perylene. Whereas the former showed decreasing concentrations since the late 1980s, no significant trends were found for the latter. Furthermore, the analyses showed that naphthalene contents decreased most strongly at rural sites featuring low population densities, while phenanthrene contents generally decreased most strongly at semi-rural sites. The deviating evolutions of light and heavy PAH were mainly attributed to their differing physico-chemical properties. Temporal evolutions in soils contradict emission inventory data suggesting PAH emissions to decline since the 1980s.

Modulation of ethoxyresorufin O-deethylase and glutathione S-transferase activities in Nile tilapia (Oreochromis niloticus) by polycyclic aromatic hydrocarbons containing two to four rings: implications in biomonitoring aquatic pollution.

PubMed

Pathiratne, Asoka; Hemachandra, Chamini K

2010-08-01

Despite ubiquity of polycyclic aromatic hydrocarbons (PAHs) in the tropical environments, little information is available concerning responses of tropical fish to PAHs and associated toxicity. In the present study, effects of five PAHs containing two to four aromatic rings on hepatic CYP1A dependent ethoxyresorufin O-deethylase (EROD), glutathione S-transferase (GST) and serum sorbitol dehydrogenase (SDH) activities in Nile tilapia, a potential fish species for biomonitoring pollution in tropical waters, were evaluated. Results showed that EROD activities were induced by the PAHs containing four aromatic rings (pyrene and chrysene) in a dose dependent manner. However PAHs with two to three aromatic rings (naphthalene, phenanthrene and fluoranthene) caused no effect or inhibition of EROD activities depending on the dose and the duration. Fluoranthene was the most potent inhibitor. SDH results demonstrated that high doses of fluoranthene induced hepatic damage. GST activity was induced by the lowest dose of phenanthrene, fluoranthene and chrysene but high doses had no effect. The results indicate that induction of EROD enzyme in Nile tilapia is a useful biomarker of exposure to PAHs such as pyrene and chrysene. However EROD inhibiting PAHs such as fluoranthene in the natural environment may modulate the EROD inducing potential of other PAHs thereby influencing PAH exposure assessments.

Degradation of phenanthrene by Trametes versicolor and its laccase.

PubMed

Han, Mun-Jung; Choi, Hyoung-Tae; Song, Hong-Gyu

2004-06-01

Phenanthrene is a three-ring polycyclic aromatic hydrocarbon and commonly found as a pollutant in various environments. Degradation of phenanthrene by white rot fungus Trametes versicolor 951022 and its laccase, isolated in Korea, was investigated. After 36 h of incubation, about 46% and 65% of 100 mg/l of phenanthrene added in shaken and static fungal cultures were removed, respectively. Phenanthrene degradation was maximal at pH 6 and the optimal temperature for phenanthrene removal was 30 degrees C. Although the removal percentage of phenanthrene was highest (76.7%) at 10 mg/l of phenanthrene concentration, the transformation rate was maximal (0.82 mg/h) at 100 mg/L of phenanthrene concentration in the fungal culture. When the purified laccase of T versicolor 951022 reacted with phenanthrene, phenanthrene was not transformed. The addition of redox mediator, 2,2'-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) or 1-hydroxybenzotriazole (HBT) to the reaction mixture increased oxidation of phenanthrene by laccase about 40% and 30%, respectively.

CROSS-INDUCTION OF PYRENE AND PHENANTHRENE IN MYCOBACTERIUM SP. ISOLATED FROM POLYCYCLIC AROMATIC HYDROCARBON CONTAMINATED RIVER SEDIMENTS

EPA Science Inventory

A polycyclic aromatic hydrocarbon (PAH)-degrading culture enriched from contaminated river sediments and a Mycobacterium sp. isolated from the enrichment were tested to investigate the possible synergistic and antagonistic interactions affecting the degradation of pyrene in the p...

Pyrene synthesis in circumstellar envelopes and its role in the formation of 2D nanostructures

NASA Astrophysics Data System (ADS)

Zhao, Long; Kaiser, Ralf I.; Xu, Bo; Ablikim, Utuq; Ahmed, Musahid; Joshi, Dharati; Veber, Gregory; Fischer, Felix R.; Mebel, Alexander M.

2018-05-01

For the past decades, the hydrogen-abstraction/acetylene-addition (HACA) mechanism has been instrumental in attempting to untangle the origin of polycyclic aromatic hydrocarbons (PAHs) as identified in carbonaceous meteorites such as Allende and Murchison. However, the fundamental reaction mechanisms leading to the synthesis of PAHs beyond phenanthrene (C14H10) are still unknown. By exploring the reaction of the 4-phenanthrenyl radical (C14H9•) with acetylene (C2H2) under conditions prevalent in carbon-rich circumstellar environments, we show evidence of a facile, isomer-selective formation of pyrene (C16H10). Along with the hydrogen-abstraction/vinylacetylene-addition (HAVA) mechanism, molecular mass growth processes from pyrene may lead through systematic ring expansions not only to more complex PAHs, but ultimately to 2D graphene-type structures. These fundamental reaction mechanisms are crucial to facilitate an understanding of the origin and evolution of the molecular universe and, in particular, of carbon in our Galaxy.

Immune effects of HFO on European sea bass, Dicentrarchus labrax, and Pacific oyster, Crassostrea gigas.

PubMed

Bado-Nilles, Anne; Quentel, Claire; Auffret, Michel; Le Floch, Stéphane; Gagnaire, Béatrice; Renault, Tristan; Thomas-Guyon, Hélène

2009-07-01

The European sea bass, Dicentrarchus labrax, and the Pacific oyster, Crassostrea gigas, were exposed to a soluble fraction of heavy fuel oil for 5 and 9 days, respectively. The organisms were then transferred to non-contaminated seawater for 1 month. The bioaccumulation and elimination of PAHs in contaminated tissues were dissimilar between species. In fish, acenaphthene and naphthalene were detected and naphthalene was still detectable 30 days after the beginning of the recovery period. In oysters, on the other hand, pyrene and phenanthrene were bioaccumulated and 14 days after exposure no more PAHs were detected. Concerning innate immune parameters, the increase of haemolytic activity of the alternative complement pathway in fish and the reduction of phenoloxidase activity in oysters endured, respectively, 1 and 2 weeks in contaminated organisms. This indicates that these two enzymatic cascades could be quite useful for monitoring pollution by oil.

Online investigations on ozonation products of pyrene and benz[ a]anthracene particles with a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer

NASA Astrophysics Data System (ADS)

Gao, Shaokai; Zhang, Yang; Meng, Junwang; Shu, Jinian

The reaction products of ozone with pyrene and benz[ a]anthracene absorbed on azelaic acid particles under the pseudo-first-order reaction conditions have been investigated with a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer (VUV-ATOFMS). The pyrene and benz[ a]anthracene particles with the initial concentrations of ˜1 mg m -3 are respectively exposed to ˜22 ppm ozone in a reaction chamber with a volume of ˜180 L. The time-of-flight mass spectra of the particulate ozonides are obtained. The assignments of the mass spectra reveal that 4-carboxy-5-phenanthrene-carboxyaldehyde (71%) and hydroxypyrene (23%) are the main solid state ozonides of pyrene, while 2-(2-formyl)phenyl-3-naphthoic acid (35%), hydroxybenz[ a]anthrone (30%), and benz[ a]anthracene-7,12-dione (18%) are the main solid state ozonides of benz[ a]anthracene. The pathways of the ozonations are proposed in the paper.

Microbial characterization and hydrocarbon biodegradation potential of natural bilge waste microflora.

PubMed

Olivera, N L; Commendatore, M G; Delgado, O; Esteves, J L

2003-09-01

Shipping operations produce oily wastes that must be managed properly to avoid environmental pollution. The aim of this study was to characterize microorganisms occurring in ship bilge wastes placed in open lagoons and, particularly, to assess their potential to degrade polycyclic aromatic hydrocarbons (PAHs). A first-order kinetic was suitable for describing hydrocarbon biodegradation after 17 days of treatment. The calculated rate constants were 0.0668 and 0.0513 day(-1) with a corresponding half-life of 10.3 and 13.5 days for the aliphatic and aromatic hydrocarbon fractions, respectively. At day 17, PAH removal percentages were: acenaphtylene 100, fluorene 95.2, phenanthrene 93.6, anthracene 70.3, and pyrene 71.5. Methyl phenanthrene removals were lower than that of their parent compound (3-methyl phenanthrene 83.6, 2-methyl phenanthrene 80.8, 1-methyl phenanthrene 77.3, 9-methyl phenanthrene 75.1, and 2,7-dimethyl phenanthrene 76.6). Neither pure cultures nor the microbial community from these wastes showed extracellular biosurfactant production suggesting that the addition of an exogenously produced biosurfactant may be important in enhancing hydrocarbon bioavailability and biodegradation. DNA analysis of bilge waste samples revealed a ubiquitous distribution of the nahAc genotype in the dump pools. Although almost all of the isolates grew on naphthalene as sole carbon source, only some of them yielded nahAc amplification under the experimental conditions used. The variety of PAHs in bilge wastes could support bacteria with multiple degradation pathways and a diversity of catabolic genes divergent from the classical nah-like type.

Reduced biodegradability of desorption-resistant fractions of polycyclic aromatic hydrocarbons in soil and aquifer solids

DOE Office of Scientific and Technical Information (OSTI.GOV)

White, J.C.; Alexander, M.

1996-11-01

Less of the desorption-resistant fractions of phenanthrene and naphthalene than freshly added phenanthrene and naphthalene was mineralized in columns of aquifer solids, loam, or muck. Slurrying columns of hydrocarbon-amended aquifer solids, loam, or muck enhanced the rate and extent of mineralization of desorption-resistant phenanthrene and naphthalene, but degradation was still less than in slurries amended with fresh compound. A substantial portion of the desorption-resistant compound remained undergraded in the slurry. A surfactant and methanol increased the mineralization of resistant phenanthrene in slurries of loam. A mixed culture of microorganisms enriched on desorption-resistant phenanthrene degraded twice as much of this fractionmore » of compound as a pseudomonad. The authors suggest that predictions of the environment fate of toxic chemicals require information on the biodegradability of the fraction of a compound that is resistant to desorption.« less

Phenanthrene

Integrated Risk Information System (IRIS)

Phenanthrene ; CASRN 85 - 01 - 8 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Effec

Use of bromodeoxyuridine immunocapture to identify psychrotolerant phenanthrene-degrading bacteria in phenanthrene-enriched polluted Baltic Sea sediments

DOE Office of Scientific and Technical Information (OSTI.GOV)

Edlund, A.; Jansson, J.

The aim of this study was to enrich and identify psychrotolerant phenanthrenedegrading bacteria from polluted Baltic Sea sediments. Polyaromatic hydrocarbon (PAH)-contaminated sediments were spiked with phenanthrene and incubated for 2 months in the presence of bromodeoxyuridine that is incorporated into the DNA of replicating cells. The bromodeoxyuridine-incorporated DNA was extracted by immunocapture and analyzed by terminal-restriction fragment length polymorphism and 16S rRNA gene cloning and sequencing to identify bacterial populations that were growing. In addition, degradation genes were quantified in the bromodeoxyuridine-incorporated DNA by real-time PCR. Phenanthrene concentrations decreased after 2 months of incubation in the phenanthrene-enriched sediments and thismore » reduction correlated to increases in copy numbers of xylE and phnAc dioxygenase genes. Representatives of Exiguobacterium, Schewanella,Methylomonas, Pseudomonas, Bacteroides and an uncultured Deltaproteobacterium and a Gammaproteobacterium dominated the growing community in the phenanthrene spiked sediments. Isolates that were closely related to three of these bacteria (two pseudomonads and an Exiguobacterium sp.) could reduce phenanthrene concentrations in pure cultures and they all harbored phnAc dioxygenase genes. These results confirm that this combination of culture-based and molecular approaches was useful for identification of actively growing bacterial species with a high potential for phenanthrene degradation.« less

Removal of polycyclic aromatic hydrocarbons from aqueous solution by raw and modified plant residue materials as biosorbents.

PubMed

Xi, Zemin; Chen, Baoliang

2014-04-01

Removal of polycyclic aromatic hydrocarbons (PAHs), e.g., naphthalene, acenaphthene, phenanthrene and pyrene, from aqueous solution by raw and modified plant residues was investigated to develop low cost biosorbents for organic pollutant abatement. Bamboo wood, pine wood, pine needles and pine bark were selected as plant residues, and acid hydrolysis was used as an easily modification method. The raw and modified biosorbents were characterized by elemental analysis, Fourier transform infrared spectroscopy and scanning electron microscopy. The sorption isotherms of PAHs to raw biosorbents were apparently linear, and were dominated by a partitioning process. In comparison, the isotherms of the hydrolyzed biosorbents displayed nonlinearity, which was controlled by partitioning and the specific interaction mechanism. The sorption kinetic curves of PAHs to the raw and modified plant residues fit well with the pseudo second-order kinetics model. The sorption rates were faster for the raw biosorbents than the corresponding hydrolyzed biosorbents, which was attributed to the latter having more condensed domains (i.e., exposed aromatic core). By the consumption of the amorphous cellulose component under acid hydrolysis, the sorption capability of the hydrolyzed biosorbents was notably enhanced, i.e., 6-18 fold for phenanthrene, 6-8 fold for naphthalene and pyrene and 5-8 fold for acenaphthene. The sorption coefficients (Kd) were negatively correlated with the polarity index [(O+N)/C], and positively correlated with the aromaticity of the biosorbents. For a given biosorbent, a positive linear correlation between logKoc and logKow for different PAHs was observed. Interestingly, the linear plots of logKoc-logKow were parallel for different biosorbents. These observations suggest that the raw and modified plant residues have great potential as biosorbents to remove PAHs from wastewater. Copyright © 2014 The Research Centre for Eco-Environmental Sciences, Chinese Academy of

Naphthalene poisoning

MedlinePlus

Naphthalene is a white solid substance with a strong smell. Poisoning from naphthalene destroys or changes red blood cells so they cannot carry oxygen. This can cause organ damage. This article is for information only. DO NOT use it ...

Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads. The ring-fission mechanism

PubMed Central

Evans, W. C.; Fernley, H. N.; Griffiths, E.

1965-01-01

1. Phenanthrene is oxidatively metabolized by soil pseudomonads through trans-3,4-dihydro-3,4-dihydroxyphenanthrene to 3,4-dihydroxyphenanthrene, which then undergoes cleavage. 2. Some properties of the ring-fission product, cis-4-(1-hydroxynaphth-2-yl)-2-oxobut-3-enoic acid, are described. The Fe2+-dependent oxygenase therefore disrupts the bond between C-4 and the angular C of the phenanthrene nucleus. 3. An enzyme of the aldolase type converts the fission product into 1-hydroxy-2-naphthaldehyde (2-formyl-1-hydroxynaphthalene). An NAD-specific dehydrogenase is also present in the cell-free extract, which oxidizes the aldehyde to 1-hydroxy-2-naphthoic acid. This is then oxidatively decarboxylated to 1,2-dihydroxynaphthalene, thus allowing continuation of metabolism via the naphthalene pathway. 4. Anthracene is similarly metabolized, through 1,2-dihydro-1,2-dihydroxyanthracene to 1,2-dihydroxyanthracene, in which ring-fission occurs to give cis-4-(2-hydroxynaphth-3-yl)-2-oxobut-3-enoic acid. The position of cleavage is again at the bond between the angular C and C-1 of the anthracene nucleus. 5. Enzymes that convert the fission product through 2-hydroxy-3-naphthaldehyde into 2-hydroxy-3-naphthoic acid were demonstrated. The further metabolism of this acid is discussed. 6. The Fe2+-dependent oxygenase responsible for cleavage of all the o-dihydroxyphenol derivatives appears to be catechol 2,3-oxygenase, and is a constitutive enzyme in the Pseudomonas strains used. PMID:14342521

Thermodynamics of phenanthrene partition into solid organic matter from water.

PubMed

Chen, Bao-liang; Zhu, Li-zhong; Tao, Shu

2005-01-01

The thermodynamic behavior of organic contaminants in soils is essential to develop remediation technologies and assess risk from alternative technologies. Thermodynamics of phenanthrene partition into four solids(three soils and a bentonite) from water were investigated. The thermodynamics parameters (deltaH, deltaG degrees, deltaS degrees) were calculated according to experimental data. The total sorption heats of phenanthrene to solids from water ranged from -7.93 to -17.1 kJ/mol, which were less exothermic than the condensation heat of phenanthrene-solid (i.e., -18.6 kJ/mol). The partition heats of phenanthrene dissolved into solid organic matter ranged from 23.1 to 32.2 kJ/mol, which were less endothermic than the aqueous dissolved heat of phenanthrene (i.e., 40.2 kJ/mol), and were more endothermic than the fusion heat of phenanthrene-solid (i.e., 18.6 kJ/mol). The standard free energy changes, deltaG degrees, are all negative which suggested that phenanthrene sorption into solid was a spontaneous process. The positive values of standard entropy changes, deltaS degrees, show a gain in entropy for the transfer of phenanthrene at the stated standard state. Due to solubility-enhancement of phenanthrene, the partition coefficients normalized by organic carbon contents decrease with increasing system temperature (i.e., ln Koc = -0.284 ln S + 9.82 (n = 4, r2 = 0.992)). The solubility of phenanthrene in solid organic matter increased with increasing temperatures. Transports of phenanthrene in different latitude locations and seasons would be predicted according to its sorption thermodynamics behavior.

Inoculation of a phenanthrene-degrading endophytic bacterium reduces the phenanthrene level and alters the bacterial community structure in wheat.

PubMed

Liu, Juan; Xiang, Yanbing; Zhang, Zhiming; Ling, Wanting; Gao, Yanzheng

2017-06-01

Colonization by polycyclic aromatic hydrocarbon (PAH)-degrading endophytic bacteria (PAHDEB) can reduce the PAH contamination risk in plant. However, little information is available on the impact of PAHDEB colonization on the endophytic bacterial community of inner plant tissues. A phenanthrene-degrading endophytic bacterium (PDEB), Massilia sp. Pn2, was inoculated onto the roots of wheat and subjected to greenhouse container experiments. The endophytic bacterial community structure in wheat was investigated using high-throughput sequencing technology. The majority of endophytic bacteria in wheat were Proteobacteria, and the dominant genus was Pseudomonas. Phenanthrene contamination clearly increased the diversity of endophytic bacteria in wheat. The cultivable endophytic bacteria counts in wheat decreased with increasing the level of phenanthrene contamination; the endophytic bacterial community structure changed correspondingly, and the bacterial richness first increased and then decreased. Inoculation of strain Pn2 reduced the phenanthrene contamination in wheat, enlarged the biomass of wheat roots, changed the bacterial community structure and enhanced the cell counts, diversity and richness of endophytic bacteria in phenanthrene-contaminated wheat in a contamination level-dependent manner. The findings of this investigation provide insight into the responses of endophytic bacterial community in plant to external PAH contamination and PAHDEB colonization.

Evaluation of ultraviolet spectrophotometry for simultaneous analysis of alkylbenzenes, alkylnaphthalenes, alkylanthracenes/phenanthrenes and total aromatics in mid-distillate fuels

NASA Technical Reports Server (NTRS)

Kim, W. S.; Seng, G. T.

1982-01-01

A rapid ultraviolet spectrophotometric method for the simultaneous determination of aromatics in middistillate fuels was developed and evaluated. In this method, alkylbenzenes, alkylnaphthalenes, alkylanthracenes/phenanthracenes and total aromatics were determined from ultraviolet spectra of the fuels. The accuracy and precision were determined using simulated standard fuels with known compositions. The total aromatics fraction accuracy was 5% for a Jet A type fuel and 0.6% for a broadened properties jet turbine type fuel. Precision, expressed as relative standard deviations, ranged from 2.9% for the alkylanthracenes/phenanthrenes to 15.3% for the alkylbenzenes. The accuracy, however, was less for actual fuel samples when compared to the results obtained by a mass spectrometric method. In addition, the ASTM D-1840 method for naphthalenes by ultraviolet spectroscopy was evaluated.

Impact of methylene chloride on microorganisms and phenanthrene mineralization in soil.

PubMed

Schwartz, Egbert; Trinh, Sinh V; Scow, Kate M

2002-01-01

This study investigated the effects of the quantity of methylene chloride, used as a carrier solvent for phenanthrene when added to soil, on phenanthrene mineralization kinetics, soil phospholipid fatty add profiles (PLFA), and phenanthrene distribution. Methylene chloride dosages of 25 microL/g soil or more resulted in an enrichment of saturated PLFAs, suggesting soil microorganisms had adjusted their cell membranes in response to the solvent. A greater fraction of phenanthrene mineralized when spiked in 5 microL/g than in 25 microL/g methylene chloride suggesting that the methylene chloride became toxic to phenanthrene-degrading organisms in soil. Phenanthrene was more equally distributed among 0.1 g soil subsamples if spiked in 25 than 5 or 1 microL methylene chloride per gram soil. Thus the amount of methylene chloride used to spike phenanthrene in soil strongly impacted the mineralization kinetics, phenanthrene distribution, and microbial community in soil. Because a variety of spiking methods are used in biodegradation research, scientists should consider the quantity of solvents used when comparing results among different studies.

Input and behavior of polycyclic aromatic hydrocarbons in arable, fallow, and forest soils of the taiga zone (Tver oblast)

NASA Astrophysics Data System (ADS)

Zhidkin, A. P.; Gennadiev, A. N.; Koshovskii, T. S.

2017-03-01

Contents of 11 most prevalent polycyclic aromatic hydrocarbons (PAHs) in snow and soils of arable, fallow, and forest areas significantly remote from impact technogenic sources of polyarenes have been examined in the Torzhok district of Tver oblast. From the analysis of snow samples, the volumes and composition of PAHs coming from the atmosphere onto the areas of different land use have been determined. Light hydrocarbons prevail in PAHs. They make up 65-70% of total PAHs; their share in soils reaches almost 95%. An increase in the content of PAHs is revealed in fallow soils compared to arable and afforested areas. A direct relationship is revealed between the lateral distribution of total PAHs and the content of organic carbon. The distribution of total PAHs is surface-accumulative in forest soils, mainly uniform in arable soils, and deepaccumulative in fallow soils. PAH groups characterized by similar radial distributions and ratios between their reserves in snow and soils are distinguished: (1) fluorene and phenanthrene, (2) biphenyl and naphthalene, (3) benzo(a)anthracene, chrysene, perylene, and benzo[ a]pyrene, and (4) anthracene and benzo[ ghi]pyrene.

Predicting bioavailability of PAHs in soils to wheat roots with triolein-embedded cellulose acetate membranes and comparison with chemical extraction.

PubMed

Tao, Yuqiang; Zhang, Shuzhen; Wang, Zijian; Christie, Peter

2008-11-26

Triolein-embedded cellulose acetate membrane (TECAM) was buried in 15 field-contaminated soils in parallel with the cultivation of wheat to predict bioavailability of naphthalene, phenanthrene, pyrene, and benzo[a]pyrene to wheat roots, and the method was compared with chemical extraction methods. Although a good linear relationship was found between PAH concentrations in chemical extractants and wheat roots, the percentage of PAH in soil removed by chemical extraction was much higher than the corresponding percentage removed by wheat roots. In contrast to chemical extraction, a nearly 1:1 relationship was found between the amount of each PAH taken up by TECAMs and wheat roots (r(2) = 0.798-0.925, P < 0.01). Furthermore, the uptake of PAHs by TECAMs and wheat roots had the same pathway of passive transport via the soil solution. Moreover, TECAM caused minimal disturbance to the soil and was easy to deploy. Therefore, TECAM is believed to be a useful tool to predict bioavailability of PAHs to wheat roots grown in contaminated soils.

Simultaneous analysis of naphthols, phenanthrols, and 1-hydroxypyrene in urine as biomarkers of polycyclic aromatic hydrocarbon exposure: intraindividual variance in the urinary metabolite excretion profiles caused by intervention with beta-naphthoflavone induction in the rat.

PubMed

Elovaara, Eivor; Väänänen, Virpi; Mikkola, Jouni

2003-04-01

Two fluorimetric HPLC methods are described for the quantification of naphthols, phenanthrols and 1-hydroxypyrene (1-OHP) in urine specimens obtained from male Wistar rats exposed to naphthalene, phenanthrene and pyrene. The polycyclic aromatic hydrocarbons (PAHs) were given intraperitoneally, either alone (1.0 mmol/kg body weight) or as an equimolar mixture (0.33 mmol/kg), using the same dosages for repeated treatments on week 1 and week 2. Between these treatments, PAH-metabolizing activities encoded by aryl hydrocarbon (Ah) receptor-controlled genes were induced in the rats with beta-naphthoflavone (betaNF). Chromatographic separation of five phenanthrols (1-, 2-, 3-, 4-, and 9-isomers) was accomplished using two different RP C-18 columns. Despite selective detection (programmable wavelengths), the quantification limits in the urine ranged widely: 1-OHP (0.18 microg/l) naphthalene, phenanthrene, and pyrene are described, as well as important factors (dose, metabolic capacity, relative urinary output) associated with biomarker validation

Isolation of Soil Bacteria Adapted To Degrade Humic Acid-Sorbed Phenanthrene

PubMed Central

Vacca, D. J.; Bleam, W. F.; Hickey, W. J.

2005-01-01

The goal of these studies was to determine how sorption by humic acids affected the bioavailability of polynuclear aromatic hydrocarbons (PAHs) to PAH-degrading microbes. Micellar solutions of humic acid were used as sorbents, and phenanthrene was used as a model PAH. Enrichments from PAH-contaminated soils established with nonsorbed phenanthrene yielded a total of 25 different isolates representing a diversity of bacterial phylotypes. In contrast, only three strains of Burkholderia spp. and one strain each of Delftia sp. and Sphingomonas sp. were isolated from enrichments with humic acid-sorbed phenanthrene (HASP). Using [14C]phenanthrene as a radiotracer, we verified that only HASP isolates were capable of mineralizing HASP, a phenotype hence termed “competence.” Competence was an all-or-nothing phenotype: noncompetent strains showed no detectable phenanthrene mineralization in HASP cultures, but levels of phenanthrene mineralization effected by competent strains in HASP and NSP cultures were not significantly different. Levels and rates of phenanthrene mineralization exceeded those predicted to be supported solely by the metabolism of phenanthrene in the aqueous phase of HASP cultures. Thus, competent strains were able to directly access phenanthrene sorbed by the humic acids and did not rely on desorption for substrate uptake. To the best of our knowledge, this is the first report of (i) a selective interaction between aerobic bacteria and humic acid molecules and (ii) differential bioavailability to bacteria of PAHs sorbed to a natural biogeopolymer. PMID:16000791

Numerical taxonomy of phenanthrene-degrading bacteria isolated from the Chesapeake Bay

DOE Office of Scientific and Technical Information (OSTI.GOV)

West, P.A.; Okpokwasili, G.C.; Brayton, P.R.

1984-11-01

Phenanthrene-degrading bacteria were isolated from Chesapeake Bay samples by the use of a solid medium which had been overlaid with an ethanol solution of phenanthrene before inoculation. Eighteen representative strains of phenanthrene-degrading bacteria with 21 type and reference bacteria were examined for 123 characteristics representing physiological, biochemical, and nutritional properties. Relationships between strains were computed with several similarity coefficients. The phenogram constructed by unweighted-pair-group arithmetic average linkage and use of the simple Jaccard (S/sub J/) coefficient was used to identify seven phena. Phenanthrene-degrading bacteria were identified as Vibrio parahaemolyticus and Vibrio fluvialis by their clustering with type and reference strains.more » Several phenanthrene-degrading bacteria resembled Enterobacteriaceae family members, although some Vibrio-like phenanthrene degraders could not be identified. 22 references, 1 figure, 2 tables.« less

Polycyclic aromatic hydrocarbon ions and the diffuse interstellar bands

NASA Technical Reports Server (NTRS)

Salama, F.; Allamandola, L. J.

1995-01-01

Neutral naphthalene (C10H8), phenanthrene (C14H10), and pyrene (C16H10) absorb strongly in the ultraviolet and may contribute to the extinction curve. High abundances are required to produce detectable structures. The cations of these Polycyclic Aromatic Hydrocarbons (PAHs) absorb in the visible. C10H8(+) has 12 discrete absorption bands which fall between 6800 and 5000 A. The strongest band at 6741 A falls close to the weak 6742 A diffuse interstellar band (DIB). Five other weaker bands also match DIBs. The possibility that C10H8(+) is responsible for some of the DIBs can be tested by searching for new DIBS at 6520, 6151, and 5965 A, other moderately strong naphthalene cation band positions. If C10H8(+) is indeed responsible for the 6742 A feature, it accounts for 0.3% of the cosmic carbon. The spectrum of C16H10(+) is dominated by a strong band at 4435 A in an Ar matrix and 4395 A in a Ne matrix, a position which falls very close to the strongest DIB, that at 4430 A. If C16H10(+), or a closely related pyrene-like ion is indeed responsible for the 4430 A feature, it accounts for 0.2% of the cosmic carbon. We also report an intense, very broad UV-to-visible continuum which is associated with both ions and could explain how PAHs convert interstellar UV and visible radiation into IR.

Neutral and ionized polycyclic aromatic hydrocarbons, diffuse interstellar bands and the ultraviolet extinction curve

NASA Technical Reports Server (NTRS)

Salama, Farid; Allamandola, Louis John

1993-01-01

Neutral naphthalene C10H8, phenanthrene C14H10 and pyrene C16H10 absorb strongly in the ultraviolet region and may contribute to the extinction curve. High abundances are required to produce detectable structures. The cations of these polycyclic aromatic hydrocarbons (PAHs) absorb in the visible C10H8(+) has 13 discrete absorption bands which fall between 6800 and 4500 A. The strongest band at 6741 A falls close to the weak 6742 A diffuse interstellar band (DIB). Five other weaker bands also match DIBs. The possibility that C10H8(+) is responsible for some of the DIBs can be tested by searching for new DIBs at 6520 and 6151 A, other strong naphthalene cation band positions. If C10H8(+) is indeed responsible for the 6742 A feature, it accounts for 0.3% of the cosmic carbon. The spectrum of C16H10(+) is dominated by a strong band at 4435 A in an Ar matrix and 4395 A in Ne, wavelengths which fall very close to the strongest DIB at 4430 A. If C16H10(+) or a closely related pyrene-like ion, is indeed responsible for the 4430 A feature, it accounts for 0.2% of the cosmic carbon. An intense, very broad UV-to-visible continuum is reported which is associated with both ions and could explain how PAHs convert interstellar UV and visible radiation into IR radiation.

The mechanisms by which phenanthrene affects the photosynthetic apparatus of cucumber leaves.

PubMed

Jin, Liqiao; Che, Xingkai; Zhang, Zishan; Li, Yuting; Gao, Huiyuan; Zhao, Shijie

2017-02-01

Phenanthrene is a polycyclic aromatic hydrocarbon (PAH) that is widely distributed in the environment and seriously affects the growth and development of plants. To clarify the mechanisms of the direct effects of phenanthrene on the plant photosynthetic apparatus, we measured short-term phenanthrene-treated cucumber leaves. Phenanthrene inhibited Rubisco carboxylation activity, decreasing photosynthesis rates (Pn). And phenanthrene inhibited photosystem II (PSII) activity, thereby blocking photosynthetic electron transport. The inhibition of the light and dark reactions decreased the photosynthetic electron transport rate (ETR) and increased the excitation pressure (1-qP). Under high light, the maximum photochemical efficiency of photosystem II (F v /F m ) in phenanthrene-treated cucumber leaves decreased significantly, but photosystem I (PSI) activity (Δ I/I o ) did not. Phenanthrene also caused a J-point rise in the OJIP curve under high light, which indicated that the acceptor side of PSII Q A to Q B electron transfer was restricted. This was primarily due to the net degradation of D1 protein, which is caused by the accumulation of reactive oxygen species (ROS) in phenanthrene-treated cucumber leaves under high light. This study demonstrated that phenanthrene could directly inhibit photosynthetic electron transport and Rubisco carboxylation activity to decrease net Pn. Under high light, phenanthrene caused the accumulation of ROS, resulting in net increases in D1 protein degradation and consequently causing PSII photoinhibition. Copyright © 2016 Elsevier Ltd. All rights reserved.

40 CFR 704.43 - Chlorinated naphthalenes.

Code of Federal Regulations, 2010 CFR

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Chlorinated naphthalenes. 704.43... § 704.43 Chlorinated naphthalenes. (a) Definitions. (1) Extent of chlorination means the percent by... means the relative amounts of each isomeric chlorinated naphthalene that composes the chemical substance...

40 CFR 704.43 - Chlorinated naphthalenes.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Chlorinated naphthalenes. 704.43... § 704.43 Chlorinated naphthalenes. (a) Definitions. (1) Extent of chlorination means the percent by... means the relative amounts of each isomeric chlorinated naphthalene that composes the chemical substance...

Sulfate-Reducing Naphthalene Degraders Are Picky Eaters.

PubMed

Wolfson, Sarah J; Porter, Abigail W; Kerkhof, Lee J; McGuinness, Lora M; Prince, Roger C; Young, Lily Y

2018-06-25

Polycyclic aromatic hydrocarbons (PAHs) are common organic contaminants found in anoxic environments. The capacity for PAH biodegradation in unimpacted environments, however, has been understudied. Here we investigate the enrichment, selection, and sustainability of a microbial community from a pristine environment on naphthalene as the only amended carbon source. Pristine coastal sediments were obtained from the Jacques Cousteau National Estuarine Research Reserve in Tuckerton, New Jersey, an ecological reserve which has no direct input or source of hydrocarbons. After an initial exposure to naphthalene, primary anaerobic transfer cultures completely degraded 500 µM naphthalene within 139 days. Subsequent transfer cultures mineralized naphthalene within 21 days with stoichiometric sulfate loss. Enriched cultures efficiently utilized only naphthalene and 2-methylnaphthalene from the hydrocarbon mixtures in crude oil. To determine the microorganisms responsible for naphthalene degradation, stable isotope probing was utilized on cultures amended with fully labeled 13 C-naphthalene as substrate. Three organisms were found to unambiguously synthesize 13 C-DNA from 13 C-naphthalene within 7 days. Phylogenetic analysis revealed that 16S rRNA genes from two of these organisms are closely related to the known naphthalene degrading isolates NaphS2 and NaphS3 from PAH-contaminated sites. A third 16S rRNA gene was only distantly related to its closest relative and may represent a novel naphthalene degrading microbe from this environment.

Naphthalene distributions and human exposure in Southern California

NASA Astrophysics Data System (ADS)

Lu, Rong; Wu, Jun; Turco, Richard P.; Winer, Arthur M.; Atkinson, Roger; Arey, Janet; Paulson, Suzanne E.; Lurmann, Fred W.; Miguel, Antonio H.; Eiguren-Fernandez, Arantzazu

The regional distribution of, and human exposure to, naphthalene are investigated for Southern California. A comprehensive approach is taken in which advanced models are linked for the first time to quantify population exposure to the emissions of naphthalene throughout Southern California. Naphthalene is the simplest and most abundant of the polycyclic aromatic hydrocarbons found in polluted urban environments, and has been detected in both outdoor and indoor air samples. Exposure to high concentrations of naphthalene may have adverse health effects, possibly causing cancer in humans. Among the significant emission sources are volatilization from naphthalene-containing products, petroleum refining, and combustion of fossil fuels and wood. Gasoline and diesel engine exhaust, with related vaporization from fuels, are found to contribute roughly half of the daily total naphthalene burden in Southern California. As part of this study, the emission inventory for naphthalene has been verified against new field measurements of the naphthalene-to-benzene ratio in a busy traffic tunnel in Los Angeles, supporting the modeling work carried out here. The Surface Meteorology and Ozone Generation (SMOG) airshed model is used to compute the spatial and temporal distributions of naphthalene and its photooxidation products in Southern California. The present simulations reveal a high degree of spatial variability in the concentrations of naphthalene-related species, with large diurnal and seasonal variations as well. Peak naphthalene concentrations are estimated to occur in the early morning hours in the winter season. The naphthalene concentration estimates obtained from the SMOG model are employed in the Regional Human Exposure (REHEX) model to calculate population exposure statistics. Results show average hourly naphthalene exposures in Southern California under summer and winter conditions of 270 and 430 ng m -3, respectively. Exposure to significantly higher concentrations

CHEMISTRY OF OXIDATION OF POLYCYCLIC AROMATIC HYDROCARBONS BY SOIL PSEUDOMONADS

PubMed Central

Rogoff, Martin H.

1962-01-01

Rogoff, Martin H. (U.S. Bureau of Mines, Pittsburgh, Pa.). Oxidation of polycyclic aromatic hydrocarbons by soil pseudomonads. J. Bacteriol. 83:998–1004. 1962.—Substitution of phenanthrene by a methyl group at the 9-carbon blocks oxidation of the compound by a resting-cell suspension of a phenanthrene-grown soil pseudomonad. When 2-methylphenanthrene is provided, the oxidation rate is considerably higher; 3-methylphenanthrene is oxidized at a rate intermediate between the other two, even though the methyl group is attached to a carbon directly involved in ring splitting. Cells grown on naphthalene or anthracene oxidize phenanthrene at a much lower rate than cells grown with phenanthrene or 2-methylnaphthalene as the source of carbon. Naphthalene-grown cells also absorb less phenanthrene from aqueous solution than do their phenanthrene-grown counterparts. The data are in keeping with the hypothesis that polynuclear aromatic hydrocarbons attach to the relevant bacterial enzymes at carbon-carbon bonds of high electron density (K regions; localized double bonds), and that the ring-splitting reactions then occur at other bonds on the substrate molecule. The actual bond that undergoes fission is determined by the electronic and steric configurations of the enzyme-substrate complex. When linearly arranged aromatic compounds such as naphthalene or anthracene are attacked, attachment to an enzyme and ring splitting may take place on the same ring; angular aromatic compounds such as phenanthrene afford attachment to an enzyme at a bond in a ring other than the one containing the ring-splitting site. PMID:14493381

Analysis of tetrahydroxylated benzo[a]pyrene isomers in hair as biomarkers of exposure to benzo[a]pyrene.

PubMed

Grova, Nathalie; Hardy, Emilie M; Meyer, Pauline; Appenzeller, Brice M R

2016-03-01

A first gas chromatography-tandem mass spectrometry (GC-MS/MS) method was designed for analysis of four tetrahydroxylated benzo[a]pyrene metabolites (benzo[a]pyrene-r-7,t-8,t-9,c-10-tetrahydrotetrol, benzo[a]pyrene-r-7,t-8,t-9,t-10-tetrahydrotetrol, benzo[a]pyrene-r-7,t-8,c-9,c-10-tetrahydrotetrol, and benzo[a]pyrene-r-7,t-8,c-9,t-10-tetrahydrotetrol) in hair. Hair powder extract was submitted to liquid-solid extraction, followed by C18 solid-phase purification. The analytes were derivatized with use of N-methyl-N-(trimethylsilyl)trifluoroacetamide and then analyzed by GC-MS/MS in negative chemical ionization mode. The calibration curve was linear from the limit of quantification (LOQ) to 20 pg/mg in hair. The coefficient of determination of the calibration curve was more than 0.975 for all the analytes investigated. The LOQs ranged from 0.075 to 0.2 pg/mg in hair. The method was afterward applied to the analysis of hair of 16 rats randomly allocated to experimental groups receiving 16 polycyclic aromatic hydrocarbons solubilized in oil at 0 or 0.8 mg/kg body weight by oral administration three times per week for 90 days. The analysis of monohydroxylated and dihydroxylated benzo[a]pyrenes was conducted in parallel by GC-MS/MS on the same samples. All tetrahydroxylated benzo[a]pyrene isomers were detected in hair samples collected from rats exposed to polycyclic aromatic hydrocarbons. Benzo[a]pyrene-r-7,t-8,t-9,c-10-tetrahydrotetrol, the most abundant isomer in hair of treated rats, was also the principal isomer released in DNA adduct hydrolysis in humans. Moreover, the benzo[a]pyrene-r-7,t-8,t-9,c-10-tetrahydrotetrol concentrations in hair were significantly greater than those of 2-hydroxybenzo[a]pyrene, 1-hydroxybenzo[a]pyrene, 7-hydroxybenzo[a]pyrene, and 4-hydroxybenzo[a]pyrene and similar to those of 9-hydroxybenzo[a]pyrene and 3-hydroxybenzo[a]pyrene. The method was also sufficiently sensitive to monitor environmental levels of exposure because two hair

Isomer discrimination of PAHs formed in sooting flames by jet-cooled laser-induced fluorescence: application to the measurement of pyrene and fluoranthene

NASA Astrophysics Data System (ADS)

Mouton, Thomas; Mercier, Xavier; Desgroux, Pascale

2016-05-01

Jet-cooled laser-induced fluorescence is a spectroscopic method, specifically developed for the study of PAHs formed in flames. This technique has already been used to measure different aromatic species in sooting low-pressure methane flames such as benzene, naphthalene, and pyrene. The use of the LIF technique to excite PAHs drastically cooled down inside a supersonic jet offers the possibility to get selective and quantitative profiles of PAHs sampled from sooting flames. In this paper, we demonstrate the ability of this experimental method to separate the contribution of two mass isomers generated in sooting flames which are the pyrene and the fluoranthene. The selectivity of the method is demonstrated by studying the spectral properties of these species. The method is then applied to the measurement of both these species in two sooting flames with different equivalence ratios and stabilized at 200 torr (26.65 kPa). The sensitivity of the technique has been found to reach a few ppb in the case of fluoranthene measurements.

Pyrene and benzo[a]pyrene metabolism by the filamentous fungus, Penicillium janthinellum

DOE Office of Scientific and Technical Information (OSTI.GOV)

Launen, L.; Pinto, L.; Kiehlmann, E.

1995-12-31

The incomplete combustion of fossil fuels generates polycyclic aromatic hydrocarbons (PAH). These include 4-5 ring PAH, of which many are potent carcinogens and mutagens that persist in soil for years. Fungi can oxidize these compounds via two mechanisms: (1) by extracellular peroxidases (Basidiomycete fungi), or (2) by a putative cytochrome P450 enzyme system. The authors have previously isolated Penicillium janthinellum from petroleum-contaminated soil and shown that it possesses high activity to oxidize pyrene, benzo(a)pyrene and chrysene in liquid culture. The purpose of this study was to evaluate the effect of changing growth condition glucose, nitrate and agitation levels, on pyrenemore » metabolism by P. janthinellum using a 3 x 2 x 2 factorial design. Spores were inoculated into minimal salts media amended with varying carbon or nitrogen concentrations and containing {sup 14}C-pyrene. The level of glucose and nitrate significantly affected the bioconversion: low glucose and nitrate levels increased the loss of parent PAH from the medium. However this effect was independent of biomass. Biometer flask experiments using {sup 14}C-pyrene showed that most pyrene became cell-associated within 7 days of incubation. Cell associated {sup 14}C-pyrene was inextractable by ethyl acetate but was recovered in methylene chloride. This result was confirmed by the mass balance result from a 10 day time course experiment using {sup 14}C-pyrene or {sup 14}C-BaP. Greater than 70% of the radiolabel in cultures containing live cells was strongly associated with the cell matter within 7 days, relative to < 1 % association with dead cells. The authors conclude that: (1) pyrene and BaP oxidation was affected by C and N levels in the growth medium independent of cell mass and (2) {sup 14}C-PAH became strongly associated with live but not dead cells within 7 days in liquid culture.« less

Electron-intramolecular-vibration interactions in positively charged phenanthrene-edge-type hydrocarbons

NASA Astrophysics Data System (ADS)

Kato, Takashi; Yamabe, Tokio

2004-02-01

Electron-phonon interactions in positively charged phenanthrene-edge-type hydrocarbons such as phenanthrene, chrysene, and picene are studied. The C-C stretching modes around 1500 cm-1 and the low-frequency modes around 500 cm-1 strongly couple to the highest occupied molecular orbitals (HOMO) in phenanthrene-edge-type hydrocarbons. The total electron-phonon coupling constants for the monocations (lHOMO) of 0.251, 0.135, and 0.149 eV for phenanthrene, chrysene, and picene, respectively, are estimated to be larger than those of 0.130, 0.107, and 0.094 eV for anthracene, tetracene, and pentacene, respectively. The phase patterns difference between the HOMO localized on carbon atoms which are located at the molecular edge in acene-edge-type hydrocarbons and the delocalized HOMO in phenanthrene-edge-type hydrocarbons is the main reason for the result. Strengths of orbital interactions between two neighboring carbon atoms in the HOMO become weaker with an increase in molecular size because the electron density on each carbon atom in the HOMO becomes smaller with an increase in molecular size in phenanthrene-edge-type hydrocarbons. On the other hand, the frontier orbitals of acene-edge-type hydrocarbons have somewhat nonbonding characters and thus cannot strongly couple to the totally symmetric vibrational modes compared with the frontier orbitals of phenanthrene-edge-type hydrocarbons. This is the reason why the lHOMO value for phenanthrene-edge-type hydrocarbons decreases with an increase in molecular size more significantly than that for acene-edge-type hydrocarbons, and the reason why the lHOMO value for polyphenanthrene with C2v geometry (0.033 eV) is estimated to be similar to that for polyacene (0.036 eV). The reorganization energies between the neutral molecules and the corresponding monocations for phenanthrene-edge-type hydrocarbons with large molecular size are estimated to be larger than those for acene-edge-type hydrocarbons with large molecular size.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Ortiz, E.; Kraatz, M.; Luthy, R.G.

The dissolution of naphthalene, phenanthrene, and pyrene from viscous organic phases into water was studied in continuous-flow systems for time periods ranging from several months to more than 1 year. By selecting nonaqueous phases ranging from low viscosity to semisolid, i.e., from a light lubricating oil to paraffin, the governance of mass transfer was shown to vary from water phase control to nonaqueous phase control. An advancing depleted-zone model is proposed to explain the dissolution of PAHs from a viscous organic phase wherein the formation of a depleted zone within the organic phase increases the organic phase resistance to themore » dissolution of PAHs. The experimental data suggest the formation of a depleted zone within the organic phase for systems comprising a high-viscosity oil, petrolatum (petroleum jelly), and paraffin. Organic phase resistance to naphthalene dissolution became dominant over aqueous phase resistance after flushing for several days. Such effects were not evident for low viscosity lubricating oil. The transition from aqueous-phase dissolution control to nonaqueous-phase dissolution control appears predictable, and this provides a more rational framework to assess long-term release of HOCs from viscous nonaqueous phase liquids and semisolids.« less

Concentration and source identification of polycyclic aromatic hydrocarbons and phthalic acid esters in the surface water of the Yangtze River Delta, China.

PubMed

Zhang, Lifei; Dong, Liang; Ren, Lijun; Shi, Shuangxin; Zhou, Li; Zhang, Ting; Huang, Yeru

2012-01-01

The pollution from polycyclic aromatic hydrocarbons (PAHs) and phthalic acid esters (PAEs) in the surface water of the rapidly urbanized Yangtze River Delta region was investigated. Fourteen surface water samples were collected in June 2010. Water samples were liquid-liquid extracted using methylene chloride and analyzed by gas chromatography-mass spectrometry. Concentrations of PAHs and PAEs ranged 12.9-638.1 ng/L and 61-28550 ng/L, respectively. Fluoranthene, naphthalene, pyrene, phenanthrene, di-2-ethylhexyl phthalate, and di-n-butyl phthalate were the most abundant compounds in the samples. The water samples were moderately polluted with benzo[a]pyrene according to China's environmental quality standard for surface water. The two highest concentrations of PAHs and PAEs occurred in samples from Taihu Lake, Wuxi City and the western section of Yangchenghu Lake. Potential sources of pollution at S7 were petroleum combustion and the plastics industry, and at Yangchenghu Lake were petroleum combustion and domestic waste. Pollution in samples from the Beijing-Hangzhou Grand Canal originated from diesel engines. There were no obvious sources of pollution for the other water samples. These results can be used as reference levels for future monitoring programs of pollution from PAHs and PAEs.

Biodegradation of low and high molecular weight hydrocarbons in petroleum refinery wastewater by a thermophilic bacterial consortium.

PubMed

Pugazhendi, Arulazhagan; Abbad Wazin, Hadeel; Qari, Huda; Basahi, Jalal Mohammad Al-Badry; Godon, Jean Jacques; Dhavamani, Jeyakumar

2017-10-01

Clean-up of contaminated wastewater remains to be a major challenge in petroleum refinery. Here, we describe the capacity of a bacterial consortium enriched from crude oil drilling site in Al-Khobar, Saudi Arabia, to utilize polycyclic aromatic hydrocarbons (PAHs) as sole carbon source at 60°C. The consortium reduced low molecular weight (LMW; naphthalene, phenanthrene, fluorene and anthracene) and high molecular weight (HMW; pyrene, benzo(e)pyrene and benzo(k)fluoranthene) PAH loads of up to 1.5 g/L with removal efficiencies of 90% and 80% within 10 days. PAH biodegradation was verified by the presence of PAH metabolites and evolution of carbon dioxide (90 ± 3%). Biodegradation led to a reduction of the surface tension to 34 ± 1 mN/m thus suggesting biosurfactant production by the consortium. Phylogenetic analysis of the consortium revealed the presence of the thermophilic PAH degrader Pseudomonas aeruginosa strain CEES1 (KU664514) and Bacillus thermosaudia (KU664515) strain CEES2. The consortium was further found to treat petroleum wastewater in continuous stirred tank reactor with 96 ± 2% chemical oxygen demand removal and complete PAH degradation in 24 days.

Determination of polycyclic aromatic hydrocarbons in urine of coke oven workers by headspace solid phase microextraction and gas chromatography-mass spectrometry.

PubMed

Waidyanatha, Suramya; Zheng, Yuxin; Rappaport, Stephen M

2003-05-06

Polycyclic aromatic hydrocarbons (PAHs) represent a complex mixture of toxic compounds that are ubiquitous in the environment. We investigated the utility of head space-solid phase microextraction (HS-SPME) to measure the following surrogate PAHs in urine: naphthalene (NAP), phenanthrene (PHE), pyrene (PYR), and benzo(a)pyrene (BAP), representing classes of 2-, 3-, 4- and 5-ring compounds, respectively. We then applied the method to urine from 28 coke oven workers (median levels (microg/l) were: NAP=3.65, PHE=1.51, PYR=0.003, BAP not detected) and 22 controls (median (microg/l) NAP=0.859, PHE=0.062, PYR=0.001, BAP not detected). Urinary levels of NAP, PHE, and PYR were all associated with exposure category (controls, side- and bottom-workers, and top-workers) but not with smoking status. Strong correlations were observed between urinary levels of NAP, PHE, and PYR in coke-oven workers. Our results indicate that unmetabolized 2-, 3- and 4-ring PAHs can be measured in urine by HS-SPME. Such measurements can be used to investigate the uptake and metabolism of complex PAH mixtures in humans.

Assessment of hydrocarbons concentration in marine fauna due to Tasman Spirit oil spill along the Clifton beach at Karachi coast.

PubMed

Siddiqi, Hina A; Ansari, Fayyaz A; Munshi, Alia B

2009-01-01

On 27 July 2003, Tasman Spirit spilled 31,000 tonnes of crude oil into the sea at the Karachi coast. This disaster badly affected the marine life (Flora and Fauna.) Present research has been proposed to ascertain the level of Polycyclic Aromatic hydrocarbons (PAHs) contamination in different fisheries including Fishes, Crustaceans; Crabs and Shrimps, Mollusks and Echinoderms along with passing time. Heavier components of crude oil such as Polycyclic Aromatic Hydrocarbons (PAHs) appear to cause most damages as these are relatively unreactive and persist in water. High concentrations of toxic PAHs were observed in all the fisheries and shellfishes caught form oil-impacted area. In this study fishes were found most contaminated than shellfishes i.e. summation operator 16 PAH = 1821.24 microg/g and summation operator 1164.34 microg/g, respectively. Naphthalene was found in the range of 0.042-602.23 microg/g. Acenaphthylene, acenaphthene, fluorene, phenanthrene and anthracene were detected in the range 0.008-80.03 microg/g, fluoranthene, pyrene, benzo(a)anthracene and chrysene 0.0008-221.32 microg/g, benzo(b) fluoranthene, benzo(k)fluoranthene and benzo(a) pyrene 0.0005-7.71 microg/g, benzo(g,h,i)perylene and indeno(1,2,3-c,d)pyrene 0.02-503.7 microg/g. Dibenzo(a,h)anthracenre was not detected in any specie.

The first-principles investigations on magnetic ground-state in Sm-doped phenanthrene

NASA Astrophysics Data System (ADS)

Han, Jia-Xing; Zhong, Guo-Hua; Wang, Xiao-Hui; Chen, Xiao-Jia; Lin, Hai-Qing

2017-05-01

Based on the density functional theory plus the effective Coulomb repulsion U, we have investigated the crystal structure, electronic properties and magnetic characteristics in Sm-doped phenanthrene, recently characterized as a superconductor with Tc˜5 -6 Kelvin. Calculated total energies of different magnetic states indicate that Sm-doped phenanthrene is stable at the ferromagnetic ground-state. Considered the strong electronic correlations effect due to the intercalation of Sm-4f electrons, we found that the Sm-4f contributes to the Fermi surface together with C-2p, which is different from K-doped phenanthrene. Compared with alkali-metal-doped phenanthrene, Sm atom has larger local magnetic moment, which suppresses the superconductivity in conventional superconductors. Our results indicate that the electron-electron correlations play an important role in superconductivity of Sm-doped phenanthrene.

Naphthalene

Integrated Risk Information System (IRIS)

Naphthalene ; CASRN 91 - 20 - 3 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Effect

Bioventing remediation and ecotoxicity evaluation of phenanthrene-contaminated soil.

PubMed

García Frutos, F Javier; Escolano, Olga; García, Susana; Babín, Mar; Fernández, M Dolores

2010-11-15

The objectives of soil remediation processes are usually based on threshold levels of soil contaminants. However, during remediation processes, changes in bioavailability and metabolite production can occur, making it necessary to incorporate an ecotoxicity assessment to estimate the risk to ecological receptors. The evolution of contaminants and soil ecotoxicity of artificially phenanthrene-contaminated soil (1000 mg/kg soil) during soil treatment through bioventing was studied in this work. Bioventing was performed in glass columns containing 5.5 kg of phenanthrene-contaminated soil and uncontaminated natural soil over a period of 7 months. Optimum conditions of mineralisation (humidity=60% WHC; C/N/P=100:20:1) were determined in a previous work. The evolution of oxygen consumption, carbon dioxide production, phenanthrene concentration and soil toxicity were studied on sacrificed columns at periods of 0, 3 and 7 months. Toxicity to soil and aquatic organisms was determined using a multispecies system in the soil columns (MS-3). In the optimal bioventing treatability test, we obtained a reduction rate in phenanthrene concentration higher that 93% after 7 months of treatment. The residual toxicity obtained at the end of the treatment was not attributed to the low phenanthrene concentration, but to the ammonia used to restore the optimal C/N ratio. Copyright © 2010 Elsevier B.V. All rights reserved.

Advances of naphthalene degradation in Pseudomonas putida ND6

NASA Astrophysics Data System (ADS)

Song, Fu; Shi, Yifei; Jia, Shiru; Tan, Zhilei; Zhao, Huabing

2018-03-01

Naphthalene is one of the most common and simple polycyclic aromatic hydrocarbons. Degradation of naphthalene has been greatly concerned due to its economic, free-pollution and its fine effect in Pseudomonas putida ND6. This review summarizes the development history of naphthalene degradation, the research progress of naphthalene degrading gene and naphthalene degradation pathway of Pseudomonas putida ND6, and the researching path of this strain. Although the study of naphthalene degradation is not consummate in Pseudomonas putida ND6, there is a potential capability for Pseudomonas putida ND6 to degrade the naphthalene in the further research.

A comparative study to evaluate natural attenuation, mycoaugmentation, phytoremediation, and microbial-assisted phytoremediation strategies for the bioremediation of an aged PAH-polluted soil.

PubMed

García-Sánchez, Mercedes; Košnář, Zdeněk; Mercl, Filip; Aranda, Elisabet; Tlustoš, Pavel

2018-01-01

Biological treatments are considered an environmentally option to clean-up polluted soil with polycyclic aromatic hydrocarbons (PAHs). A pot experiment was conducted to comparatively evaluate four different strategies, including natural attenuation (NA), mycoaugmentation (M) by using Crucibulum leave, phytoremediation (P) using maize plants, and microbial-assisted phytoremediation (MAP) for the bioremediation of an aged PAH-polluted soil at 180 days. The P treatment had higher affinity degrading 2-3 and 4 ring compounds than NA and M treatments, respectively. However, M and P treatments were more efficient in regards to naphthalene, indeno[l,2,3-c,d]pyrene and benzo[g,h,i]perylene degradation respect to NA. However, 4, 5-6 rings undergo a strong decline during the microbe-assisted phytoremediation, being the treatment which determined the highest rates of PAHs degradation. Sixteen PAH compounds, except fluorene and dibenzo[a,h]anthracene, were found in maize roots, whereas the naphthalene, phenanthrene, anthracene, fluoranthene, and pyrene were accumulated in the shoots, in both P and MAP treatments. However, higher PAH content in maize biomass was achieved during the MAP treatment respect to P treatment. The bioconversion and translocation factors were less than 1, indicating that phystabilization/phytodegradation processes occurred rather than phytoextraction. The microbial biomass, activity and ergosterol content were significantly boosted in the MAP treatment respect to the other treatments at 180 days. Ours results demonstrated that maize-C. laeve association was the most profitable technique for the treatment of an aged PAH-polluted soil when compared to other bioremediation approaches. Copyright © 2017 Elsevier Inc. All rights reserved.

Removal of pyrene and benzo(a)pyrene micropollutant from water via adsorption by green synthesized iron oxide nanoparticles

NASA Astrophysics Data System (ADS)

Hassan, Saad S. M.; Abdel-Shafy, Hussein I.; Mansour, Mona S. M.

2018-03-01

Polycyclic aromatic hydrocarbons (PAHs) in water are classified as organic micropollutants, which are carcinogenic even in very low concentration (ppb). In this study the green synthesized iron oxide nanoparticles (IONPs) were green synthesized at room temperature by using pomegranate peel extract. The green synthesized IONPs were used for adsorbing benzo(a)pyrene and pyrene (PAHs) from water. Factors affecting the adsorption were investigated. These factors are: nanoparticles dose, pH, temperature, and initial concentration of PAHs. The overall results showed that the maximum adsorption capacities of IONPs towards pyrene and benzo(a)pyrene were 2.8 and 0.029 mg g-1, respectively. The thermodynamic study indicated an exothermic adsorption process of pyrene and benzo(a)pyrene. The kinetic and isotherm studies were carried out. The obtained data revealed that the adsorption process follows a pseudo-second order mechanism and obeys Langmuir isotherm model. In addition, the IONPs proved to be a potential candidate for the adsorption of pyrene and benzo(a)pyrene even after five cycles of use and regeneration. The investigation was extended using semi-pilot plant to remove the studied PAHs from artificially contaminated water. The results showed that the IONPs was capable to remove the pyrene and benzo (a) pyrene at the rate of 98.5 and 99%, respectively. It also can be used as disinfectant.

Extracellular polymeric substances govern the development of biofilm and mass transfer of polycyclic aromatic hydrocarbons for improved biodegradation.

PubMed

Zhang, Yinping; Wang, Fang; Zhu, Xiaoshu; Zeng, Jun; Zhao, Qiguo; Jiang, Xin

2015-10-01

The hypothesis that extracellular polymeric substances (EPS) affect the formation of biofilms for subsequent enhanced biodegradation of polycyclic aromatic hydrocarbons was tested. Controlled formation of biofilms on humin particles and biodegradation of phenanthrene and pyrene were performed with bacteria and EPS-extracted bacteria of Micrococcus sp. PHE9 and Mycobacterium sp. NJS-P. Bacteria without EPS extraction developed biofilms on humin, in contrast the EPS-extracted bacteria could not attach to humin particles. In the subsequent biodegradation of phenanthrene and pyrene, the biodegradation rates by biofilms were significantly higher than those of EPS-extracted bacteria. Although, both the biofilms and EPS-extracted bacteria showed increases in EPS contents, only the EPS contents in biofilms displayed significant correlations with the biodegradation efficiencies of phenanthrene and pyrene. It is proposed that the bacterial-produced EPS was a key factor to mediate bacterial attachment to other surfaces and develop biofilms, thereby increasing the bioavailability of poorly soluble PAH for enhanced biodegradation. Copyright © 2015. Published by Elsevier Ltd.

[Immobilization of introduced bacteria and degradation of pyrene and benzo(alpha) pyrene in soil by immobilized bacteria].

PubMed

Wang, Xin; Li, Peijun; Song, Shouzhi; Zhong, Yong; Zhang, Hui; Verkhozina, E V

2006-11-01

In this study, introduced bacteria were applied in the bioremediation of pyrene and benzo (alpha) pyrene in organic pollutants-contaminated soils, aimed to test whether it was feasible to introduce bacteria to environmental engineering. Three introduced bacteria were immobilized separately or together to degrade the pyrene and benzo (alpha) pyrene in soil, taking dissociated bacteria as the control, and comparing with three indigenous bacteria. The results showed that immobilized introduced bacteria, either single or mixed, had higher degradation efficiency than dissociated bacteria. Compared with indigenous bacteria, some introduced bacteria had predominance to some degree. The introduced bacteria-mixture had better degradation efficiency after being immobilized. The degradation rate of pyrene and benzo(alpha) pyrene after treated with immobilized bacteria-( B61-B67)-mixture for 96 hours was 43.49% and 38.55%, respectively.

Mechanisms for naphthalene removal during electrolytic aeration.

PubMed

Goel, Ramesh K; Flora, Joseph R V; Ferry, John

2003-02-01

Batch tests were performed to investigate chemical and physical processes that may result during electrolytic aeration of a contaminated aquifer using naphthalene as a model contaminant. Naphthalene degradation of 58-66% took place electrolytically and occurred at the same rates at a pH of 4 and 7. 1,4-naphthoquinone was identified as a product of the electrolysis. Stripping due to gases produced at the electrodes did not result in any naphthalene loss. Hydrogen peroxide (which may be produced at the cathode) did not have any effect on naphthalene, but the addition of ferrous iron (which may be present in aquifers) resulted in 67-99% disappearance of naphthalene. Chlorine (which may be produced from the anodic oxidation of chloride) can effectively degrade naphthalene at pH of 4, but not at a pH of 7. Mono-, di- and poly chloronaphthalenes were identified as oxidation products. Ferric iron coagulation (due to the oxidation of ferrous iron) did not significantly contribute to naphthalene loss. Overall, electrolytic oxidation and chemical oxidation due to the electrolytic by-products formed are significant abiotic processes that could occur and should be accounted for if bioremediation of PAH-contaminated sites via electrolytic aeration is considered. Possible undesirable products such as chlorinated compounds may be formed when significant amounts of chlorides are present.

Synthesis and photophysical characterizations of thermal-stable naphthalene benzimidazoles.

PubMed

Erten-Ela, Sule; Ozcelik, Serdar; Eren, Esin

2011-07-01

Microwave-assisted synthesis, photophysical and electrochemical properties of thermal-stable naphthalene benzimidazoles and naphthalimides are studied in this paper. Microwave-assisted synthesis of naphthalene benzimidazoles provide higher yields than the conventional thermal synthesis. Comparative photophysical properties of naphthalene benzimidazoles and naphthalimides are revealed that conjugation of electron-donating group onto naphthalimide moiety increases fluorescence quantum yields. Fluorophore-solvent interactions are also investigated using Lippert-Mataga equation for naphthalimides and naphthalene benzimidazoles. Thermal stabilities of naphthalene benzimidazoles are better than naphthalimides due to increased aromaticity. The experimental E(LUMO) levels of naphthalene benzimidazoles are found to be between 3.15 and 3.28 eV. Therefore, naphthalene benzimidazole derivatives consisting of anchoring groups are promising materials in organic dye sensitized solar cells. © Springer Science+Business Media, LLC 2011

Which persistent organic pollutants in the rivers of the Bohai Region of China represent the greatest risk to the local ecosystem?

PubMed

Zhang, Yueqing; Johnson, Andrew C; Su, Chao; Zhang, Meng; Jürgens, Monika D; Shi, Yajuan; Lu, Yonglong

2017-07-01

Freshwater aquatic organisms can be exposed to hundreds of persistent organic pollutants (POPs) discharged by natural and anthropogenic activities. Given our limited resources it is necessary to identify, from the existing evidence, which is the greatest threat so that control measures can be targeted wisely. The focus of this study was to rank POPs according to the relative risk they represent for aquatic organisms in rivers in the Bohai Region, China. A list of 14 POPs was compiled based on the available data on their presence in these rivers and ecotoxicological data. Those that were widely detected were benzo[a]pyrene, p,p'-DDE, p,p'-DDT, endrin, fluoranthene, heptachlor, hexabromocyclododecane, hexachlorobenzene, α-hexachlorocyclohexane, γ-hexachlorocyclohexane, naphthalene, perfluorooctanoic acid, perfluorooctane sulfonate and phenanthrene. Effect concentrations were compiled for Chinese relevant and standard test species and compared with river aqueous concentrations. Only bed-sediment concentrations were available so water levels were calculated based on the known local sediment organic carbon concentration and the K oc . The POPs were ranked on the ratio between the median river and median effect concentrations. Of the POPs studied, fluoranthene was ranked as the highest threat, followed by phenanthrene, naphthalene and p,p'-DDE. The risk from p,p'-DDE may be magnified due to being highly bioaccumulative. However, the greatest overlap between river concentrations and effect levels was for lindane. Overall, fish was the most sensitive species group to the risks from POPs. Hotspots with the highest concentrations and hence risk were mainly associated with watercourses draining in Tianjin, the biggest city in the Bohai Region. Copyright © 2017 Elsevier Ltd. All rights reserved.

Experimental Electronic Spectroscopy of Two PAHs: Naphthalene and 2-METHYL Naphthalene

NASA Astrophysics Data System (ADS)

Friha, H.; Feraud, G.; Pino, T.; Brechignac, Ph.; Parneix, P.; Dhaoudi, Z.; Jaidane, N.; Galila, H.; Troy, T.; Schmidt, T.

2011-06-01

The presence of polycyclic aromatic hydrocarbons (PAHs) in the interstellar medium (ISM) was suggested in the mid-80's. Since then, their important role in the physico-chemical evolution of the ISM has been confirmed. Interstellar PAHs have been in particular proposed as possible carriers of some Diffuse Interstellar Bands (DIBs). These absorption bands are seen in the spectra of reddened stars from the visible to the near infrared and constitute a major astrophysical issue. Our purpose is to obtain electronic spectra of gas phase PAHs which will be used to probe their participation to the interstellar extinction curve from the visible (DIBs) to the UV (bump). For this goal PAHs cations represent an excellent set of target species. A new way of forming PAH+-Ar_n clusters cations has been implemented in the experimental set-up 'ICARE' at ISMO (Orsay) giving us the capability to measure the electronic spectra of cold PAH cations in the gas phase through the "Ar tagging" trick. Two molecules have been investigated in this way: naphthalene (C_1_0H_8) and 2- methyl naphthalene (C_1_1H_1_0). Clusters of naphthalene and (or 2-methyl-naphthalene) with Ar atoms are first formed in a supersonic jet, before being hit by a 281 nm laser beam which photo-ionizes the clusters which are then injected in a molecular beam through a skimmer. A tunable laser beam crossing downstream photo-dissociates the cations. The bare PAH fragments are detected using a Time-Of-Flight spectrometer while scanning the visible laser wavelength from 470 to 690 nm.

2-(Naphthalen-1-yl)-4-(naphthalen-1-yl­methyl­idene)-1,3-oxazol-5(4H)-one

PubMed Central

Gündoğdu, Cevher; Alp, Serap; Ergün, Yavuz; Tercan, Barış; Hökelek, Tuncer

2011-01-01

In the title compound, C24H15NO2, the oxazole ring is oriented at dihedral angles of 10.09 (4) and 6.04 (4)° with respect to the mean planes of the naphthalene ring systems, while the two naphthalene ring systems make a dihedral angle of 4.32 (3)°. Intra­molecular C—H⋯N hydrogen bonds link the oxazole N atom to the naphthalene ring systems. In the crystal, inter­molecular weak C—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers. π–π contacts between the oxazole and naphthalene rings and between the naphthalene ring systems [centroid–centroid distances = 3.5947 (9) and 3.7981 (9) Å] may further stabilize the crystal structure. Three weak C—H⋯π inter­actions also occur. PMID:21754548

Succession of Phenotypic, Genotypic, and Metabolic Community Characteristics during In Vitro Bioslurry Treatment of Polycyclic Aromatic Hydrocarbon-Contaminated Sediments

PubMed Central

Ringelberg, David B.; Talley, Jeffrey W.; Perkins, Edward J.; Tucker, Samuel G.; Luthy, Richard G.; Bouwer, Edward J.; Fredrickson, Herbert L.

2001-01-01

Dredged harbor sediment contaminated with polycyclic aromatic hydrocarbons (PAHs) was removed from the Milwaukee Confined Disposal Facility and examined for in situ biodegradative capacity. Molecular techniques were used to determine the successional characteristics of the indigenous microbiota during a 4-month bioslurry evaluation. Ester-linked phospholipid fatty acids (PLFA), multiplex PCR of targeted genes, and radiorespirometry techniques were used to define in situ microbial phenotypic, genotypic, and metabolic responses, respectively. Soxhlet extractions revealed a loss in total PAH concentrations of 52%. Individual PAHs showed reductions as great as 75% (i.e., acenapthene and fluorene). Rates of 14C-PAH mineralization (percent/day) were greatest for phenanthrene, followed by pyrene and then chrysene. There was no mineralization capacity for benzo[a]pyrene. Ester-linked phospholipid fatty acid analysis revealed a threefold increase in total microbial biomass and a dynamic microbial community composition that showed a strong correlation with observed changes in the PAH chemistry (canonical r2 of 0.999). Nucleic acid analyses showed copies of genes encoding PAH-degrading enzymes (extradiol dioxygenases, hydroxylases, and meta-cleavage enzymes) to increase by as much as 4 orders of magnitude. Shifts in gene copy numbers showed strong correlations with shifts in specific subsets of the extant microbial community. Specifically, declines in the concentrations of three-ring PAH moieties (i.e., phenanthrene) correlated with PLFA indicative of certain gram-negative bacteria (i.e., Rhodococcus spp. and/or actinomycetes) and genes encoding for naphthalene-, biphenyl-, and catechol-2,3-dioxygenase degradative enzymes. The results of this study suggest that the intrinsic biodegradative potential of an environmental site can be derived from the polyphasic characterization of the in situ microbial community. PMID:11282603

Unimolecular reaction energies for polycyclic aromatic hydrocarbon ions.

PubMed

West, Brandi; Rodriguez Castillo, Sarah; Sit, Alicia; Mohamad, Sabria; Lowe, Bethany; Joblin, Christine; Bodi, Andras; Mayer, Paul M

2018-03-07

Imaging photoelectron photoion coincidence spectroscopy was employed to explore the unimolecular dissociation of the ionized polycyclic aromatic hydrocarbons (PAHs) acenaphthylene, fluorene, cyclopenta[d,e,f]phenanthrene, pyrene, perylene, fluoranthene, dibenzo[a,e]pyrene, dibenzo[a,l]pyrene, coronene and corannulene. The primary reaction is always hydrogen atom loss, with the smaller species also exhibiting loss of C 2 H 2 to varying extents. Combined with previous work on smaller PAH ions, trends in the reaction energies (E 0 ) for loss of H from sp 2 -C and sp 3 -C centres, along with hydrocarbon molecule loss were found as a function of the number of carbon atoms in the ionized PAHs ranging in size from naphthalene to coronene. In the case of molecules which possessed at least one sp 3 -C centre, the activation energy for the loss of an H atom from this site was 2.34 eV, with the exception of cyclopenta[d,e,f]phenanthrene (CPP) ions, for which the E 0 was 3.44 ± 0.86 eV due to steric constraints. The hydrogen loss from PAH cations and from their H-loss fragments exhibits two trends, depending on the number of unpaired electrons. For the loss of the first hydrogen atom, the energy is consistently ca. 4.40 eV, while the threshold to lose the second hydrogen atom is much lower at ca. 3.16 eV. The only exception was for the dibenzo[a,l]pyrene cation, which has a unique structure due to steric constraints, resulting in a low H loss reaction energy of 2.85 eV. If C 2 H 2 is lost directly from the precursor cation, the energy required for this dissociation is 4.16 eV. No other fragmentation channels were observed over a large enough sample set for trends to be extrapolated, though data on CH 3 and C 4 H 2 loss obtained in previous studies is included for completeness. The dissociation reactions were also studied by collision induced dissociation after ionization by atmospheric pressure chemical ionization. When modeled with a simple temperature-based theory for the

Acute intravascular hemolysis and methemoglobinemia following naphthalene ball poisoning.

PubMed

Kapoor, Rajan; Suresh, P; Barki, Satish; Mishra, Mayank; Garg, M K

2014-09-01

Naphthalene (C10H8) is a natural component of fossil fuels such as petroleum, diesel and coal. The common consumer products made from naphthalene are moth repellents, in the form of mothballs or crystals, and toilet deodorant blocks. Major toxic effects of naphthalene are due to precipitation of acute intravascular hemolysis. Very few cases of naphthalene poisoning and its effects have been reported from India. We report a case of accidental naphthalene poisoning, who presented with intravascular hemolysis and methemoglobinemia.

Monitoring benzo(a)pyrene exposure using laser-excited Shpol'skii spectroscopy of benzo(a)pyrene metabolites

NASA Astrophysics Data System (ADS)

Ariese, Freek; Kok, S. J.; Verkaik, M.; Hoornweg, Gerard P.; Gooijer, Cees; Velthorst, Nel H.; Hofstraat, Johannes W.

1993-03-01

Exposure to polycyclic aromatic hydrocarbons (PAHs) is considered a serious threat to the health of animals and humans and should be thoroughly monitored. Next to chemical analysis of PAHs in the various environmental compartments, PAH metabolites in body fluids (e.g., bile and urine) could be measured to determine the actual uptake. Although pyrene is not considered particularly toxic, its metabolite 1-hydroxy pyrene is often used as a biomarker because it is usually found at considerable concentrations and the analysis is relatively simple. As the result of differences in volatility and/or solubility, the uptake of more relevant carcinogens like benzo(a)pyrene may be some orders of magnitude lower and is far more difficult to measure. Determination of benzo(a)pyrene metabolites requires a very selective and sensitive method, and so far these compounds could only be detected after exposure to heavy pollution. In this paper it will be shown how several hydroxy benzo(a)pyrene metabolites are selectively determined using Shpol'skii spectroscopy. With this method, highly resolved fluorescence spectra are obtained upon cooling the sample in a suitable solvent to cryogenic temperatures. When a tunable laser system is employed as an excitation source, sub- femtomole amounts can be detected. Applications of the technique to marine monitoring (benzo(a)pyrene metabolites in fish bile) and to occupational hygienics (benzo(a)pyrene metabolites in workers' urine) are discussed. The data will be compared with 1-hydroxy pyrene concentrations to evaluate the routine use of the latter compound as a biomarker.

Analysis of particle and vapour phase PAHs from the personal air samples of bus garage workers exposed to diesel exhaust.

PubMed

Kuusimaki, Leea; Peltonen, Kimmo; Mutanen, Pertti; Savela, Kirsti

2003-07-01

The levels of particle and vapour phase polycyclic aromatic hydrocarbons (PAHs) derived from the diesel exhaust compounds in bus garage work were measured in winter and in summer. Five personal air samples were collected from the breathing zones of 22 garage workers every other day of consecutive weeks. Control samples (n = 22) were collected from office workers in Helsinki. Fifteen PAHs in the air samples were analysed by HPLC using a fluorescence detector. Statistically significant differences were observed between total PAH levels of the exposed workers (2241 and 1245 ng/m(3)) and the control group (254 and 275 ng/m(3)) in both winter (P < 0.001) and summer (P < 0.001). Phenanthrene, pyrene, benzo[ghi]perylene and fluoranthene were the major compounds in the particle phase, and naphthalene, phenanthrene and fluorene in the vapour phase. About 98% of PAHs measured were related to the vapour phase compounds, whereas the high molecular weight PAH compounds were detected only in the particle phase. The PAH levels in the garages were twice as high (P < 0.001) in winter as in summer. Even though the exposure levels were low in the bus garages, the low level does not allow conclusions to be drawn about the possible adverse health effects due to exposure to diesel exhaust.

Polycyclic aromatic hydrocarbons bioaccessibility in seafood: Culinary practices effects on dietary exposure.

PubMed

Dos Santos Fogaça, Fabíola Helena; Soares, Cristina; Oliveira, Marta; Alves, Ricardo N; Maulvault, Ana L; Barbosa, Vera L; Anacleto, Patrícia; Magalhães, João Avelar; Bandarra, Narcisa M; Ramalhosa, Maria João; Morais, Simone; Marques, António

2018-07-01

This work aimed to determine the effect of culinary practices on the contamination level and bioaccessibility of polycyclic aromatic hydrocarbons (PAHs) in seafood. The selected farmed seafood species (marine shrimp, clams and seaweed) were commercially available in Portugal. The mean concentrations of PAHs varied between 0.23 and 51.8 µg kg -1 , with the lowest value being observed in raw shrimp and the highest in dried seaweed. The number of compounds detected in seaweed and clams (naphthalene, acenaphthene, fluorene, phenanthrene, benzo(b)fluoranthene and benzo(j)fluoranthene) were higher than in shrimp (fluorene and pyrene). Among the PAHs measured, fluorene was the predominant one. There was a significant interaction effect between species and culinary treatment (p < 0.05), thus boiled and dried seaweed samples presented the lowest and the highest levels of fluorene (0.13 and 1.8 µg kg -1 ), respectively. The daily intake of PAHs decreased with bioaccessibility, varying from 22% for benzo(k)fluoranthene (in raw clam) to 84% for phenanthrene (in steamed clam). According to the potency equivalent concentrations, screening values and bioaccessibility of PAHs, the consumption of marine shrimp, clam and seaweed is considered as safe for consumers. Copyright © 2018 Elsevier Inc. All rights reserved.

Polycyclic aromatic hydrocarbons (PAHs) in yogurt samples.

PubMed

Battisti, Chiara; Girelli, Anna Maria; Tarola, Anna Maria

2015-01-01

The concentrations and distributions of major polycyclic aromatic hydrocarbons (PAHs) were determined in 20 kinds of yogurt specimens collected from Italian supermarkets using reversed phase high-performance liquid chromatography equipped with fluorescence detection. The method was validated by determination of recovery percentages, precision (repeatability) and sensitivity (limits of detection) with yogurt samples fortified at 0.25, 0.5 and 1 µg/kg concentration levels. The recovery of 13 PAHs, with the exception of naphthalene and acenaphthene, ranged from 61% to 130% and from 60% to 97% at all the levels for yogurts with low (0.1%) and high (3.9%) fat content, respectively. The method is repeatable with relative standard deviation values <20% for all analytes. The results obtained demonstrate that acenaphthene, fluorantene, phenanthrene, anthracene, fluoranthene and pyrene were found in all samples with a similar distribution, but different content when yogurts with low and high fats were compared.

Predicting the equilibrium solubility of solid polycyclic aromatic hydrocarbons and dibenzothiophene using a combination of MOSCED plus molecular simulation or electronic structure calculations

NASA Astrophysics Data System (ADS)

Phifer, Jeremy R.; Cox, Courtney E.; da Silva, Larissa Ferreira; Nogueira, Gabriel Gonçalves; Barbosa, Ana Karolyne Pereira; Ley, Ryan T.; Bozada, Samantha M.; O'Loughlin, Elizabeth J.; Paluch, Andrew S.

2017-06-01

Methods to predict the equilibrium solubility of non-electrolyte solids are important for the design of novel separation processes. Here we demonstrate how conventional molecular simulation free energy calculations or electronic structure calculations in a continuum solvent, here SMD or SM8, can be used to predict parameters for the MOdified Separation of Cohesive Energy Density (MOSCED) method. The method is applied to the solutes naphthalene, anthracene, phenanthrene, pyrene and dibenzothiophene, compounds of interested to the petroleum industry and for environmental remediation. Adopting the melting point temperature and enthalpy of fusion of these compounds from experiment, we are able to predict equilibrium solubilities. Comparing to a total of 422 non-aqueous and 193 aqueous experimental solubilities, we find the proposed method is able to well correlate the data. The use of MOSCED is additionally advantageous as it is a solubility parameter-based method useful for intuitive solvent selection and formulation.

Microbial Degradation of Phenanthrene in Pristine and Contaminated Sandy Soils.

PubMed

Schwarz, Alexandra; Adetutu, Eric M; Juhasz, Albert L; Aburto-Medina, Arturo; Ball, Andrew S; Shahsavari, Esmaeil

2018-05-01

Phenanthrene mineralisation studies in both pristine and contaminated sandy soils were undertaken through detailed assessment of the activity and diversity of the microbial community. Stable isotope probing (SIP) was used to assess and identify active 13 C-labelled phenanthrene degraders. Baseline profiling indicated that there was little difference in fungal diversity but a significant difference in bacterial diversity dependent on contamination history. Identification of dominant fungal and bacterial species highlighted the presence of organisms capable of degrading various petroleum-based compounds together with other anthropogenic compounds, regardless of contamination history. Community response following a simulated contamination event ( 14 C-phenanthrene) showed that the microbial community in deep pristine and shallow contaminated soils adapted most to the presence of phenanthrene. The similarity in microbial community structure of well-adapted soils demonstrated that a highly adaptable fungal community in these soils enabled a rapid response to the introduction of a contaminant. Ten fungal and 15 bacterial species were identified as active degraders of phenanthrene. The fungal degraders were dominated by the phylum Basidiomycota including the genus Crypotococcus, Cladosporium and Tremellales. Bacterial degraders included the genera Alcanivorax, Marinobacter and Enterococcus. There was little synergy between dominant baseline microbes, predicted degraders and those that were determined to be actually degrading the contaminant. Overall, assessment of baseline microbial community in contaminated soils provides useful information; however, additional laboratory assessment of the microbial community's ability to degrade pollutants allows for better prediction of the bioremediation potential of a soil.

Determination of phenanthrene bioavailability by using a self-dying reporter bacterium: test with model solids and soil.

PubMed

Shin, Doyun; Nam, Kyoungphile

2012-02-20

The present study was conducted to investigate the performance and feasibility of a self-dying reporter bacterium to visualize and quantify phenanthrene bioavailability in soil. The self-dying reporter bacterium was designed to die on the initiation of phenanthrene biodegradation. The viability of the reporter bacterium was determined by a fluorescence live/dead cell staining method and visualized by confocal laser scanning microscopic observation. Phenanthrene was spiked into four types of model solids and a sandy loam. The bioavailability of phenanthrene to the reporter bacterium was remarkably declined with the hydrophobicity of the model solids: essentially no phenanthrene was biodegraded in the presence of 9-nm pores and about 35.8% of initial phenanthrene was biodegraded without pores. Decrease in bioavailability was not evident in the nonporous hydrophilic bead, but a small decrease was observed in the porous hydrophilic bead at 1000 mg/kg of phenanthrene. The fluorescence intensity was commensurate with the extent of phenanthrene biodegradation by the reporter bacterium at the concentration range from 50 to 500 mg/kg. Such a quantitative relationship was also confirmed with a sandy loam spiked up to 1000 mg/kg of phenanthrene. This reporter bacterium may be a useful means to determine phenanthrene bioavailability in soil. Copyright © 2011 Elsevier B.V. All rights reserved.

Extractive biodegradation and bioavailability assessment of phenanthrene in the cloud point system by Sphingomonas polyaromaticivorans.

PubMed

Pan, Tao; Deng, Tao; Zeng, Xinying; Dong, Wei; Yu, Shuijing

2016-01-01

The biological treatment of polycyclic aromatic hydrocarbons is an important issue. Most microbes have limited practical applications because of the poor bioavailability of polycyclic aromatic hydrocarbons. In this study, the extractive biodegradation of phenanthrene by Sphingomonas polyaromaticivorans was conducted by introducing the cloud point system. The cloud point system is composed of a mixture of (40 g/L) Brij 30 and Tergitol TMN-3, which are nonionic surfactants, in equal proportions. After phenanthrene degradation, a higher wet cell weight and lower phenanthrene residue were obtained in the cloud point system than that in the control system. According to the results of high-performance liquid chromatography, the residual phenanthrene preferred to partition from the dilute phase into the coacervate phase. The concentration of residual phenanthrene in the dilute phase (below 0.001 mg/L) is lower than its solubility in water (1.18 mg/L) after extractive biodegradation. Therefore, dilute phase detoxification was achieved, thus indicating that the dilute phase could be discharged without causing phenanthrene pollution. Bioavailability was assessed by introducing the apparent logP in the cloud point system. Apparent logP decreased significantly, thus indicating that the bioavailability of phenanthrene increased remarkably in the system. This study provides a potential application of biological treatment in water and soil contaminated by phenanthrene.

Evaluating environmental modeling and sampling data with biomarker data to identify sources and routes of exposure

NASA Astrophysics Data System (ADS)

Shin, Hyeong-Moo; McKone, Thomas E.; Bennett, Deborah H.

2013-04-01

Exposure to environmental chemicals results from multiple sources, environmental media, and exposure routes. Ideally, modeled exposures should be compared to biomonitoring data. This study compares the magnitude and variation of modeled polycyclic aromatic hydrocarbons (PAHs) exposures resulting from emissions to outdoor and indoor air and estimated exposure inferred from biomarker levels. Outdoor emissions result in both inhalation and food-based exposures. We modeled PAH intake doses using U.S. EPA's 2002 National Air Toxics Assessment (NATA) county-level emissions data for outdoor inhalation, the CalTOX model for food ingestion (based on NATA emissions), and indoor air concentrations from field studies for indoor inhalation. We then compared the modeled intake with the measured urine levels of hydroxy-PAH metabolites from the 2001-2002 National Health and Nutrition Examination Survey (NHANES) survey as quantifiable human intake of PAH parent-compounds. Lognormal probability plots of modeled intakes and estimated intakes inferred from biomarkers suggest that a primary route of exposure to naphthalene, fluorene, and phenanthrene for the U.S. population is likely inhalation from indoor sources. For benzo(a)pyrene, the predominant exposure route is likely from food ingestion resulting from multi-pathway transport and bioaccumulation due to outdoor emissions. Multiple routes of exposure are important for pyrene. We also considered the sensitivity of the predicted exposure to the proportion of the total naphthalene production volume emitted to the indoor environment. The comparison of PAH biomarkers with exposure variability estimated from models and sample data for various exposure pathways supports that both indoor and outdoor models are needed to capture the sources and routes of exposure to environmental contaminants.

Effect of land use activities on PAH contamination in urban soils of Rawalpindi and Islamabad, Pakistan.

PubMed

Ud Din, Ikhtiar; Rashid, Audil; Mahmood, Tariq; Khalid, Azeem

2013-10-01

Urbanization can increase the vulnerability of soils to various types of contamination. Increased contamination of urban soils with polycyclic aromatic hydrocarbon (PAH) could relate to increased number of petrol pump stations and mechanical workshops-a phenomenon that needs to be constantly monitored. This study was undertaken to explore the soil PAH levels in Rawalpindi and Islamabad urban areas in relation to land use activities. Composite soil samples from petrol pump stations and mechanical workshops (n = 32) areas were evaluated for five PAHs--naphthalene, phenanthrene, pyrene, benzo[a]pyrene, and indeno(1,2,3-cd)pyrene-and compared with control area locations with minimum petroleum-related activity (n = 16). Surface samples up to 3 cm depth were collected and extraction of analytes was carried out using n-hexane and dichloromethane. Prior to running the samples, standards (100 μg ml(-1)) were run on HPLC to optimize signal to noise ratio using acetonitrile as mobile phase at a flow rate of 1.25 ml/min at 40 °C. Significant differences between petrol pump stations and mechanical workshop areas were observed for individual PAH as well as with control area soil samples. Naphthalene was found to be the most abundant PAH in soil, ranging from 2.47 to 24.36 mg kg(-1). Correlation between the benzo[a]pyrene (BaP) level in soil and the total PAH concentration (r = 0.82, P < 0.0001) revealed that BaP can be used as a potential marker for PAH pollution. A clear segregation between petrogenic and pyrogenic sources of contamination was observed when low molecular weight PAHs detected in soil was plotted against high molecular weight PAHs. The former source comprised lubricants and used engine oil found at mechanical workshops, whereas the latter could be mostly attributed to vehicular emission at petrol pumps. The results indicate that PAH contamination in urban areas of Rawalpindi and Islamabad has direct relevance with land use for petroleum

Proteomic analysis of plasma membrane proteins in wheat roots exposed to phenanthrene.

PubMed

Shen, Yu; Du, Jiangxue; Yue, Le; Zhan, Xinhua

2016-06-01

Polycyclic aromatic hydrocarbons (PAHs) are potentially carcinogenic and toxic to humans through ingestion of contaminated food crops. PAHs can enter crop roots through proton/PAH symporters; however, to date, the symporter remains unclear. Here we reveal, for the first time, the plasma membrane proteome of Triticum aestivum seedling roots in response to phenanthrene (a model PAH) exposure. Two-dimensional gel electrophoresis (2-DE) coupled with MALDI-TOF/TOF-MS and protein database search engines were employed to analyze and identify phenanthrene-responsive proteins. Over 192 protein spots are reproducibly detected in each gel, while 8 spots are differentially expressed under phenanthrene treatment. Phenanthrene induces five up-regulated proteins distinguished as 5-methyltetrahydropteroyltriglutamate-homocysteine methyltransferase 2, enolase, heat shock protein 80-2, probable mediator of RNA polymerase II transcription subunit 37e (heat shock 70-kDa protein 1), and lactoylglutathione lyase. Three proteins identified as adenosine kinase 2, 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1c, and glyceraldehyde-3-phosphate dehydrogenase 3 are down-regulated under exposure to phenanthrene. The up-regulated proteins are related to plant defense response, antioxidant system, and glycolysis. The down-regulated proteins involve the metabolism of high-energy compounds and plant growth. Magnesium, which is able to bind to enolase, can enhance the transport of phenanthrene into wheat roots. Therefore, it is concluded that phenanthrene can induce differential expression of proteins in relation to carbohydrate metabolism, self-defense, and plant growth on wheat root plasma membrane. This study not only provides novel insights into PAH uptake by plant roots and PAH stress responses, but is also a good starting point for further determination and analyses of their functions using genetic and other approaches.

Pyrene degradation by yeasts and filamentous fungi.

PubMed

Romero, M Cristina; Salvioli, Mónica L; Cazau, M Cecilia; Arambarri, A M

2002-01-01

The saprotrophic soil fungi Fusarium solani (Mart.) Sacc., Cylindrocarpon didymum (Hartig) Wollenw, Penicillium variabile Sopp. and the yeasts Rhodotorula glutinis (Fresenius) Harrison and Rhodotorula minuta (Saito) Harrison were cultured in mineral medium with pyrene. The remaining pyrene concentrations were periodically determined during 20 incubation days, using HPLC. To assess the metabolism of pyrene degradation we added 0.1 microCi of [4,5,9,10] 14C-pyrene to each fungi culture and measured the radioactivity in the volatile organic substances, extractable, aqueous phase, biomass and 14CO2 fractions. The assays demonstrated that F. solani and R. glutinis metabolized pyrene as a sole source of carbon. Differences in their activities at the beginning of the cultures disappeared by the end of the experiment, when 32 and 37% of the original pyrene concentration was detected, for the soil fungi and yeasts, respectively. Among the filamentous fungi, F. solani was highly active and oxidized pyrene; moreover, small but significant degradation rates were observed in C. didymum and P. variahile cultures. An increase in the 14CO2 evolution was observed at the 17th day with cosubstrate. R. glutinis and R. minuta cultures showed similar ability to biotransform pyrene, and that 35% of the initial concentration was consumed at the end of the assay. The same results were obtained in the experiments with or without glucose as cosubstrate.

Homology modeling, simulation and molecular docking studies of catechol-2, 3-Dioxygenase from Burkholderia cepacia: Involved in degradation of Petroleum hydrocarbons.

PubMed

Ajao, At; Kannan, M; Yakubu, Se; Vj, Umoh; Jb, Ameh

2012-01-01

Catechol 2, 3-dioxygenase is present in several types of bacteria and undergoes degradation of environmental pollutants through an important key biochemical pathways. Specifically, this enzyme cleaves aromatic rings of several environmental pollutants such as toluene, xylene, naphthalene and biphenyl derivatives. Hence, the importance of Catechol 2, 3-dioxygenase and its role in the degradation of environmental pollutants made us to predict the three-dimensional structure of Catechol 2, 3-dioxygenase from Burkholderia cepacia. The 10ns molecular dynamics simulation was carried out to check the stability of the modeled Catechol 2, 3- dioxygenase. The results show that the model was energetically stable, and it attains their equilibrium within 2000 ps of production MD run. The docking of various petroleum hydrocarbons into the Catechol 2,3-dioxygenase reveals that the benzene, O-xylene, Toluene, Fluorene, Naphthalene, Carbazol, Pyrene, Dibenzothiophene, Anthracene, Phenanthrene, Biphenyl makes strong hydrogen bond and Van der waals interaction with the active site residues of H150, L152, W198, H206, H220, H252, I254, T255, Y261, E271, L276 and F309. Free energy of binding and estimated inhibition constant of these compounds demonstrates that they are energetically stable in their binding cavity. Chrysene shows positive energy of binding in the active site atom of Fe. Except Pyrene all the substrates made close contact with Fe atom by the distance ranges from 1.67 to 2.43 Å. In addition to that, the above mentioned substrate except pyrene all other made π-π stacking interaction with H252 by the distance ranges from 3.40 to 3.90 Å. All these docking results reveal that, except Chrysene all other substrate has good free energy of binding to hold enough in the active site and makes strong VdW interaction with Catechol-2,3-dioxygenase. These results suggest that, the enzyme is capable of catalyzing the above-mentioned substrate.

Homology modeling, simulation and molecular docking studies of catechol-2, 3-Dioxygenase from Burkholderia cepacia: Involved in degradation of Petroleum hydrocarbons

PubMed Central

Ajao, AT; Kannan, M; Yakubu, SE; VJ, Umoh; JB, Ameh

2012-01-01

Catechol 2, 3-dioxygenase is present in several types of bacteria and undergoes degradation of environmental pollutants through an important key biochemical pathways. Specifically, this enzyme cleaves aromatic rings of several environmental pollutants such as toluene, xylene, naphthalene and biphenyl derivatives. Hence, the importance of Catechol 2, 3-dioxygenase and its role in the degradation of environmental pollutants made us to predict the three-dimensional structure of Catechol 2, 3-dioxygenase from Burkholderia cepacia. The 10ns molecular dynamics simulation was carried out to check the stability of the modeled Catechol 2, 3- dioxygenase. The results show that the model was energetically stable, and it attains their equilibrium within 2000 ps of production MD run. The docking of various petroleum hydrocarbons into the Catechol 2,3-dioxygenase reveals that the benzene, O-xylene, Toluene, Fluorene, Naphthalene, Carbazol, Pyrene, Dibenzothiophene, Anthracene, Phenanthrene, Biphenyl makes strong hydrogen bond and Van der waals interaction with the active site residues of H150, L152, W198, H206, H220, H252, I254, T255, Y261, E271, L276 and F309. Free energy of binding and estimated inhibition constant of these compounds demonstrates that they are energetically stable in their binding cavity. Chrysene shows positive energy of binding in the active site atom of Fe. Except Pyrene all the substrates made close contact with Fe atom by the distance ranges from 1.67 to 2.43 Å. In addition to that, the above mentioned substrate except pyrene all other made π-π stacking interaction with H252 by the distance ranges from 3.40 to 3.90 Å. All these docking results reveal that, except Chrysene all other substrate has good free energy of binding to hold enough in the active site and makes strong VdW interaction with Catechol-2,3-dioxygenase. These results suggest that, the enzyme is capable of catalyzing the above-mentioned substrate. PMID:23144539

Levels of PAHs in the Waters, Sediments, and Shrimps of Estero de Urias, an Estuary in Mexico, and Their Toxicological Effects

PubMed Central

Jaward, Foday M.; Alegria, Henry A.; Galindo Reyes, Jose G.; Hoare, Armando

2012-01-01

PAHs were measured in water, sediment, and shrimps of Estero de Urias, an estuary in Sinaloa, Mexico, during the rainy and dry seasons, and analyzed for eleven PAHs routinely detected in samples. Phenanthrene was the most dominant congener in the water, sediment, and shrimp samples comprising about 38, 24, and 25%, respectively, of the eleven PAHs detected, followed by pyrene and naphthalene in water and sediment samples, and pyrene and fluorine in the shrimp samples. Total PAH concentrations ranged from 9 to 347 ng/L in water, 27 to 418 ng/g in sediments, and 36 to 498 ng/g in shrimps. The sources of contamination are closely related to human activities such as domestic and industrial discharge, automobile exhausts, and street runoff. High concentrations were also measured during the rainy season and during the first quarter of the year. Toxicity tests were also carried out, exposing fish embryos and juvenile shrimps to some of these PAHs. Fish embryos exposed to PAHs showed exogastrulation, while juvenile shrimps showed significantly lower growth rates than controls. DNA and protein alterations were also observed. These toxicity tests indicate that PAH concentrations measured could be dangerous to some aquatic organisms, particularly during early stages of development. PMID:22997501

Pyrene

Integrated Risk Information System (IRIS)

Pyrene ; CASRN 129 - 00 - 0 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Effects )

FRET based integrated pyrene-AgNPs system for detection of Hg (II) and pyrene dimer: Applications to environmental analysis

NASA Astrophysics Data System (ADS)

Walekar, Laxman S.; Hu, Peidong; Vafaei Molamahmood, Hamed; Long, Mingce

2018-06-01

The integrated system of pyrene and cetyltrimethyl ammonium bromide (CTAB) capped silver nanoparticles (AgNPs) with a distance (r) of 2.78 nm has been developed for the detection of Hg (II) and pyrene dimer. The interaction between pyrene and AgNPs results in the fluorescence quenching of pyrene due to the energy transfer, whose mechanism can be attributed to the Forster Resonance Energy Transfer (FRET) supported by experimental observation and theoretical calculations. The developed probe shows a highly selective and sensitive response towards Hg (II) probably due to the amalgam formation, which results in the fluorescence recovery (90%) of pyrene and color change of solution from yellowish brown to colorless. The addition of Hg (II) may increase the distance between pyrene and AgNPs undergoes the 'FRET OFF' process. This system gives a selective response towards Hg (II) over other competing metal ions. Under the optimal condition, the system offers good linearity between 0.1 and 0.6 μg mL-1 with a detection limit of 62 ng mL-1. In addition, the system also provides an effective platform for detection of pyrene in its dimer form even at very low concentrations (10 ng mL-1) on the surface of AgNPs. Therefore, it could be used as effective alternatives for the detection of Hg (II) as well as pyrene simultaneously.

Effect of amphiphilic polyurethane nanoparticles on sorption-desorption of phenanthrene in aquifer material.

PubMed

Kim, Ju-Young; Shim, Sun-Bo; Shim, Jin-Kie

2003-03-17

Micelle-like amphiphilic nano-sized polyurethane (APU) nanoparticles were synthesized via chemical cross-linking reaction of nano-aggregates of urethane acrylate nonionomer (UAN) chain and were tested for extraction efficiency of sorbed phenanthrene from aquifer material. Even though the solubilizing performance and interfacial activity of APU nanoparticles were inferior to that of Triton X-100, in the low concentration region, APU nanoparticles could effectively reduce phenanthrene sorption on the aquifer material and extracted sorbed phenanthrene from the aquifer material, whereas Triton X-100 could not extract sorbed phenanthrene and rather increased phenanthrene sorption onto the aquifer materials. At higher concentrations, APU nanoparticles and Triton X-100 had almost the same soil washing effectiveness. This interesting result is mainly due to a lower degree of sorption of APU nanoparticles onto the aquifer material. The sorption of APU nanoparticles onto aquifer sand is largely hindered by their chemically cross-linked nature, resulting in better soil-washing performance of APU nanoparticles than Triton X-100. Copyright 2003 Elsevier Science B.V.

Removal of anthracene and phenanthrene by filamentous fungi capable of cortexolone 11-hydroxylation.

PubMed

Lisowska, K; Długoński, J

1999-01-01

Nine fungal strains showing ability of cortexolone hydroxylation to epicortisol and/or cortisol were screened in this work for anthracene and phenanthrene elimination (250 mg/l). All of the strains (Cylindrocladium simplex IM 2358, C. simplex IM 2358/650, Monosporium olivaceum IM 484, Curvularia lunata IM 2901, C. lunata IM 2901/366, C. tuberculata IM 4417, Cunninghamella elegans IM 1785, C. elegans IM 1785/21Gp, C. elegans IM 1785/10Gi) significantly removed anthracene and phenanthrene. During incubation with anthracene formation of intermediate products was observed. The amount of the main intermediate product, identified as 9, 10-anthraquinone, was not greater than 22.2% of the anthracene introduced to the fungal cultures. C. elegans IM 1785/21Gp was the best degrader of both anthracene and phenanthrene, removing 81.6 and 99.4% of these compounds after 7 days, respectively. Phenanthrene removal by C. elegans IM 1785/21Gp was preceded by PAHs accumulation in mycelium and growth inhibition. Elimination of phenanthrene started after one day of incubation and was related to the fungus growth.

Bioavailability of atrazine, pyrene and benzo[a]pyrene in European river waters

USGS Publications Warehouse

Akkanen, J.; Penttinen, S.; Haitzer, M.; Kukkonen, J.V.K.

2001-01-01

Thirteen river waters and one humic lake water were characterized. The effects of dissolved organic matter (DOM) on the bioavailability of atrazine, pyrene and benzo[a]pyrene (B[a]P) was evaluated. Binding of the chemicals by DOM was analyzed with the equilibrium dialysis technique. For each of the water samples, 24 h bioconcentration factors (BCFs) of the chemicals were measured in Daphnia magna. The relationship between DOM and other water characteristics (including conductivity, water hardness and pH), and bioavailability of the chemicals was studied by performing several statistical analyses, including multiple regression analyses, to determine how much of the variation of BCF values could be explained by the quantity and quality of DOM. The bioavailability of atrazine was not affected by DOM or any other water characteristics. Although equilibrium dialysis showed binding of pyrene to DOM, the bioavailability of pyrene was not significantly affected by DOM. The bioavailability of B[a]P was significantly affected by both the quality and quantity of DOM. Multiple regression analyses, using the quality (ABS270 and HbA%) and quantity of DOM as variables, explainedup to 70% of the variation in BCF of B[a]P in the waters studied. ?? 2001 Elsevier Science Ltd. All rights reserved.

Interplay of localized pyrene chromophores and π-conjugation in novel poly(2,7-pyrene) ladder polymers

NASA Astrophysics Data System (ADS)

Rudnick, Alexander; Kass, Kim-Julia; Preis, Eduard; Scherf, Ullrich; Bässler, Heinz; Köhler, Anna

2017-05-01

We present a detailed spectroscopic study, along with the synthesis, of conjugated, ladder-type 2,7-linked poly(pyrene)s. We observe a delocalization of the first singlet excited state along the polymer backbone, i.e., across the 2,7 linkage in the pyrene moiety, in contrast to earlier studies on conjugated 2,7-linked poly(pyrene)s without ladder structure. The electronic signature of the pyrene unit is, however, manifested in an increased lifetime and reduced oscillator strength as well as a modified vibronic progression in absorption of the singlet state compared to a ladder-type poly(para-phenylene) (MeLPPP). Furthermore, the reduced oscillator strength and increased lifetime slow down Förster-type energy transfer in films, where this transfer occurs to sites with increasing inter-chain coupling of H-type nature.

IRIS Toxicological Review of Naphthalene (1998 Final)

EPA Science Inventory

EPA announced the release of the final report, Toxicological Review of Naphthalene: in support of the Integrated Risk Information System (IRIS). The updated Summary for Naphthalene and accompanying toxicological review have been added to the IRIS Database.

Solubilization of phenanthrene above cloud point of Brij 30: a new application in biodegradation.

PubMed

Pantsyrnaya, T; Delaunay, S; Goergen, J L; Guseva, E; Boudrant, J

2013-06-01

In the present study a new application of solubilization of phenanthrene above cloud point of Brij 30 in biodegradation was developed. It was shown that a temporal solubilization of phenanthrene above cloud point of Brij 30 (5wt%) permitted to obtain a stable increase of the solubility of phenanthrene even when the temperature was decreased to culture conditions of used microorganism Pseudomonas putida (28°C). A higher initial concentration of soluble phenanthrene was obtained after the cloud point treatment: 200 against 120μM without treatment. All soluble phenanthrene was metabolized and a higher final concentration of its major metabolite - 1-hydroxy-2-naphthoic acid - (160 against 85μM) was measured in the culture medium in the case of a preliminary cloud point treatment. Therefore a temporary solubilization at cloud point might have a perspective application in the enhancement of biodegradation of polycyclic aromatic hydrocarbons. Copyright © 2013 Elsevier Ltd. All rights reserved.

Biodiversity of polycyclic aromatic hydrocarbon-degrading bacteria from deep sea sediments of the Middle Atlantic Ridge.

PubMed

Cui, Zhisong; Lai, Qiliang; Dong, Chunming; Shao, Zongze

2008-08-01

The bacteria involved in the biodegradation of polycyclic aromatic hydrocarbons (PAHs) in deep sea subsurface environments are largely unknown. In order to reveal their biodiversity, sediments from 2.2 m under the bottom surface at a water depth of 3542 m were sampled on the Middle Atlantic Ridge with a gravity column sampler. The sediments were promptly enriched with either crude oil or a mixture of PAHs (naphthalene, phenanthrene and pyrene) as the sole carbon source, and further enriched with the PAH mixture mentioned above in the lab. The resulting consortia were named C2CO and C2PPN respectively. Their bacterial composition was analysed with plate cultivation, PCR-DGGE and 16S rDNA library analysis. On plates, isolates belonging to Pseudoalteromonas, Halomonas, Marinobacter, Thalassospira and Tistrella dominated the culturable populations. With PCR-DGGE, five major bands closely related to Cycloclasticus, Alteromonas, Thalassospira, Alcanivorax and Rhodospirillaceae were detected in consortium C2CO, while only one major band of Cycloclasticus was detected in consortium C2PPN. In addition, the dynamics of community structure in response to aromatic substrate alterations were examined. As a result, three ribotypes of Cycloclasticus were detected by 16S rDNA library analysis, one which played a key role in phenanthrene degradation; two Alteromonas bacteria dominated the naphthalene reselected consortium. Although bacteria of the two genera grew as the main members of the communities, none of them were isolated, probably owing to their poor cultivability. These results confirm that bacteria of Cycloclasticus are important obligate PAH degraders in marine environments, and coexist with other degrading bacteria that inhabit the deep subsurface sediment of the Atlantic. This supports the view that PAH accumulation and bioattenuation occur in remote areas consistently and continuously.

Biodiversity of polycyclic aromatic hydrocarbon-degrading bacteria from deep sea sediments of the Middle Atlantic Ridge

PubMed Central

Cui, Zhisong; Lai, Qiliang; Dong, Chunming; Shao, Zongze

2008-01-01

The bacteria involved in the biodegradation of polycyclic aromatic hydrocarbons (PAHs) in deep sea subsurface environments are largely unknown. In order to reveal their biodiversity, sediments from 2.2 m under the bottom surface at a water depth of 3542 m were sampled on the Middle Atlantic Ridge with a gravity column sampler. The sediments were promptly enriched with either crude oil or a mixture of PAHs (naphthalene, phenanthrene and pyrene) as the sole carbon source, and further enriched with the PAH mixture mentioned above in the lab. The resulting consortia were named C2CO and C2PPN respectively. Their bacterial composition was analysed with plate cultivation, PCR-DGGE and 16S rDNA library analysis. On plates, isolates belonging to Pseudoalteromonas, Halomonas, Marinobacter, Thalassospira and Tistrella dominated the culturable populations. With PCR-DGGE, five major bands closely related to Cycloclasticus, Alteromonas, Thalassospira, Alcanivorax and Rhodospirillaceae were detected in consortium C2CO, while only one major band of Cycloclasticus was detected in consortium C2PPN. In addition, the dynamics of community structure in response to aromatic substrate alterations were examined. As a result, three ribotypes of Cycloclasticus were detected by 16S rDNA library analysis, one which played a key role in phenanthrene degradation; two Alteromonas bacteria dominated the naphthalene reselected consortium. Although bacteria of the two genera grew as the main members of the communities, none of them were isolated, probably owing to their poor cultivability. These results confirm that bacteria of Cycloclasticus are important obligate PAH degraders in marine environments, and coexist with other degrading bacteria that inhabit the deep subsurface sediment of the Atlantic. This supports the view that PAH accumulation and bioattenuation occur in remote areas consistently and continuously. PMID:18445026

Leaching of polycyclic aromatic hydrocarbons from oil shale processing waste deposit: a long-term field study.

PubMed

Jefimova, Jekaterina; Irha, Natalya; Reinik, Janek; Kirso, Uuve; Steinnes, Eiliv

2014-05-15

The leaching behavior of selected polycyclic aromatic hydrocarbons (PAHs) from an oil shale processing waste deposit was monitored during 2005-2009. Samples were collected from the deposit using a special device for leachate sampling at field conditions without disturbance of the upper layers. Contents of 16 priority PAHs in leachate samples collected from aged and fresh parts of the deposit were determined by GC-MS. The sum of the detected PAHs in leachates varied significantly throughout the study period: 19-315 μg/l from aged spent shale, and 36-151 μg/l from fresh spent shale. Among the studied PAHs the low-molecular weight compounds phenanthrene, naphthalene, acenaphthylene, and anthracene predominated. Among the high-molecular weight PAHs benzo[a]anthracene and pyrene leached in the highest concentrations. A spent shale deposit is a source of PAHs that could infiltrate into the surrounding environment for a long period of time. Copyright © 2014 Elsevier B.V. All rights reserved.

Multivariate analysis of mixed contaminants (PAHs and heavy metals) at manufactured gas plant site soils.

PubMed

Thavamani, Palanisami; Megharaj, Mallavarapu; Naidu, Ravi

2012-06-01

Principal component analysis (PCA) was used to provide an overview of the distribution pattern of polycyclic aromatic hydrocarbons (PAHs) and heavy metals in former manufactured gas plant (MGP) site soils. PCA is the powerful multivariate method to identify the patterns in data and expressing their similarities and differences. Ten PAHs (naphthalene, acenapthylene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene, pyrene, chrysene, benzo[a]pyrene) and four toxic heavy metals - lead (Pb), cadmium (Cd), chromium (Cr) and zinc (Zn) - were detected in the site soils. PAH contamination was contributed equally by both low and high molecular weight PAHs. PCA was performed using the varimax rotation method in SPSS, 17.0. Two principal components accounting for 91.7% of the total variance was retained using scree test. Principle component 1 (PC1) substantially explained the dominance of PAH contamination in the MGP site soils. All PAHs, except anthracene, were positively correlated in PC1. There was a common thread in high molecular weight PAHs loadings, where the loadings were inversely proportional to the hydrophobicity and molecular weight of individual PAHs. Anthracene, which was less correlated with other individual PAHs, deviated well from the origin which can be ascribed to its lower toxicity and different origin than its isomer phenanthrene. Among the four major heavy metals studied in MGP sites, Pb, Cd and Cr were negatively correlated in PC1 but showed strong positive correlation in principle component 2 (PC2). Although metals may not have originated directly from gaswork processes, the correlation between PAHs and metals suggests that the materials used in these sites may have contributed to high concentrations of Pb, Cd, Cr and Zn. Thus, multivariate analysis helped to identify the sources of PAHs, heavy metals and their association in MGP site, and thereby better characterise the site risk, which would not be possible if one uses chemical analysis

Visible light photodegradation of phenanthrene catalyzed by Fe(III)-smectite: role of soil organic matter.

PubMed

Jia, Hanzhong; Li, Li; Fan, Xiaoyun; Liu, Mingdeng; Deng, Wenye; Wang, Chuanyi

2013-07-15

In the present study, phenanthrene is employed as a model to explore the roles played by three soil organic matter (SOM) fractions, i.e., dissolved organic matter (DOM), humic acid (HA), and fulvic acid (FA), in its photodegradation with assistance of Fe(III)-smectite under visible-light. Slight decrease in phenanthrene photodegradation rate was observed in the presence of DOM, which is explained in terms of oxidative-radical competition between DOM and target phenanthrene molecules due to the high electron-donor capacity of phenolic moieties in DOM. On the other hand, a critic content is observed with FA (0.70mg/g) and HA (0.65mg/g). Before reaching the critic content, the removal of phenanthrene is accelerated; while after that, the photodegradation rate is suppressed. The acceleration of phenanthrene degradation can be attributed to the photosensitization of FA and HA. Due to the strong interaction between phenanthrene and the phenyl rings, however, the retention of phenanthrene on SOM-Fe(III)-smectite in the presence of high content of HA or FA is enhanced, thus slowing down its photodegradation. Those observations provide valuable insights into the transformation and fate of PAHs in the natural soil environment and open a window for using clay-humic substances complexes for remediation of contaminated soil. Copyright © 2013 Elsevier B.V. All rights reserved.

Enrichment and identification of naphthalene-degrading bacteria from the Persian Gulf.

PubMed

Hassanshahian, Mehdi; Boroujeni, Negar Amini

2016-06-15

Naphthalene is a ubiquitous pollutant of the marine environment, and naphthalene biodegradation has been receiving constant scientific consideration. For cleanup of aromatic contaminated sites, bioremediation methods are considered as economical and safe approaches for the marine environment. The aims of this research are isolation and characterization of naphthalene-degrading bacteria from some marine samples of the Persian Gulf. Fifty four naphthalene-degrading bacteria were isolated from marine samples (sediment and seawater) that are enriched in ONR7a medium with naphthalene as the only carbon source. Some screening tests such as growth at high concentration of naphthalene, bioemulsifier production and surface hydrophobicity were done to select the best and prevalent strains for naphthalene degradation. Determination of the nucleotide sequence of the gene encoding for 16S rRNA shows that these isolated strains belong to these genera: Shewanella, Salegentibacter, Halomonas, Marinobacter, Oceanicola, Idiomarina and Thalassospira. These strains can degrade half of the percentage of naphthalene in 10days of incubation. This research is the first report on isolation of these genera from the Persian Gulf as naphthalene-degrader. Copyright © 2016 Elsevier Ltd. All rights reserved.

Specific adsorption of cadmium on surface-engineered biocompatible organoclay under metal-phenanthrene mixed-contamination.

PubMed

Biswas, Bhabananda; Sarkar, Binoy; Mandal, Asit; Naidu, Ravi

2016-11-01

Bioremediation of polycyclic aromatic hydrocarbons (PAHs) is extremely challenging when they coexist with heavy metals. This constrain has led to adsorption-based techniques that help immobilize the metals and reduce toxicity. However, the adsorbents can also non-selectively bind the organic compounds, which reduces their bioavailability. In this study we developed a surface-engineered organoclay (Arquad ® 2HT-75-bentonite-palmitic acid) which enhanced bacterial proliferation and adsorbed cadmium, but elevated phenanthrene bioavailability. Adsorption models of single and binary solutes revealed that the raw bentonite adsorbed cadmium and phenanthrene non-selectively at the same binding sites and sequestrated phenanthrene. In contrast, cadmium selectively bound to the deprotonated state of carboxyl groups in the organoclay and phenanthrene on the outer surface of the adsorbent led to a microbially congenial microenvironment with a higher phenanthrene bioavailability. This study provided valuable information which would be highly important for developing a novel clay-modulated bioremediation technology for cleaning up PAHs under mixed-contaminated situations. Copyright © 2016 Elsevier Ltd. All rights reserved.

Linking of Microorganisms to Phenanthrene Metabolism in Soil by Analysis of 13C-Labeled Cell Lipids

PubMed Central

Johnsen, Anders R.; Winding, Anne; Karlson, Ulrich; Roslev, Peter

2002-01-01

Phenanthrene-metabolizing soil microbial communities were characterized by examining mineralization of [14C]phenanthrene, by most-probable-number (MPN) counting, by 16S-23S spacer DNA analysis of the numerically dominant, culturable phenanthrene-degrading isolates, and by examining incorporation of [13C]phenanthrene-derived carbon into sterols and polar lipid fatty acids (PLFAs). An unpolluted agricultural soil, a roadside soil diffusely polluted with polycyclic aromatic hydrocarbons (PAHs), and two highly PAH-polluted soils from industrial sites were analyzed. Microbial phenanthrene degraders were not detected by MPN counting in the agricultural soil and the roadside soil. In the industrial soils, phenanthrene degraders constituted 0.04 and 3.6% of the total number of CFU. 16S-23S spacer DNA analysis followed by partial 16S DNA sequencing of representative isolates from one of the industrial soils showed that one-half of the isolates belonged to the genus Sphingomonas and the other half were closely related to an unclassified beta-proteobacterium. The 13C-PLFA profiles of the two industrial soils were relatively similar and resembled the profiles of phenanthrene-degrading Sphingomonas reference strains and unclassified beta-proteobacterium isolates but did not match the profiles of Pseudomonas, Mycobacterium, or Nocardia reference strains. The 13C-PLFA profiles of phenanthrene degraders in the agricultural soil and the roadside soil were different from each other and different from the profiles of the highly polluted industrial soils. Only in the roadside soil were 10me/12me18:0 PLFAs enriched in 13C, suggesting that actinomycetes metabolized phenanthrene in this soil. The 13C-PLFA profiles of the unpolluted agricultural soil did not resemble the profiles of any of the reference strains. In all of the soils investigated, no excess 13C was recovered in the 18:2ω6,9 PLFA, suggesting that fungi did not contribute significantly to assimilation of [13C]phenanthrene

Remediation of phenanthrene from contaminated kaolinite by electroremediation-Fenton technology.

PubMed

Alcantara, T; Pazos, M; Gouveia, S; Cameselle, C; Sanroman, M A

2008-07-01

Polycyclic aromatic hydrocarbons (PAHs) cause a high environmental impact when released into the environment. The objective of this study was to evaluate the capacity to decontaminate polluted soils with phenanthrene as a model PAH using a combination of two technologies: electrokinetic remediation and Fenton process. Kaolinite was used as a model sample that was artificially polluted at the laboratory at an initial concentration of phenanthrene of 500 mg kg(-1) of dried kaolinite. The standard electrokinetic process resulted in negligible removal of phenanthrene from the kaolinite sample. Faster and more efficient degradation of this compound can be promoted by introduction of a strong oxidant into the soil such as hydroxyl radicals. For this reason, the Fenton reactions have been induced in several experiments in which H(2)O(2) (10%) was used as flushing solution, and kaolinite polluted with iron was used. When anode and cathode chambers were filled with H(2)O(2) (10%), the kaolinite pH is maintained at an acid value around 3.5 without pH control and an overall removal and destruction efficiency of phenanthrene of 99% was obtained in 14 days by applying a voltage gradient of 3 V cm(-1). Therefore, it is evident that a combined technology of electrokinetic remediation and Fenton reaction is capable of simultaneously removing and degrading of PAHs in polluted model samples with kaolinite.

Novel Phenanthrene-Degrading Bacteria Identified by DNA-Stable Isotope Probing

PubMed Central

Luo, Chunling; Zhang, Dayi; Zhang, Gan

2015-01-01

Microorganisms responsible for the degradation of phenanthrene in a clean forest soil sample were identified by DNA-based stable isotope probing (SIP). The soil was artificially amended with either 12C- or 13C-labeled phenanthrene, and soil DNA was extracted on days 3, 6 and 9. Terminal restriction fragment length polymorphism (TRFLP) results revealed that the fragments of 219- and 241-bp in HaeIII digests were distributed throughout the gradient profile at three different sampling time points, and both fragments were more dominant in the heavy fractions of the samples exposed to the 13C-labeled contaminant. 16S rRNA sequencing of the 13C-enriched fraction suggested that Acidobacterium spp. within the class Acidobacteria, and Collimonas spp. within the class Betaproteobacteria, were directly involved in the uptake and degradation of phenanthrene at different times. To our knowledge, this is the first report that the genus Collimonas has the ability to degrade PAHs. Two PAH-RHDα genes were identified in 13C-labeled DNA. However, isolation of pure cultures indicated that strains of Staphylococcus sp. PHE-3, Pseudomonas sp. PHE-1, and Pseudomonas sp. PHE-2 in the soil had high phenanthrene-degrading ability. This emphasizes the role of a culture-independent method in the functional understanding of microbial communities in situ. PMID:26098417

Isolation and Characterization of Phenanthrene Degrading Bacteria from Diesel Fuel-Contaminated Antarctic Soils

PubMed Central

Gran-Scheuch, Alejandro; Fuentes, Edwar; Bravo, Denisse M.; Jiménez, Juan Cristobal; Pérez-Donoso, José M.

2017-01-01

Antarctica is an attractive target for human exploration and scientific investigation, however the negative effects of human activity on this continent are long lasting and can have serious consequences on the native ecosystem. Various areas of Antarctica have been contaminated with diesel fuel, which contains harmful compounds such as heavy metals and polycyclic aromatic hydrocarbons (PAH). Bioremediation of PAHs by the activity of microorganisms is an ecological, economical, and safe decontamination approach. Since the introduction of foreign organisms into the Antarctica is prohibited, it is key to discover native bacteria that can be used for diesel bioremediation. By following the degradation of the PAH phenanthrene, we isolated 53 PAH metabolizing bacteria from diesel contaminated Antarctic soil samples, with three of these isolates exhibiting a high phenanthrene degrading capacity. In particular, the Sphingobium xenophagum D43FB isolate showed the highest phenanthrene degradation ability, generating up to 95% degradation of initial phenanthrene. D43FB can also degrade phenanthrene in the presence of its usual co-pollutant, the heavy metal cadmium, and showed the ability to grow using diesel-fuel as a sole carbon source. Microtiter plate assays and SEM analysis revealed that S. xenophagum D43FB exhibits the ability to form biofilms and can directly adhere to phenanthrene crystals. Genome sequencing analysis also revealed the presence of several genes involved in PAH degradation and heavy metal resistance in the D43FB genome. Altogether, these results demonstrate that S. xenophagum D43FB shows promising potential for its application in the bioremediation of diesel fuel contaminated-Antarctic ecosystems. PMID:28894442

Fate of phenanthrene and mineralization of its non-extractable residues in an oxic soil.

PubMed

Wang, Yongfeng; Xu, Jun; Shan, Jun; Ma, Yini; Ji, Rong

2017-05-01

The fate of organic pollutants in the environment, especially the formation and stability of non-extractable (i.e., bound) residues (NERs) determines their environmental risk. Using 14 C-tracers, we studied the fate of the carcinogen phenanthrene in active or sterilized oxic loamy soil in the absence and presence of the geophagous earthworm Metaphire guillelmi and characterized the NERs derived from phenanthrene. After incubation of 14 C-phenanthrene in active soil for 28 days, 40 ± 3.1% of the initial amount was mineralized and 70.1 ± 1.9% was converted to NERs. Most of the NERs (>92%) were bound to soil humin. Silylation of the humin-bound residues released 45.3 ± 5.3% of these residues, which indicated that they were physically entrapped, whereas the remainder of the residues were chemically bound or biogenic. By contrast, in sterilized soil, only 43.4 ± 12.6% of the phenanthrene was converted to NERs and all of these residues were completely released upon silylation, which underlines the essential role of microbial activity in NER formation. The presence of M. guillelmi in active soil significantly inhibited phenanthrene mineralization (24.4 ± 2.6% mineralized), but NER formation was not significantly affected. Only a small amount of phenanthrene-derived residues (1.9-5.3% of the initial amount) accumulated in the earthworm body. When humin-bound residues were mixed with fresh soil, 33.9% (humin recovered from active soils) and 12.4% (humin recovered from sterilized soils) of the residues were mineralized after 75 days of incubation, respectively, which indicated a high bioavailability of NERs, albeit lower than the initial addition of phenanthrene. Our results indicated that many phenanthrene-derived NERs, especially those physically entrapped, are still bioavailable and may pose a toxic threat to soil organisms. Copyright © 2017 Elsevier Ltd. All rights reserved.

Uptake of aromatic hydrocarbon vapors (benzene and phenanthrene) at the air-water interface of micron-size water droplets.

PubMed

Raja, Suresh; Valsaraj, Kalliat T

2004-12-01

Uptake of aromatic hydrocarbon vapors (benzene and phenanthrene) by typical micrometer-sized fog-water droplets was studied using a falling droplet reactor at temperatures between 296 and 316 K. Uptake of phenanthrene vapor greater than that predicted by bulk (air-water)-phase equilibrium was observed for diameters less than 200 microm, and this was attributed to surface adsorption. The experimental values of the droplet-vapor partition constant were used to obtain the overall mass transfer coefficient and the mass accommodation coefficient for both benzene and phenanthrene. Mass transfer of phenanthrene was dependent only on gas-phase diffusion and mass accommodation at the interface. However, for benzene, the mass transfer was limited by liquid-phase diffusion and mass accommodation. A large value of the mass accommodation coefficient, alpha = (1.4 +/- 0.4) x 10(-2) was observed for the highly surface-active (hydrophobic) phenanthrene, whereas a small alpha = (9.7 +/- 1.8) x 10(-5) was observed for the less hydrophobic benzene. Critical cluster numbers ranging from 2 for benzene to 5.7 for phenanthrene were deduced using the critical cluster nucleation theory for mass accommodation. The enthalpy of mass accommodation was more negative for phenanthrene than it was for benzene. Consequently, the temperature effect was more pronounced for phenanthrene. A linear correlation was observed for the enthalpy of accommodation with the excess enthalpy of solution. A natural organic carbon surrogate (Suwannee Fulvic acid) in the water droplet increased the uptake for phenanthrene and benzene, the effect being more marked for phenanthrene. A characteristic time constant analysis showed that uptake and droplet scavenging would compete for the fog deposition of phenanthrene, whereas deposition would be unimpeded by the uptake rate for benzene vapor. For both compounds, the characteristic atmospheric reaction times were much larger and would not impact fog deposition.

Constraint on the potassium content for the superconductivity of potassium-intercalated phenanthrene.

PubMed

Huang, Qiao-Wei; Zhong, Guo-Hua; Zhang, Jiang; Zhao, Xiao-Miao; Zhang, Chao; Lin, Hai-Qing; Chen, Xiao-Jia

2014-03-21

Raman-scattering measurements were performed on K(x)phenanthrene (0 ⩽ x ⩽ 6.0) at room temperature. Three phases (x = 3.0, 3.5, and 4.0) are identified based on the obtained Raman spectra. Only the K3phenanthrene phase is found to exhibit the superconducting transition at 5 K. The C-C stretching modes are observed to broaden and become disordered in K(x)phenanthrene with x = 2.0, 2.5, 6.0, indicating some molecular disorder in the metal intercalation process. This disorder is expected to influence the nonmetallic nature of these materials. The absence of metallic character in these nonsuperconducting phases is found from the calculated electronic structures based on the local density approximation.

Communication: Ion mobility of the radical cation dimers: (Naphthalene)2+• and naphthalene+•-benzene: Evidence for stacked sandwich and T-shape structures

NASA Astrophysics Data System (ADS)

Platt, Sean P.; Attah, Isaac K.; Aziz, Saadullah; El-Shall, M. Samy

2015-05-01

Dimer radical cations of aromatic and polycyclic aromatic molecules are good model systems for a fundamental understanding of photoconductivity and ferromagnetism in organic materials which depend on the degree of charge delocalization. The structures of the dimer radical cations are difficult to determine theoretically since the potential energy surface is often very flat with multiple shallow minima representing two major classes of isomers adopting the stacked parallel or the T-shape structure. We present experimental results, based on mass-selected ion mobility measurements, on the gas phase structures of the naphthalene+ṡ ṡ naphthalene homodimer and the naphthalene+ṡ ṡ benzene heterodimer radical cations at different temperatures. Ion mobility studies reveal a persistence of the stacked parallel structure of the naphthalene+ṡ ṡ naphthalene homodimer in the temperature range 230-300 K. On the other hand, the results reveal that the naphthalene+ṡ ṡ benzene heterodimer is able to exhibit both the stacked parallel and T-shape structural isomers depending on the experimental conditions. Exploitation of the unique structural motifs among charged homo- and heteroaromatic-aromatic interactions may lead to new opportunities for molecular design and recognition involving charged aromatic systems.

Mechanistic Studies on the Dibenzofuran Formation from Phenanthrene, Fluorene and 9–Fluorenone

PubMed Central

Li, Shanqing; Zhang, Qingzhu

2015-01-01

We carried out molecular orbital theory calculations for the homogeneous gas‑phase formation of dibenzofuran from phenanthrene, fluorene, 9-methylfluorene and 9-fluorenone. Dibenzofuran will be formed if ∙OH adds to C8a, and the order of reactivity follows as 9-fluorenone > 9-methylfluorene > fluorene > phenanthrene. The oxidations initiated by ClO∙ are more favorable processes, considering that the standard reaction Gibbs energies are at least 21.63 kcal/mol lower than those of the equivalent reactions initiated by ∙OH. The adding of ∙OH and then O2 to phenanthrene is a more favorable route than adding ∙OH to C8a of phenanthrene, when considering the greater reaction extent. The reaction channel from fluorene and O2 to 9-fluorenone and H2O seems very important, not only because it contains only three elementary reactions, but because the standard reaction Gibbs energies are lower than −80.07 kcal/mol. PMID:25756381

Effects of nanoplastics and microplastics on toxicity, bioaccumulation, and environmental fate of phenanthrene in fresh water.

PubMed

Ma, Yini; Huang, Anna; Cao, Siqi; Sun, Feifei; Wang, Lianhong; Guo, Hongyan; Ji, Rong

2016-12-01

Contamination of fine plastic particles (FPs), including micrometer to millimeter plastics (MPs) and nanometer plastics (NPs), in the environment has caught great concerns. FPs are strong adsorbents for hydrophobic toxic pollutants and may affect their fate and toxicity in the environment; however, such information is still rare. We studied joint toxicity of FPs with phenanthrene to Daphnia magna and effects of FPs on the environmental fate and bioaccumulation of 14 C-phenanthrene in fresh water. Within the five sizes particles we tested (from 50 nm to 10 μm), 50-nm NPs showed significant toxicity and physical damage to D. magna. The joint toxicity of 50-nm NPs and phenanthrene to D. magna showed an additive effect. During a 14-days incubation, the presence of NPs significantly enhanced bioaccumulation of phenanthrene-derived residues in daphnid body and inhibited the dissipation and transformation of phenanthrene in the medium, while 10-μm MPs did not show significant effects on the bioaccumulation, dissipation, and transformation of phenanthrene. The differences may be attributed to higher adsorption of phenanthrene on 50-nm NPs than 10-μm MPs. Our findings underlined the high potential ecological risks of FPs, and suggested that NPs should be given more concerns, in terms of their interaction with hydrophobic pollutants in the environment. Copyright © 2016 Elsevier Ltd. All rights reserved.

21 CFR 172.824 - Sodium mono- and dimethyl naphthalene sulfonates.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Sodium mono- and dimethyl naphthalene sulfonates... sulfonates. The food additive sodium mono- and dimethyl naphthalene sulfonates may be safely used in... statement declaring the presence of sodium mono- and dimethyl naphthalene sulfonates. [42 FR 14491, Mar. 15...

Infrared spectroscopy of matrix-isolated polycyclic aromatic hydrocarbon cations. 2. The members of the thermodynamically most favorable series through coronene

NASA Technical Reports Server (NTRS)

Hudgins, D. M.; Allamandola, L. J.

1995-01-01

Gaseous, ionized polycyclic aromatic hydrocarbons (PAHs) are thought to be responsible for a very common family of interstellar infrared emission bands. Here the near- and mid-infrared spectra of the cations of the five most thermodynamically favored PAHs up to coronene:phenanthrene, pyrene, benzo[e]pyrene, benzo[ghi]perylene, and coronene, are presented to test this hypothesis. For those molecules that have been studied previously (pyrene, pyrene-d10, and coronene), band positions and relative intensities are in agreement. In all of these cases we report additional features. Absolute integrated absorbance values are given for the phenanthrene, perdeuteriophenanthrene, pyrene, benzo[ghi]perylene, and coronene cations. With the exception of coronene, the cation bands corresponding to the CC modes are typically 2-5 times more intense than those of the CH out-of-plane bending vibrations. For the cations, the CC stretching and CH in-plane bending modes give rise to bands that are an order of magnitude stronger than those of the neutral species, and the CH out-of-plane bends produce bands that are 5-20 times weaker than those of the neutral species. This behavior is similar to that found in most other PAH cations studied to date. The astronomical implications of these PAH cation spectra are also discussed.

Analysis of Benzo[a]pyrene in Vegetable Oils Using Molecularly Imprinted Solid Phase Extraction (MISPE) Coupled with Enzyme-Linked Immunosorbent Assay (ELISA)

PubMed Central

Pschenitza, Michael; Hackenberg, Rudolf; Niessner, Reinhard; Knopp, Dietmar

2014-01-01

This paper describes the development of a molecularly imprinted polymer-based solid phase extraction (MISPE) method coupled with enzyme-linked immunosorbent assay (ELISA) for determination of the PAH benzo[a]pyrene (B[a]P) in vegetable oils. Different molecularly imprinted polymers (MIPs) were prepared using non-covalent 4-vinylpyridine/divinylbenzene co-polymerization at different ratios and dichloromethane as porogen. Imprinting was done with a template mixture of phenanthrene and pyrene yielding a broad-specific polymer for PAHs with a maximum binding capacity (Q) of ∼32 μg B[a]P per 50 mg of polymer. The vegetable oil/n-hexane mixture (1:1, (v/v)) was pre-extracted with acetonitrile, the solvent evaporated, the residue reconstituted in n-hexane and subjected to MISPE. The successive washing with n-hexane and isopropanol revealed most suitable to remove lipid matrix constituents. After elution of bound PAHs from MISPE column with dichloromethane, the solvent was evaporated, the residue reconstituted with dimethyl sulfoxide and diluted 100-fold with methanol/water (10:90, (v/v)) for analysis of B[a]P equivalents with an ELISA. The B[a]P recovery rates in spiked vegetable oil samples of different fatty acid composition were determined between 63% and 114%. The presence of multiple PAHs in the oil sample, because of MIP selectivity and cross-reactivity of the ELISA, could yield overestimated B[a]P values. PMID:24887045

Binding of Diverse Environmental Chemicals with Human Cytochromes P450 2A13, 2A6, and 1B1 and Enzyme Inhibition

PubMed Central

Shimada, Tsutomu; Kim, Donghak; Murayama, Norie; Tanaka, Katsuhiro; Takenaka, Shigeo; Nagy, Leslie D.; Folkman, Lindsay M.; Foroozesh, Maryam K.; Komori, Masayuki; Yamazaki, Hiroshi; Guengerich, F. Peter

2014-01-01

A total of 68 chemicals including derivatives of naphthalene, phenanthrene, fluoranthene, pyrene, biphenyl, and flavone were examined for their abilities to interact with human P450s 2A13 and 2A6. Fifty-one of these 68 chemicals induced stronger Type I binding spectra (iron low- to high-spin state shift) with P450 2A13 than those seen with P450 2A6, i.e. the spectral binding intensities (ΔAmax/Ks ratio) determined with these chemicals were always higher for P450 2A13. In addition, benzo[c]phenanthrene, fluoranthene, 2,3-dihydroxy-2,3-dihydrofluoranthene, pyrene, 1-hydroxypyrene, 1-nitropyrene, 1-acetylpyrene, 2-acetylpyrene, 2,5,2’,5’-tetrachlorobiphenyl, 7-hydroxyflavone, chrysin, and galangin were found to induce a Type I spectral change only with P450 2A13. Coumarin 7-hydroxylation, catalyzed by P450 2A13, was strongly inhibited by 2’-methoxy-5,7-dihydroxyflavone, 2-ethynylnaphthalene, 2’-methoxyflavone, 2-naphththalene propargyl ether, acenaphthene, acenaphthylene, naphthalene, 1-acetylpyrene, flavanone, chrysin, 3-ethynylphenanthrene, flavone, and 7-hydroxyflavone; these chemicals induced Type I spectral changes with low Ks values. On the basis of the intensities of the spectral changes and inhibition of P450 2A13, we classified the 68 chemicals into eight groups based on the order of affinities for these chemicals and inhibition of P450 2A13. The metabolism of chemicals by P450 2A13 during the assays explained why some of the chemicals that bound well were poor inhibitors of P450 2A13. Finally, we compared the 68 chemicals for their abilities to induce Type I spectral changes of P450 2A13 with the Reverse Type I binding spectra observed with P450 1B1: 45 chemicals interacted with both P450s 2A13 and 1B1, indicating that the two enzymes have some similarty of structural features regarding these chemicals. Molecular docking analyses suggest similarities at the active sites of these P450 enzymes. These results indicate that P450 2A13, as well as Family

Fate of pyrene in the rhizosphere

DOE Office of Scientific and Technical Information (OSTI.GOV)

Lee, E.; Banks, M.K.; Schwab, A.P.

The objective of this research is to investigate the impact of vegetation on the fate of toxic and recalcitrant pyrene in soil as well as the influence of different plant species (alfalfa (Meticago sativa) and fescue (Festuca arundinacea)). The effect of vegetation will be evaluated by determining the distribution of {sup 14}C among soil, plant tissue, leachate, and CO{sub 2} evolved in planted and unplanted soils using highly controlled plant growth chambers during a 6-month experiment. The influence of plant species on the fate of pyrene will be estimated by comparing the dissipation rate of the {sup 14}C-target compound betweenmore » alfalfa and fescue. These data will be analyzed to ascertain if there are differences between vegetated and nonvegetated soils, also between plant species with regard to leaching, degradation, plant uptake, mineralization of the {sup 14}C-labelled pyrene. The beneficial effects of vegetation planted in soil contaminated by pyrene is anticipated.« less

Indigenous 14C-phenanthrene biodegradation in "pristine" woodland and grassland soils from Norway and the United Kingdom.

PubMed

Okere, Uchechukwu V; Schuster, Jasmin K; Ogbonnaya, Uchenna O; Jones, Kevin C; Semple, Kirk T

2017-11-15

In this study, the indigenous microbial mineralisation of 14 C-phenanthrene in seven background soils (four from Norwegian woodland and three from the UK (two grasslands and one woodland)) was investigated. ∑PAHs ranged from 16.39 to 285.54 ng g -1 dw soil. Lag phases (time before 14 C-phenanthrene mineralisation reached 5%) were longer in all of the Norwegian soils and correlated positively with TOC, but negatively with ∑PAHs and phenanthrene degraders for all soils. 14 C-phenanthrene mineralisation in the soils varied due to physicochemical properties. The results show that indigenous microorganisms can adapt to 14 C-phenanthrene mineralisation following diffuse PAH contamination. Considering the potential of soil as a secondary PAH source, these findings highlight the important role of indigenous microflora in the processing of PAHs in the environment.

Naphthalene biodegradation in temperate and arctic marine microcosms.

PubMed

Bagi, Andrea; Pampanin, Daniela M; Lanzén, Anders; Bilstad, Torleiv; Kommedal, Roald

2014-02-01

Naphthalene, the smallest polycyclic aromatic hydrocarbon (PAH), is found in abundance in crude oil, its major source in marine environments. PAH removal occurs via biodegradation, a key process determining their fate in the sea. Adequate estimation of PAH biodegradation rates is essential for environmental risk assessment and response planning using numerical models such as the oil spill contingency and response (OSCAR) model. Using naphthalene as a model compound, biodegradation rate, temperature response and bacterial community composition of seawaters from two climatically different areas (North Sea and Arctic Ocean) were studied and compared. Naphthalene degradation was followed by measuring oxygen consumption in closed bottles using the OxiTop(®) system. Microbial communities of untreated and naphthalene exposed samples were analysed by polymerase chain reaction denaturing gradient gel electrophoresis (PCR-DGGE) and pyrosequencing. Three times higher naphthalene degradation rate coefficients were observed in arctic seawater samples compared to temperate, at all incubation temperatures. Rate coefficients at in situ temperatures were however, similar (0.048 day(-1) for temperate and 0.068 day(-1) for arctic). Naphthalene biodegradation rates decreased with similar Q10 ratios (3.3 and 3.5) in both seawaters. Using the temperature compensation method implemented in the OSCAR model, Q10 = 2, biodegradation in arctic seawater was underestimated when calculated from the measured temperate k1 value, showing that temperature difference alone could not predict biodegradation rates adequately. Temperate and arctic untreated seawater communities were different as revealed by pyrosequencing. Geographic origin of seawater affected the community composition of exposed samples.

Naphthalene and Naphthoquinone: Distributions and Human Exposure in the Los Angeles Basin

NASA Astrophysics Data System (ADS)

Lu, R.; Wu, J.; Turco, R.; Winer, A. M.; Atkinson, R.; Paulson, S.; Arey, J.; Lurmann, F.

2003-12-01

Naphthalene is the simplest and most abundant of the polycyclic aromatic hydrocarbons (PAHs). Naphthalene is found primarily in the gas-phase and has been detected in both outdoor and indoor samples. Evaporation from naphthalene-containing products (including gasoline), and during refining operations, are important sources of naphthalene in air. Naphthalene is also emitted during the combustion of fossil fuels and wood, and is a component of vehicle exhaust. Exposure to high concentrations of naphthalene can damage or destroy red blood cells, causing hemolytic anemia. If inhaled over a long period of time, naphthalene may cause kidney and liver damage, skin allergy and dermatitis, cataracts and retinal damage, as well as attack the central nervous system. Naphthalene has been found to cause cancer as a result of inhalation in animal tests. Naphthoquinones are photooxidation products of naphthalene and the potential health effects of exposure to these quinones are a current focus of research. We are developing and applying models that can be used to assess human exposure to naphthalene and its photooxidation products in major air basins such as California South Coast Air Basin (SoCAB). The work utilizes the Surface Meteorology and Ozone Generation (SMOG) airshed model, and the REgional Human EXposure (REHEX) model, including an analysis of individual exposure. We will present and discuss simulations of basin-wide distributions of, and human exposures to, naphthalene and naphthoquinone, with emphasis on the uncertainties in these estimates of atmospheric concentrations and human exposure. Regional modeling of pollutant sources and exposures can lead to cost-effective and optimally health-protective emission control strategies.

A Comparative Study of the Metabolism of 6-Methylbenzo [A] Pyrene and Benzo [A] Pyrene by Rat Liver Microsomes

DTIC Science & Technology

1984-02-24

147. Dewhurst, F., and Kitchen, D. A. (1972). Synthesis and properties of 6-substituted benzo [a] pyrene derivatives. J_. £. 1 . Perkins I, 710-712...group results in the formation of 6-hydroxymathylbenzo[a]pyrene (6-OHMBaP) which can be further metabolized to both the 1 - and 3-phenols of 6...LIST OF TABLES LIST OF FIGURES xi BACKGROUND 1 Introduction 1 Metabolism of PAH 1 Microsomal Metabolism of Benzo[a]pyrene 2 Inducers of

Degradation of naphthalene-2,6- and naphthalene-1,6-disulfonic acid by a Moraxella sp

DOE Office of Scientific and Technical Information (OSTI.GOV)

Wittich, R.M.; Tast, H.G.; Knackmuss, H.J.

1988-07-01

A naphthalene-2,6-disulfonic acid (2,6NDS)-degrading Moraxella strain was isolated from an industrial sewage plant. This culture could also be adapted to naphthalene-1,6-disulfonic acid as growth substrate. Regioselective 1,2-dioxygenation effected desulfonation and catabolism to 5-sulfosalicylic acid (5SS), which also could be used a the sole carbon source. 5SS-grown cells exhibited high gentisate 1,2-dioxygenase activity. Neither 5SS- nor gentisate-grown cells oxidized 2,6NDS; therefore, 2,6NDS or an early metabolite must serve as an inducer of the initial catabolic enzymes(s).

Identification of petroleum hydrocarbons using a reduced number of PAHs selected by Procrustes rotation.

PubMed

Fernández-Varela, R; Andrade, J M; Muniategui, S; Prada, D; Ramírez-Villalobos, F

2010-04-01

Identifying petroleum-related products released into the environment is a complex and difficult task. To achieve this, polycyclic aromatic hydrocarbons (PAHs) are of outstanding importance nowadays. Despite traditional quantitative fingerprinting uses straightforward univariate statistical analyses to differentiate among oils and to assess their sources, a multivariate strategy based on Procrustes rotation (PR) was applied in this paper. The aim of PR is to select a reduced subset of PAHs still capable of performing a satisfactory identification of petroleum-related hydrocarbons. PR selected two subsets of three (C(2)-naphthalene, C(2)-dibenzothiophene and C(2)-phenanthrene) and five (C(1)-decahidronaphthalene, naphthalene, C(2)-phenanthrene, C(3)-phenanthrene and C(2)-fluoranthene) PAHs for each of the two datasets studied here. The classification abilities of each subset of PAHs were tested using principal components analysis, hierarchical cluster analysis and Kohonen neural networks and it was demonstrated that they unraveled the same patterns as the overall set of PAHs. (c) 2009 Elsevier Ltd. All rights reserved.

Phenanthrene binding by humic acid-protein complexes as studied by passive dosing technique.

PubMed

Zhao, Jian; Wang, Zhenyu; Ghosh, Saikat; Xing, Baoshan

2014-01-01

This work investigated the binding behavior of phenanthrene by humic acids (HA-2 and HA-5), proteins (bovine serum albumin (BSA)), lysozyme and pepsin), and their complexes using a passive dosing technique. All sorption isotherms were fitted well with Freundlich model and the binding capability followed an order of HA-5 > HA-2 > BSA > pepsin > lysozyme. In NaCl solution, phenanthrene binding to HA-BSA complexes was much higher than the sum of binding to individual HA and BSA, while there was no enhancement for HA-pepsin. Positively charged lysozyme slightly lowered phenanthrene binding on both HAs due to strong aggregation of HA-lysozyme complexes, leading to reduction in the number of binding sites. The binding enhancement by HA-BSA was observed under all tested ion species and ionic strengths. This enhancement can be explained by unfolding of protein, reduction of aggregate size and formation of HA-BSA complexes with favorable conformations for binding phenanthrene. Copyright © 2013 Elsevier Ltd. All rights reserved.

Theoretical investigation on the mechanism of NO3 radical-initiated atmospheric reactions of phenanthrene

NASA Astrophysics Data System (ADS)

Zhao, Nan; Shi, Xiangli; Xu, Fei; Zhang, Qingzhu; Wang, Wenxing

2017-07-01

Phenanthrene is a polycyclic aromatic hydrocarbon from fossil fuel combustion with toxic properties. The products arising from atmospheric reaction can be more mutagenic and carcinogenic compared to unmodified phenanthrene, and are therefore important to be studied. The products of the specific NO3-radical reactions with phenanthrene where therefore investigated in this study by means of Density Functional Theory (DFT). The results show that the main products are proposed to be 10-(nitrooxy)-10-hydro-phenanthrene-9-one, 2,2‧-diformylbiphenyl, 9,10-phenanthrenequinone, 9-fluorenone and dibenzopyranone. 10-(nitrooxy)-10-hydro-phenanthrene-9-one and 2,2‧-diformylbiphenyl are classified as first-generation products which are subject to secondary reactions to produce 9,10-phenanthrenequinone, 9-fluorenone and dibenzopyranone. The rate constants of elementary reactions were assessed by Rice-Ramsperger-Kassel-Marcus (RRKM) theory. The atmospheric lifetime of Phe determined by the gas-phase reaction with NO3 is estimated to be 1.8 h, based on the calculated overall rate constant of 3.04 × 10-13 cm3 molecule-1 s-1 at 298 K and 1 atm. Combined with available experimental observation, this work should help to clarify the transformation and potential health risk of Phe in the atmosphere.

Biochemical and genotoxic response of naphthalene to fingerlings of milkfish Chanos chanos.

PubMed

Palanikumar, L; Kumaraguru, A K; Ramakritinan, C M

2013-09-01

The present study investigated the acute toxicity, sub-lethal toxicity and biochemical response of naphthalene in fingerlings of milkfish Chanos chanos. The 96 h acute toxicity LC50 values for C. chanos exposed to naphthalene was 5.18 μg l(-1). The estimated no observed effect concentration and lowest observed effect concentration values for naphthalene in C. chanos were 0.42 and 0.69 μg l(-1) respectively for 30 days. The estimated maximum allowable toxicant concentration for naphthalene was 0.53 μg l(-1). Biochemical enzyme markers such as lipid peroxidation, catalase, glutathione S transferase and reduced glutathione were measured in gills and liver tissues of C. chanos exposed to sub-lethal concentrations of naphthalene. Fluctuation in lipid peroxidation and catalase level suggests that naphthalene concentrations play a vital role in induction of oxidative stress in fish. Induction of reduced glutathione level and inhibition of glutathione S-transferase level was observed in naphthalene exposed C. chanos suggesting that there may be enhanced oxidative damage due to free radicals. Increasing concentration increases in number of nuclear abnormalities. The formation of micronuclei and binucleated micronuclei induction by naphthalene confirm its genotoxic potential. The highest levels of DNA damage (% tail length) were observed at 1.24 μg l(-1) of naphthalene. The study suggests that biochemical enzymes, nuclear abnormalities and DNA damage index can serve as a biological marker for naphthalene contamination.

Comparative transcriptomic evidence for Tween80-enhanced biodegradation of phenanthrene by Sphingomonas sp. GY2B.

PubMed

Liu, Shasha; Guo, Chuling; Lin, Weijia; Wu, Fengji; Lu, Guining; Lu, Jing; Dang, Zhi

2017-12-31

Previous study of the effects of surfactants on the biodegradation of phenanthrene focused on investigating alterations of the cell characteristics of Sphingomonas sp. GY2B. However, genes regulation associated with biodegradation and biological processes in response to the presence of surfactants, remains unclear. In this study, comparative transcriptome analysis was conducted to observe the gene expression of GY2B during phenanthrene biodegradation in the presence and absence of Tween80. A diverse set of genes was regulated by Tween80, leading to increased biodegradation of phenanthrene by GY2B: (i) Tween80 increased expression of genes related to H + transport in the plasma membrane to provide a driving force (i.e., ATP) for accelerating transmembrane transport of phenanthrene with increasing Tween80 concentrations, thereby enhancing the uptake and degradation of phenanthrene by GY2B; (ii) Tween80 (1 and 8 CMC) promoted intracellular biodegradation of phenanthrene by stimulating expression of genes encoding dioxygenases and monooxygenase, increasing expression of genes involved in intracellular metabolic processes (e.g., TCA cycle); and (iii) Tween80 likely increased GY2B vitality and growth by inducing expression of genes associated with ABC transporters and protein transport, regulating genes involved in other biological processes (e.g., transcription, translation). Copyright © 2017. Published by Elsevier B.V.

Biodegradation Ability and Catabolic Genes of Petroleum-Degrading Sphingomonas koreensis Strain ASU-06 Isolated from Egyptian Oily Soil

PubMed Central

Mostafa, Yasser M.; Shoreit, Ahmed

2014-01-01

Polycyclic aromatic hydrocarbons (PAHs) are serious pollutants and health hazards. In this study, 15 PAHs-degrading bacteria were isolated from Egyptian oily soil. Among them, one Gram-negative strain (ASU-06) was selected and biodegradation ability and initial catabolic genes of petroleum compounds were investigated. Comparison of 16S rRNA gene sequence of strain ASU-06 to published sequences in GenBank database as well as phylogenetic analysis identified ASU-06 as Sphingomonas koreensis. Strain ASU-06 degraded 100, 99, 98, and 92.7% of 100 mg/L naphthalene, phenanthrene, anthracene, and pyrene within 15 days, respectively. When these PAHs present in a mixed form, the enhancement phenomenon appeared, particularly in the degradation of pyrene, whereas the degradation rate was 98.6% within the period. This is the first report showing the degradation of different PAHs by this species. PCR experiments with specific primers for catabolic genes alkB, alkB1, nahAc, C12O, and C23O suggested that ASU-06 might possess genes for aliphatic and PAHs degradation, while PAH-RHDαGP gene was not detected. Production of biosurfactants and increasing cell-surface hydrophobicity were investigated. GC/MS analysis of intermediate metabolites of studied PAHs concluded that this strain utilized these compounds via two main pathways, and phthalate was the major constant product that appeared in each day of the degradation period. PMID:25177681

SYNTHESIS OF p-TRIFLUOROMETHYL-TOLUENE AND 3,6-BIS(TRIFLUOROMETHYL) PHENANTHRENE USING SULFUR TETRAFLUORIDE

DTIC Science & Technology

studies on the soxhlet extractors showed promise that separation and isolation is possible. Corrosion data gathered during the course of the p-toluic...production of 3, 6-bis(trifluoromethyl) phenanthrene based on a 20% conversion to 3,6- bis(trifluoromethyl) phenanthrene plus an additional 30% yield of

Tissue distribution and depuration kinetics of waterborne 14C-labeled light PAHs in mummichog (Fundulus heteroclitus).

PubMed

Valdez Domingos, F X; Oliveira Ribeiro, C A; Pelletier, É; Rouleau, C

2011-04-01

Light polycyclic aromatic hydrocarbons (PAHs) of petrogenic origin are commonly found in estuaries and coastal areas. Though they are known to be toxic to fish, little is known about their uptake and tissue distribution. This paper reports on the results of a study on uptake, elimination, and tissue distribution of three waterborne 14C-labeled PAHs in the mummichog, Fundulus heteroclitus, using whole-body autoradiography. After a 24 h exposure to 1 μCi·L(-1) of 14C-naphthalene, 14C-1-naphthol, and 14C-phenanthrene, fish were transferred to clean water and tissue distribution examined after 0, 1, 3, 7, 14, and 21 days of depuration. All compounds were readily accumulated by fish and were also rapidly eliminated (t0.5 range=1.1 to 3.0 days). Most of the radioactivity in naphthalene- and phenanthrene-treated fish was found in gall bladder≫liver>intestinal lumen. In naphthol-exposed fish, an important labeling of some brain areas was observed. Brain of naphthalene-exposed fish was also labeled after 24 h depuration, indicating that exposure to naphthalene may result in metabolite accumulation in the brain. This is the first study showing that naphthalene, naphthol, and/or unidentified metabolite(s) can accumulate in brain tissues, which may impair normal brain function.

Sorption of phenanthrene and benzene on differently structural kerogen: important role of micropore-filling.

PubMed

Zhang, Yulong; Ma, Xiaoxuan; Ran, Yong

2014-02-01

Shale was thermally treated to obtain a series of kerogen with varied maturation. Their chemical, structural and porous properties were related to the sorption and/or desorption behaviors of phenanthrene and benzene. As the treatment temperature increases, aliphatic and carbonyl carbon of the kerogen samples decrease, while their aromaticity and maturation increase. Meanwhile, the isothermal nonlinearity of phenanthrene and benzene increases whereas the sorption capacity and micropore adsorption volumes (Vo,d) initially increase and then decrease. The Vo,d of benzene is significantly correlated with, but higher than that of phenanthrene, suggesting similar micropore filling mechanism and molecular sieve effect. The benzene desorption exhibits hysteresis, which is related to the pore deformation of the kerogen and the entrapment of solute in the kerogen matrix. The Vo,d of phenanthrene and benzene on the kerogen samples accounts for 23-46% and 36-65% of the maximum sorption volumes, respectively, displaying the importance of the micropore filling. Copyright © 2013 Elsevier Ltd. All rights reserved.

Spatial Distribution of Bacterial Communities and Phenanthrene Degradation in the Rhizosphere of Lolium perenne L.

PubMed Central

Corgié, S. C.; Beguiristain, T.; Leyval, C.

2004-01-01

Rhizodegradation of organic pollutants, such as polycyclic aromatic hydrocarbons, is based on the effect of root-produced compounds, known as exudates. These exudates constitute an important and constant carbon source that selects microbial populations in the plant rhizosphere, modifying global as well as specific microbial activities. We conducted an experiment in two-compartment devices to show the selection of bacterial communities by root exudates and phenanthrene as a function of distance to roots. Using direct DNA extraction, PCR amplification, and thermal gradient gel electrophoresis screening, bacterial population profiles were analyzed in parallel to bacterial counts and quantification of phenanthrene biodegradation in three layers (0 to 3, 3 to 6, and 6 to 9 mm from root mat) of unplanted-polluted (phenanthrene), planted-polluted, and planted-unpolluted treatments. Bacterial community differed as a function of the distance to roots, in both the presence and the absence of phenanthrene. In the planted and polluted treatment, biodegradation rates showed a strong gradient with higher values near the roots. In the nonplanted treatment, bacterial communities were comparable in the three layers and phenanthrene biodegradation was high. Surprisingly, no biodegradation was detected in the section of planted polluted treatment farthest from the roots, where the bacterial community structure was similar to those of the nonplanted treatment. We conclude that root exudates and phenanthrene induce modifications of bacterial communities in polluted environments and spatially modify the activity of degrading bacteria. PMID:15184156

Preliminary physiologically based pharmacokinetic models for benzo[a]pyrene and dibenzo[def,p]chrysene in rodents

DOE Office of Scientific and Technical Information (OSTI.GOV)

Crowell, Susan Ritger, E-mail: Susan.crowell@pnnl.gov; Amin, Shantu G.; Anderson, Kim A.

2011-12-15

Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous environmental contaminants generated as byproducts of natural and anthropogenic combustion processes. Despite significant public health concern, physiologically based pharmacokinetic (PBPK) modeling efforts for PAHs have so far been limited to naphthalene, plus simpler PK models for pyrene, nitropyrene, and benzo[a]pyrene (B[a]P). The dearth of published models is due in part to the high lipophilicity, low volatility, and myriad metabolic pathways for PAHs, all of which present analytical and experimental challenges. Our research efforts have focused upon experimental approaches and initial development of PBPK models for the prototypic PAH, B[a]P, and the more potent, albeitmore » less studied transplacental carcinogen, dibenzo[def,p]chrysene (DBC). For both compounds, model compartments included arterial and venous blood, flow limited lung, liver, richly perfused and poorly perfused tissues, diffusion limited fat, and a two compartment theoretical gut (for oral exposures). Hepatic and pulmonary metabolism was described for both compounds, as were fractional binding in blood and fecal clearance. Partition coefficients for parent PAH along with their diol and tetraol metabolites were estimated using published algorithms and verified experimentally for the hydroxylated metabolites. The preliminary PBPK models were able to describe many, but not all, of the available data sets, comprising multiple routes of exposure (oral, intravenous) and nominal doses spanning several orders of magnitude. Supported by Award Number P42 ES016465 from the National Institute of Environmental Health Sciences. -- Highlights: Black-Right-Pointing-Pointer We present PBPK models for benzo[a]pyrene (B[a]P) and dibenzo[def,p]chrysene (DBC). Black-Right-Pointing-Pointer B[a]P model accurately predicts data from multiple sources over a wide dose range. Black-Right-Pointing-Pointer DBC model was based on the B[a]P model as less chemical

Anti-inflammatory phenanthrene derivatives from stems of Dendrobium denneanum.

PubMed

Lin, Yuan; Wang, Fei; Yang, Li-Juan; Chun, Ze; Bao, Jin-Ku; Zhang, Guo-Lin

2013-11-01

Cultivated Dendrobium denneanum has been substituted for other endangered Dendrobium species in recent years, but there have been few studies regarding either its chemical constituents or pharmacological effects. In this study, three phenanthrene glycosides, three 9,10-dihydrophenanthrenes, two 9,10-dihydrophenanthrenes glycosides, and four known phenanthrene derivatives, were isolated from the stems of D. denneanum. Their structures were elucidated on the basis of MS and NMR spectroscopic data. Ten compounds were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated mouse macrophage RAW264.7 cells with IC50 values of 0.7-41.5 μM, and exhibited no cytotoxicity in RAW264.7, HeLa, or HepG2 cells. Additionally, it was found that 2,5-dihydroxy-4-methoxy-phenanthrene 2-O-β-d-glucopyranoside, and 5-methoxy-2,4,7,9S-tetrahydroxy-9,10-dihydrophenanthrene suppressed LPS-induced expression of inducible NO synthase (iNOS) inhibited phosphorylation of p38, JNK as well as mitogen-activated protein kinase (MAPK), and inhibitory kappa B-α (IκBα). This indicated that both compounds exert anti-inflammatory effects by inhibiting MAPKs and nuclear factor κB (NF-κB) pathways. Copyright © 2013 Elsevier Ltd. All rights reserved.

ADDITIVITY OF IN VIVO MUTATION INDUCTION BY CUMULATIVE EXPOSURES TO BENZO[A]PYRENE OR DIBENZO[A,L]PYRENE

EPA Science Inventory

Dibenzo[a,l]pyrene (DB[a,l]P) and benzo[a]pyrene (B[a]P) are polycyclic aromatic hydrocarbons (PAH) found in cigarette smoke condensate, coal combustion processes and in some environmental pollutants. In this study, we investigated the effect of dosing regimen on the mutagenicity...

Contrasting effects of a nonionic surfactant on the biotransformation of polycyclic aromatic hydrocarbons to cis-dihydrodiols by soil bacteria

DOE Office of Scientific and Technical Information (OSTI.GOV)

Allen, C.C.R.; Boyd, D.R.; Hempenstall, F.

The biotransformation of the polycyclic aromatic hydrocarbons (PAHs) naphthalene and phenanthrene was investigated by using two dioxygenase-expressing bacteria, Pseudomonas sp. strain 9816/11 and Sphingomonas yanoikuyae B8/36, under conditions which facilitate mass-transfer limited substrate oxidation. Both of these strains are mutants that accumulate cis-dihydrodiol metabolites under the reaction conditions used. The effects of the nonpolar solvent 2,2,4,4,6,8,8-heptamethylnonane (HMN) and the nonionic surfactant Triton X-100 on the rate of accumulation of these metabolites were determined. HMN increased the rate of accumulation of metabolites for both microorganisms, with both substrates. The enhancement effect was most noticeable with phenanthrene, which has a lower aqueousmore » solubility than naphthalene. Triton X-100 increased the rate of oxidation of the PAHs with strain 9816/11 with the effect being most noticeable when phenanthrene was used as a substrate. However, the surfactant inhibited the biotransformation of both naphthalene and phenanthrene with strain B8/36 under the same conditions. The observation that a nonionic surfactant could have such contrasting effects on PAH oxidation by different bacteria, which are known to be important for the degradation of these compounds in the environment, may explain why previous research on the application of the surfactants to PAH bioremediation has yielded inconclusive results. The surfactant inhibited growth of the wild-type strain S. yanoikuyae B1 on aromatic compounds but did not inhibit B8/36 dioxygenase enzyme activity in vitro.« less

Excretion of 3-hydroxy-benzo(a)pyrene and mutagenicity in rat urine after exposure to benzo(a)pyrene.

PubMed

Jongeneelen, F J; Leijdekkers, C M; Bos, R P; Theuws, J L; Henderson, P T

1985-10-01

3-hydroxy-benzo(a)pyrene (3-OH-B(a)P) and mutagenic activity in rat urine were determined after the oral administration of benzo(a)pyrene given in three repeated doses of 10, 20 and 50 mumol kg-1. The procedure for the determination of 3-OH-B(a)P consisted of enzymic hydrolysis, separation and HPLC-analysis. The mutagenic activity of concentrated urine samples was assayed with the Salmonella typhimurium strain TA98 in the presence of S9 mix and beta-glucuronidase. The urinary excretion of 3-OH-B(a)P and mutagens showed a correlation and both increased dose-dependently during the sampling period of 6 days. Data indicated that 3-OH-B(a)P can be regarded as a reliable representative of all urinary (pre)-mutagens derived from benzo(a)pyrene and exposure of rats to benzo(a)pyrene could be detected with greater sensitivity by the HPLC assay of 3-OH-B(a)P than with the non-specific mutagenicity assay.

[Risk analysis of naphthalene pollution in soils of Tianjin].

PubMed

Yang, Yu; Shi, Xuan; Xu, Fu-liu; Tao, Shu

2004-03-01

Three approaches were applied and evaluated for probabilistic risk assessment of naphthalene in soils of Tianjin, China, based on the observed naphthalene concentration of 188 top soil samples from the area and LC50 of naphthalene to ten typical soil fauna species from the literature. It was found that the overlapping area of the two probability density functions of concentration and LC50 was 6.4%, the joint probability curve bend towards and very close to the bottom and left axis, and the calculated probability that exposure concentration exceeds LC50 of various species was as low as 1.67%, all indicating a very much acceptable risk of naphthalene to the soil fauna ecosystem and only some of very sensitive species or individual animals are threaten by localized extremely high concentration. The three approaches revealed similar results from different viewpoints.

Effects of the inoculant strain Sphingomonas paucimobilis 20006FA on soil bacterial community and biodegradation in phenanthrene-contaminated soil.

PubMed

Coppotelli, B M; Ibarrolaza, A; Del Panno, M T; Morelli, I S

2008-02-01

The effects of the inoculant strain Sphingomonas paucimobilis 20006FA (isolated from a phenanthrene-contaminated soil) on the dynamics and structure of microbial communities and phenanthrene elimination rate were studied in soil microcosms artificially contaminated with phenanthrene. The inoculant managed to be established from the first inoculation as it was evidenced by denaturing gradient gel electrophoresis analysis, increasing the number of cultivable heterotrophic and PAH-degrading cells and enhancing phenanthrene degradation. These effects were observed only during the inoculation period. Nevertheless, the soil biological activity (dehydrogenase activity and CO(2) production) showed a late increase. Whereas gradual and successive changes in bacterial community structures were caused by phenanthrene contamination, the inoculation provoked immediate, significant, and stable changes on soil bacterial community. In spite of the long-term establishment of the inoculated strain, at the end of the experiment, the bioaugmentation did not produce significant changes in the residual soil phenanthrene concentration and did not improve the residual effects on the microbial soil community.

Metabolism of a Representative Oxygenated Polycyclic Aromatic Hydrocarbon (PAH) Phenanthrene-9,10-quinone in Human Hepatoma (HepG2) Cells

PubMed Central

2014-01-01

Exposure to polycyclic aromatic hydrocarbons (PAHs) in the food chain is the major human health hazard associated with the Deepwater Horizon oil spill. Phenanthrene is a representative PAH present in crude oil, and it undergoes biological transformation, photooxidation, and chemical oxidation to produce its signature oxygenated derivative, phenanthrene-9,10-quinone. We report the downstream metabolic fate of phenanthrene-9,10-quinone in HepG2 cells. The structures of the metabolites were identified by HPLC–UV–fluorescence detection and LC–MS/MS. O-mono-Glucuronosyl-phenanthrene-9,10-catechol was identified, as reported previously. A novel bis-conjugate, O-mono-methyl-O-mono-sulfonated-phenanthrene-9,10-catechol, was discovered for the first time, and evidence for both of its precursor mono conjugates was obtained. The identities of these four metabolites were unequivocally validated by comparison to authentic enzymatically synthesized standards. Evidence was also obtained for a minor metabolic pathway of phenanthrene-9,10-quinone involving bis-hydroxylation followed by O-mono-sulfonation. The identification of 9,10-catechol conjugates supports metabolic detoxification of phenanthrene-9,10-quinone through interception of redox cycling by UGT, COMT, and SULT isozymes and indicates the possible use of phenanthrene-9,10-catechol conjugates as biomarkers of human exposure to oxygenated PAH. PMID:24646012

Infrared Spectroscopy of Matrix-Isolated Polycyclic Aromatic Hydrocarbon Cations. Part 2; The Members of the Thermodynamically Most Favorable Series through Coronene

NASA Technical Reports Server (NTRS)

Hudgins, D. M.; Allamandola, L. J.

1995-01-01

Gaseous, ionized polycyclic aromatic hydrocarbons (PAHS) are thought to be responsible for a very common family of interstellar infrared emission bands. Here the near- and mid-infrared spectra of the cations of the five most thermodynamically favored PAHs up to coronene: phenanthrene, pyrene, benzo[e]pyrene, benzo-[ghi]perylene, and coronene, are presented to test this hypothesis. For those molecules that have been studied previously (pyrene, pyrene-d(sub 10), and coronene), band positions and relative intensities are in agreement. In all of these cases we report additional features. Absolute integrated absorbance values are given for the phenanthrene, perdeuteriophenanthrene, pyrene, benzo[ghi]perylene, and coronene cations. With the exception of coronene, the cation bands corresponding to the CC modes are typically 2-5 times more intense than those of the CH out-of-plane bending vibrations. For the cations, the CC stretching and CH in-plane bending modes give rise to bands that are an order of magnitude stronger than those of the neutral species, and the CH out-of-plane bends produce bands that are 5-20 times weaker than those of the neutral species. This behavior is similar to that found in most other PAH cations studied to date. The astronomical implications of these PAH cation spectra are also discussed.

Infrared Spectroscopy of Matrix-Isolated Polycyclic Aromatic Hydrocarbon Cations

NASA Technical Reports Server (NTRS)

Hudgins, D. M.; Allamandola, L. J.

1995-01-01

Gaseous, ionized polycyclic aromatic hydrocarbons (PAHs) are thought to be responsible for a very common family of interstellar infrared emission bands. Here the near- and mid-infrared spectra of the cations of the five most thermodynamically favored PAHs up to coronene: phenanthrene, pyrene, benzo(e)pyrene, benzo-(ghi)perylene, and coronene, are presented to test this hypothesis. For those molecules that have been studied previously (pyrene, pyrene-d(sub 10), and coronene), band positions and relative intensities are in agreement. In all of these cases we report additional features. Absolute integrated absorbance values are given for the phenanthrene, perdeuteriophenanthrene, pyrene, benzo(ghi]perylene, and coronene cations. With the exception of coronene, the cation bands corresponding to the CC modes are typically 2-5 times more intense than those of the CH out-of-plane bending vibrations. For the cations, the CC stretching and CH in-plane bending modes give rise to bands that are an order of magnitude stronger than those of the neutral species, and the CH out-of-plane bends produce bands that are 5-20 times weaker than those of the neutral species. This behavior is similar to that found in most other PAH cations studied to date. The astronomical implications of these PAH cation spectra are also discussed.

Temperature-dependent vibrational spectroscopy to study order-disorder transitions in charge transfer complexes

NASA Astrophysics Data System (ADS)

Isaac, Rohan; Goetz, Katelyn P.; Roberts, Drew; Jurchescu, Oana D.; McNeil, L. E.

2018-02-01

Charge-transfer (CT) complexes are a promising class of materials for the semiconductor industry because of their versatile properties. This class of compounds shows a variety of phase transitions, which are of interest because of their potential impact on the electronic characteristics. Here temperature-dependent vibrational spectroscopy is used to study structural phase transitions in a set of organic CT complexes. Splitting and broadening of infrared-active phonons in the complex formed between pyrene and pyromellitic dianhydride (PMDA) confirm the structural transition is of the order-disorder type and complement previous x-ray diffraction (XRD) results. We show that this technique is a powerful tool to characterize transitions, and apply it to a range of binary CT complexes composed of polyaromatic hyrdocarbons (anthracene, perylene, phenanthrene, pyrene, and stilbene) and PMDA. We extend the understanding of transitions in perylene-PMDA and pyrene-PMDA, and show that there are no order-disorder transitions present in anthracene-PMDA, stilbene-PMDA and phenanthrene-PMDA in the temperature range investigated here.

Anthracene + Pyrene Solid Mixtures: Eutectic and Azeotropic Character

PubMed Central

Rice, James W.; Fu, Jinxia; Suuberg, Eric M.

2010-01-01

To better characterize the thermodynamic behavior of a binary polycyclic aromatic hydrocarbon mixture, thermochemical and vapor pressure experiments were used to examine the phase behavior of the anthracene (1) + pyrene (2) system. A solid-liquid phase diagram was mapped for the mixture. A eutectic point occurs at 404 K at x1 = 0.22. A model based on eutectic formation can be used to predict the enthalpy of fusion associated with the mixture. For mixtures that contain x1 < 0.90, the enthalpy of fusion is near that of pure pyrene. This and X-ray diffraction results indicate that mixtures of anthracene and pyrene have pyrene-like crystal structures and energetics until the composition nears that of pure anthracene. Solid-vapor equilibrium studies show that mixtures of anthracene and pyrene form solid azeotropes at x1 of 0.03 and 0.14. Additionally, mixtures at x1 = 0.99 sublime at the vapor pressure of pure anthracene, suggesting that anthracene behavior is not significantly influenced by x2 = 0.01 in the crystal structure. PMID:21116474

The endophytic bacterium Serratia sp. PW7 degrades pyrene in wheat.

PubMed

Zhu, Xuezhu; Wang, Wanqing; Crowley, David E; Sun, Kai; Hao, Shupeng; Waigi, Michael Gatheru; Gao, Yanzheng

2017-03-01

This research was conducted to isolate polycyclic aromatic hydrocarbon-degrading (PAH-degrading) endophytic bacteria and investigate their potential in protecting plants against PAH contamination. Pyrene-degrading endophytic bacteria were isolated from plants grown in PAH-contaminated soil. Among these endophytic bacteria, strain PW7 (Serratia sp.) isolated from Plantago asiatica was selected to investigate the suppression of pyrene accumulation in Triticum aestivum L. In the in vitro tests, strain PW7 degraded 51.2% of the pyrene in the media within 14 days. The optimal biodegradation conditions were pH 7.0, 30 °C, and MS medium supplemented with additional glucose, maltose, sucrose, and peptones. In the in vivo tests, strain PW7 successfully colonized the roots and shoots of inoculated (E + ) wheat plants, and its colonization decreased pyrene accumulation and pyrene transportation from roots to shoots. Remarkably, the concentration of pyrene in shoots decreased much more than that in roots, suggesting that strain PW7 has the potential for protecting wheat against pyrene contamination and mitigating the threat of pyrene to human health via food consumption.

Distribution of phenanthrene between soil and an aqueous phase in the presence of anionic micelle-like amphiphilic polyurethane particles.

PubMed

Lee, Kangtaek; Choi, Heon-Sik; Kim, Ju-Young; Ahn, Ik-Sung

2003-12-12

Sorption of micelle-like amphiphilic polyurethane (APU) particles to soil was studied and compared to that of a model anionic surfactant, sodium dodecyl sulfate (SDS). Three types of APU particles with different hydrophobicity were synthesized from urethane acrylate anionomers (UAA) and used in this study. Due to the chemically cross-linked structure, APU exhibited less sorption to the soil than SDS and a greater reduction in the sorption of phenanthrene, a model soil contaminant, to the soil was observed in the presence of APU than SDS even though the solubility of phenanthrene was higher in the presence of SDS than APU. A mathematical model was developed to describe the phenanthrene distribution between soil and an aqueous phase containing APU particles. The sorption of phenanthrene to the test soil could be well described by Linear isotherm. APU sorption to the soil was successfully described by Langmuir and Freundlich isotherms. The partition of phenanthrene between water and APU were successfully explained with a single partition coefficient. The model, which accounts for the limited solubilization of phenanthrene in sorbed APU particles, successfully described the experimental data for the distribution of phenanthrene between the soil and the aqueous phase in the presence of APU.

Different effects of copper (II), cadmium (II) and phosphate on the sorption of phenanthrene on the biomass of cyanobacteria.

PubMed

Tao, Yuqiang; Li, Wei; Xue, Bin; Zhong, Jicheng; Yao, Shuchun; Wu, Qinglong

2013-10-15

Due to the large surface area and high organic carbon content of cyanobacteria, organic contaminants can be readily sorbed on cyanobacteria during algal blooms, and then be transferred to the food web. This process is likely to be affected by the coexisting metals and nutrients, however, the possible impacts remain unclear. Effects of Cu(2+), Cd(2+), and phosphate on the sorption of phenanthrene on cyanobacterial biomass collected from an algal bloom were therefore studied. Continuous decrease in phenanthrene sorption was observed in the presence of low concentrations of Cu(2+), and Cd(2+) (<0.04 mmol L(-1)), because Cu(2+) and Cd(2+) were coadsorbed with phenanthrene on the surface of cyanobacteria as suggested by scanning electron microscopy-energy dispersive X-ray (SEM-EDX) and Fourier transform infrared (FTIR) analyses. Phenanthrene sorption began to increase with the further increase in Cu(2+) concentration, but remained lower than that in the absence of Cu(2+). This increase in sorption was ascribed to the cation-π interaction between Cu(2+) and phenanthrene, as suggested by the enhanced ultraviolet absorbance at 251 nm. In contrast, sorption rebounding of phenanthrene did not occur in the presence of higher concentrations of Cd(2+). The different effects of Cu(2+) and Cd(2+) on phenanthrene sorption were attributed to that Cd(2+) required much more energy than Cu(2+) to form cation-π complexes with phenanthrene in the solutions. Phenanthrene sorption decreased continuously with the increase in phosphate concentration. Phosphate blocked the binding sites, modified the cell morphology, and increased the negative charge as well as the hydrophilicity of the cyanobacterial surface, thereby suppressing phenanthrene sorption. This study indicates that sorption of aromatic organic compounds by cyanobacteria could be significantly alerted by concentrations and properties of the coexisting transition metals and phosphates, which may subsequently affect their

Fluorene and Phenanthrene Uptake and Accumulation by Wheat, Alfalfa and Sunflower from the Contaminated Soil.

PubMed

Salehi-Lisar, Seyed Yahya; Deljoo, Somaye; Harzandi, Ahmad Mosen

2015-01-01

Polycyclic Aromatic Hydrocarbons (PAHs) are diverse organic contaminants released into the environment by both natural and anthropogenic activities. These compounds have negative impacts on plants growth and development. Although there are many reports on their existence in different parts of plant, their uptake and translocation pathways and mechanisms are not well understood yet. This paper highlights the uptake, translocation and accumulation of PAHs by wheat, sunflower and alfalfa through an experimental study under controlled conditions. Seeds were cultivated in a soil containing 50 mg/kg of phenanthrene and fluorene and their concentrations in plants roots and shoots were determined using a gas chromatograph after 7 and 14 days. The results showed that phenanthrene and fluorene concentrations in the treated plants were increased over the time. PAHs bioavailability was time and species dependent and generally, phenanthrene uptake and translocation was faster than that of fluorene, probably due to their higher Kow. Fluorene tended to accumulate in roots, but phenanthrene was transported to aerial parts of plants.

Preparation and characterization of a novel graphene/biochar composite for aqueous phenanthrene and mercury removal.

PubMed

Tang, Jingchun; Lv, Honghong; Gong, Yanyan; Huang, Yao

2015-11-01

A graphene/biochar composite (G/BC) was synthesized via slow pyrolysis of graphene (G) pretreated wheat straw, and tested for the sorption characteristics and mechanisms of representative aqueous contaminants (phenanthrene and mercury). Structure and morphology analysis showed that G was coated on the surface of biochar (BC) mainly through π-π interactions, resulting in a larger surface area, more functional groups, greater thermal stability, and higher removal efficiency of phenanthrene and mercury compared to BC. Pseudo second-order model adequately simulated sorption kinetics, and sorption isotherms of phenanthrene and mercury were simulated well by dual-mode and BET models, respectively. FTIR and SEM analysis suggested that partitioning and surface sorption were dominant mechanisms for phenanthrene sorption, and that surface complexation between mercury and C-O, CC, -OH, and OC-O functional groups was responsible for mercury removal. The results suggested that the G/BC composite is an efficient, economic, and environmentally friendly multifunctional adsorbent for environmental remediation. Copyright © 2015 Elsevier Ltd. All rights reserved.

Evidence of polycyclic aromatic hydrocarbon biodegradation in a contaminated aquifer by combined application of in situ and laboratory microcosms using (13)C-labelled target compounds.

PubMed

Bahr, Arne; Fischer, Anko; Vogt, Carsten; Bombach, Petra

2015-02-01

The number of approaches to evaluate the biodegradation of polycyclic aromatic hydrocarbons (PAHs) within contaminated aquifers is limited. Here, we demonstrate the applicability of a novel method based on the combination of in situ and laboratory microcosms using (13)C-labelled PAHs as tracer compounds. The biodegradation of four PAHs (naphthalene, fluorene, phenanthrene, and acenaphthene) was investigated in an oxic aquifer at the site of a former gas plant. In situ biodegradation of naphthalene and fluorene was demonstrated using in situ microcosms (BACTRAP(®)s). BACTRAP(®)s amended with either [(13)C6]-naphthalene or [(13)C5/(13)C6]-fluorene (50:50) were incubated for a period of over two months in two groundwater wells located at the contaminant source and plume fringe, respectively. Amino acids extracted from BACTRAP(®)-grown cells showed significant (13)C-enrichments with (13)C-fractions of up to 30.4% for naphthalene and 3.8% for fluorene, thus providing evidence for the in situ biodegradation and assimilation of those PAHs at the field site. To quantify the mineralisation of PAHs, laboratory microcosms were set up with BACTRAP(®)-grown cells and groundwater. Naphthalene, fluorene, phenanthrene, or acenaphthene were added as (13)C-labelled substrates. (13)C-enrichment of the produced CO2 revealed mineralisation of between 5.9% and 19.7% for fluorene, between 11.1% and 35.1% for acenaphthene, between 14.2% and 33.1% for phenanthrene, and up to 37.0% for naphthalene over a period of 62 days. Observed PAH mineralisation rates ranged between 17 μg L(-1) d(-1) and 1639 μg L(-1) d(-1). The novel approach combining in situ and laboratory microcosms allowed a comprehensive evaluation of PAH biodegradation at the investigated field site, revealing the method's potential for the assessment of PAH degradation within contaminated aquifers. Copyright © 2014 Elsevier Ltd. All rights reserved.

Human biomonitoring of polycyclic aromatic hydrocarbonsand metals in the general population residing near the municipal solid waste incinerator of Modena, Italy.

PubMed

Gatti, Maria Giulia; Bechtold, Petra; Campo, Laura; Barbieri, Giovanna; Quattrini, Giulia; Ranzi, Andrea; Sucato, Sabrina; Olgiati, Luca; Polledri, Elisa; Romolo, Michael; Iacuzio, Laura; Carrozzi, Giuliano; Lauriola, Paolo; Goldoni, Carlo A; Fustinoni, Silvia

2017-11-01

A cross-sectional biomonitoring study was carried out to investigate exposure to incinerator emission in relation to the body burden of selected biomarkers in the population living around the plant. Approximately 500 people, aged 18-69 yrs, living within 4 km from the incinerator were randomly selected form the population register. Exposure was measured through fall-out maps of particulate matter (PM), used as tracer for incinerator emissions. Ten metabolized polycyclic aromatic hydrocarbons (PAHs), from naphthalene to chrysene, 1-hydroxypyrene and twelve metals (Cd, Cr, Cu, Hg, Ni, Pb, Ni, Zn, V, Tl, As, Sn) were measured in spot urine samples. Confounders, such as diet, smoking, traffic, occupation and personal characteristics were assessed by questionnaires and objective measurements, and included into multivariate linear regression models. Metal concentrations in urine were in line with or higher than Italian reference limits, besides Cr and V with more than twofold concentrations. Metal levels did not show clear association to exposure categories. Most abundant PAHs were naphthalene (median 26.2 ng/L) and phenanthrene (7.4 ng/L). All PAHs, but benz[a]anthracene and 1-hydroxypyrene, were found in more than 52% of samples, and included in regression models. Significant associations between urinary PAHs and exposure were found, strong for fluorene, and weaker for naphthalene, fluoranthene and pyrene. Results were confirmed by sensitivity analyses. Correlation with variables reported in literature were observed. The study indicates that the emissions were very low and highlights that specific urinary PAHs provided useful information about the internal dose arising from incinerator emission. Copyright © 2017 Elsevier Ltd. All rights reserved.

IRIS Toxicological Review of Benzo[a]pyrene (Final Report) ...

EPA Pesticide Factsheets

EPA has finalized the Integrated Risk Information System (IRIS) assessment of benzo[a]pyrene. This assessment addresses the potential cancer and noncancer human health effects from long-term exposure to benzo[a]pyrene. Now final, this assessment will update the toxicological information on benzo[a]pyrene posted in 1987. EPA’s program and regional offices may use this assessment to inform decisions to protect human health. EPA is undertaking an update of the Integrated Risk Information System (IRIS) health assessment for benzo[a]pyrene (BaP). The outcome of this project is an updated Toxicological Review and IRIS Summary for BaP that will be entered into the IRIS database.

Aromatic hydrocarbon biodegradation activates neutral lipid biosynthesis in oleaginous yeast.

PubMed

Deeba, Farha; Pruthi, Vikas; Negi, Yuvraj S

2018-05-01

In this study, the biodegradation ability of oleaginous yeast Cryptococcus psychrotolerans IITRFD for aromatic hydrocarbons (AHs) was investigated. It was found to completely degrade range of AHs such as 1 g/L phenol, 0.75 g/L naphthalene, 0.50 g/L anthracene and 0.50 g/L pyrene with lipid productivity (g/L/h) of 0.0444, 0.0441, 0.0394 and 0.0383, respectively. This work demonstrated the ring cleavage pathways of AHs by this yeast which follow ortho route for phenol and naphthalene while meta route for anthracene and pyrene degradation. The end products generated during biodegradation of AHs are feed as precursors for de novo triacylglycerols (TAG) biosynthesis pathway of oleaginous yeast. A high quantity of lipid content (46.54%) was observed on phenol as compared to lipid content on naphthalene (46.38%), anthracene (44.97%) and pyrene (44.16%). The lipid profile revealed by GC-MS analysis shows elevated monounsaturated fatty acid (MUFA) content with improved biodiesel quality. Copyright © 2018 Elsevier Ltd. All rights reserved.

Contamination of polycyclic aromatic hydrocarbons (PAHs) in surface sediments and plants of mangrove swamps in Shenzhen, China.

PubMed

Li, Fenglan; Zeng, Xiaokang; Yang, Junda; Zhou, Kai; Zan, Qijie; Lei, Anping; Tam, Nora F Y

2014-08-30

The concentrations of 16 individual and total polycyclic aromatic hydrocarbons (∑PAHs) in sediments, roots and leaves of three mangrove swamps in Shenzhen, China, namely Futian, Baguang and Waterlands, were determined. The mean concentration of ∑PAHs in Futian (4480 ng g(-1)) was significantly higher than that in Baguang (1262 ng g(-1)) and Waterlands (2711 ng g(-1)). Among the 16 PAHs, the concentration of naphthalene was the highest. Based on the ratios of phenanthrene/anthracene and fluoranthene/pyrene, PAHs in Futian and Waterlands came from petrogenic and pyrolytic sources, while Baguang was mainly from pyrolytic. More PAHs were accumulated in leaves, as reflected by its higher mean concentration of ∑PAHs (3697 ng g(-1)) and bioconcentration factor of PAHs (BCF) (>1.5) than that in roots. The BCF values in plants collected from Futian were significantly higher than that from Waterlands. These results indicated that more attention should be paid to the PAH contamination in Futian. Copyright © 2014 Elsevier Ltd. All rights reserved.

Influence of fuel composition on polycyclic aromatic hydrocarbon emissions from a fleet of in-service passenger cars

NASA Astrophysics Data System (ADS)

Lim, McKenzie C. H.; Ayoko, Godwin A.; Morawska, Lidia.; Ristovski, Zoran D.; Jayaratne, E. Rohan

The composition of exhaust emissions from eight in-service passenger cars powered by liquefied petroleum gas (LPG) and unleaded petrol (ULP) were measured on a chassis dynamometer at two driving speeds (60 and 80 km h -1) with the aims of evaluating their polycyclic aromatic hydrocarbon (PAH) contents and investigating the effects of the type of fuel on vehicle performance, ambient air quality and associated health risks. Naphthalene, fluorene, phenanthrene, anthracene, pyrene, chrysene, benzo(a)anthracene and benzo(b)fluoranthene were the most prominent PAHs emitted by both ULP and LPG powered cars. The total emission factors of PAHs from LPG cars were generally lower than (but statistically comparable with) those of ULP cars. Similarly, the total BAP eq of the PAHs emitted by LPG cars were lower than those from ULP cars. Multi-criteria decision making (MCDM) methods showed that cars powered by LPG fuel performed better than those powered by ULP fuel in term of PAH levels. The implications of these observations on the advantages and disadvantages of using ULP and LPG fuels are discussed.

Comparison between Soil- and Biochar-Derived Humic Acids: Composition, Conformation, and Phenanthrene Sorption.

PubMed

Jin, Jie; Sun, Ke; Yang, Yan; Wang, Ziying; Han, Lanfang; Wang, Xiangke; Wu, Fengchang; Xing, Baoshan

2018-02-20

Biochar-derived organic matter (BDOM) plays an important role in determining biochar's application potential in soil remediation. However, little is known about the physicochemical properties of BDOM and its sorption of hydrophobic organic compounds (HOCs). Humic acids (HAs) were extracted from oxidized biochars produced from plant straws and animal manures at 450 °C, and their sorption of phenanthrene, a representative of HOCs, was investigated. The organic carbon recovery of biochar-derived HAs (BDHAs) was 13.9-69.3%. The 13 C NMR spectra of BDHAs mainly consisted of aromatic and carboxylic C, while those of soil-derived HAs (SDHAs) contained abundant signals in aliphatic region. BDHAs and SDHAs had comparable CO 2 cumulative surface areas. BDHAs were found to exhibit higher phenanthrene sorption than SDHAs. After the removal of amorphous aromatic components, the logK oc values of BDHAs were significantly decreased, implying that amorphous aromatic C regulated phenanthrene sorption by BDHAs. In contrast, aliphatic moieties dominated phenanthrene sorption by SDHAs, as evidenced by the enhanced sorption after the removal of amorphous aromatics. This study clearly demonstrated the contrasting characteristics and sorption behaviors of BDHA and SDHA, indicating that biochar addition and subsequent weathering could greatly affect native organic matter properties and the fate of HOCs in biochar-amended soils.

Toxicity and photoactivation of PAH mixtures in marine sediment

DOE Office of Scientific and Technical Information (OSTI.GOV)

Swartz, R.; Ferraro, S.; Lamberson, J.

1995-12-31

The toxicity and toxicological photoactivation of mixtures of sediment-associated fluoranthene, phenanthrene, pyrene, and acenaphthene were determined using standard 10 d sediment toxicity tests with the marine amphipod, Rhepoxynius abronius. The four PAHs were spiked into sediment in a concentration series of either single compounds or an equitoxic mixture. Spiked sediment was stored at 4 C for 28 d before testing. Toxicity tests were conducted under fluorescent lighting. Survivors after 10 d in PAH-contaminated sediment were exposed for 1 h to UV light in the absence of sediment and then tested for their ability to bury in clean sediment. The 10more » d LC50s for single PAHs were 3.3, 2.2, 2.8, and 2.3 mg/g oc for fluoranthene, phenanthrene, pyrene, and acenaphthene, respectively. These LC50s were used to calculate the sum of toxic units ({Sigma}TU) of the four PAHs in the equitoxic mixture treatments. The {Sigma}TU LC50 was then calculated for the mixture treatments. If the toxicological interaction of the four PAHs in the mixture was additive, the {Sigma}TU LC50 should equal 1.0. The observed {Sigma}TU LC50 in the mixture was 1.55, indicating the interaction was slightly less than additive. UV enhancement of toxic effects of individual PAHs was correctly predicted by photophysical properties, i.e. pyrene and fluoranthene were photoactivated and phenanthrene and acenaphthene were not. UV effects in the mixture of four PAHs can be explained by the photoactivation of pyrene and fluoranthene alone.« less

Modeling of experimental data on trace elements and organic compounds content in industrial waste dumps.

PubMed

Smoliński, Adam; Drobek, Leszek; Dombek, Václav; Bąk, Andrzej

2016-11-01

The main objective of the study presented was to investigate the differences between 20 mine waste dumps located in the Silesian Region of Poland and Czech Republic, in terms of trace elements and polycyclic aromatic hydrocarbons contents. The Principal Component Analysis and Hierarchical Clustering Analysis were applied in exploration of the studied data. Since the data set was affected by outlying objects, the employment of a relevant analysis strategy was necessary. The final PCA model was constructed with the use of the Expectation-Maximization iterative approach preceded by a correct identification of outliers. The analysis of the experimental data indicated that three mine waste dumps located in Poland were characterized by the highest concentrations of dibenzo(g,h,i)anthracene and benzo(g,h,i)perylene, and six objects located in Czech Republic and three objects in Poland were distinguished by high concentrations of chrysene and indeno (1.2.3-cd) pyrene. Three of studied mine waste dumps, one located in Czech Republic and two in Poland, were characterized by low concentrations of Cr, Ni, V, naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthen, benzo(a)anthracene, chrysene, benzo (b) fluoranthene, benzo (k) fluoranthene, benzo(a)pyrene, dibenzo(g,h,i)anthracene, benzo(g,h,i)perylene and indeno (1.2.3-cd) pyrene in comparison with the remaining ones. The analysis contributes to the assessment and prognosis of ecological and health risks related to the emission of trace elements and organic compounds (PAHs) from the waste dumps examined. No previous research of similar scope and aims has been reported for the area concerned. Copyright © 2016 Elsevier Ltd. All rights reserved.

Polycyclic Aromatic Hydrocarbons In Edible Mushrooms from Niger Delta, Nigeria: Carcinogenic and Non-Carcinogenic Health Risk Assessment

PubMed

Igbiri, Sorbari; Udowelle, Nnaemeka Arinze; Ekhator, Osazuwa Clinton; Asomugha, Rose Ngozi; Igweze, Zelinjo Nkeiruka; Orisakwe, Orish Ebere

2017-02-01

In the oil-rich Niger Delta, hydrocarbon pollution and oil spillages, gas flaring and sundry anthropogenic activities constitute sources of polycyclic aromatic hydrocarbons (PAHs), with food contamination playing a major role in human exposure. In this study we assessed PAH levels in wild and cultivated edible mushroom species consumed by the general population from the oil producing Niger Delta, Nigeria. The concentrations of USEPA-16 PAHs were determined by gas chromatography and carcinogenic and non-carcinogenic health risks were calculated. The concentrations of USEPA-16 PAHs ranged from 0.02 mg/kg – 3.37 mg/kg. The dietary intake of carcinogenic and non-carcinogenic USEPA-16 PAHs (Naphthalene, Acenaphthylene, Acenaphthene, Anthracene, Phenanthrene, Flourene, Flouranthene, Pyrene, Benzo[a]Anthracene, Chrysene, Benzo[a]Pyrene, Benzo[b]Flouranthene, Benzo[K]Flouranthene, Benzo[g,h,i] Perylene, Dibenz[a,h]Anthracene and Ideno[1,2,3-cd]Pyrene) for adults, adolescents and seniors ranged from 0.00 – 0.05 mg/kg/day, 0.00 – 0.06 mg/kg/day and 0.00 – 0.07 mg/kg/day. The BaPeq ranged from 0.02 – 2.76 with margin of exposure MOE values of BaP ranging from 3,500,000 to 700,000, 3,500,000 and 3,500,000 to 7,000,000 for adults, adolescents and seniors indicating very insignificant health risk. The incremental lifetime cancer risk was within the safe range of 1.56x10-8 – 1.73x10-6 with the highest calculated risk found for wild Pleurotus ostreatus mushroom species from the study area. Creative Commons Attribution License

Extended Hansen solubility approach: naphthalene in individual solvents.

PubMed

Martin, A; Wu, P L; Adjei, A; Beerbower, A; Prausnitz, J M

1981-11-01

A multiple regression method using Hansen partial solubility parameters, delta D, delta p, and delta H, was used to reproduce the solubilities of naphthalene in pure polar and nonpolar solvents and to predict its solubility in untested solvents. The method, called the extended Hansen approach, was compared with the extended Hildebrand solubility approach and the universal-functional-group-activity-coefficient (UNIFAC) method. The Hildebrand regular solution theory was also used to calculate naphthalene solubility. Naphthalene, an aromatic molecule having no side chains or functional groups, is "well-behaved', i.e., its solubility in active solvents known to interact with drug molecules is fairly regular. Because of its simplicity, naphthalene is a suitable solute with which to initiate the difficult study of solubility phenomena. The three methods tested (Hildebrand regular solution theory was introduced only for comparison of solubilities in regular solution) yielded similar results, reproducing naphthalene solubilities within approximately 30% of literature values. In some cases, however, the error was considerably greater. The UNIFAC calculation is superior in that it requires only the solute's heat of fusion, the melting point, and a knowledge of chemical structures of solute and solvent. The extended Hansen and extended Hildebrand methods need experimental solubility data on which to carry out regression analysis. The extended Hansen approach was the method of second choice because of its adaptability to solutes and solvents from various classes. Sample calculations are included to illustrate methods of predicting solubilities in untested solvents at various temperatures. The UNIFAC method was successful in this regard.

4-(Naphthalene-2-carboxamido)­pyridin-1-ium thio­cyanate–N-(pyridin-4-yl)naphthalene-2-carboxamide (1/1)

PubMed Central

Saeed, Sohail; Rashid, Naghmana; Butcher, Ray J.; Öztürk Yildirim, Sema; Hussain, Rizwan

2012-01-01

The asymmetric unit of the title compound, C16H13N2O+·NCS−·C16H12N2O, contains two N-(pyridin-4-yl)naphthalene-2-carboxamide mol­ecules, both are partially protonated in the pyridine moiety, i.e. the H atom attached to the pyridine N atom is partially occupied with an occupancy factor of 0.61 (3) and 0.39 (3), respectively. In the crystal, protonated and neutral N-(pyridin-4-yl)naphthalene-2-carboxamide mol­ecules are linked by N—H⋯N hydrogen bonding; the thio­cyanate counter-ion links with both protonated and neutral N-(pyridin-4-yl)naphthalene-2-carboxamide mol­ecules via N—H⋯S and N—H⋯N hydrogen bonding. The dihedral angles between the pyridine ring and naphthalene ring systems are 11.33 (6) and 9.51 (6)°, respectively. π–π stacking is observed in the crystal structure, the shortest centroid–centroid distance being 3.5929 (8) Å. The crystal structure was determined from a nonmerohedral twin {ratio of the twin components = 0.357 (1):0.643 (1) and twin law [-100 0-10 -101]}. PMID:23125774

Effect of short-chain organic acids on the enhanced desorption of phenanthrene by rhamnolipid biosurfactant in soil-water environment.

PubMed

An, Chun-jiang; Huang, Guo-he; Wei, Jia; Yu, Hui

2011-11-01

This study investigated the effect of short-chain organic acids on biosurfactant-enhanced mobilization of phenanthrene in soil-water system. The desorption characteristics of phenanthrene by soils were assessed in the presence of rhamnolipid and four SCOAs, including acetic acid, oxalic acid, tartaric acid and citric acid. The tests with rhamnolipid and different organic acids could attain the higher desorption of phenanthrene compared to those with only rhamnolipid. Among the different combinations, the series with rhamnolipid and citric acid exhibited more significant effect on the desorption performance. The removal of phenanthrene using rhamnolipid and SCOAs gradually increased as the SCOA concentration increased up to a concentration of 300 mmol/L. The effects of pH, soil dissolved organic matter and ionic strength were further evaluated in the presence of both biosurfactant and SCOAs. The results showed that the extent of phenanthrene desorption was more significant at pH 6 and 9. Desorption of phenanthrene was relatively lower in the DOM-removed soils with the addition of biosurfactant and SCOAs. The presence of more salt ions made phenanthrene more persistent on the solid phase and adversely affected its desorption from contaminated soil. The results from this study may have important implications for soil washing technologies used to treat PAH-contaminated soil and groundwater. Copyright © 2011 Elsevier Ltd. All rights reserved.

Comparative Biochemistry and Metabolism. Part 2. Naphthalene Lung Toxicity.

DTIC Science & Technology

1985-11-01

Metabolites to Intra- and Extracellular Proteins .............. ........ 18 Thiol Status in Isolated Hepatocytes Incubated with Naphthalene or Menadione ...Viabilities of isolated hepatocytes incubated with menadione and varying concentrations of n aphthalene...23 15 Intracellular reduced glutathione levels in hepa- tocytes incubated in the presence of menadione or varying concentrations of naphthalene

Yields of Bacterial Cells from Hydrocarbons

PubMed Central

Wodzinski, Richard S.; Johnson, Marvin J.

1968-01-01

A strain of Nocardia and one of Pseudomonas, both isolated on pristane (2,6,10,14-tetramethylpentadecane), gave cell yields of approximately 100% on n-octadecane and pristane. Both organisms grew more rapidly on the n-octadecane than on the pristane. A mixed culture, isolated on 3-methylheptane, whose two components were identified as species of Pseudomonas and of Nocardia, gave approximately 100% cell yields and grew with generation times of about 5 hr on n-heptane, n-octane, and 2-methylheptane. The generation time on 3-methylheptane was 8.6 hr and the cell yield was only 79%. A strain of Pseudomonas isolated from naphthalene enrichments and one from phenanthrene enrichments both gave a cell yield of 50% on naphthalene. The phenanthrene isolate gave a cell yield of 40% on phenanthrene. A Nocardia species isolated on benzene gave a 79% cell yield on benzene. The generation times of the bacteria isolated on aromatic hydrocarbons were related to the solubility of the aromatic hydrocarbons on which they were grown; the more insoluble hydrocarbons gave slower growth. PMID:5726161

Toxicity of Naphthalene and Benzene on Tribollium castaneum Herbst.

PubMed

Pajaro-Castro, Nerlis; Caballero-Gallardo, Karina; Olivero-Verbel, Jesus

2017-06-21

Naphthalene and benzene are widely-used volatile organic compounds. The aim of this research was to examine the toxicological effects of naphthalene and benzene against Tribolium castaneum as an animal model. Adult insects were exposed to these aromatic compounds to assess mortality after 4-48 h of exposure. The lethal concentration 50 (LC 50 ) for naphthalene, naphthalin, and benzene were 63.6 µL/L, 20.0 µL/L, and 115.9 µL/L in air, respectively. Real-time polymerase chain reaction (PCR) analysis revealed expression changes in genes related to oxidative stress and metabolism [Glutathione S-Transferase (Gst), and Cytochrome P450 6BQ8 (Cyp6bq8)]; reproduction and metamorphosis [Hormone receptor in 39-like protein (Hr39), Ecdysone receptor: (Ecr), and Chitin synthase 2 (Chs2)]; and neurotransmission [Histamine-gated chloride channel 2 (Hiscl2)] in insects exposed for 4 h to 70.2 µL/L naphthalene. Adults exposed to benzene (80 µL/L; 4 h) overexpressed genes related to neurotransmission [GABA-gated anion channel (Rdl), Hiscl2, and GABA-gated ion channel (Grd)]; reproduction and metamorphosis [Ultraspiracle nuclear receptor (USP), Ecr; and Hr39]; and development (Chs2). The data presented here provides evidence that naphthalene and benzene inhalation are able to induce alterations on reproduction, development, metamorphosis, oxidative stress, metabolism, neurotransmission, and death of the insect.

The phn Genes of Burkholderia sp. Strain RP007 Constitute a Divergent Gene Cluster for Polycyclic Aromatic Hydrocarbon Catabolism

PubMed Central

Laurie, Andrew D.; Lloyd-Jones, Gareth

1999-01-01

Cloning and molecular ecological studies have underestimated the diversity of polycyclic aromatic hydrocarbon (PAH) catabolic genes by emphasizing classical nah-like (nah, ndo, pah, and dox) sequences. Here we report the description of a divergent set of PAH catabolic genes, the phn genes, which although isofunctional to the classical nah-like genes, show very low homology. This phn locus, which contains nine open reading frames (ORFs), was isolated on an 11.5-kb HindIII fragment from phenanthrene-degrading Burkholderia sp. strain RP007. The phn genes are significantly different in sequence and gene order from previously characterized genes for PAH degradation. They are transcribed by RP007 when grown at the expense of either naphthalene or phenanthrene, while in Escherichia coli the recombinant phn enzymes have been shown to be capable of oxidizing both naphthalene and phenanthrene to predicted metabolites. The locus encodes iron sulfur protein α and β subunits of a PAH initial dioxygenase but lacks the ferredoxin and reductase components. The dihydrodiol dehydrogenase of the RP007 pathway, PhnB, shows greater similarity to analogous dehydrogenases from described biphenyl pathways than to those characterized from naphthalene/phenanthrene pathways. An unusual extradiol dioxygenase, PhnC, shows no similarity to other extradiol dioxygenases for naphthalene or biphenyl oxidation but is the first member of the recently proposed class III extradiol dioxygenases that is specific for polycyclic arene diols. Upstream of the phn catabolic genes are two putative regulatory genes, phnR and phnS. Sequence homology suggests that phnS is a LysR-type transcriptional activator and that phnR, which is divergently transcribed with respect to phnSFECDAcAdB, is a member of the ς54-dependent family of positive transcriptional regulators. Reverse transcriptase PCR experiments suggest that this gene cluster is coordinately expressed and is under regulatory control which may involve

Hydration of a Large Anionic Charge Distribution - Naphthalene-Water Cluster Anions

NASA Astrophysics Data System (ADS)

Weber, J. Mathias; Adams, Christopher L.

2010-06-01

We report the infrared spectra of anionic clusters of naphthalene with up to three water molecules. Comparison of the experimental infrared spectra with theoretically predicted spectra from quantum chemistry calculations allow conclusions regarding the structures of the clusters under study. The first water molecule forms two hydrogen bonds with the π electron system of the naphthalene moiety. Subsequent water ligands interact with both the naphthalene and the other water ligands to form hydrogen bonded networks, similar to other hydrated anion clusters. Naphthalene-water anion clusters illustrate how water interacts with negative charge delocalized over a large π electron system. The clusters are interesting model systems that are discussed in the context of wetting of graphene surfaces and polyaromatic hydrocarbons.

Combination of degradation pathways for naphthalene utilization in Rhodococcus sp. strain TFB

PubMed Central

Tomás-Gallardo, Laura; Gómez-Álvarez, Helena; Santero, Eduardo; Floriano, Belén

2014-01-01

Rhodococcus sp. strain TFB is a metabolic versatile bacterium able to grow on naphthalene as the only carbon and energy source. Applying proteomic, genetic and biochemical approaches, we propose in this paper that, at least, three coordinated but independently regulated set of genes are combined to degrade naphthalene in TFB. First, proteins involved in tetralin degradation are also induced by naphthalene and may carry out its conversion to salicylaldehyde. This is the only part of the naphthalene degradation pathway showing glucose catabolite repression. Second, a salicylaldehyde dehydrogenase activity that converts salicylaldehyde to salicylate is detected in naphthalene-grown cells but not in tetralin-or salicylate-grown cells. Finally, we describe the chromosomally located nag genes, encoding the gentisate pathway for salicylate conversion into fumarate and pyruvate, which are only induced by salicylate and not by naphthalene. This work shows how biodegradation pathways in Rhodococcus sp. strain TFB could be assembled using elements from different pathways mainly because of the laxity of the regulatory systems and the broad specificity of the catabolic enzymes. PMID:24325207

Phase Behavior of Pyrene and Vinyl Polymers with Aromatic Side Groups

DOE Office of Scientific and Technical Information (OSTI.GOV)

Kangovi, Gagan N.; Lee, Sangwoo

The phase behavior and thermodynamic properties of mixtures of pyrene and model vinyl polymers with and without aromatic side groups are investigated using differential scanning calorimetry (DSC) measurements. The melting temperature and associated heat of melting of the pyrene crystals in the mixtures are utilized to extract the effective interaction parameters χ and the composition of polymer-rich phases, respectively. The χ of pyrene mixed with polymers with aromatic side groups investigated in this study, polystyrene, poly(2-vinylpyridine), and poly(3-vinylanisole), is less than 0.5 at the melting point of the pyrene crystals, suggesting that pyrene and the polymers with aromatic sides groupsmore » are enthalpically compatible, likely due to aromatic π–π interactions. In contrast, the χ of pyrene mixed with poly(1,4-isoprene) or poly(ethylene-alt-propylene) is larger than 0.5. The DSC measurements also enable characterization of the composition of polymer-rich phases. Interestingly, the polymers with aromatic side groups are found to have more pronounced miscibility with pyrene at symmetric compositions.« less

Isolation, plant colonization potential, and phenanthrene degradation performance of the endophytic bacterium Pseudomonas sp. Ph6-gfp

PubMed Central

Sun, Kai; Liu, Juan; Gao, Yanzheng; Jin, Li; Gu, Yujun; Wang, Wanqing

2014-01-01

This investigation provides a novel method of endophyte-aided removal of polycyclic aromatic hydrocarbons (PAHs) from plant bodies. A phenanthrene-degrading endophytic bacterium Pseudomonas sp. Ph6 was isolated from clover (Trifolium pratense L.) grown in a PAH-contaminated site. After being marked with the GFP gene, the colonization and distribution of strain Ph6-gfp was directly visualized in plant roots, stems, and leaves for the first time. After ryegrass (Lolium multiflorum Lam.) roots inoculation, strain Ph6-gfp actively and internally colonized plant roots and transferred vertically to the shoots. Ph6-gfp had a natural capacity to cope with phenanthrene in vitro and in planta. Ph6-gfp degraded 81.1% of phenanthrene (50 mg·L−1) in a culture solution within 15 days. The inoculation of plants with Ph6-gfp reduced the risks associated with plant phenanthrene contamination based on observations of decreased concentration, accumulation, and translocation factors of phenanthrene in ryegrass. Our results will have important ramifications in the assessment of the environmental risks of PAHs and in finding ways to circumvent plant PAH contamination. PMID:24964867

Quantifying the biodegradation of phenanthrene by Pseudomonas stutzeri P16 in the presence of a nonionic surfactant.

PubMed Central

Grimberg, S J; Stringfellow, W T; Aitken, M D

1996-01-01

The low water solubility of polycyclic aromatic hydrocarbons is believed to limit their availability to microorganisms, which is a potential problem for bioremediation of polycyclic aromatic hydrocarbon-contaminated sites. Surfactants have been suggested to enhance the bioavailability of hydrophobic compounds, but both negative and positive effects of surfactants on biodegradation have been reported in the literature. Earlier, we presented mechanistic models of the effects of surfactants on phenanthrene dissolution and on the biodegradation kinetics of phenanthrene solubilized in surfactant micelles. In this study, we combined the biodegradation and dissolution models to quantify the influence of the surfactant Tergitol NP-10 on biodegradation of solid-phase phenanthrene by Pseudomonas stutzeri P16. Although micellized phenanthrene does not appear to be available directly to the bacterium, the ability of the surfactant to increase the phenanthrene dissolution rate resulted in an overall increase in bacterial growth rate in the presence of the surfactant. Experimental observations could be predicted well by the derived model with measured biokinetic and dissolution parameters. The proposed model therefore can serve as a base case for understanding the physical-chemical effects of surfactants on nonaqueous hydrocarbon bioavailability. PMID:8779577

ASSOCIATION BETWEEN MUTATION SPECTRUM AND PERSISTENT DNA ADDUCT PROFILE IN SALMONELLA FOR BENZO[A]PYRENE AND DIBENZO[A]PYRENE

EPA Science Inventory

Dibenzo[a,l]pyrene (DB[a1]P) is less prevalent in the environment but 100-200X more carcinogenic in rodents than benzo[a]pyrene (B[a]P) .B[a]P induces most of its adducts on G, whereas DB[a,1]P produces most its adducts on A. Using the Salmonella mutagenicity assay, we have exami...

Bacterial chemotaxis along vapor-phase gradients of naphthalene.

PubMed

Hanzel, Joanna; Harms, Hauke; Wick, Lukas Y

2010-12-15

The role of bacterial growth and translocation for the bioremediation of organic contaminants in the vadose zone is poorly understood. Whereas air-filled pores restrict the mobility of bacteria, diffusion of volatile organic compounds in air is more efficient than in water. Past research, however, has focused on chemotactic swimming of bacteria along gradients of water-dissolved chemicals. In this study we tested if and to what extent Pseudomonas putida PpG7 (NAH7) chemotactically reacts to vapor-phase gradients forming above their swimming medium by the volatilization from a spot source of solid naphthalene. The development of an aqueous naphthalene gradient by air-water partitioning was largely suppressed by means of activated carbon in the agar. Surprisingly, strain PpG7 was repelled by vapor-phase naphthalene although the steady state gaseous concentrations were 50-100 times lower than the aqueous concentrations that result in positive chemotaxis of the same strain. It is thus assumed that the efficient gas-phase diffusion resulting in a steady, and possibly toxic, naphthalene flux to the cells controlled the chemotactic reaction rather than the concentration to which the cells were exposed. To our knowledge this is the first demonstration of apparent chemotactic behavior of bacteria in response to vapor-phase effector gradients.

21 CFR 172.824 - Sodium mono- and dimethyl naphthalene sulfonates.

Code of Federal Regulations, 2010 CFR

2010-04-01

... SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Multipurpose Additives § 172.824 Sodium mono- and dimethyl naphthalene sulfonates. The food additive sodium mono- and dimethyl naphthalene sulfonates may be safely used in...

Comparative Biochemistry and Metabolism: Part 2. Naphthalene Lung Toxicity

DTIC Science & Technology

1984-10-14

naphthalene, produces a highly selective lesion of the pulmonary bronchiolar epithelium in mice. This lesion appears to depend upon the cytochrome P450...predominating. The rates of metabolism were lower than in rodent lung and there were marked interindividual differences. Pulmonary microsome...54 Effect of Cobalt Protoporphyrin on Naphthalene and 2-Methylnaphthalene-Induced Pulmonary Bronchiolar Necrosis

Sources, concentrations, and risks of naphthalene in indoor and outdoor air.

PubMed

Batterman, S; Chin, J-Y; Jia, C; Godwin, C; Parker, E; Robins, T; Max, P; Lewis, T

2012-08-01

Naphthalene is a ubiquitous pollutant, and very high concentrations are sometimes encountered indoors when this chemical is used as a pest repellent or deodorant. This study describes the distribution and sources of vapor-phase naphthalene concentrations in four communities in southeast Michigan, USA. Outdoors, naphthalene was measured in the communities and at a near-road site. Indoors, naphthalene levels were characterized in 288 suburban and urban homes. The median outdoor concentration was 0.15 μg/m(3), and a modest contribution from rush-hour traffic was noted. The median indoor long-term concentration was 0.89 μg/m(3), but concentrations were extremely skewed and 14% of homes exceeded 3 μg/m(3), the chronic reference concentration for non-cancer effects, 8% exceeded 10 μg/m(3), and levels reached 200 μg/m(3). The typical excess individual lifetime cancer risk was about 10(-4) and reached 10(-2) in some homes. Important sources include naphthalene's use as a pest repellent and deodorant, migration from attached garages and, to lesser extents, cigarette smoke and vehicle emissions. Excessive use as a repellent caused the highest concentrations. Naphthalene presents high risks in a subset of homes, and policies and actions to reduce exposures, for example, sales bans or restrictions, improved labeling, and consumer education, should be considered. Long-term average concentrations of naphthalene in most homes fell into the 0.2-1.7 μg/m(3) range reported as representative in earlier studies. The highly skewed distribution of concentrations results in a subset of homes with elevated concentrations and health risks that greatly exceed US EPA and World Health Organization (WHO) guidelines. The most important indoor source is the use of naphthalene as a pest repellant or deodorant; secondary sources include presence of an attached garage, cigarette smoking, and outdoor sources. House-to-house variation was large, reflecting differences among the residences and

Unraveling the early molecular and physiological mechanisms involved in response to phenanthrene exposure.

PubMed

Dumas, Anne-Sophie; Taconnat, Ludivine; Barbas, Evangelos; Rigaill, Guillem; Catrice, Olivier; Bernard, Delphine; Benamar, Abdelilah; Macherel, David; El Amrani, Abdelhak; Berthomé, Richard

2016-10-21

Higher plants have to cope with increasing concentrations of pollutants of both natural and anthropogenic origin. Given their capacity to concentrate and metabolize various compounds including pollutants, plants can be used to treat environmental problems - a process called phytoremediation. However, the molecular mechanisms underlying the stabilization, the extraction, the accumulation and partial or complete degradation of pollutants by plants remain poorly understood. Here, we determined the molecular events involved in the early plant response to phenanthrene, used as a model of polycyclic aromatic hydrocarbons. A transcriptomic and a metabolic analysis strongly suggest that energy availability is the crucial limiting factor leading to high and rapid transcriptional reprogramming that can ultimately lead to death. We show that the accumulation of phenanthrene in leaves inhibits electron transfer and photosynthesis within a few minutes, probably disrupting energy transformation. This kinetic analysis improved the resolution of the transcriptome in the initial plant response to phenanthrene, identifying genes that are involved in primary processes set up to sense and detoxify this pollutant but also in molecular mechanisms used by the plant to cope with such harmful stress. The identification of first events involved in plant response to phenanthrene is a key step in the selection of candidates for further functional characterization, with the prospect of engineering efficient ecological detoxification systems for polycyclic aromatic hydrocarbons.

Does a concomitant exposure to lead influence unfavorably the naphthalene subchronic toxicity and toxicokinetics?

PubMed

Katsnelson, Boris A; Minigaliyeva, Ilzira A; Degtyareva, Tamara D; Privalova, Larisa I; Beresneva, Tatyana A

2014-01-01

Rats were given 20 times during 40 d either naphthalene per gavage or the same and lead acetate intraperitoneally in single doses corresponding to 5% of the respective 50% lethal doses. The concomitant exposure to lead not only added some typical indicators of lead toxicity to the moderate naphthalene intoxication picture but also exaggerated some less specific indices for intoxication. However, a number of such indices testified to attenuation of naphthalene's adverse effects under the impact of lead. Lead also lowered urinary excretion of both total and conjugated naphthalene, while the free- to total naphthalene ratio in urine sharply increased. These results corroborate implicitly the initial hypothesis that lead, being an inhibitor of cytochrome P450, hinders phase I of the naphthalene biotransformation and, thus, the formation of derivates which can be more toxic but are capable of entering into reactions of conjugation with resulting detoxication and elimination of naphthalene from the body. © 2013 SETAC.

Characterization of naphthalene degradation by Streptomyces sp. QWE-5 isolated from active sludge.

PubMed

Xu, Peng; Ma, Wencheng; Han, Hongjun; Hou, Baolin; Jia, Shengyong

2014-01-01

A bacterial strain, QWE-5, which utilized naphthalene as its sole carbon and energy source, was isolated and identified as Streptomyces sp. It was a Gram-positive, spore-forming bacterium with a flagellum, with whole, smooth, convex and wet colonies. The optimal temperature and pH for QWE-5 were 35 °C and 7.0, respectively. The QWE-5 strain was capable of completely degrading naphthalene at a concentration as high as 100 mg/L. At initial naphthalene concentrations of 10, 20, 50, 80 and 100 mg/L, complete degradation was achieved within 32, 56, 96, 120 and 144 h, respectively. Kinetics of naphthalene degradation was described using the Andrews equation. The kinetic parameters were as follows: qmax (maximum specific degradation rate) = 1.56 h⁻¹, Ks (half-rate constant) = 60.34 mg/L, and KI (substrate-inhibition constant) = 81.76 mg/L. Metabolic intermediates were identified by gas chromatography and mass spectrometry, allowing a new degradation pathway for naphthalene to be proposed. In this pathway, monooxygenation of naphthalene yielded naphthalen-1-ol. Further degradation by Streptomyces sp. QWE-5 produced acetophenone, followed by adipic acid, which was produced as a combination of decarboxylation and hydroxylation processes.

Evaluating phenanthrene sorption on various wood chars

USGS Publications Warehouse

James, G.; Sabatini, D.A.; Chiou, C.T.; Rutherford, D.; Scott, A.C.; Karapanagioti, H.K.

2005-01-01

A certain amount of wood char or soot in a soil or sediment sample may cause the sorption of organic compounds to deviate significantly from the linear partitioning commonly observed with soil organic matter (SOM). Laboratory produced and field wood chars have been obtained and analyzed for their sorption isotherms of a model solute (phenanthrene) from water solution. The uptake capacities and nonlinear sorption effects with the laboratory wood chars are similar to those with the field wood chars. For phenanthrene aqueous concentrations of 1 ??gl-1, the organic carbon-normalized sorption coefficients (log Koc) ranging from 5.0 to 6.4 for field chars and 5.4-7.3 for laboratory wood chars, which is consistent with literature values (5.6-7.1). Data with artificial chars suggest that the variation in sorption potential can be attributed to heating temperature and starting material, and both the quantity and heterogeneity of surface-area impacts the sorption capacity. These results thus help to corroborate and explain the range of log Koc values reported in previous research for aquifer materials containing wood chars. ?? 2004 Elsevier Ltd. All rights reserved.

Sources, Concentrations and Risks of Naphthalene in Indoor and Outdoor Air

PubMed Central

Batterman, Stuart; Chin, Jo-Yu; Jia, Chunrong; Godwin, Christopher; Parker, Edith; Robins, Thomas; Max, Paul; Lewis, Toby

2011-01-01

Naphthalene is a ubiquitous pollutant, and very high concentrations are sometimes encountered indoors when this chemical is used as a pest repellent or deodorant. This study describes the distribution and sources of vapor phase naphthalene concentrations in four communities in southeast Michigan, USA. Outdoors, naphthalene was measured in the communities and at a near-road site. Indoors, naphthalene levels were characterized in 288 suburban and urban homes. The median outdoor concentration was 0.15 µg m−3, and a modest contribution from rush-hour traffic was noted. The median indoor long-term concentration was 0.89 µg m−3, but concentrations were extremely skewed and 14% of homes exceeded 3 µg m−3, the chronic reference concentration for non-cancer effects, 8% exceeded 10 µg m−3, and levels reached 200 µg m−3. The typical individual lifetime cancer risk was about 10−4, and reached 10−2 in some homes. Important sources include naphthalene's use as a pest repellent and deodorant, migration from attached garages, and to lesser extents, cigarette smoke and vehicle emissions. Excessive use as a repellent caused the highest concentrations. Naphthalene presents high risks in a subset of homes, and policies and actions to reduce exposures, e.g., sales bans or restrictions, improved labeling and consumer education, should be considered. PMID:22145682

Longitudinal Study of [D10]Phenanthrene Metabolism by the Diol Epoxide Pathway in Smokers

PubMed Central

Hecht, Stephen S.; Hochalter, J. Bradley; Carmella, Steven G.; Zhang, Yan; Rauch, Diane M.; Fujioka, Naomi; Jensen, Joni; Hatsukami, Dorothy K.

2013-01-01

The extent of metabolism of [D10]phenanthrene to [D10]r-1,t-2,3,c-4-tetrahydroxy-1,2,3,4-tetradeuterophenanthrene ([D10]PheT) could be a biomarker of human metabolic activation of carcinogenic polycyclic aromatic hydrocarbons, leading to identification of smokers particularly susceptible to lung cancer. The longitudinal stability of [D10]PheT was evaluated in 24 cigarette smokers given 7 – 8 oral doses of [D10]phenanthrene (10 μg) over 5.5 months. [D10]PheT in 6 h urine was quantified after each dose. The overall coefficient of variation for 24 subjects was (mean ± S.D.) 27.4 ± 8.83%. Thus, a single administration of [D10]phenanthrene is likely sufficient to determine a smoker’s ability to metabolize it to [D10]PheT. PMID:23336104

Solubility prediction of naphthalene in carbon dioxide from crystal microstructure

NASA Astrophysics Data System (ADS)

Sang, Jiarong; Jin, Junsu; Mi, Jianguo

2018-03-01

Crystals dissolved in solvents are ubiquitous in both natural and artificial systems. Due to the complicated structures and asymmetric interactions between the crystal and solvent, it is difficult to interpret the dissolution mechanism and predict solubility using traditional theories and models. Here we use the classical density functional theory (DFT) to describe the crystal dissolution behavior. As an example, naphthalene dissolved in carbon dioxide (CO2) is considered within the DFT framework. The unit cell dimensions and microstructure of crystalline naphthalene are determined by minimizing the free-energy of the crystal. According to the microstructure, the solubilities of naphthalene in CO2 are predicted based on the equality of naphthalene's chemical potential in crystal and solution phases, and the interfacial structures and free-energies between different crystal planes and solution are determined to investigate the dissolution mechanism at the molecular level. The theoretical predictions are in general agreement with the available experimental data, implying that the present model is quantitatively reliable in describing crystal dissolution.

Microwave-assisted extraction and ultrasonic extraction to determine polycyclic aromatic hydrocarbons in needles and bark of Pinus pinaster Ait. and Pinus pinea L. by GC-MS.

PubMed

Ratola, Nuno; Lacorte, Sílvia; Barceló, Damià; Alves, Arminda

2009-01-15

Two different extraction strategies (microwave-assisted extraction (MAE) and ultrasonic extraction (USE)) were tested in the extraction of the 16 US Environmental Protection Agency (EPA) polycyclic aromatic hydrocarbons (PAHs) from pine trees. Extraction of needles and bark from two pine species common in the Iberian Peninsula (Pinus pinaster Ait. and Pinus pinea L.) was optimized using two amounts of sample (1g and 5 g) and two PAHs spiking levels (20 ng/g and 100 ng/g). In all cases, the clean-up procedure following extraction consisted in solid-phase extraction (SPE) with alumina cartridges. Quantification was done by gas chromatography (GC) with mass spectrometry (MS), using five deuterated PAH surrogate standards as internal standards. Limits of detection were globally below 0.2 ng/g. The method was robust for the matrices studied regardless of the extraction procedures. Recovery values between 70 and 130% were reached in most cases, except for high molecular weight PAHs (indeno[1,2,3-cd]pyrene, dibenzo[a,h]anthracene and benzo[ghi]perylene). A field study with naturally contaminated samples from eight sites (four in Portugal and four in Catalonia, Spain) showed that needles are more suitable biomonitors for PAHs, yielding concentrations from 2 to 17 times higher than those found in bark. The levels varied according to the sampling site, with the sum of the individual PAH concentrations between 213 and 1773 ng/g (dry weight). Phenanthrene was the most abundant PAH, followed by fluoranthene, naphthalene and pyrene.

Association between Mutation Spectra and Stable and Unstable DNA Adduct Profiles in Salmonella for Benzo[a]pyrene and Dibenzo[a.l]pyrene

EPA Science Inventory

Benzo[a]pyrene (BP) and dibenzo[a,l]pyrene (DBP) are two polycyclic aromatic hydrocarbons (PAHs) that exhibit distinctly different mutagenicity and carcinogenicity profiles. Although some studies show that these PAHs produce unstable DNA adducts, conflicting data and arguments ha...

Comparative proteomics reveal the mechanism of Tween80 enhanced phenanthrene biodegradation by Sphingomonas sp. GY2B.

PubMed

Liu, Shasha; Guo, Chuling; Dang, Zhi; Liang, Xujun

2017-03-01

Previous study concerning the effects of surfactants on phenanthrene biodegradation focused on observing the changes of cell characteristics of Sphingomonas sp. GY2B. However, the impact of surfactants on the expression of bacterial proteins, controlling phenanthrene transport and catabolism, remains obscure. To overcome the knowledge gap, comparative proteomic approaches were used to investigate protein expressions of Sphingomonas sp. GY2B during phenanthrene biodegradation in the presence and absence of a nonionic surfactant, Tween80. A total of 23 up-regulated and 19 down-regulated proteins were detected upon Tween80 treatment. Tween80 could regulate ion transport (e.g. H + ) in cell membrane to provide driving force (ATP) for the transmembrane transport of phenanthrene thus increasing its uptake and biodegradation by GY2B. Moreover, Tween80 probably increased GY2B vitality and growth by inducing the expression of peptidylprolyl isomerase to stabilize cell membrane, increasing the abundances of proteins involved in intracellular metabolic pathways (e.g. TCA cycle), as well as decreasing the abundances of translation/transcription-related proteins and cysteine desulfurase, thereby facilitating phenanthrene biodegradation. This study may facilitate a better understanding of the mechanisms that regulate surfactants-enhanced biodegradation of PAHs at the proteomic level. Copyright © 2016 Elsevier Inc. All rights reserved.

Assigning ecological roles to the populations belonging to a phenanthrene-degrading bacterial consortium using omic approaches

PubMed Central

Coppotelli, Bibiana Marina; Madueño, Laura; Loviso, Claudia Lorena; Macchi, Marianela; Neme Tauil, Ricardo Martin; Valacco, María Pía; Morelli, Irma Susana

2017-01-01

The present study describes the behavior of a natural phenanthrene-degrading consortium (CON), a synthetic consortium (constructed with isolated strains from CON) and an isolated strain form CON (Sphingobium sp. AM) in phenanthrene cultures to understand the interactions among the microorganisms present in the natural consortium during phenanthrene degradation as a sole carbon and energy source in liquid cultures. In the contaminant degradation assay, the defined consortium not only achieved a major phenanthrene degradation percentage (> 95%) but also showed a more efficient elimination of the intermediate metabolite. The opposite behavior occurred in the CON culture where the lowest phenanthrene degradation and the highest HNA accumulation were observed, which suggests the presence of positive and also negative interaction in CON. To consider the uncultured bacteria present in CON, a metagenomic library was constructed with total CON DNA. One of the resulting scaffolds (S1P3) was affiliated with the Betaproteobacteria class and resulted in a significant similarity with a genome fragment from Burkholderia sp. HB1 chromosome 1. A complete gene cluster, which is related to one of the lower pathways (meta-cleavage of catechol) involved in PAH degradation (ORF 31–43), mobile genetic elements and associated proteins, was found. These results suggest the presence of at least one other microorganism in CON besides Sphingobium sp. AM, which is capable of degrading PAH through the meta-cleavage pathway. Burkholderiales order was further found, along with Sphingomonadales order, by a metaproteomic approach, which indicated that both orders were metabolically active in CON. Our results show the presence of negative interactions between bacterial populations found in a natural consortium selected by enrichment techniques; moreover, the synthetic syntrophic processing chain with only one microorganism with the capability of degrading phenanthrene was more efficient in

Biodegradability of nonaqueous-phase liquids affects the mineralization of phenanthrene in soil because of microbial competition

DOE Office of Scientific and Technical Information (OSTI.GOV)

Morrison, D.E.; Alexander, M.

1997-08-01

A study was conducted to determine the effects of biodegradability of nonaqueous-phase liquids (NAPLs) and microbial competition on the biodegradation in soil of a constituent of the NAPLs. The rates of mineralization of phenanthrene dissolved in 8 mg of 2,2,4,4,6,8,8-heptamethylnonane (HMN), di(2-ethylhexyl) phthalate (DEHP), or pristane per g of soil were faster than the rates when the compound was dissolved in hexadecane or dodecane. Addition of inorganic N and P to the soil increased the mineralization rate in the first two but not the last two NAPLs. N and P addition did not enhance mineralization of phenanthrene when added inmore » 500 {micro}g of hexadecane, pristane, or HMN per g of soil. Hexadecane was rapidly degraded, pristane was slowly metabolized, DEHP was still slower, and HMN was not mineralized in the test period. Mixing the soil stimulated mineralization of phenanthrene dissolved in HMN but not in hexadecane. Mineralization of phenanthrene dissolved in HMN was the same if the gas phase contained 21%, 2.1%, or traces of O{sub 2}. In contrast, the biodegradation of phenanthrene dissolved in hexadecane, although the same at 21 and 2.1% O{sub 2}, was not observed if traces of O{sub 2} were present. The mineralization was slower in unshaken soil-water mixtures if phenanthrene was added in hexadecane than in HMN or pristane, but the rates with the 3 NAPLs were increased by shaking the suspensions. The authors suggest that the biodegradability of major components of NAPLs and microbial competition for N, P, or O{sub 2} will have a major impact on the rate of transformation of minor constituents of NAPLs.« less

Source apportionment of elevated wintertime PAHs by compound-specific radiocarbon analysis

NASA Astrophysics Data System (ADS)

Sheesley, R. J.; Kruså, M.; Krecl, P.; Johansson, C.; Gustafsson, Ã.-.

2008-12-01

Natural abundance radiocarbon analysis facilitates distinct source apportionment between contemporary biomass/biofuel (14C "alive") versus fossil fuel (14C "dead") combustion. Here, the first compound-specific radiocarbon analysis (CSRA) of atmospheric polycylic aromatic hydrocarbons (PAHs) was demonstrated for a set of samples collected in Lycksele, Sweden a small town with frequent episodes of severe atmospheric pollution in the winter. Renewed interest in residential wood combustion means than this type of seasonal pollution is of increasing concern in many areas. Five individual/paired PAH isolates from three pooled fortnight-long filter collections were analyzed by CSRA: phenanthrene, fluoranthene, pyrene, benzo[b+k]fluoranthene and indeno[cd]pyrene plus benzo[ghi]perylene; phenanthrene was the only compound also analyzed in the gas phase. The measured Δ14C for PAHs spanned from -138.3‰ to 58.0‰. A simple isotopic mass balance model was applied to estimate the fraction biomass (fbiomass) contribution that was constrained to a range of 71% for indeno[cd]pyrene+benzo[ghi]perylene to 87% for the gas phase phenanthrene and particulate fluoranthene, respectively. Indeno[cd]pyrene plus benzo[ghi]perylene, known to be enhanced in gasoline-powered motor vehicle exhaust compared to diesel exhaust, had the lowest contribution of biomass combustion of the measured PAHs by 9%. The total organic carbon (TOC, defined as carbon remaining after removal of inorganic carbon) fbiomass was estimated to be 77%, which falls within the range for PAHs. This CSRA data of atmospheric PAHs demonstrate the non-uniformity of biomass combustion contribution to different PAHs even in a location with limited local emission sources and illustrates that regulatory efforts would not evenly reduce all PAHs.

Photoactivation and toxicity of mixtures of polycyclic aromatic hydrocarbon compounds in marine sediment

DOE Office of Scientific and Technical Information (OSTI.GOV)

Swartz, R.C.; Ferraro, S.P.; Lamberson, J.O.

1997-10-01

The direct toxicity and photoinduced toxicity of sediment-associated acenaphthene, phenanthrene, fluoranthene, and pyrene were determined for the marine amphipod Rhepoxynius abronius. The four polycyclic aromatic hydrocarbons (PAHs) were spiked into sediment in a concentration series of either single compounds or as approximately equitoxic mixtures of all four compounds. Standard 10-d sediment toxicity tests were conducted under fluorescent lighting. After 10 d, survivors were exposed for 1 h to ultraviolet (UV) radiation in the absence of sediment and then tested for their ability to bury in uncontaminated sediment. The 10-d median lethal concentrations (LC50s) were 2.31 mg acenaphthene/g organic carbon (OC),more » 2.22 mg phenanthrene/g OC, 3.31 mg fluoranthene/g OC, and 2.81 mg pyrene/g OC. These LC50s were used to calculate the sum of toxic units ({Sigma}TU) of the four PAHs in the approximately equitoxic mixtures. The {Sigma}TU LC50 was then calculated for the mixture treatments. If the toxicologic interaction of a mixture of contaminants is additive, {Sigma}TU LC50 = 1.0. The observed LC50 (1.55 {Sigma}TU) was slightly, but significantly, greater than unity, indicating that the interaction of PAHs in the mixture was less than additive. Exposure to UV radiation enhanced the toxic effects of fluoranthene and pyrene, but did not affect the toxicity of acenaphthene and phenanthrene. Effects of UV radiation on the toxicity of the mixture of four PAHs could be explained by the photoactivation of fluoranthene and pyrene alone. These results are consistent with predictions based on photophysical properties of PAH compounds.« less

Comparative Biochemistry and Metabolism. Part 2. Naphthalene Lung Toxicity

DTIC Science & Technology

1983-08-01

Amounts of Supernatant Enzyme Protein on the Rates of Formation of a Polar Metabolite and NapY-’ halene - Glutathione Adducts...demonstrating the regio- and stereospecific formation of glutathione adducts from aromatic and aliphatic epoxides (Yagen et al., 1981; Van Bladeren et al...butylated hydroxyanisole, Cancer Res. 41:4309-4315. Bock, K.W., Van Ackeren, G., Lorch, "L., Birke, F., (1976), Metabolism of naphthalene to naphthalene

Cometabolic Degradation of Dibenzofuran and Dibenzothiophene by a Naphthalene-Degrading Comamonas sp. JB.

PubMed

Ji, Xiangyu; Xu, Jing; Ning, Shuxiang; Li, Nan; Tan, Liang; Shi, Shengnan

2017-12-01

Comamonas sp. JB was used to investigate the cometabolic degradation of dibenzofuran (DBF) and dibenzothiophene (DBT) with naphthalene as the primary substrate. Dehydrogenase and ATPase activity of the growing system with the presence of DBF and DBT were decreased when compared to only naphthalene in the growing system, indicating that the presence of DBF and DBT inhibited the metabolic activity of strain JB. The pathways and enzymes involved in the cometabolic degradation were tested. Examination of metabolites elucidated that strain JB cometabolically degraded DBF to 1,2-dihydroxydibenzofuran, subsequently to 2-hydroxy-4-(3'-oxo-3'H-benzofuran-2'-yliden)but-2-enoic acid, and finally to catechol. Meanwhile, strain JB cometabolically degraded DBT to 1,2-dihydroxydibenzothiophene and subsequently to the ring cleavage product. A series of naphthalene-degrading enzymes including naphthalene dioxygenase, 1,2-dihydroxynaphthalene dioxygenase, salicylaldehyde dehydrogenase, salicylate hydroxylase, and catechol 2,3-oxygenase have been detected, confirming that naphthalene was the real inducer of expression the degradation enzymes and metabolic pathways were controlled by naphthalene-degrading enzymes.

A pyrene formulation for fluorometric visualization of latent fingermarks

NASA Astrophysics Data System (ADS)

Kumari Sharma, Kirti; Harsha Kannikanti, Gavash; Ramachandra Rao Baggi, Tulsidas; Rao Vaidya, Jayathirtha

2018-07-01

Present work is conducted to demonstrate the use of pyrene for the development of latent fingermarks. Pyrene formulation with binders can be efficiently used for developing latent fingermarks on porous, non-porous and semi-porous surfaces. The effectiveness of pyrene formulation for the detection of latent fingermarks present on a large variety of objects was systematically and comparatively carried out. To optimize the working formulation, studies were carried out using different pyrene concentrations followed by various substrate study, time dependent study, temperature study, depleted fingermark development and the stability of the proposed formulation. When illuminated at 366 nm, the developed fingermarks showed clear, high contrast primary, secondary and tertiary level ridge details. This work reveals that the fluorescent molecules having high quantum yield are a versatile fluorescent label and can find their applications in forensic latent fingermark development.

Infrared Spectroscopy of Naphthalene Aggregation and Cluster Formation in Argon Matrices

NASA Technical Reports Server (NTRS)

Roser, J. E.; Allamondola, L. J.

2011-01-01

Fourier-transform mid-infrared absorption spectra of mixed argon/naphthalene matrices at 5 K are shown with ratios of argon-to-naphthalene that vary from 1000 to 0. These spectra show the changes as naphthalene clustering and aggregation occurs, with moderate spectral shifts affecting the C-H vibrational modes and relatively small or no shifts to the C-C and C-C-C vibrational modes. The possible contribution of homogeneous naphthalene clusters to the interstellar unidentified infrared bands is discussed. The contribution of polycyclic aromatic hydrocarbon (PAH) clusters to the 7.7 micron emission plateau and the blue shading of the 12.7 micron emission band are identified as promising candidates for future research. In addition, since PAH clusters are model components of Jupiter and Titan's atmospheres, the information presented here may also be applicable to the spectroscopy of these objects.

Secondary Organic Aerosol Formation from the Photooxidation of Naphthalene

NASA Astrophysics Data System (ADS)

Zhou, S.; Chen, Y.; Wenger, J.

2009-04-01

Polycyclic aromatic hydrocarbons (PAHs) are ubiquitous air pollutants that are released into the atmosphere as a by-product of combustion processes. The gas-phase PAHs can be chemically transformed via reaction with the hydroxyl radical to produce a range of oxidised organic compounds and other pollutants such as ozone and secondary organic aerosol (SOA). Epidemiological studies have established that exposure to this type of air pollution is associated with damaging effects on the respiratory and cardiovascular systems, and can lead to asthma, oxidative stress, health deterioration and even death. The major anthropogenic source of SOA in urban areas is believed to be aromatic hydrocarbons, which are present in automobile fuels and are used as solvents. As a result, research is currently being performed on the characterisation of SOA produced from aromatic hydrocarbons such as toluene, the xylenes and trimethylbenzenes. However, significant amounts of PAHs are also released into urban areas from automobile emissions and the combustion of fossil fuels for home heating. Naphthalene is regularly cited as the most abundant PAH in polluted urban air, with typical ambient air concentrations of 0.05 - 0.20 parts per billion (ppbV) in European cities, comparable to the xylenes. Since naphthalene reacts in an analogous manner to monocyclic aromatic compounds then it is also expected to make a significant contribution to ambient SOA. However, the yield and chemical composition of SOA produced from the atmospheric degradation of naphthalene is not well known. In this presentation, the effects of NOx level and relative humidity on the SOA formation from the phootooixdation of naphthalene will be presented. A series of experiments has been performed in a large atmospheric simulation chamber equipped with a gas chromatograph and analyzers for monitoring nitrogen oxides (NOx) and ozone. SOA formation from the photooxidation of naphthalene was measured using a scanning mobility

PHOTOACTIVATION AND TOXICITY OF MIXTURES OF POLYCYCLIC AROMATIC HYDROCARBON COMPOUNDS IN MARINE SEDIMENT

EPA Science Inventory

The direct toxicity and photoinduced toxicity of sediment-associated acenaphthene, phenanthrene, fluoranthene, and pyrene were determined for the marine amphipod Rhepoxynius abronius. The four polycyclic aromatic hydrocarbons (PAHs) were spiked into sediment in a concentration se...

Effects of secondary carbon supplement on biofilm-mediated biodegradation of naphthalene by mutated naphthalene 1, 2-dioxygenase encoded by Pseudomonas putida strain KD9.

PubMed

Dutta, Kunal; Shityakov, Sergey; Khalifa, Ibrahim; Mal, Arpan; Moulik, Satya Priya; Panda, Amiya Kumar; Ghosh, Chandradipa

2018-05-18

Polycyclic aromatic hydrocarbons (PAHs) belong to a diverse group of environmental pollutants distributed ubiquitously in the environment. The carcinogenic properties of PAHs are the main causes of harm to human health. The green technology, biodegradation have become convenient options to address the environmental pollution. In this study, we analyzed the biodegradation potential of naphthalene with secondary carbon supplements (SCSs) in carbon deficient media (CSM) by Pseudomonas putida strain KD9 isolated from oil refinerary waste. The rigid-flexible molecular docking method revealed that the mutated naphthalene 1,2-dioxygenase had lower affinity for naphthalene than that found in wild type strain. Moreover, analytical methods (HPLC, qRT-PCR) and soft agar chemotaxis suggest sucrose (0.5 wt%) to be the best chemo-attractant and it unequivocally caused enhanced biodegradation of naphthalene (500 mg L -1 ) in both biofilm-mediated and shake-flask biodegradation methods. In addition, the morphological analysis detected from microscopy clearly showed KD9 to change its size and shape (rod to pointed) during biodegradation of naphthalene in CSM as sole source of carbon and energy. The forward versus side light scatter plot of the singlet cells obtained from flow cytometry suggests smaller cell size in CSM and lower florescence intensity of the total DNA content of cells. This study concludes that sucrose may be used as potential bio-stimulation agent. Copyright © 2018 Elsevier B.V. All rights reserved.

SEQUESTERING AGENTS FOR ACTIVE CAPS - REMEDIATION OF METALS AND ORGANICS

DOE Office of Scientific and Technical Information (OSTI.GOV)

Knox, A; Michael Paller, M; Danny D. Reible, D

2007-05-10

This research evaluated organoclays, zeolites, phosphates, and a biopolymer as sequestering agents for inorganic and organic contaminants. Batch experiments were conducted to identify amendments and mixtures of amendments for metal and organic contaminants removal and retention. Contaminant removal was evaluated by calculating partitioning coefficients. Metal retention was evaluated by desorption studies in which residue from the removal studies was extracted with 1 M MgCl{sub 2} solution. The results indicated that phosphate amendments, some organoclays, and the biopolymer, chitosan, were very effective sequestering agents for metals in fresh and salt water. Organoclays were very effective sorbents for phenanthrene, pyrene, and benzo(a)pyrene.more » Partitioning coefficients for the organoclays were 3000-3500 ml g{sup -1} for benzo(a)pyrene, 400-450 ml g{sup -1} for pyrene, and 50-70 ml g{sup -1} for phenanthrene. Remediation of sites with a mixture of contaminants is more difficult than sites with a single contaminant because metals and organic contaminants have different fate and transport mechanisms in sediment and water. Mixtures of amendments (e.g., organoclay and rock phosphate) have high potential for remediating both organic and inorganic contaminants under a broad range of environmental conditions, and have promise as components in active caps for sediment remediation.« less

Polycyclic aromatic hydrocarbons and their derivatives in indoor and outdoor air in an eight-home study

NASA Astrophysics Data System (ADS)

Chuang, Jane C.; Mack, Gregory A.; Kuhlman, Michael R.; Wilson, Nancy K.

A pilot field study was performed in Columbus, OH, during the winter of 1986/1987. The objectives were to determine the feasibility of the use of a newly developed quiet sampler in indoor air sampling for particles and semivolatile organic compounds (SVOC) and to measure the concentrations of polycyclic aromatic hydrocarbons (PAH), PAH derivatives, and nicotine in air in selected residences. Eight homes were chosen for sampling on the basis of these characteristics: electric/gas heating system, electric/gas cooking appliances, and the absence/presence of environmental tobacco smoke (ETS). The indoor sampler was equipped with a quartz-fiber filter to collect particles followed by XAD-4 resin to trap SVOC. A PS-1 sampler with a similar sampling module was used outdoors. The indoor air was sampled in the kitchen and living room areas over two consecutive 8-h periods. The outdoor air was sampled concurrently with the indoor samples over a 16-h period. Fifteen PAH, five nitro-PAH, five oxygenated PAH, and three nitrogen heterocyclic compounds were determined in these samples. The most abundant PAH found indoors was naphthalene. The indoor concentrations of PAH derivatives were lower than those of their parent compounds. Average concentrations of all but three target compounds (naphthalene dicarboxylic acid anhydride, pyrene dicarboxylic acid anhydride, and 2-nitrofluoranthene) were higher indoors than outdoors. Environmental tobacco smoke was the most significant influence on indoor pollutant levels. Homes with gas heating systems had higher indoor pollutant levels than homes with electric heating systems. However, the true effects of heating and cooking systems were not characterized as accurately as the effects of ETS because of the small sample sizes and the lack of statistical significance for most pollutant differences in the absence of ETS. The concentrations of PAH marker compounds (phenanthrene, fluoranthene, and pyrene) correlated well with the concentrations

IRIS Toxicological Review of Benzo[a]pyrene (Final Report)

EPA Science Inventory

EPA has finalized the Integrated Risk Information System (IRIS) assessment of benzo[a]pyrene. This assessment addresses the potential cancer and noncancer human health effects from long-term exposure to benzo[a]pyrene. Now final, this assessment will update the toxicological info...

MEASUREMENT OF HEMOGLOBIN AND ALBUMIN ADDUCTS OF NAPHTHALENE-1,2-OXIDE, 1,2-NAPHTHOQUINONE AND 1,4-NAPHTHOQUINONE AFTER ADMINISTRATION OF NAPHTHALENE TO F344 RATS

EPA Science Inventory

Naphthalene-1,2-oxide (NPO), 1,2-naphthoquinone (1,2-NPQ) and 1,4-naphthoquinone (1,4-NPQ) are the major metabolites of naphthalene that are thought to be responsible for the cytotoxicity and genotoxicity of this chemical. We measured cysteinyl adducts of these metabolites in ...

Visualization of Capsule Reentry Vehicle Heat Shield Ablation Using Naphthalene PLIF

NASA Technical Reports Server (NTRS)

Combs, Christopher S.; Clemens, Noel T.; Danehy, Paul M.

2014-01-01

The Orion Multi-Purpose Crew Vehicle (MPCV) will use an ablative heat shield and improved understanding of the ablation process would be beneficial for design purposes. Given that ablation is a multi-physics process involving heat and mass transfer, codes aiming to predict heat shield ablation are in need of experimental data pertaining to the turbulent transport of ablation products for validation. At The University of Texas at Austin, a technique is being developed that uses planar laser-induced fluorescence (PLIF) of a low-temperature sublimating ablator (naphthalene) to visualize the transport of ablation products in a supersonic flow. Since ablation at reentry temperatures can be difficult to recreate in a laboratory setting it is desirable to create a limited physics problem and simulate the ablation process at relatively low temperature conditions using naphthalene. A scaled Orion MPCV model with a solid naphthalene heat shield has been tested in a Mach 5 wind tunnel at various angles of attack in the current work. PLIF imaging reveals the distribution of the ablation products as they are transported into the heat-shield boundary layer and over the capsule shoulders into the separated shear layer and backshell recirculation region. Visualizations of the capsule shear layer using both naphthalene PLIF and Schlieren imaging compared favorably. High concentrations of naphthalene in the capsule separated flow region, intermittent turbulent structures on the heat shield surface, and interesting details of the capsule shear layer structure were observed using the naphthalene PLIF technique. The capsule shear layer was also shown to generally appear to be more turbulent at lower angles of attack. Furthermore, the PLIF signal increased steadily over the course of a run indicating that during a wind tunnel run the model heated up and the rate of naphthalene ablation increased. The shear layer showed increasing signs of turbulence over the course of a wind tunnel run

Sensitizing of pyrene fluorescence by β-cyclodextrin-modified TiO2 nanoparticles.

PubMed

Shown, Indrajit; Ujihara, Masaki; Imae, Toyoko

2010-12-15

TiO(2) nanoparticles were synthesized by hydrolysis of tetraisopropyl orthotitanate in an aqueous solution of cyclodextrin. The β-cyclodextrin-modified spherical TiO(2) nanoparticles were water-dispersible and had an average particle diameter of 4.4 ± 1 nm. Pyrene fluorescence was enhanced by increasing the concentration of β-cyclodextrin-modified TiO(2) nanoparticle and the sensitization effect was triply stronger than the case of the β-cyclodextrin only. The increase in a concentration of host (β-cyclodextrin) changes its microenvironment for guest (pyrene), that is, the interaction of pyrene with apolar cavity of β-cyclodextrin increases, resulting in enhancement of fluorescence. The sensitization behavior of pyrene fluorescence in the presence of TiO(2) nanoparticles occurs from the increase in the extinction coefficient of pyrene, demonstrating the charge transfer between pyrene and metal oxide nanoparticle. Crown Copyright © 2010. Published by Elsevier Inc. All rights reserved.

Circularly polarized luminescence of helically assembled pyrene π-stacks on RNA and DNA duplexes.

PubMed

Nakamura, Mitsunobu; Ota, Fuyuki; Takada, Tadao; Akagi, Kazuo; Yamana, Kazushige

2018-05-01

In this report, we describe the circularly polarized luminescence (CPL) of the RNA duplexes having one to four 2'-O-pyrene modified uridines (Upy) and the DNA duplexes having two, four, and six pyrene modified non-nucleosidic linkers (Py). Both the pyrene π-stack arrays formed on the RNA and DNA double helical structures exhibited pyrene excimer fluorescence. In the pyrene-modified RNA systems, the RNA duplex having four Upys gives CPL emission with g lum value of <0.01 at 480 nm. The structure of pyrene stacks on the RNA duplex may be rigidly regulated with increase in the Upy domains, which resulted in the CPL emission. In the DNA systems, the pyrene-modified duplexes containing two and four Pys exhibited CPL emission with g lum values of <0.001 at 505 nm. The pyrene π-stack arrays presented here show CPL emission. However, the g lum values are relatively small when compared with our previous system consisting of the pyrene-zipper arrays on RNA. © 2018 Wiley Periodicals, Inc.

Effects of shape, size, and pyrene doping on electronic properties of graphene nanoflakes.

PubMed

Kuamit, Thanawit; Ratanasak, Manussada; Rungnim, Chompoonut; Parasuk, Vudhichai

2017-11-25

Effects of size, shape, and pyrene doping on electronic properties of graphene nanoflakes (GNFs) were theoretically investigated using density functional theory method with PBE, B3PW91, and M06-2X functionals and cc-pVDZ basis set. Two shapes of zigzag GNFs, hexagonal (HGN) and rhomboidal (RGN), were considered. The energy band gap of GNF depends on shape and decreases with size. The HGN has larger band gap energy (1.23-3.96 eV) than the RGN (0.13-2.12 eV). The doping of pyrene and pyrene derivatives on both HGN and RGN was also studied. The adsorption energy of pyrene and pyrene derivatives on GNF does not depend on the shape of GNFs with energies between 21 and 27 kcal mol -1 . The substituent on pyrene enhances the binding to GNF but the strength does not depend on electron withdrawing or donating capability. The doping by pyrene and pyrene derivatives also shifts the HOMO and LUMO energies of GNFs. Both positive (destabilizing) and negative (stabilizing) shifts on HOMO and LUMO of GNFs were seen. The direction and magnitude of the shift do not follow the electron withdrawing and donating capability of pyrene substituents. However, only a slight shift was observed for doped RGN. A shift of 0.19 eV was noticed for HOMO of HGN doped with 1-aminopyrene (pyNH 2 ) and of 0.04 eV for LUMO of HGN doped with 1-pyrenecarboxylic acid (pyCOOH). Graphical Abstract HOMO and LUMO Energies of pyrene/pyrene derivatives doped Graphene Nanoflakes.

Thermodynamic study of (anthracene + benzo[a]pyrene) solid mixtures

PubMed Central

Rice, James W.; Suuberg, Eric M.

2010-01-01

To characterize better the thermodynamic behavior of a binary polycyclic aromatic hydrocarbon mixture, thermochemical and vapor pressure experiments were used to examine the phase behavior of the {anthracene (1) + benzo[a]pyrene (2)} system. A solid-liquid phase diagram was mapped for the mixture. A eutectic point occurs at x1 = 0.26. The eutectic mixture is an amorphous solid that lacks organized crystal structure and melts between T = (414 and 420) K. For mixtures that contain 0.10 < x1 < 0.90, the enthalpy of fusion is dominated by that of the eutectic. Solid-vapor equilibrium studies show that mixtures of anthracene and benzo[a]pyrene at x1 < 0.10 sublime at the vapor pressure of pure benzo[a]pyrene. These results suggest that the solid-vapor equilibrium of benzo[a]pyrene is not significantly influenced by moderate levels of anthracene in the crystal structure. PMID:20814451

Ultrafast third-order nonlinear optical response of pyrene derivatives

NASA Astrophysics Data System (ADS)

Shi, Yufang; Li, Zhongguo; Fang, Yu; Sun, Jinyu; Zhao, Minggen; Song, Yinglin

2017-05-01

Two mono-substituted pyrene derivatives with delocalized electron system 1-(pyren-1-yl)-3-(4-Methyl thiophene-2-yl) acrylic ketone (13#) and 1-(pyren-1-yl)-3-(4-bromo thiophene-2-yl) acrylic ketone (15#) were successfully synthesized. The resultant compounds were characterized by nuclear magnetic resonance (NMR), infrared spectroscopy (IR), high resolution mass spectrum (HR-MS), and UV-vis spectra. The third-order nonlinear optical properties of the compounds were investigated using Z-scan technique with femtosecond laser pulses at 500 nm and 700 nm, respectively. Both of the compounds showed a decrease in transmittance about the focus, which are typical of two-photon absorption. It was found that the two-photon absorption behavior of the pyrene derivatives were modified by substituents on thiophene ring. These results indicate that both compounds can be promising candidates for future optoelectronic and bio-imaging applications.

Simultaneous Quantification of Multiple Urinary Naphthalene Metabolites by Liquid Chromatography Tandem Mass Spectrometry

PubMed Central

Ayala, Daniel C.; Morin, Dexter; Buckpitt, Alan R.

2015-01-01

Naphthalene is an environmental toxicant to which humans are exposed. Naphthalene causes dose-dependent cytotoxicity to murine airway epithelial cells but a link between exposure and human pulmonary disease has not been established. Naphthalene toxicity in rodents depends on P450 metabolism. Subsequent biotransformation results in urinary elimination of several conjugated metabolites. Glucuronide and sulfate conjugates of naphthols have been used as markers of naphthalene exposure but, as the current studies demonstrate, these assays provide a limited view of the range of metabolites generated from the parent hydrocarbon. Here, we present a liquid chromatography tandem mass spectrometry method for measurement of the glucuronide and sulfate conjugates of 1-naphthol as well as the mercapturic acids and N-acetyl glutathione conjugates from naphthalene epoxide. Standard curves were linear over 2 log orders. On column detection limits varied from 0.91 to 3.4 ng; limits of quantitation from 1.8 to 6.4 ng. The accuracy of measurement of spiked urine standards was -13.1 to + 5.2% of target and intra-day and inter-day variability averaged 7.2 (± 4.5) and 6.8 (± 5.0) %, respectively. Application of the method to urine collected from mice exposed to naphthalene at 15 ppm (4 hrs) showed that glutathione-derived metabolites accounted for 60-70% of the total measured metabolites and sulfate and glucuronide conjugates were eliminated in equal amounts. The method is robust and directly measures several major naphthalene metabolites including those derived from glutathione conjugation of naphthalene epoxide. The assays do not require enzymatic deconjugation, extraction or derivatization thus simplifying sample work up. PMID:25853821

KINETICS OF CHROMATE REDUCTION DURING NAPHTHALENE DEGRADATION IN A MIXED CULTURE

EPA Science Inventory

A mixed culture of Bacillus sp. K1 and Sphingomonas paucimobilis EPA 505 was exposed to chromate and naphthalene. Batch experiments showed that chromate was reduced and naphthalene was degraded by the mixed culture. Chromate reduction occurred initially at a high rate followed by...

ORGANIC COSOLVENT EFFECTS ON THE SORPTION AND TRANSPORT OF NEUTRAL ORGANIC CHEMICALS

EPA Science Inventory

Soil column miscible displacement techniques were used to investigate the effects of an organic cosolvent (methanol) on the sorption and transport of three neutral organic chemicals; naphthalene, phenanthrene, and the herbicide diuron, through a sandy surface soil. A two-domain, ...

GROUNDWATER TRANSPORT OF HYDROPHOBIC ORGANIC COMPOUNDS IN THE PRESENCE OF DISSOLVED ORGANIC MATTER

EPA Science Inventory

The effects of dissolved organic matter (DOM) on the transport of hydrophobic organic compounds in soil columns were investigated. Three compounds (naphthalene, phenanthrene and DDT) that spanned three orders of magnitude in water solubility were used. Instead of humic matter, mo...

COSOLVENT EFFECTS ON SORPTION AND MOBILITY OF ORGANIC CONTAMINANTS IN SOILS

EPA Science Inventory

Batch equilibrium and column miscible displacement techniques were used to investigate the influence of an organic cosolvent (methanol) on the sorption and transport of three hydrophobic organic chemicals (HOCs) — naphthalene, phenanthrene, and diuron herbicide — in a sandy surfa...

Acute photo-induced toxicity and toxicokinetics of single compounds and mixtures of polycyclic aromatic hydrocarbons in zebrafish.

PubMed

Willis, Alison M; Oris, James T

2014-09-01

The present study examined photo-induced toxicity and toxicokinetics for acute exposure to selected polycyclic aromatic hydrocarbons (PAHs) in zebrafish. Photo-enhanced toxicity from co-exposure to ultraviolet (UV) radiation and PAHs enhanced the toxicity and exhibited toxic effects at PAH concentrations orders of magnitude below effects observed in the absence of UV. Because environmental exposure to PAHs is usually in the form of complex mixtures, the present study examined the photo-induced toxicity of both single compounds and mixtures of PAHs. In a sensitive larval life stage of zebrafish, acute photo-induced median lethal concentrations (LC50s) were derived for 4 PAHs (anthracene, pyrene, carbazole, and phenanthrene) to examine the hypothesis that phototoxic (anthracene and pyrene) and nonphototoxic (carbazole and phenanthrene) pathways of mixtures could be predicted from single exposures. Anthracene and pyrene were phototoxic as predicted; however, carbazole exhibited moderate photo-induced toxicity and phenanthrene exhibited weak photo-induced toxicity. The toxicity of each chemical alone was used to compare the toxicity of mixtures in binary, tertiary, and quaternary combinations of these PAHs, and a predictive model for environmental mixtures was generated. The results indicated that the acute toxicity of PAH mixtures was additive in phototoxic scenarios, regardless of the magnitude of photo-enhancement. Based on PAH concentrations found in water and circumstances of high UV dose to aquatic systems, there exists potential risk of photo-induced toxicity to aquatic organisms. © 2014 SETAC.

Polyaniline nanotubes and their dendrites doped with different naphthalene sulfonic acids

DOE Office of Scientific and Technical Information (OSTI.GOV)

Zhang Zhiming; Chemistry and Chemical Engineering College, Ocean University of China, Qingdao 266003; Wei Zhixiang

2005-03-01

Polyaniline (PANI) nanotubes (130-250 nm in average diameter) doped with {alpha}-naphthalene sulfonic acid ({alpha}-NSA), {beta}-naphthalene sulfonic acid ({beta}-NSA) and 1,5-naphthalene disulfonic acid were synthesized via a self-assembly process. It was found that the formation yield, morphology (hollow or solid), size, crystalline and electrical properties of the nanostructures are affected by the position and number of -SO{sub 3}H groups attached to the naphthalene ring of NSA as well as the synthesis conditions. Moreover, these nanotubes aggregate to form a dendritic morphology when the polymerization is performed at a static state. The micelles composed of dopant or dopant/anilinium cations might act inmore » a template-like fashion in forming self-assembled PANI nanotubes, which was further confirmed by X-ray diffraction measurements, while the aggregated morphology of the nanotubes might result from polymer chain interactions including {pi}-{pi} interactions, hydrogen and ionic bonds.« less

Phytoremediation of polycyclic aromatic hydrocarbons (PAH) by cv. Crioula: A Brazilian alfalfa cultivar.

PubMed

Alves, Wilber S; Manoel, Evelin A; Santos, Noemi S; Nunes, Rosane O; Domiciano, Giselli C; Soares, Marcia R

2018-07-03

This work aimed to evaluate the phytoremediation capacity of the alfalfa cultivar Crioula in soils contaminated with polycyclic aromatic hydrocarbons (PAHs), primary pollutants with mutagenic and carcinogenic potential. Alfalfa was grown from seed for 40 days on soil amended with anthracene, pyrene, and phenanthrene. Soil and plant tissue was collected for biometric assay, dry mass analysis, and PAH analysis by liquid chromatography. Increased total PAH concentration was associated with decreases in plant biomass, height, and internode length. The Crioula cultivar had a satisfactory phytoremediation effect, reducing total PAH concentration (300 ppm) in the experimental soil by 85% in 20 days, and by more than 95% in 40 days. The PAH showed a tendency to be removed in the temporal order: phenanthrene before pyrene before anthracene, and the removal ratio was influenced by the initial soil concentration of each PAH.

A comparative intracellular proteomic profiling of Pseudomonas aeruginosa strain ASP-53 grown on pyrene or glucose as sole source of carbon and identification of some key enzymes of pyrene biodegradation pathway.

PubMed

Mukherjee, Ashis K; Bhagowati, Pabitra; Biswa, Bhim Bahadur; Chanda, Abhishek; Kalita, Bhargab

2017-09-07

Pseudomonas aeruginosa strain ASP-53, isolated from a petroleum oil-contaminated soil sample, was found to be an efficient degrader of pyrene. PCR amplification of selected hydrocarbon catabolic genes (alkB gene, which encodes for monooxygenase, and the C12O, C23O, and PAH-RHDα genes encoding for the dioxygenase enzyme) from the genomic DNA of P. aeruginosa strain ASP-53 suggested its hydrocarbon degradation potential. The GC-MS analysis demonstrated 30.1% pyrene degradation by P. aeruginosa strain ASP-53 after 144h of incubation at pH6.5, 37°C. Expressions of 115 and 196 intracellular proteins were unambiguously identified and quantitated by shotgun proteomics analysis when the isolate was grown in medium containing pyrene and glucose, respectively. The pyrene-induced uniquely expressed and up-regulated proteins in P. aeruginosa strain ASP-53 in addition to substrate (pyrene) metabolism are also likely to be associated with different cellular functions for example-related to protein folding (molecular chaperone), stress response, metabolism of carbohydrate, proteins and amino acids, and fatty acids; transport of metabolites, energy generation such as ATP synthesis, electron transport and nitrate assimilation, and other oxidation-reduction reactions. Proteomic analyses identified some important enzymes involved in pyrene degradation by P. aeruginosa ASP-53 which shows that this bacterium follows the salicylate pathway of pyrene degradation. This study is the first report on proteomic analysis of pyrene biodegradation pathway by Pseudomonas aeruginosa, isolated from a petroleum-oil contaminated soil sample. The pathway displays partial similarity with deduced pyrene degradation mechanisms of Mycobacterium vanbaalenii PYR-1. The GC-MS analysis as well as PCR amplification of hydrocarbon catabolic genes substantiated the potency of the bacterium under study to effectively degrade high molecular weight, toxic PAH such as pyrene for its filed scale bioremediation

[Effects of naphthalene on soil respiration, nutrients and enzyme activities in the subalpine forest of western Sichuan, China].

PubMed

Yang, Fan; Yang, Wan Qin; Wu, Fu Zhong; Wang, Hui; Lan, Li Ying; Liu, Yu Wei; Guo, Cai Hong; Tan, Bo

2017-06-18

As a biocide to reduce soil and litter faunal populations in field experiments, naphthalene has been widely used in the study of ecological functions of soil fauna, but the non-target effects of naphthalene bring about enormous uncertainty to its application. In order to understand whether there were non-target effects of naphthalene in subalpine forest soil, soil in the subalpine forests of west Qinghai-Tibet Plateau was taken as study object. The short-term responses of soil respiration rate, nutrient content and enzyme activity to naphthalene were studied in microcosms. The results showed that soil respiration rate was significantly suppressed by application of naphthalene within 0-10 days, and then showed a significant promotion effect. Naphthalene significantly affected the dynamics of soil NH 4 + -N and NO 3 - -N contents. With application of naphthalene, the highest contents of NH 4 + -N and NO 3 - -N occurred at the 3rd and 7th day, respectively. But they were observed at the 45th and 52nd day with no-naphthalene, respectively. Moreover, soil dissolved carbon content in the naphthalene microcosms showed a sharp increase and then decrease dynamic at the 3rd day, while small change was detected in the no-naphthalene microcosms. Dissolved nitrogen content in both the naphthalene and no-naphthalene microcosms showed an increase at first and then decreased subsequently during the study period. Similar dynamics were found for the soil enzyme activities in both the naphthalene and no-naphthalene microcosms. The highest activities of urease, nitrate reductase and nitrite reductase in both the naphthalene and no-naphthalene microcosms were at the 45th, 38th and 10th day, respectively. In addition, the interaction of naphthalene treatment and sampling time had significant effects on soil respiration rate, the contents of NH 4 + -N, NO 3 - -N and dissolved nitrogen, but had no significant effects on soil dissolved carbon content, and the activities of invertase

Accelerated removal of pyrene and benzo[a]pyrene in freshwater sediments with amendment of cyanobacteria-derived organic matter.

PubMed

Yan, Zaisheng; Jiang, Helong; Li, Xiaohong; Shi, Yuan

2014-05-15

The removal of pyrene and benzo[a]pyrene (BaP) were investigated in freshwater sediments with amendment of seven different organic matters including cyanobacteria-derived organic matter (COM), plant-derived organic matter (POM), and humic substances (HS). During the 210 days of experiments, the amendment of COM or HS enhanced significantly the removal of pyrene and BaP in sediments, especially with fresh COM (FCOM) treatment much superior to HS. On the contrary, degradation of these polycyclic aromatic hydrocarbons (PAHs) was not significantly improved and even inhibited in POM-amended sediments. The first-order rate constants of pyrene and BaP degradation in the FCOM-amended sediments reached 0.00540±0.00017d(-1) and 0.00517±0.00057d(-1), respectively, and were about three and five folds of those in the control treatment. The enhanced PAHs degradation in FCOM-amended sediments was related to higher PAH-degrading bacteria number and bioavailability with a result of biostimulation and priming effect by labile carbon and high-value nutrition in FCOM. Thus, this study improved our understanding about effects of settled biomass from cyanobacterial blooms, which occurred frequently in eutrophic aquatic ecosystems, on the natural attenuation of PAHs in sediments. Furthermore, this study would also help develop a new promising approach to remediate PAH-contaminated sediments through utilization of cyanobacterial bloom biomass. Copyright © 2014 Elsevier B.V. All rights reserved.

Solubilization of pyrene by anionic-nonionic mixed surfactants.

PubMed

Zhou, Wenjun; Zhu, Lizhong

2004-06-18

Surfactant-enhanced remediation (SER) is an effective approach for the removal of sorbed hydrophobic organic compounds from contaminated soils. The solubilization of pyrene by four anionic-nonionic mixed surfactants, sodium dodecyl sulfate (SDS) with Triton X-405 (TX405), Brij35, Brij58, and Triton X-100 (TX100), has been studied from measurements of the molar solubilization ratio (MSR), the micelle-water partition coefficient (Kmc), and the critical micelle concentration (CMC). The MSRs of pyrene in mixed surfactants are found to be larger than those predicted according to an ideal mixing rule. The mixing effect of anionic and nonionic surfactants on MSR for pyrene follows the order of SDS-TX405 > SDS-Brij35 > SDS-Brij58 > SDS-TX100 and increases with an increase in the hydrophile-lipophile balance (HLB) value of nonionic surfactant in mixed systems. In addition, the mixture of anionic and nonionic surfactants cause the Kmc value for pyrene to be greater than the ideal value in SDS-TX405 mixed system, but to be smaller than the ideal value in SDS-Brij35, SDS-Brij58, and SDS-TX100 mixed systems. Meanwhile, in the four mixed systems, the experimental CMCs are lower than the ideal CMCs at almost all mixed surfactant solution compositions. The mixing effect of anionic and nonionic surfactants on MSR for pyrene can be attributed to the conjunct or the net result of the negative deviation of the CMCs from ideal mixture and the increasing or decreasing Kmc.

[Degradation characteristics of naphthalene with a Pseudomonas aeruginosa strain isolated from soil contaminated by diesel].

PubMed

Liu, Wen-Chao; Wu, Bin-Bin; Li, Xiao-Sen; Lu, Dian-Nan; Liu, Yong-Min

2015-02-01

Abstract: A naphthalene-degrading bacterium (referred as HD-5) was isolated from the diesel-contaminated soil and was assigned to Pseudomonas aeruginosa according to 16S rDNA sequences analysis. Gene nah, which encodes naphthalene dioxygenase, was identified from strain HD-5 by PCR amplification. Different bioremediation approaches, including nature attenuation, bioaugmentation with strain Pseudomonas aeruginosa, biostimulation, and an integrated degradation by bioaugmentation and biostimulation, were evaluated for their effectiveness in the remediating soil containing 5% naphthalene. The degradation rates of naphthalene in the soil were compared among the different bioremediation approaches, the FDA and dehydrogenase activity in bioremediation process were measured, and the gene copy number of 16S rRNA and nah in soil were dynamically monitored using real-time PCR. It was shown that the naphthalene removal rate reached 71.94%, 62.22% and 83.14% in approaches of bioaugmentation (B), biostimulation(S) and integrated degradation composed of bioaugmentation and biostimulation (BS), respectively. The highest removal rate of naphthalene was achieved by using BS protocol, which also gives the highest FDA and dehydrogenase activity. The gene copy number of 16S rRNA and nah in soil increased by about 2.67 x 10(11) g(-1) and 8.67 x 10(8) g(-1) after 31 days treatment using BS protocol. Above-mentioned results also demonstrated that the screened bacterium, Pseudomonas aeruginosa, could grow well in naphthalene-contaminated soil and effectively degrade naphthalene, which is of fundamental importance for bioremediation of naphthalene-contaminated soil.

Simplified MPN method for enumeration of soil naphthalene degraders using gaseous substrate.

PubMed

Wallenius, Kaisa; Lappi, Kaisa; Mikkonen, Anu; Wickström, Annika; Vaalama, Anu; Lehtinen, Taru; Suominen, Leena

2012-02-01

We describe a simplified microplate most-probable-number (MPN) procedure to quantify the bacterial naphthalene degrader population in soil samples. In this method, the sole substrate naphthalene is dosed passively via gaseous phase to liquid medium and the detection of growth is based on the automated measurement of turbidity using an absorbance reader. The performance of the new method was evaluated by comparison with a recently introduced method in which the substrate is dissolved in inert silicone oil and added individually to each well, and the results are scored visually using a respiration indicator dye. Oil-contaminated industrial soil showed slightly but significantly higher MPN estimate with our method than with the reference method. This suggests that gaseous naphthalene was dissolved in an adequate concentration to support the growth of naphthalene degraders without being too toxic. The dosing of substrate via gaseous phase notably reduced the work load and risk of contamination. The result scoring by absorbance measurement was objective and more reliable than measurement with indicator dye, and it also enabled further analysis of cultures. Several bacterial genera were identified by cloning and sequencing of 16S rRNA genes from the MPN wells incubated in the presence of gaseous naphthalene. In addition, the applicability of the simplified MPN method was demonstrated by a significant positive correlation between the level of oil contamination and the number of naphthalene degraders detected in soil.

Bioactive Phenanthrene and Bibenzyl Derivatives from the Stems of Dendrobium nobile.

PubMed

Zhou, Xue-Ming; Zheng, Cai-Juan; Gan, Li-She; Chen, Guang-Ying; Zhang, Xiao-Peng; Song, Xiao-Ping; Li, Gao-Nan; Sun, Chong-Ge

2016-07-22

A new enantiomeric pair of spirodiketones, (+)- and (-)-denobilone A (1 and 2), three new phenanthrene derivatives (3-5), and three new biphenanthrenes (22-24), along with 11 known phenanthrene derivatives (6-16), five known bibenzyl derivatives (17-21), and four known biphenanthrenes (25-28), were isolated from Dendrobium nobile. The structures of 1-5 and 22-24 were elucidated using comprehensive spectroscopic methods. (+)-Denobilone and (-)-denobilone A (1 and 2) were isolated as a pair of enantiomers by chiral HPLC. The absolute configurations of (+)- and (-)-denobilone A (1 and 2) were determined by comparing their experimental and calculated electronic circular dichroism spectra. The absolute configuration of denobilone B (3) was determined by X-ray crystallographic analysis. The inhibitory activities of all compounds against nine phytopathogenic fungi and three cancer cell lines were evaluated.

IRIS Toxicological Review of Benzo[a]pyrene (Interagency ...

EPA Pesticide Factsheets

In January 2017, EPA finalized the IRIS assessment of Benzo[a]pyrene. The Toxicological Review was reviewed internally by EPA and by other federal agencies and White House Offices before public release. Consistent with the May 2009 IRIS assessment development process, all written comments on IRIS assessments submitted by other federal agencies and White House Offices are made publicly available. Accordingly, interagency comments and the interagency science discussion materials provided to other agencies, including interagency review drafts of the IRIS Toxicological Review of Benzo[a]pyrene are posted on this site. EPA is undertaking an update of the Integrated Risk Information System (IRIS) health assessment for benzo[a]pyrene (BaP). The outcome of this project is an updated Toxicological Review and IRIS Summary for BaP that will be entered into the IRIS database.

Cold and drought stress in combination with pyrene exposure: studies with Protaphorura armata (Collembola: Onychiuridae).

PubMed

Sjursen, Heidi; Holmstrup, Martin

2004-02-01

Adult survival of the springtail Protaphorura armata exposed to pyrene, a common soil pollutant, was investigated in combination with cold and drought stress, in three separate experiments. (1) A drought stress imposed subsequent to pyrene exposure in soil resulted in a significant decrease in springtail survival, when compared with controls exposed to pyrene and subsequently to 100% relative humidity. (2) A previous exposure to drought stress resulted in slightly improved survival of pyrene exposure at a concentration of 10mg/kg, but not at higher pyrene concentrations. When comparing tests 1 and 2, better survival was found in the latter test. When comparing the drought survival of springtails that had been previously exposed to pyrene with drought survival of springtails with no previous history of pyrene exposure, survival was significantly lower in the former. (3) Springtail survival of pyrene exposure was investigated at several temperatures. Springtails showed a significant improvement in survival at temperatures fluctuating between +1 degrees C and -1 degrees C in 12:12-h cycles, and at a constant -3 degrees C, at the highest pyrene concentration (300 mg/kg), while survival remained the same at all temperatures when springtails were exposed to lower pyrene concentrations. It is concluded that temperature and water availability are important factors when assessing the springtails' susceptibility to pyrene exposure.

The coupling of the plant and microbial catabolisms of phenanthrene in the rhizosphere of Medicago sativa.

PubMed

Muratova, Anna; Dubrovskaya, Ekaterina; Golubev, Sergey; Grinev, Vyacheslav; Chernyshova, Marina; Turkovskaya, Olga

2015-09-01

We studied the catabolism of the polycyclic aromatic hydrocarbon phenanthrene by four rhizobacterial strains and the possibility of enzymatic oxidation of this compound and its microbial metabolites by the root exudates of alfalfa (Medicago sativa L.) in order to detect the possible coupling of the plant and microbial metabolisms under the rhizospheric degradation of the organic pollutant. A comparative study of phenanthrene degradation pathways in the PAH-degrading rhizobacteria Ensifer meliloti, Pseudomonas kunmingensis, Rhizobium petrolearium, and Stenotrophomonas sp. allowed us to identify the key metabolites from the microbial transformation of phenanthrene, including 9,10-phenanthrenequinone, 2-carboxybenzaldehyde, and 1-hydroxy-2-naphthoic, salicylic, and o-phthalic acids. Sterile alfalfa plants were grown in the presence and absence of phenanthrene (0.03 g kg(-1)) in quartz sand under controlled environmental conditions to obtain plant root exudates. The root exudates were collected, concentrated by ultrafiltration, and the activity of oxidoreductases was detected spectrophotometrically by the oxidation rate for various substrates. The most marked activity was that of peroxidase, whereas the presence of oxidase and tyrosinase was detected on the verge of the assay sensitivity. Using alfalfa root exudates as a crude enzyme preparation, we found that in the presence of the synthetic mediator, the plant peroxidase could oxidize phenanthrene and its microbial metabolites. The results indicate the possibility of active participation of plants in the rhizospheric degradation of polycyclic aromatic hydrocarbons and their microbial metabolites, which makes it possible to speak about the coupling of the plant and microbial catabolisms of these contaminants in the rhizosphere. Copyright © 2015 Elsevier GmbH. All rights reserved.

Preservation of commonly applied fluorescent tracers in complex water samples

NASA Astrophysics Data System (ADS)

Cao, Viet; Schaffer, Mario; Jin, Yulan; Licha, Tobias

2017-06-01

Water sample preservation and pre-treatment are important steps for achieving accurate and reproductive results from tracer tests. However, this is particularly challenging for complex water mixtures prior to fluorescence analysis. In this study, the interference of iron and calcium precipitation with nine commonly applied conservative tracers, uranine, eosin, 1-naphthalene sulfonate, 1,5-naphthalene disulfonate, 2,6-naphthalene disulfonate, 4-amino-1-naphthalene sulfonate, 6-hydroxy-2-naphthalene sulfonate, 1,3,6-naphthalene trisulfonate, and 1,3,6,8-pyrene tetrasulfonate, was investigated in batch experiments. In general, the observed results are influenced by precipitates. A technique consisting of pH adjustment and centrifugation is described for preserving samples and avoiding the impact of these precipitates on the tracer test results.

Soil mineral composition matters: response of microbial communities to phenanthrene and plant litter addition in long-term matured artificial soils.

PubMed

Babin, Doreen; Vogel, Cordula; Zühlke, Sebastian; Schloter, Michael; Pronk, Geertje Johanna; Heister, Katja; Spiteller, Michael; Kögel-Knabner, Ingrid; Smalla, Kornelia

2014-01-01

The fate of polycyclic aromatic hydrocarbons (PAHs) in soil is determined by a suite of biotic and abiotic factors, and disentangling their role in the complex soil interaction network remains challenging. Here, we investigate the influence of soil composition on the microbial community structure and its response to the spiked model PAH compound phenanthrene and plant litter. We used long-term matured artificial soils differing in type of clay mineral (illite, montmorillonite) and presence of charcoal or ferrihydrite. The soils received an identical soil microbial fraction and were incubated for more than two years with two sterile manure additions. The matured artificial soils and a natural soil were subjected to the following spiking treatments: (I) phenanthrene, (II) litter, (III) litter + phenanthrene, (IV) unspiked control. Total community DNA was extracted from soil sampled on the day of spiking, 7, 21, and 63 days after spiking. Bacterial 16S rRNA gene and fungal internal transcribed spacer amplicons were quantified by qPCR and subjected to denaturing gradient gel electrophoresis (DGGE). DGGE analysis revealed that the bacterial community composition, which was strongly shaped by clay minerals after more than two years of incubation, changed in response to spiked phenanthrene and added litter. DGGE and qPCR showed that soil composition significantly influenced the microbial response to spiking. While fungal communities responded only in presence of litter to phenanthrene spiking, the response of the bacterial communities to phenanthrene was less pronounced when litter was present. Interestingly, microbial communities in all artificial soils were more strongly affected by spiking than in the natural soil, which might indicate the importance of higher microbial diversity to compensate perturbations. This study showed the influence of soil composition on the microbiota and their response to phenanthrene and litter, which may increase our understanding of

Soil Mineral Composition Matters: Response of Microbial Communities to Phenanthrene and Plant Litter Addition in Long-Term Matured Artificial Soils

PubMed Central

Babin, Doreen; Vogel, Cordula; Zühlke, Sebastian; Schloter, Michael; Pronk, Geertje Johanna; Heister, Katja; Spiteller, Michael; Kögel-Knabner, Ingrid; Smalla, Kornelia

2014-01-01

The fate of polycyclic aromatic hydrocarbons (PAHs) in soil is determined by a suite of biotic and abiotic factors, and disentangling their role in the complex soil interaction network remains challenging. Here, we investigate the influence of soil composition on the microbial community structure and its response to the spiked model PAH compound phenanthrene and plant litter. We used long-term matured artificial soils differing in type of clay mineral (illite, montmorillonite) and presence of charcoal or ferrihydrite. The soils received an identical soil microbial fraction and were incubated for more than two years with two sterile manure additions. The matured artificial soils and a natural soil were subjected to the following spiking treatments: (I) phenanthrene, (II) litter, (III) litter + phenanthrene, (IV) unspiked control. Total community DNA was extracted from soil sampled on the day of spiking, 7, 21, and 63 days after spiking. Bacterial 16S rRNA gene and fungal internal transcribed spacer amplicons were quantified by qPCR and subjected to denaturing gradient gel electrophoresis (DGGE). DGGE analysis revealed that the bacterial community composition, which was strongly shaped by clay minerals after more than two years of incubation, changed in response to spiked phenanthrene and added litter. DGGE and qPCR showed that soil composition significantly influenced the microbial response to spiking. While fungal communities responded only in presence of litter to phenanthrene spiking, the response of the bacterial communities to phenanthrene was less pronounced when litter was present. Interestingly, microbial communities in all artificial soils were more strongly affected by spiking than in the natural soil, which might indicate the importance of higher microbial diversity to compensate perturbations. This study showed the influence of soil composition on the microbiota and their response to phenanthrene and litter, which may increase our understanding of

Effect of linear alkyl benzene sulfonates (LAS) on the fate of phenanthrene in a model ecosystem (water-lava-plant-air).

PubMed

Jiang, Xia; Jin, Xiang-can; Yan, Chang-zhou; Yediler, Ayfer; Ou, Zi-qing; Kettrup, Antonius

2004-01-01

Advanced closed chamber system was used to study the fate of phenanthrene (3-rings PAHs) in the presence of linear alkylbenzene sulphonates (LAS). The results showed mineralization and metabolism of phenanthrene are fast in the "culture solution-lava-plant-air" model ecological system. The distribution proportions of applied 14C-activity in this simulative ecological system were 41%-45%, 14% to 10% and 1% in plant, lava and culture solution respectively, and 18% to 29%, 11% to 8% recovered in the forms of VOCs and CO2. Main parts of the applied 14C-activity exist in two forms, one is polar metabolites (25%) which mainly distribute in the root (23%), the other is unextractable part (23%) which have been constructed into plant root (8.98%), shoot (0.53%) or bonded to lava (13.2%). The main metabolites of phenanthrene were polar compounds (25% of applied 14C-activity), and small portion of 14C-activity was identified as non-polar metabolites (6% of applied 14C-activity) and apparent phenanthrene (1.91% of applied 14C-activity). Phenanthrene and its metabolites can be taken up through plant roots and translocated to plant shoots. The presence of LAS significantly increased the the concentration of 14C-activity in the plant and production of VOCs, at the same time it decreased the phenanthrene level in the plant and the production of CO2 at the concentration of 200 mg/L.

A novel Pseudomonas gessardii strain LZ-E simultaneously degrades naphthalene and reduces hexavalent chromium.

PubMed

Huang, Haiying; Wu, Kejia; Khan, Aman; Jiang, Yiming; Ling, Zhenmin; Liu, Pu; Chen, Yong; Tao, Xuanyu; Li, Xiangkai

2016-05-01

Combined pollutants with polycyclic aromatic hydrocarbons (PAHs) and heavy metals have been identified as toxic and unmanageable contaminates. In this work, Pseudomonas gessardii strain LZ-E isolated from wastewater discharge site of a petrochemical company degrades naphthalene and reduces Cr(VI) simultaneously. 95% of 10mgL(-1) Cr(VI) was reduced to Cr(III) while 77% of 800mgL(-1) naphthalene was degraded when strain LZ-E was incubated in BH medium for 48h. Furthermore, naphthalene promotes Cr(VI) reduction in strain LZ-E as catechol and phthalic acid produced in naphthalene degradation are able to reduce Cr(VI) abiotically. An aerated bioreactor system was setup to test strain LZ-E's remediation ability. Strain LZ-E continuously remediated naphthalene and Cr(VI) at rates of 15mgL(-1)h(-1) and 0.20mgL(-1)h(-1) of 800mgL(-1) naphthalene and 10mgL(-1) Cr(VI) addition with eight batches in 16days. In summary, strain LZ-E is a potential applicant for combined pollution remediation. Copyright © 2016 The Authors. Published by Elsevier Ltd.. All rights reserved.

Assessing the environmental impact of phenanthrene in different types of land use based on the binding characteristics with dissolved organic matter.

PubMed

Chen, Xiao-Meng; Zhao, Yue; Ma, Ying-Ying; Zhu, Long-Ji; Yang, Tian-Xue; Wei, Zi-Min; Dong, Ying-Li; Wei, Qing-Bin

2018-01-01

The binding characteristics of phenanthrene with dissolved organic matter (DOM) were studied by the excitation emission matrix fluorescence spectroscopy with parallel factor analysis in four types of land use which derived from forest (F), meadow (M), cropland (C), and greenhouse (G). The results showed that the humification degree and binding characteristics of phenanthrene with DOM were distinct differences in the four soils. The binding capacities of humic-like components with phenanthrene were stronger than those of protein-like components. The log K derived from the Stern-Volmer equation significantly correlated with the humification degree of DOM (p < 0.05) in different types of land use. Besides, correlation analysis demonstrated that the potential binding index (Fk) obtained from the modified Stern-Volmer model was a more accurate parameter to describe the combination degree of DOM with phenanthrene than log K, which presented a decrease order of C > F > M > G. Therefore, the environmental impact of phenanthrene in different types of land use could be assessed deeply based on the Fk and DOM concentration. Copyright © 2017 Elsevier Inc. All rights reserved.

Diversity of metabolic capacities among strains degrading polycyclic aromatic hydrocarbons

DOE Office of Scientific and Technical Information (OSTI.GOV)

Bouchez, M.; Besnaienou, B.; Blanchet, D.

1995-12-31

Strains of Pseudomonas and Rhodococcus genera were isolated for their capacity to use, as a sole carbon and energy source, one of the following polycyclic aromatic hydrocarbons (PAHs): naphthalene (NAP), fluorene (FLU), phenanthrene (PHE), anthracene (ANT), fluoranthene (FLT), and pyrene (PYR). The range of PAHs supporting growth of these pure strains was usually restricted, but several other hydrocarbons were used by Rhodococcus sp. All strains could grow on simple organic acids. Maximal specific growth rates ({mu}{sub max}) of all strains on their PAH growth substrates were determined by respirometry. No clear relationships between {mu}{sub max} values and the molecular weightmore » or water solubility of PAHs were apparent, but Pseudomonas sp. exhibited the highest {mu}{sub max} values. Carbon balances for PAH biodegradation were established. Differences between strains were observed, but high mineralization rates and low production of soluble metabolites were obtained for all PAHs. Bacterial biomass represented 16% to 35% of the carbon consumed. Strain diversity was also apparent in the interactions observed in the degradation of a mixture of two PAHs by individual strains, which often involved inhibition of PAH substrate degradation, with or without cometabolization of the second PAH.« less

Solubilization of polycyclic aromatic hydrocarbons in micellar nonionic surfactant solutions

DOE Office of Scientific and Technical Information (OSTI.GOV)

Edwards, D.A.; Luthy, R.G.; Liu, Zhongbao

1991-01-01

Experimental data are presented on the enhanced apparent solubilities of naphthalene, phenanthrene, and pyrene resulting from solubilization in aqueous solutions of four commercial, nonionic surfactants: an alkyl polyoxyethylene (POE) type, two octylphenol POE types, and a nonylphenol POE type. Apparent solubilities of the polycyclic aromatic hydrocarbon (PAH) compounds in surfactant solutions were determined by radiolabeled techniques. Solubilization of each PAH compound commenced at the surfactant critical micelle concentration and was proportional to the concentration of surfactant in micelle form. The partitioning of organic compounds between surfactant micelles and aqueous solution is characterized by a mole fraction micelle-phase/aqueous-phase partition coefficient, K{submore » m}. Values of log K{sub m} for PAH compounds in surfactant solutions of this study range from 4.57 to 6.53. Log K{sub m} appears to be a linear function of log K{sub ow} for a given surfactant solution. A knowledge of partitioning in aqueous surfactant systems is a prerequisite to understanding mechanisms affecting the behavior of hydrophobic organic compounds in soil-water systems in which surfactants play a role in contaminant remediation or facilitated transport.« less

First-Principles DFT Studies of the Vibrational Properties of Germanene Nanoflakes

NASA Astrophysics Data System (ADS)

Richardson, Steven; Peroparde, Borja; Andrade, Xavier; Aspuru-Guzik, AláN.

The germanium analogue of graphene, germanene, is a potentially new atomically thin quantum material which theory predicts will possess unique transport and optoelectronic properties. Recently, there have been a number of experimental efforts to successfully grow two-dimensional films of germanene on noble metal substrates using molecular beam epitaxy. In addition to this top-down approach of synthesizing large scale films of germanene, we would like to focus on a bottom-up approach where nanoflakes of germanene could be used as molecular seeds or precursors to grow large films of two-dimensional germanene. A knowledge of their infrared and Raman spectra will be critical for characterizing these germanene nanoflakes in future experiments. In this work we used density-functional theory (DFT) to compute the vibrational spectra of a selected number of lower order germanene nanoflakes (e.g. hexagermabenzene, germa-naphthalene, germa-anthracene, germa-phenanthrene, germa-pyrene, germa-tetracene, and germa-pentacene). Our DFT studies also reveal that these germanene nanoflakes are vibrationally stable with buckling of these molecules from their normal two-dimensional planar forms which exist in graphene nanoflakes. This research is supported by NSF Grant No. DMR-1231319.

High-Sensitivity Surface-Enhanced Raman Scattering (SERS) Substrate Based on a Gold Colloid Solution with a pH Change for Detection of Trace-Level Polycyclic Aromatic Hydrocarbons in Aqueous Solution.

PubMed

Shi, Xiaofeng; Liu, Shu; Han, Xiaohong; Ma, Jun; Jiang, Yongchao; Yu, Guifeng

2015-05-01

In this study, a gold colloid solution whose parameters were optimized, and without any surfactants, was developed as a surface-enhanced Raman scattering (SERS) substrate for the detection of trace-level polycyclic aromatic hydrocarbons (PAHs). A gold colloid solution with 57 nm gold particles and pH 13 was prepared to be the SERS substrate. It had impressive enhancement that was two orders of magnitude higher than that of a gold colloid solution with 57 nm gold particles and without pH change (pH 6). Even with a compact field-based Raman spectrometer, naphthalene, phenanthrene, anthracene, fluoranthene, and pyrene were detected, with limits of detection at 6.8 nM, 3.4 nM, 1.8 nM, 0.68 nM (680 pM), and 0.44 nM (440 pM), respectively. The significant enhancement was ascribed to an electromagnetic mechanism and a charge-transfer mechanism. Quantitative analyses for these five PAHs in water were also performed. The SERS intensities of PAHs were found to have good linear dependence relations with the concentrations in low concentration. This high-sensitivity, easily prepared substrate offers a promising technology for the quantitative detection of trace-level PAHs.

Quantifying the equilibrium partitioning of substituted polycyclic aromatic hydrocarbons in aerosols and clouds using COSMOtherm.

PubMed

Awonaike, Boluwatife; Wang, Chen; Goss, Kai-Uwe; Wania, Frank

2017-03-22

Functional groups attached to polycyclic aromatic hydrocarbons (PAHs) can significantly modify the environmental fate of the parent compound. Equilibrium partition coefficients, which are essential for describing the environmental phase distribution of a compound, are largely unavailable for substituted PAHs (SPAHs). Here, COSMOtherm, a software based on quantum-chemical calculations is used to estimate the atmospherically relevant partition coefficients between the gas phase, the aqueous bulk phase, the water surface and the water insoluble organic matter phase, as well as the salting-out coefficients, for naphthalene, anthracene, phenanthrene, benz(a)anthracene, benzo(a)pyrene and dibenz(a,h)anthracene and 62 of their substituted counterparts. They serve as input parameters for the calculation of equilibrium phase distribution of these compounds in aerosols and clouds. Our results, which were compared with available experimental data, show that the effect of salts, the adsorption to the water surface and the dissolution in a bulk aqueous phase can be safely neglected when estimating the gas-particle partitioning of SPAHs in aerosols. However, for small PAHs with more than one polar functional group the aqueous phase can be the dominant reservoir in a cloud.

Pyrene-Tagged Ionic Liquids: Separable Organic Catalysts for SN2 Fluorination.

PubMed

Taher, Abu; Lee, Kyo Chul; Han, Hye Ji; Kim, Dong Wook

2017-07-07

We prepared pyrene-substituted imidazolium-based ionic liquids (PILs) as organic catalysts for the S N 2 fluorination using alkali metal fluoride (MF). In this system, the PIL significantly enhanced the reactivity of MF due to the phase-transfer catalytic effect of the imidazolium moiety as well as the metal cation-π (pyrene) interactions. Furthermore, this homogeneous catalyst PIL was easily separated from the reaction mixture using reduced graphene oxide by π-π stacking with the pyrene of PIL.

Environmental Assessment for Restoration and Stabilization of Eastern Shoreline MacDill AFB, Florida

DTIC Science & Technology

2005-12-01

heal stress , and machinery injuries. Construction would not involve any unique hazards and all construction methods would comply with Occupational...slips, heat stress , and machinery injuries. Construction would not involve any unique hazards, and all construction methods would comply with OSHA...Chloropropane, Benzene, Cumine , Naphthalene, benzo(b)flouranthene, toluene Soils: Benzo(a)pyrene, dibenzo(a,h)anthracene, Pb, naphthalene, toluene Surface

Flame-retardant EPDM compounds containing phenanthrene to enhance radiation resistance

NASA Astrophysics Data System (ADS)

Chen, Jian; Huang, Wei; Jiang, Shu-Bin; Li, Xiao-Yan; An, You; Li, Chuang; Gao, Xiao-Ling; Chen, Hong-Bing

2017-01-01

Ethylene propylene diene monomer (EPDM) compounds with good flame-retardant and γ-ray radiation resistant properties were prepared by adding complex flame retardants and phenathrene. The resultant EPDM formulations have a long time to ignition (TTI >46 s), a low peak heat release rate (PHRR 341 kW/m2) and a high limited oxygen index (LOI >30). Effects of γ-ray radiation on the resultant flame-retardant EPDM was investigated. The formulated EPDM is a crosslinking dominated polymer under γ-ray radiation. The γ-ray radiation resistant property of EPDM was enhanced by adding phenanthrene. Elongation at break of EPDM formulated with phenanthrene could retain 91% after being irradiated to 0.3 MGy and still retains 40% elongation even after being irradiated to 0.9 MGy, which is much better the control. It is expected that the formulated flame-retardant and radiation resistant EPDM materials could meet the requirements for use in radiation environments.

Naphthalene metabolism in relation to target tissue anatomy, physiology, cytotoxicity and tumorigenic mechanism of action

PubMed Central

Bogen, Kenneth T.; Benson, Janet M.; Yost, Garold S.; Morris, John B.; Dahl, Alan R.; Clewell, Harvey J.; Krishnan, Kannan; Omiecinski, Curtis J.

2014-01-01

This report provides a summary of deliberations conducted under the charge for members of Module C Panel participating in the Naphthalene State-of-the-Science Symposium (NS3), Monterey, CA, October 9–12, 2006. The panel was charged with reviewing the current state of knowledge and uncertainty about naphthalene metabolism in relation to anatomy, physiology and cytotoxicity in tissues observed to have elevated tumor incidence in these rodent bioassays. Major conclusions reached concerning scientific claims of high confidence were that: (1) rat nasal tumor occurrence was greatly enhanced, if not enabled, by adjacent, histologically related focal cellular proliferation; (2) elevated incidence of mouse lung tumors occurred at a concentration (30 ppm) cytotoxic to the same lung region at which tumors occurred, but not at a lower and less cytotoxic concentration (tumorigenesis NOAEL = 10 ppm); (3) naphthalene cytotoxicity requires metabolic activation (unmetabolized naphthalene is not a proximate cause of observed toxicity or tumors); (4) there are clear regional and species differences in naphthalene bioactivation; and (5) target tissue anatomy and physiology is sufficiently well understood for rodents, non-human primates and humans to parameterize species-specific physiologically based pharmacokinetic (PBPK) models for nasal and lung effects. Critical areas of uncertainty requiring resolution to enable improved human cancer risk assessment were considered to be that: (1) cytotoxic naphthalene metabolites, their modes of cytotoxic action, and detailed low-dose dose–response need to be clarified, including in primate and human tissues, and neonatal tissues; (2) mouse, rat, and monkey inhalation studies are needed to better define in vivo naphthalene uptake and metabolism in the upper respiratory tract; (3) in vivo validation studies are needed for a PBPK model for monkeys exposed to naphthalene by inhalation, coupled to cytotoxicity studies referred to above; and (4

IRIS Toxicological Review of Benzo[a]pyrene (External Review Draft)

EPA Science Inventory

The IRIS Toxicological Review of Benzo[a]pyrene was released for external peer review in September 2014. The EPA’s Science Advisory Board’s (SAB) Chemical Assessment Advisory Committee (CAAC) conducted a peer review of the scientific basis supporting the benzo[a]pyrene assessmen...

Differentiation of naphthalene and paradichlorobenzene mothballs based on their difference in specific gravity.

PubMed

Fukuda, T; Koyama, K; Yamashita, M; Koichi, N; Takeda, M

1991-08-01

The present study was conducted to measure the specific gravities of paradichlorobenzene and naphthalene mothballs and compare them with the specific gravity of a saturated aqueous solution of sodium chloride (1.197). The specific gravities of 450 paradichlorobenzene mothballs from 5 manufactures and 150 naphthalene mothballs from 2 manufactures were measured with a specific gravity meter. The mean specific gravities of paradichlorobenzene mothballs were between 1.429 and 1.437 (p = 0.99). On the other hand, the mean specific gravities of naphthalene mothballs were between 1.094 and 1.100 (p = 0.99). Based on the fact that paradichlorobenzene mothballs sink in a saturated solution of salt whereas naphthalene mothballs float on it, these 2 kinds of mothballs ought to be rapidly and accurately distinguished in clinical settings.

Binding mode dependent signaling for the detection of Cu2 +: An experimental and theoretical approach with practical applications

NASA Astrophysics Data System (ADS)

Ghosh, Soumen; Khan, Mehebub Ali; Ganguly, Aniruddha; Masum, Abdulla Al; Alam, Md. Akhtarul; Guchhait, Nikhil

2018-02-01

Two amido-schiff bases (3-Hydroxy-naphthalene-2-carboxylic acid pyren-1-ylmethylene-hydrazide and Naphthalene-2-carboxylic acid pyren-1-ylmethylene-hydrazide) have been synthesized having a common structural unit and only differs by a -OH group in the naphthalene ring. Both of them can detect Cu2 + ion selectively in semi-aqueous medium in distinctly different output modes (one detects Cu2 + by naked-eye color change where as the other detects Cu2 + by fluorescence enhancement). The difference in the binding of Cu 2 + with the compounds is the reason for this observation. The detection limit is found to be micromolar region for compound which contains -OH group whereas the compound without -OH group detects copper in nano-molar region. DFT calculations have been performed in order to demonstrate the structure of the compounds and their copper complexes. Practical utility has been explored by successful paper strip response of both the compounds. The biological applications have been evaluated in RAW 264.7.

Hydroxypropyl cyclic β-(1 → 2)-D-glucans and epichlorohydrin β-cyclodextrin dimers as effective carbohydrate-solubilizers for polycyclic aromatic hydrocarbons.

PubMed

Choi, Jae Min; Jeong, Daham; Piao, Jinglan; Kim, Kyoungtea; Nguyen, Andrew Bao Loc; Kwon, Nak-Jung; Lee, Mi-Kyung; Lee, Im Soon; Yu, Jae-Hyuk; Jung, Seunho

2015-01-12

The removal of polycyclic aromatic hydrocarbons by soil washing using water is extremely difficult due to their intrinsic hydrophobic nature. In this study, the effective aqueous solubility enhancements of seven polycyclic aromatic hydrocarbons by chemically modified hydroxypropyl rhizobial cyclic β-(1 → 2)-D-glucans and epichlorohydrin β-cyclodextrin dimer have been investigated for the first time. In the presence of hydroxypropyl cyclic β-(1 → 2)-D-glucans, the solubility of benzo[a]pyrene is increased up to 38 fold of its native solubility. The solubility of pyrene and phenanthrene dramatically increased up to 160 and 359. Coronene, chrysene, perylene, and fluoranthene also show an increase of 11, 23, 23, and 97 fold, respectively, of enhanced solubility by complexation with synthetic epichlorohydrin β-cyclodextrin dimer. The physicochemical properties of the complex are characterized by Fourier-transform infrared spectra and differential scanning calorimetry. Utilizing a scanning electron microscopy, the morphological structures of native benzo[a]pyrene, pyrene, phenanthrene, coronene, chrysene, perylene, fluoranthene and their complex with novel carbohydrate-solubilizers are studied. These results elucidate that polycyclic aromatic hydrocarbons are able to form an efficient complex with hydroxypropyl cyclic β-(1 → 2)-D-glucans and β-cyclodextrin dimer, suggesting the potential usage of chemically modified novel carbohydrate-solubilizers. Copyright © 2014 Elsevier Ltd. All rights reserved.

Interrelation of nonequivalent Csbnd C bonds of naphthalene frame and spatial orientation of substituents: Beta-naphthalene sulfonyl fluoride and beta-naphthalene sulfonyl chloride

NASA Astrophysics Data System (ADS)

Giricheva, Nina I.; Petrov, Vjacheslav M.; Oberhammer, Heinz; Petrova, Valentina N.; Dakkouri, Marwan; Ivanov, Sergey N.; Girichev, Georgiy V.

2013-06-01

β-naphthalene sulfonyl fluoride, β-NaphSF, and β-naphthalene sulfonyl chloride, β-NaphSCl, were studied by gas-phase electron diffraction (GED) and quantum chemical calculations (B3LYP and MP2 in combination with cc-pVDZ, aug-cc-pVDZ and cc-pVTZ basis sets). For each compound the calculations predicted the existence of two conformers which are enantiomers. On the basis of the experimental data it was found that the gas phase over β-NaphSF and NaphSCl at 357(5) K and 395(5) K, respectively, consists of molecular species of C1 symmetry in which the Cβsbnd Ssbnd Hal plane deviates from the perpendicular orientation relative to the naphthalene skeleton plane. The following geometrical parameters (Å and degrees) were obtained from the experiment (uncertainties are in parentheses): rh1(Csbnd H)aver. = 1.097(7), rh1(Csbnd C)aver. = 1.410(3), rh1(Csbnd S) = 1.753(6), rh1(Ssbnd O)aver. = 1.414(4), rh1(Ssbnd F) = 1.559(5), ∠Csbnd Cβsbnd C = 122.8(3), ∠Cβsbnd Ssbnd F = 103.3(30); Φ(Cαsbnd Cβsbnd Ssbnd F) = 104(6) for β-NaphSF, and rh1(Csbnd H)aver. = 1.089(4), rh1(Csbnd C)aver. = 1.411(3), rh1(Csbnd S) = 1.757(5), rh1(Ssbnd O)aver. = 1.419(3), rh1(Ssbnd Сl) = 2.053(4), ∠Csbnd Cβsbnd C = 122.8(1), ∠Cβsbnd Ssbnd Cl = 102.2(7), Φ(Cαsbnd Cβsbnd Ssbnd Cl) = 108(3) for β-NaphSCl. The calculated barriers to internal rotation of the sulfonyl halide groups exceed considerably the thermal energy values corresponding to the temperatures of the GED experiments. Natural bond orbital (NBO) analyses of the electron density distribution were applied to explain the peculiarities of the molecular structure of the studied compounds and the deviation from the structures of their benzene analogs.

CLASSIFICATION OF PAH-DEGRADING BACTERIA BY PAH UTILIZATION PATTERNS AND THE COMPARISON OF METABOLIC PRODUCTS

EPA Science Inventory

Bacterial strains capable of using either phenanthrene, fluoranthene, or pyrene as sole carbon and energy sources were isolated from 16 different soil samples collected from the United States, Germany, and Norway. Thirty one strains were isolated on fluoranthene and the other twe...

Removal of phenanthrene from soil by co-cultures of bacteria and fungi pregrown on sugarcane bagasse pith.

PubMed

Chávez-Gómez, B; Quintero, R; Esparza-García, F; Mesta-Howard, A M; Zavala Díaz de la Serna, F J; Hernández-Rodríguez, C H; Gillén, T; Poggi-Varaldo, H M; Barrera-Cortés, J; Rodríguez-Vázquez, R

2003-09-01

Sixteen co-cultures composed of four bacteria and four fungi grown on sugarcane bagasse pith were tested for phenanthrene degradation in soil. The four bacteria were identified as Pseudomonas aeruginose, Ralstonia pickettii, Pseudomonas sp. and Pseudomonas cepacea. The four fungi were identified as: Penicillium sp., Trichoderma viride, Alternaria tenuis and Aspergillus terrus that were previously isolated from different hydrocarbon-contaminated soils. Fungi had a statistically significant positive (0.0001phenanthrene removal, that ranged from 35% to 50% and bacteria removed the compound by an order of 20%. Co-cultures B. cepacea-Penicillium sp., R. pickettii-Penicillium sp., and P. aeruginose-Penicillium sp. exhibited synergism for phenanthrene removal, reaching 72.84+/-3.85%, 73.61+/-6.38% and 69.47+/-4.91%; in 18 days, respectively.

Biodegradation of polycyclic aromatic hydrocarbons by Trichoderma species: a mini review.

PubMed

Zafra, German; Cortés-Espinosa, Diana V

2015-12-01

Fungi belonging to Trichoderma genus are ascomycetes found in soils worldwide. Trichoderma has been studied in relation to diverse biotechnological applications and are known as successful colonizers of their common habitats. Members of this genus have been well described as effective biocontrol organisms through the production of secondary metabolites with potential applications as new antibiotics. Even though members of Trichoderma are commonly used for the commercial production of lytic enzymes, as a biological control agent, and also in the food industry, their use in xenobiotic biodegradation is limited. Trichoderma stands out as a genus with a great range of substrate utilization, a high production of antimicrobial compounds, and its ability for environmental opportunism. In this review, we focused on the recent advances in the research of Trichoderma species as potent and efficient aromatic hydrocarbon-degrading organisms, as well as aimed to provide insight into its potential role in the bioremediation of soils contaminated with heavy hydrocarbons. Several Trichoderma species are associated with the ability to metabolize a variety of both high and low molecular weight polycyclic aromatic hydrocarbons (PAHs) such as naphthalene, phenanthrene, chrysene, pyrene, and benzo[a]pyrene. PAH-degrading species include Trichoderma hamatum, Trichoderma harzianum, Trichoderma reesei, Trichoderma koningii, Trichoderma viride, Trichoderma virens, and Trichoderma asperellum using alternate enzyme systems commonly seen in other organisms, such as multicooper laccases, peroxidases, and ring-cleavage dioxygenases. Within these species, T. asperellum stands out as a versatile organism with remarkable degrading abilities, high tolerance, and a remarkable potential to be used as a remediation agent in polluted soils.

Responses of metabolic pathways to polycyclic aromatic compounds in flounder following oil spill in the Baltic Sea near the Estonian coast.

PubMed

Kreitsberg, Randel; Zemit, Irina; Freiberg, Rene; Tambets, Meelis; Tuvikene, Arvo

2010-09-15

In January 2006 an oil spill that involved approximately 40tons of heavy fuel oil affected more than 30km of the north-west coast of Estonia. The aquatic pollution of the coastal area of the Baltic Sea was monitored by measuring the content of selected polycyclic aromatic hydrocarbons (PAHs and PAH metabolites) in flounder (Platichthys flesus trachurus Duncker). One hundred and thirty-one fish were collected: muscle and liver tissues were analyzed by high-performance liquid chromatography (HPLC); bile and urine samples were analyzed using fixed wavelengths fluorescence. Fifteen different types of PAHs were analyzed in liver and muscle, and four types of PAH metabolites were analyzed in bile and urine (2-, 3-, 4- and 5-ringed PAH metabolites represented by naphthalene, phenanthrene, pyrene and benzo(a)pyrene). Fluorescence analyses were carried out using excitation/emission wavelength pairs: 290/380, 256/380, 341/383 and 380/430nm, respectively. There was a time-dependent decrease of PAH concentrations in liver (83%), bile (82%) and urine (113%). HPLC analysis of muscle tissues demonstrated low concentrations of single PAHs, but a decrease of concentrations during the study period was not observed. During the analyses concentrations of PAH metabolites in bile and urine were compared. Liver metabolic transformation activity is believed to exceed that of the kidney but the analyses demonstrated high metabolite concentration in fish urine, particularly of 4- and 5-ring PAH metabolites. The results indicate remarkable buffer capacity of hydrodynamically active sea as well as considerable importance of kidney-urine metabolic pathways in flounder physiology. 2010 Elsevier B.V. All rights reserved.

Toxicological effects of polycyclic aromatic hydrocarbons and their derivatives on respiratory cells

NASA Astrophysics Data System (ADS)

Koike, Eiko; Yanagisawa, Rie; Takano, Hirohisa

2014-11-01

Polycyclic aromatic hydrocarbons (PAHs) are found in ambient aerosols and particulate matter. Experimental studies have shown that PAHs and related chemicals can induce toxicological effects. The present study aimed to investigate the effects of PAHs and their derivatives on the respiratory and immune systems and the underlying mechanisms. The human bronchial epithelial cell line BEAS-2B was exposed to PAHs and their derivatives, and the cytotoxicity and proinflammatory protein expression were then investigated. A cytotoxic effect was observed in BEAS-2B exposed to PAH derivatives such as naphthoquinone (NQ), phenanthrenequinone (PQ), 1-nitropyrene (1-NP), and 1-aminopyrene (1-AP). In addition, 1,2-NQ and 9,10-PQ showed more effective cytotoxicity than 1,4-NQ and 1,4-PQ, respectively. Pyrene showed a weak cytotoxic effect. On the other hand, naphthalene and phenanthrene showed no significant effects. Pyrene, 1-NP, and 1-AP also increased intercellular adhesion molecule-1 expression and interleukin-6 production in BEAS-2B. The increase was partly suppressed by protein kinase inhibitors such as the epidermal growth factor receptor-selective tyrosine kinase inhibitor and nuclear receptor antagonists such as the thyroid hormone receptor antagonist. The present study suggests that the toxicological effects of chemicals may be related to the different activities resulting from their structures, such as numbers of benzene rings and functional groups. Furthermore, the chemical-induced increase in proinflammatory protein expression in bronchial epithelial cells was possibly a result of the activation of protein kinase pathways and nuclear receptors. The increase may partly contribute to the adverse health effects of atmospheric PAHs.

The variability of standard artificial soils: cadmium and phenanthrene sorption measured by a batch equilibrium method.

PubMed

Bielská, Lucie; Hovorková, Ivana; Kuta, Jan; Machát, Jiří; Hofman, Jakub

2017-01-01

Artificial soil (AS) is used in soil ecotoxicology as a test medium or reference matrix. AS is prepared according to standard OECD/ISO protocols and components of local sources are usually used by laboratories. This may result in significant inter-laboratory variations in AS properties and, consequently, in the fate and bioavailability of tested chemicals. In order to reveal the extent and sources of variations, the batch equilibrium method was applied to measure the sorption of 2 model compounds (phenanthrene and cadmium) to 21 artificial soils from different laboratories. The distribution coefficients (K d ) of phenanthrene and cadmium varied over one order of magnitude: from 5.3 to 61.5L/kg for phenanthrene and from 17.9 to 190L/kg for cadmium. Variations in phenanthrene sorption could not be reliably explained by measured soil properties; not even by the total organic carbon (TOC) content which was expected. Cadmium logK d values significantly correlated with cation exchange capacity (CEC), pH H2O and pH KCl , with Pearson correlation coefficients of 0.62, 0.80, and 0.79, respectively. CEC and pH H2O together were able to explain 72% of cadmium logK d variability in the following model: logK d =0.29pH H2O +0.0032 CEC -0.53. Similarly, 66% of cadmium logK d variability could be explained by CEC and pH KCl in the model: logKd=0.27pH KCl +0.0028 CEC -0.23. Variable cadmium sorption in differing ASs could be partially treated with these models. However, considering the unpredictable variability of phenanthrene sorption, a more reliable solution for reducing the variability of ASs from different laboratories would be better harmonization of AS preparation and composition. Copyright © 2016 Elsevier Inc. All rights reserved.

Enrichment and characterization of sulfate reducing, naphthalene degrading microorganisms

NASA Astrophysics Data System (ADS)

Steffen, Kümmel; Florian-Alexander, Herbst; Márcia, Duarte; Dietmar, Pieper; Jana, Seifert; Bergen Martin, von; Hans-Hermann, Richnow; Carsten, Vogt

2014-05-01

Polycyclic aromatic hydrocarbons (PAH) are pollutants of great concern due to their potential toxicity, mutagenicity and carcinogenicity. PAH are widely distributed in the environment by accidental discharges during the transport, use and disposal of petroleum products, and during forest and grass fires. Caused by their hydrophobic nature, PAH basically accumulate in sediments from where they are slowly released into the groundwater. Although generally limited by the low water solubility of PAH, microbial degradation is one of the major mechanisms leading to the complete clean-up of PAH-contaminated sites. Whereas organisms and biochemical pathways responsible for the aerobic breakdown of PAH are well known, anaerobic PAH biodegradation is less understood; only a few anaerobic PAH degrading cultures have been described. We studied the anaerobic PAH degradation in a microcosm approach to enrich anaerobic PAH degraders. Anoxic groundwater and sediment samples were used as inoculum. Groundwater samples were purchased from the erstwhile gas works facility and a former wood impregnation site. In contrast, sources of sediment samples were a former coal refining area and an old fuel depot. Samples were incubated in anoxic mineral salt medium with naphthalene as sole carbon source and sulfate as terminal electron acceptor. Grown cultures were characterized by feeding with 13C-labeled naphthalene, 16S rRNA gene sequencing using an Illumina® approach, and functional proteome analyses. Finally, six enrichment cultures able to degrade naphthalene under anoxic conditions were established. First results point to a dominance of identified sequences affiliated to the freshwater sulfate-reducing strain N47, which is a known anaerobic naphthalene degrader, in four out of the six enrichments. In those enrichments, peptides related to the pathway of anoxic naphthalene degradation in N47 were abundant. Overall the data underlines the importance of Desulfobacteria for natural

Quantity and quality of stormwater collected from selected stormwater outfalls at industrial sites, Fort Gordon, Georgia, 2012

USGS Publications Warehouse

Nagle, Doug D.

2013-01-01

Samples from sites SWR11–3, SWR11–4, and SWR11–5 were analyzed for 83 volatile and semivolatile organic compounds. Eight polycyclic aromatic hydrocarbon compounds, benzo[a]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[k]fluoranthene, chrysene, indeno[1,2,3-cd]pyrene, phenanthrene, and pyrene, were detected at all three sites. Of the 86 volatile and semivolatile organic compounds that were analyzed in stormwater samples from heating and cooling sites, 15 (18 percent) were detected at site SWR11–3, 12 (14 percent) were detected at site SWR11–4, and 17 (20 percent) were detected at site SWR11–5.

Hypothesis-based weight-of-evidence evaluation and risk assessment for naphthalene carcinogenesis

PubMed Central

Bailey, Lisa A.; Nascarella, Marc A.; Kerper, Laura E.; Rhomberg, Lorenz R.

2016-01-01

Inhalation of naphthalene causes olfactory epithelial nasal tumors in rats (but not in mice) and benign lung adenomas in mice (but not in rats). The limited available human data have not identified an association between naphthalene exposure and increased respiratory cancer risk. Assessing naphthalene's carcinogenicity in humans, therefore, depends entirely on experimental evidence from rodents. We evaluated the respiratory carcinogenicity of naphthalene in rodents, and its potential relevance to humans, using our Hypothesis-Based Weight-of-Evidence (HBWoE) approach. We systematically and comparatively reviewed data relevant to key elements in the hypothesized modes of action (MoA) to determine which is best supported by the available data, allowing all of the data from each realm of investigation to inform interpretation of one another. Our analysis supports a mechanism that involves initial metabolism of naphthalene to the epoxide, followed by GSH depletion, cytotoxicity, chronic inflammation, regenerative hyperplasia, and tumor formation, with possible weak genotoxicity from downstream metabolites occurring only at high cytotoxic doses, strongly supporting a non-mutagenic threshold MoA in the rat nose. We also conducted a dose–response analysis, based on the likely MoA, which suggests that the rat nasal MoA is not relevant in human respiratory tissues at typical environmental exposures. Our analysis illustrates how a thorough WoE evaluation can be used to support a MoA, even when a mechanism of action cannot be fully elucidated. A non-mutagenic threshold MoA for naphthalene-induced rat nasal tumors should be considered as a basis to determine human relevance and to guide regulatory and risk-management decisions. PMID:26202831

Source apportionment of elevated wintertime PAHs by compound-specific radiocarbon analysis

NASA Astrophysics Data System (ADS)

Sheesley, R. J.; Kruså, M.; Krecl, P.; Johansson, C.; Gustafsson, Ã.-.

2009-05-01

Natural abundance radiocarbon analysis facilitates distinct source apportionment between contemporary biomass/biofuel (14C "alive") versus fossil fuel (14C "dead") combustion. Here, the first compound-specific radiocarbon analysis (CSRA) of atmospheric polycyclic aromatic hydrocarbons (PAHs) was demonstrated for a set of samples collected in Lycksele, Sweden a small town with frequent episodes of severe atmospheric pollution in the winter. Renewed interest in using residential wood combustion (RWC) means that this type of seasonal pollution is of increasing concern in many areas. Five individual/paired PAH isolates from three pooled fortnight-long filter collections were analyzed by CSRA: phenanthrene, fluoranthene, pyrene, benzo[b+k]fluoranthene and indeno[cd]pyrene plus benzo[ghi]perylene; phenanthrene was the only compound also analyzed in the gas phase. The measured Δ14C for PAHs spanned from -138.3‰ to 58.0‰. A simple isotopic mass balance model was applied to estimate the fraction biomass (fbiomass) contribution, which was constrained to 71-87% for the individual PAHs. Indeno[cd]pyrene plus benzo[ghi]perylene had an fbiomass of 71%, while fluoranthene and phenanthrene (gas phase) had the highest biomass contribution at 87%. The total organic carbon (TOC, defined as carbon remaining after removal of inorganic carbon) fbiomass was estimated to be 77%, which falls within the range for PAHs. This CSRA data of atmospheric PAHs established that RWC is the dominating source of atmospheric PAHs to this region of the boreal zone with some variations among RWC contributions to specific PAHs.

Effects of soil amendment with different carbon sources and other factors on the bioremediation of an aged PAH-contaminated soil.

PubMed

Teng, Ying; Luo, Yongming; Ping, Lifeng; Zou, Dexun; Li, Zhengao; Christie, Peter

2010-04-01

Carbon supplementation, soil moisture and soil aeration are believed to enhance in situ bioremediation of PAH-contaminated soils by stimulating the growth of indigenous microorganisms. However, the effects of added carbon and nitrogen together with soil moisture and soil aeration on the dissipation of PAHs and on associated microbial counts have yet to be fully assessed. In this study the effects on bioremediation of carbon source, carbon-to-nitrogen ratio, soil moisture and aeration on an aged PAH-contaminated agricultural soil were studied in microcosms over a 90-day period. Additions of starch, glucose and sodium succinate increased soil bacterial and fungal counts and accelerated the dissipation of phenanthrene and benzo(a)pyrene in soil. Decreases in phenanthrene and benzo(a)pyrene concentrations were effective in soil supplemented with glucose and sodium succinate (both 0.2 g C kg(-1) dry soil) and starch (1.0 g C kg(-1) dry soil). The bioremediation effect at a C/N ratio of 10:1 was significantly higher (P < 0.05) than at a C/N of either 25:1 or 40:1. Soil microbial counts and PAH dissipation were lower in the submerged soil but soil aeration increased bacterial and fungal counts, enhanced indigenous microbial metabolic activities, and accelerated the natural degradation of phenanthrene and benzo(a)pyrene. The results suggest that optimizing carbon source, C/N ratio, soil moisture and aeration conditions may be a feasible remediation strategy in certain PAH contaminated soils with large active microbial populations.

STABILITY OF HEMOGLOBIN AND ALBUMIN ADDUCTS OF NAPHTHALENE OXIDE, 1,2-NAPHTHOQUINONE, AND 1,4-NAPHTHOQUINONE

EPA Science Inventory

Naphthalene is an important industrial chemical, which has recently been shown to cause tumors of the respiratory tract in rodents. It is thought that one or more reactive metabolites of naphthalene, namely, naphthalene-1,2-oxide (NPO), 1,2-naphthoquinone (1,2-NPQ), and 1,4-na...

The influence of mechanochemical modification on prevention of toxic ability of humic acids towards phenanthrene in aquatic environment

NASA Astrophysics Data System (ADS)

Shekhovtsova, N. S.; Maltseva, E. V.; Glyzina, T. S.; Ovchinnikova, I. S.

2015-11-01

The aim of the research work is to quantify interaction between phenanthrene with modified humic acids in aquatic environment. The changes in the structure and properties of humic acids after modifications were studied with 1H NMR spectroscopy and potentiometric titration methods. Our research demonstrates that the application of thiourea as a modified agent increases the binding capacity of humic acids towards phenanthrene.

Biodegradation of naphthalene and anthracene by chemo-tactically active rhizobacteria of populus deltoides

PubMed Central

Bisht, Sandeep; Pandey, Piyush; Sood, Anchal; Sharma, Shivesh; Bisht, N. S.

2010-01-01

Several naphthalene and anthracene degrading bacteria were isolated from rhizosphere of Populus deltoides, which were growing in non-contaminated soil. Among these, four isolates, i.e. Kurthia sp., Micrococcus varians, Deinococcus radiodurans and Bacillus circulans utilized chrysene, benzene, toluene and xylene, in addition to anthracene and naphthalene. Kurthia sp and B. circulans showed positive chemotactic response for naphthalene and anthracene. The mean growth rate constant (K) of isolates were found to increase with successive increase in substrate concentration (0.5 to 1.0 mg/50ml). B. circulans SBA12 and Kurthia SBA4 degraded 87.5% and 86.6% of anthracene while, Kurthia sp. SBA4, B. circulans SBA12, and M. varians SBA8 degraded 85.3 %, 95.8 % and 86.8 % of naphthalene respectively after 6 days of incubation as determined by HPLC analysis. PMID:24031572

Health Effects Assessment for Pyrene

EPA Science Inventory

The document represents a brief, quantitatively oriented scientific summary of health effects data for pyrene. It was developed by the Environmental Criteria and Assessment Office to assist the Office of Emergency and Remedial Response in establishing chemical-specific health-rel...

Alkylation effects on the energy transfer of highly vibrationally excited naphthalene.

PubMed

Hsu, Hsu Chen; Tsai, Ming-Tsang; Dyakov, Yuri A; Ni, Chi-Kung

2011-11-04

The energy transfer of highly vibrationally excited isomers of dimethylnaphthalene and 2-ethylnaphthalene in collisions with krypton were investigated using crossed molecular beam/time-of-flight mass spectrometer/time-sliced velocity map ion imaging techniques at a collision energy of approximately 300 cm(-1). Angular-resolved energy-transfer distribution functions were obtained directly from the images of inelastic scattering. The results show that alkyl-substituted naphthalenes transfer more vibrational energy to translational energy than unsubstituted naphthalene. Alkylation enhances the V→T energy transfer in the range -ΔE(d)=-100~-1500 cm(-1) by approximately a factor of 2. However, the maximum values of V→T energy transfer for alkyl-substituted naphthalenes are about 1500~2000 cm(-1), which is similar to that of naphthalene. The lack of rotation-like wide-angle motion of the aromatic ring and no enhancement in very large V→T energy transfer, like supercollisions, indicates that very large V→T energy transfer requires special vibrational motions. This transfer cannot be achieved by the low-frequency vibrational motions of alkyl groups. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Rapid Mineralization of Benzo[a]pyrene by a Microbial Consortium Growing on Diesel Fuel

PubMed Central

Kanaly, Robert A.; Bartha, Richard; Watanabe, Kazuya; Harayama, Shigeaki

2000-01-01

A microbial consortium which rapidly mineralized the environmentally persistent pollutant benzo[a]pyrene was recovered from soil. The consortium cometabolically converted [7-14C]benzo[a]pyrene to 14CO2 when it was grown on diesel fuel, and the extent of benzo[a]pyrene mineralization was dependent on both diesel fuel and benzo[a]pyrene concentrations. Addition of diesel fuel at concentrations ranging from 0.007 to 0.2% (wt/vol) stimulated the mineralization of 10 mg of benzo[a]pyrene per liter 33 to 65% during a 2-week incubation period. When the benzo[a]pyrene concentration was 10 to 100 mg liter−1 and the diesel fuel concentration was 0.1% (wt/vol), an inoculum containing 1 mg of cell protein per liter (small inoculum) resulted in mineralization of up to 17.2 mg of benzo[a]pyrene per liter in 16 days. This corresponded to 35% of the added radiolabel when the concentration of benzo[a]pyrene was 50 mg liter−1. A radiocarbon mass balance analysis recovered 25% of the added benzo[a]pyrene solubilized in the culture suspension prior to mineralization. Populations growing on diesel fuel most likely promoted emulsification of benzo[a]pyrene through the production of surface-active compounds. The consortium was also analyzed by PCR-denaturing gradient gel electrophoresis of 16S rRNA gene fragments, and 12 dominant bands, representing different sequence types, were detected during a 19-day incubation period. The onset of benzo[a]pyrene mineralization was compared to changes in the consortium community structure and was found to correlate with the emergence of at least four sequence types. DNA from 10 sequence types were successfully purified and sequenced, and that data revealed that eight of the consortium members were related to the class Proteobacteria but that the consortium also included members which were related to the genera Mycobacterium and Sphingobacterium. PMID:11010861

IMMOBILIZATION OF AQUEOUS PYRENE BY DISSOLVED HUMIC ACID (R822832)

EPA Science Inventory

Abstract

Pyrene is frequently used as a fluorescent probe in the study of solution environments. Purging with nitrogen is a common practice for the elimination of oxygen from solutions, but this procedure leads to the loss of pyrene through carry-over in the nitrogen s...

Effects of oil dispersants on photodegradation of pyrene in marine water.

PubMed

Gong, Yanyan; Fu, Jie; O'Reilly, S E; Zhao, Dongye

2015-04-28

This work investigated effects of a popular oil dispersant (Corexit EC9500A) on UV- or sunlight-mediated photodegradation of pyrene (a model polycyclic aromatic hydrocarbon) in seawater. The presence of 18 and 180mg/L of the dispersant increased the first-order photodegradation rate by 5.5% and 16.7%, respectively, and reduced or ceased pyrene volatilization. By combining individual first-order rate laws for volatilization and photodegradation, we proposed an integrated kinetic model that can adequately predict the overall dissipation of pyrene from seawater. Mechanistic studies indicated that superoxide radicals played a predominant role in pyrene photodegradation, and the dispersant enhanced formation of superoxide radicals. 1-Hydroxypyrene was the main intermediate regardless of the dispersant, suggesting that electrons were transferred from excited pyrene to oxygen. In the presence of 18mg/L of the dispersant, the photodegradation rate increased with increasing ionic strength and temperature, but decreased with increasing HA concentration, and remained independent of solution pH. The results are important in understanding roles of oil dispersants on environmental fate of persistent oil components in natural and engineered systems. Copyright © 2015 Elsevier B.V. All rights reserved.

MEASURING GROWTH OF A PHENANTHRENE DEGRADING BACTERIAL INOCULUM IN SOIL WITH A QUANTITATIVE COMPETITIVE POLYMERASE CHAIN REACTION METHOD. (R825433)

EPA Science Inventory

We measured growth of a phenanthrene-degrading bacterium, Arthrobacter, strain RP17, in Forbes soil, amended with 500 g g⁻¹ phenanthrene using a quantitati...

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene-derived aminophosphonates.

PubMed

Lewkowski, Jarosław; Rodriguez Moya, Maria; Wrona-Piotrowicz, Anna; Zakrzewski, Janusz; Kontek, Renata; Gajek, Gabriela

2016-01-01

A large series of variously substituted amino(pyren-1-yl)methylphosphonic acid derivatives was synthesized using a modified aza-Pudovik reaction in 20-97% yields. The fluorescence properties of the obtained compounds were investigated revealing that N-alkylamino(pyren-1-yl)methylphosphonic derivatives are stronger emissive compounds than the corresponding N-aryl derivatives. N-Benzylamino(pyren-1-yl)methylphosphonic acid displayed strong fluorescence (ΦF = 0.68) in phosphate-buffered saline (PBS). The influence of a series of derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC50 = 20.8 μM), simultaneously showing weak toxicity towards normal lymphocytes (IC50 = 230.8 µM).

Dynamic behavior of semivolatile organic compounds in indoor air. 2. Nicotine and phenanthrene with carpet and wallboard.

PubMed

Van Loy, M D; Riley, W J; Daisey, J M; Nazaroff, W W

2001-02-01

The surface interactions of nicotine and phenanthrene with carpet, painted wallboard, and stainless steel were investigated in a room-sized environmental test chamber. Adsorption kinetics were tested by flash evaporating a known mass of each compound into a sealed 20 m3 chamber containing one or more of the tested sorbents. In each experiment, one or more emissions were performed after the gas-phase concentration had reached an apparent plateau. At the end of each experiment, the chamber was ventilated and resealed to monitor reemission of the compound from the sorbents. Kinetic sorption parameters were determined by fitting a mass-balance model to the experimental results. The sorption capacity of stainless steel was of similar magnitude for nicotine and phenanthrene. Sorption of nicotine on carpet and wallboard was much stronger, with equilibrium partitioning values 2-3 orders of magnitude higher. The sorption capacities of phenanthrene on carpet and wallboard were smaller, approximately 10-20% of the stainless steel values. The rates of uptake are of similar magnitude for all sorbate--sorbent pairs and are consistent with the limit imposed by gas-phase boundary-layer mass transport. The rates of desorption are much faster for phenanthrene than for nicotine. Model simulations predict average nicotine levels in a typical smoking residence that are consistent with published data.

IRIS Toxicological Review of Benzo[a]pyrene (Public ...

EPA Pesticide Factsheets

EPA is developing an Integrated Risk Information System (IRIS) assessment of benzo[a]pyrene and has released the draft assessment for public comment and external peer review. When final, the assessment will appear on the IRIS database. EPA is undertaking an update of the Integrated Risk Information System (IRIS) health assessment for benzo[a]pyrene (BaP). The outcome of this project is an updated Toxicological Review and IRIS Summary for BaP that will be entered into the IRIS database.

Combined remediation of Cd-phenanthrene co-contaminated soil by Pleurotus cornucopiae and Bacillus thuringiensis FQ1 and the antioxidant responses in Pleurotus cornucopiae.

PubMed

Jiang, Juan; Liu, Hongying; Li, Qiao; Gao, Ni; Yao, Yuan; Xu, Heng

2015-10-01

Remediation of soil co-contaminated with heavy metals and PAHs by mushroom and bacteria is a novel technique. In this study, the combined remediation effect of mushroom (Pleurotus cornucopiae) and bacteria (FQ1, Bacillus thuringiensis) on Cd and phenanthrene co-contaminated soil was investigated. The effect of bacteria (B. thuringiensis) on mushroom growth, Cd accumulation, phenanthrene degradation by P. cornucopiae and antioxidative responses of P. cornucopiae were studied. P. cornucopiae could adapt easily and grow well in Cd-phenanthrene co-contaminated soil. It was found that inoculation of FQ1 enhanced mushroom growth (biomass) and Cd accumulation with the increment of 26.68-43.58% and 14.29-97.67% respectively. Up to 100% and 95.07% of phenanthrene were removed in the bacteria-mushroom (B+M) treatment respectively spiked with 200mg/kg and 500mg/kg phenanthrene. In addition, bacterial inoculation alleviated oxidative stress caused by co-contamination with relative decreases in lipid peroxidation and enzyme activity, including malondialdehyde (MDA), superoxide dismutase (SOD), catalase (CAT), and peroxidase (POD). This study demonstrated that the integrated remediation strategy of bacteria and mushroom is an effective and promising method for Cd-phenanthrene co-contaminated soil bioremediation. Copyright © 2015 Elsevier Inc. All rights reserved.

Nucleoside adducts from the in vitro reaction of benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide or benzo[a]pyrene 4,5-oxide with nucleic acids.

PubMed

Jennette, K W; Jeffrey, A M; Blobstein, S H; Beland, F A; Harvey, R G; Weinstein, I B

1977-03-08

The covalent binding of benzo[a]pyrene 4,5-oxide and benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide isomer I and isomer II to nucleic acids in aqueous acetone solution has been investigated. Benzo[a]pyrene 4,5-oxide reacted preferentially with guanosine residues. On the other hand, benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide isomer I and II reacted extensively with guanosine, adenosine, and cytidine residues. Time course studies showed that the reactivity of isomer I or isomer II with homopolyribonucleotides followed the order poly(G) greater than poly(A) greater than poly(C). Alkaline or enzymatic hydrolysis of the modified nucleic acids and subsequent chromatography on Sephadex LH-20 columns yielded benzo[a]pyrene-nucleotide adducts. These were enzymatically converted to the corresponding nucleosides which were resolved into several distinct components by high-pressure liquid chromatography. Evidence was obtained for the presence of multiple nucleoside adducts of guanosine, adenosine, cytidine, deoxyguanosine, deoxyadenosine, and deoxycytidine. The HPLC profiles of adducts formed with isomer I were different from the corresponding profiles of adducts formed with isomer II. Structural aspects of these nucleoside adducts are discussed.

Naphthalene SOA: redox activity and naphthoquinone gas-particle partitioning

NASA Astrophysics Data System (ADS)

McWhinney, R. D.; Zhou, S.; Abbatt, J. P. D.

2013-10-01

Chamber secondary organic aerosol (SOA) from low-NOx photooxidation of naphthalene by hydroxyl radical was examined with respect to its redox cycling behaviour using the dithiothreitol (DTT) assay. Naphthalene SOA was highly redox-active, consuming DTT at an average rate of 118 ± 14 pmol per minute per μg of SOA material. Measured particle-phase masses of the major previously identified redox active products, 1,2- and 1,4-naphthoquinone, accounted for only 21 ± 3% of the observed redox cycling activity. The redox-active 5-hydroxy-1,4-naphthoquinone was identified as a new minor product of naphthalene oxidation, and including this species in redox activity predictions increased the predicted DTT reactivity to 30 ± 5% of observations. These results suggest that there are substantial unidentified redox-active SOA constituents beyond the small quinones that may be important toxic components of these particles. A gas-to-SOA particle partitioning coefficient was calculated to be (7.0 ± 2.5) × 10-4 m3 μg-1 for 1,4-naphthoquinone at 25 °C. This value suggests that under typical warm conditions, 1,4-naphthoquinone is unlikely to contribute strongly to redox behaviour of ambient particles, although further work is needed to determine the potential impact under conditions such as low temperatures where partitioning to the particle is more favourable. Also, higher order oxidation products that likely account for a substantial fraction of the redox cycling capability of the naphthalene SOA are likely to partition much more strongly to the particle phase.

IRIS Toxicological Review of Benzo[a]pyrene (Interagency ...

EPA Pesticide Factsheets

On August 21, 2013, the draft Toxicological Review of Benzo[a]pyrene and the draft charge to external peer reviewers were released for public review and comment. The Toxicological Review and charge were reviewed internally by EPA and by other federal agencies and White House Offices before public release. Consistent with the May 2009 IRIS assessment development process, all written comments on IRIS assessments submitted by other federal agencies and White House Offices are made publicly available. Accordingly, interagency comments and the interagency science consultation materials provided to other agencies, including interagency review drafts of the IRIS Toxicological Review of Benzo[a]pyrene and the charge to external peer reviewers, are posted on this site. EPA is undertaking an update of the Integrated Risk Information System (IRIS) health assessment for benzo[a]pyrene (BaP). The outcome of this project is an updated Toxicological Review and IRIS Summary for BaP that will be entered into the IRIS database.

COSOLVENT EFFECTS ON PHENANTHRENE SORPTION-DESORPTION ON A FRESH-WATER SEDIMENT

EPA Science Inventory

This study evaluated the effects of the water-miscible cosolvent methanol on the sorption-desorption of phenanthrene by the natural organic matter (NOM) of a fresh-water sediment. A biphasic pattern was observed in the relationship between the log of the carbon-normalized sorpti...

Naphthalene, an insect repellent, is produced by Muscodor vitigenus, a novel endophytic fungus

Treesearch

Bryn H. Daisy; Gary A. Strobel; Uvidelio Castillo; David Ezra; Joe Sears; David K. Weaver; Justin B. Runyon

2002-01-01

Muscodor vitigenus is a recently described endophytic fungus of Paullinia paullinioides, a liana growing in the understorey of the rainforests of the Peruvian Amazon. This fungus produces naphthalene under certain cultural conditions. Naphthalene produced by M. vitigenus was identified by gas chromatography/mass...

A Thermal Dehydrogenative Diels–Alder Reaction of Styrenes for the Concise Synthesis of Functionalized Naphthalenes

PubMed Central

Kocsis, Laura S.; Benedetti, Erica

2012-01-01

Functionalized naphthalenes are valuable building blocks in many important areas. A microwave-assisted, intramolecular dehydrogenative Diels-Alder reaction of styrenyl derivatives to provide cyclopenta[b]naphthalene substructures not previously accessible using existing synthetic methods is described. The synthetic utility of these uniquely functionalized naphthalenes was demonstrated by a single-step conversion of one of these cycloadducts to a fluorophore bearing a structural resemblance to Prodan. PMID:22913473

A thermal dehydrogenative Diels-Alder reaction of styrenes for the concise synthesis of functionalized naphthalenes.

PubMed

Kocsis, Laura S; Benedetti, Erica; Brummond, Kay M

2012-09-07

Functionalized naphthalenes are valuable building blocks in many important areas. A microwave-assisted, intramolecular dehydrogenative Diels-Alder reaction of styrenyl derivatives to provide cyclopenta[b]naphthalene substructures not previously accessible using existing synthetic methods is described. The synthetic utility of these uniquely functionalized naphthalenes was demonstrated by a single-step conversion of one of these cycloadducts to a fluorophore bearing a structural resemblance to Prodan.

Benzene and naphthalene in air and breath as indicators of exposure to jet fuel

PubMed Central

Egeghy, P; Hauf-Cabalo, L; Gibson, R; Rappaport, S

2003-01-01

Aims: To estimate exposures to benzene and naphthalene among military personnel working with jet fuel (JP-8) and to determine whether naphthalene might serve as a surrogate for JP-8 in studies of health effects. Methods: Benzene and naphthalene were measured in air and breath of 326 personnel in the US Air Force, who had been assigned a priori into low, moderate, and high exposure categories for JP-8. Results: Median air concentrations for persons in the low, moderate, and high exposure categories were 3.1, 7.4, and 252 µg benzene/m3 air, 4.6, 9.0, and 11.4 µg benzene/m3 breath, 1.9, 10.3, and 485 µg naphthalene/m3 air, and 0.73, 0.93, and 1.83 µg naphthalene/m3 breath, respectively. In the moderate and high exposure categories, 5% and 15% of the benzene air concentrations, respectively, were above the 2002 threshold limit value (TLV) of 1.6 mg/m3. Multiple regression analyses of air and breath levels revealed prominent background sources of benzene exposure, including cigarette smoke. However, naphthalene exposure was not unduly influenced by sources other than JP-8. Among heavily exposed workers, dermal contact with JP-8 contributed to air and breath concentrations along with several physical and environmental factors. Conclusions: Personnel having regular contact with JP-8 are occasionally exposed to benzene at levels above the current TLV. Among heavily exposed workers, uptake of JP-8 components occurs via both inhalation and dermal contact. Naphthalene in air and breath can serve as useful measures of exposure to JP-8 and uptake of fuel components in the body. PMID:14634191

High levels of PAH-metabolites in urine of e-waste recycling workers from Agbogbloshie, Ghana.

PubMed

Feldt, Torsten; Fobil, Julius N; Wittsiepe, Jürgen; Wilhelm, Michael; Till, Holger; Zoufaly, Alexander; Burchard, Gerd; Göen, Thomas

2014-01-01

The informal recycling of electronic waste (e-waste) is an emerging source of environmental pollution in Africa. Among other toxins, polycyclic aromatic hydrocarbons (PAHs) are a major health concern for exposed individuals. In a cross-sectional study, the levels of PAH metabolites in the urine of individuals working on one of the largest e-waste recycling sites of Africa, and in controls from a suburb of Accra without direct exposure to e-waste recycling activities, were investigated. Socioeconomic data, basic health data and urine samples were collected from 72 exposed individuals and 40 controls. In the urine samples, concentrations of the hydroxylate PAH metabolites (OH-PAH) 1-hydroxyphenanthrene (1-OH-phenanthrene), the sum of 2- and 9-hydroxyphenanthrene (2-/9-OH-phenanthrene), 3-hydroxyphenanthrene (3-OH-phenanthrene), 4-hydroxyphenanthrene (4-OH-phenanthrene) and 1-hydroxypyrene (1-OH-pyrene), as well as cotinine and creatinine, were determined. In the exposed group, median urinary concentrations were 0.85 μg/g creatinine for 1-OH-phenanthrene, 0.54 μg/g creatinine for 2-/9-OH-phenanthrene, 0.99 μg/g creatinine for 3-OH-phenanthrene, 0.22 μg/g creatinine for 4-OH-phenanthrene, and 1.33 μg/g creatinine for 1-OH-pyrene, all being significantly higher compared to the control group (0.55, 0.37, 0.63, 0.11 and 0.54 μg/g creatinine, respectively). Using a multivariate linear regression analysis including sex, cotinine and tobacco smoking as covariates, exposure to e-waste recycling activities was the most important determinant for PAH exposure. On physical examination, pathological findings were rare, but about two thirds of exposed individuals complained about cough, and one quarter about chest pain. In conclusion, we observed significantly higher urinary PAH metabolite concentrations in individuals who were exposed to e-waste recycling compared to controls who were not exposed to e-waste recycling activities. The impact of e-waste recycling on exposure to

Biodegradation and adsorption of C1- and C2-phenanthrenes and C1- and C2-dibenzothiophenes in the presence of clay minerals: effect on forensic diagnostic ratios.

PubMed

Ugochukwu, Uzochukwu C; Head, Ian M; Manning, David A C

2014-07-01

The impact of modified montmorillonites on adsorption and biodegradation of crude oil C1-phenanthrenes, C1-dibenzothiophenes, C2-phenanthrenes and C2-dibenzothiophenes was investigated in aqueous clay/oil microcosm experiments with a hydrocarbon degrading microorganism community. Consequently, the effect on C1-dibenzothiophenes/C1-phenanthrenes, C2-dibenzothiophenes/C2-phenanthrenes, 2+3-methyldibenzothiophene/4-methyldibenzothiophene and 1-methyldibenzothiophene/4-methyldibenzothiophene ratios commonly used as diagnostic ratios for oil forensic studies was evaluated. The clay mineral samples were treated to produce acid activated montmorillonite, organomontmorillonite and homoionic montmorillonite which were used in this study. The different clay minerals (modified and unmodified) showed varied degrees of biodegradation and adsorption of the C1-phenanthrenes, C1-dibenzothiophenes, C2-phenanthrenes and C2-dibenzothiophenes. The study indicated that as opposed to biodegradation, adsorption has no effect on the diagnostic ratios. Among the diagnostic ratios reviewed, only C2-dibenzothiophenes/C2-phenanthrenes ratio was neither affected by adsorption nor biodegradation making this ratio very useful in forensic studies of oil spills and oil-oil correlation.

Benzo[a]pyrene (BaP)

Integrated Risk Information System (IRIS)

EPA / 635 / R - 17 / 003Fc www.epa.gov / iris Toxicological Review of Benzo [ a ] pyrene Executive Summary [ CASRN 50 - 32 - 8 ] January 2017 Integrated Risk Information System National Center for Environmental Assessment Office of Research and Development U.S . Environmental Protection Agency Washi

Optical Sensing Properties of Pyrene-Schiff Bases toward Different Acids.

PubMed

Babgi, Bandar A; Alzahrani, Asma

2016-07-01

A set of (4-substituted-phenyl)-pyren-1-ylmethylene-amine (PMA) was prepared by the reaction of pyrene-1-carboxaldehyde and the corresponding 4-substituted aniline. The structure of the PMA compounds were confirmed by spectroscopic data (IR, (1)HNMR, (13)CNMR, ISI-MS and elemental analysis. The structure of (4-bromo-phenyl)-pyren-1-ylmethylene-amine (BrPMA) was further confirmed by the single X-ray crystallography. The absorption and emission spectroscopic behaviors were investigated in variant acids. The compounds showed dramatic spectroscopic changes upon acidifying with strong acids and negligible effects when weak acids are used in the acidifications. Hence, the PMA compounds can be used as sensors to distinguish between weak and strong acids.

Evaluation of Benzo[a]pyrene in Food from China by High-Performance Liquid Chromatography-Fluorescence Detection

PubMed Central

Chen, Yong-Hong; Xia, En-Qin; Xu, Xiang-Rong; Li, Sha; Ling, Wen-Hua; Wu, Shan; Deng, Gui-Fang; Zou, Zhi-Fei; Zhou, Jing; Li, Hua-Bin

2012-01-01

The occurrence and levels of benzo[a]pyrene in various heat-treated foods from China were evaluated by high-performance liquid chromatography-fluorescence detection. In a total of 119 samples, 105 were found to contain benzo[a]pyrene at levels of 0.03 to 19.75 µg/kg. The benzo[a]pyrene contents in 12 animal source foods were higher than the Chinese maximum permissible level in food (5 µg/kg) and the highest level was 19.75 µg/kg, nearly four times the maximum permissible level. The results revealed a widespread carinogenic public health risk from benzo[a]pyrene in heat-treated foods. The highest benzo[a]pyrene levels were found in animal source samples such as charcoal-grilled and smoked meats, especially pork, beef and sausage, while trace levels of benzo[a]pyrene were present in grain food. Charcoal-grilled vegetables were found to also contain certain levels of benzo[a]pyrene. This study provided new information on benzo[a]pyrene content of a variety of heat-treated foods from China. PMID:23202838

Effects of alfalfa and organic fertilizer on benzo[a]pyrene dissipation in an aged contaminated soil.

PubMed

Fu, Dengqiang; Teng, Ying; Luo, Yongming; Tu, Chen; Li, Shixing; Li, Zhengao; Christie, Peter

2012-06-01

A climate-controlled pot experiment was conducted to investigate the effects of planting alfalfa and applying organic fertilizer on the dissipation of benzo[a]pyrene from an aged contaminated agricultural soil. Short-term planting of alfalfa inhibited the dissipation of benzo[a]pyrene from the soil by 8.9%, and organic fertilizer enhanced benzo[a]pyrene removal from the soil by 11.6% compared with the unplanted and unfertilized treatments, respectively. No significant interaction was observed between alfalfa and organic fertilizer on benzo[a]pyrene dissipation. Sterilization completely inhibited the removal of benzo[a]pyrene from the soil indicating that its degradation by indigenous microorganisms may have been the main mechanism of dissipation. Furthermore, significant positive relationships were observed between benzo[a]pyrene removal and the contents of soil ammonium nitrogen, nitrate nitrogen, and total mineral nitrogen at the end of the experiment, suggesting that competition between plants and microorganisms for nitrogen may have inhibited benzo[a]pyrene dissipation in the rhizosphere of alfalfa and the addition of organic fertilizer may facilitate microbial degradation of benzo[a]pyrene in the soil.

Effect of low-molecular-weight organic acids on photo-degradation of phenanthrene catalyzed by Fe(III)-smectite under visible light.

PubMed

Jia, Hanzhong; Chen, Hongxia; Nulaji, Gulimire; Li, Xiyou; Wang, Chuanyi

2015-11-01

The photolysis of polycyclic aromatic hydrocarbons (PAHs) is potentially an important process for its transformation and fate on contaminated soil surfaces. In this study, phenanthrene is employed as a model to explore PAH photodegradation with the assistance of Fe(III)-smectite under visible-light while focusing on roles played by five low-molecular-weight organic acids (LMWOAs), i.e., malic acid, oxalic acid, citric acid, ethylenediaminetetraacetic acid (EDTA), and nitrilotriacetic acid. Our results show that oxalic acid is most effective in promoting the photodegradation of phenanthrene, while only a slight increase in the rate of phenanthrene photodegradation is observed in the presence of malic acid. Electron paramagnetic resonance experiments confirm the formation of CO2(-) radicals in the presence of malic and oxalic acid, which provides strong evidence for generating OH and subsequent photoreaction pathways. The presence of EDTA or nitrilotriacetic acid significantly inhibits both Fe(II) formation and phenanthrene photodegradation because these organic anions tend to chelate with Fe(III), leading to decreases in the electron-accepting potential of Fe(III)-smectite and a weakened interaction between phenanthrene and Fe(III)-smectite. These observations provide valuable insights into the transformation and fate of PAHs in the natural soil environment and demonstrate the potential for using some LMWOAs as additives for the remediation of contaminated soil. Copyright © 2015 Elsevier Ltd. All rights reserved.

Analysis of benzo(a)pyrene in airborne particulates by gas chromatography

NASA Technical Reports Server (NTRS)

Luedecke, E.

1976-01-01

A routine method was developed to measure benzo(a)pyrene in airborne particulates. Samples were collected on a filter and the organic portion was extracted with cyclohexane. The polynuclear hydrocarbon (PNHC) fraction was separated from the aliphatics by column chromatography. An internal standard was added to the extract and a portion of it was injected into a gas chromatograph. Although the gas chromatographic method has often been reported in the literature, satisfactory separation of benzo(a)pyrene and benzo(e)pyrene has not been achieved. With the introduction of a nematic liquid crystal as the stationary phase good separation is now possible.

Squamocin, an annonaceous acetogenin, enhances naphthalene degradation mediated by Bacillus atrophaeus CN4.

PubMed

Parellada, Eduardo A; Igarza, Mercedes; Isacc, Paula; Bardón, Alicia; Ferrero, Marcela; Ameta, Keshav Lalit; Neske, Adriana

Squamocin belongs to a group of compounds called annonaceous acetogenins. They are secondary products of Annonaceae metabolism and can be isolated from Annona cherimolia seeds. This paper deals with the stimulation of biofilm formation of Bacillus atrophaeus CN4 by employing low squamocin concentrations to increase naphthalene degradation. Bacillus atrophaeus CN4, isolated from contaminated soil, has the ability to degrade naphthalene as the only source of carbon and energy. In the absence of additional carbon sources, the strain removed 69% of the initial concentration of naphthalene (approx. 0.2mmol/l) in the first 12h of incubation. The addition of squamocin in LB medium stimulated Bacillus atrophaeus CN4 biofilm formation and enhanced naphthalene removal. Squamocin (2.5μg/ml) does not affect planktonic growth and therefore, the observed increases are solely due to the stimulation of biofilm formation. Copyright © 2017 Asociación Argentina de Microbiología. Publicado por Elsevier España, S.L.U. All rights reserved.

Energy transfer of highly vibrationally excited naphthalene: collisions with CHF3, CF4, and Kr.

PubMed

Chen Hsu, Hsu; Tsai, Ming-Tsang; Dyakov, Yuri A; Ni, Chi-Kung

2011-08-07

Energy transfer of highly vibrationally excited naphthalene in the triplet state in collisions with CHF(3), CF(4), and Kr was studied using a crossed-beam apparatus along with time-sliced velocity map ion imaging techniques. Highly vibrationally excited naphthalene (2.0 eV vibrational energy) was formed via the rapid intersystem crossing of naphthalene initially excited to the S(2) state by 266 nm photons. The shapes of the collisional energy-transfer probability density functions were measured directly from the scattering results of highly vibrationally excited naphthalene. In comparison to Kr atoms, the energy transfer in collisions between CHF(3) and naphthalene shows more forward scatterings, larger cross section for vibrational to translational (V → T) energy transfer, smaller cross section for translational to vibrational and rotational (T → VR) energy transfer, and more energy transferred from vibration to translation, especially in the range -ΔE(d) = -100 to -800 cm(-1). On the other hand, the difference of energy transfer properties between collisional partners Kr and CF(4) is small. The enhancement of the V → T energy transfer in collisions with CHF(3) is attributed to the large attractive interaction between naphthalene and CHF(3) (1-3 kcal/mol).

Development of Naphthalene PLIF for Making Quantitative Measurements of Ablation Products Transport in Supersonic Flows

NASA Astrophysics Data System (ADS)

Combs, Christopher; Clemens, Noel

2014-11-01

Ablation is a multi-physics process involving heat and mass transfer and codes aiming to predict ablation are in need of experimental data pertaining to the turbulent transport of ablation products for validation. Low-temperature sublimating ablators such as naphthalene can be used to create a limited physics problem and simulate ablation at relatively low temperature conditions. At The University of Texas at Austin, a technique is being developed that uses planar laser-induced fluorescence (PLIF) of naphthalene to visualize the transport of ablation products in a supersonic flow. In the current work, naphthalene PLIF will be used to make quantitative measurements of the concentration of ablation products in a Mach 5 turbulent boundary layer. For this technique to be used for quantitative research in supersonic wind tunnel facilities, the fluorescence properties of naphthalene must first be investigated over a wide range of state conditions and excitation wavelengths. The resulting calibration of naphthalene fluorescence will be applied to the PLIF images of ablation from a boundary layer plug, yielding 2-D fields of naphthalene mole fraction. These images may help provide data necessary to validate computational models of ablative thermal protection systems for reentry vehicles. Work supported by NASA Space Technology Research Fellowship Program under grant NNX11AN55H.

Infrared spectroscopy of hydrated naphthalene cluster anions.

PubMed

Knurr, Benjamin J; Adams, Christopher L; Weber, J Mathias

2012-09-14

We present infrared spectra of mass-selected C(10)H(8)(-)·(H(2)O)(n)·Ar(m) cluster anions (n = 1-6) obtained by Ar predissociation spectroscopy. The experimental spectra are compared with predicted spectra from density functional theory calculations. The OH groups of the water ligands are involved in H-bonds to other water molecules or to the π system of the naphthalene anion, which accommodates the excess electron. The interactions in the water network are generally found to be more important than those between water molecules and the ion. For 2 ≤ n ≤ 4 the water molecules form single layer water networks on one side of the naphthalene anion, while for n = 5 and 6, cage and multilayer structures become more energetically favorable. For cluster sizes with more than 3 water molecules, multiple conformers are likely to be responsible for the experimental spectra.

Influence of low oxygen tensions and sorption to sediment black carbon on biodegradation of pyrene.

PubMed

Ortega-Calvo, José-Julio; Gschwend, Philip M

2010-07-01

Sorption to sediment black carbon (BC) may limit the aerobic biodegradation of polycyclic aromatic hydrocarbons (PAHs) in resuspension events and intact sediment beds. We examined this hypothesis experimentally under conditions that were realistic in terms of oxygen concentrations and BC content. A new method, based on synchronous fluorescence observations of (14)C-pyrene, was developed for continuously measuring the uptake of dissolved pyrene by Mycobacterium gilvum VM552, a representative degrader of PAHs. The effect of oxygen and pyrene concentrations on pyrene uptake followed Michaelis-Menten kinetics, resulting in a dissolved oxygen half-saturation constant (K(om)) of 14.1 microM and a dissolved pyrene half-saturation constant (K(pm)) of 6 nM. The fluorescence of (14)C-pyrene in air-saturated suspensions of sediments and induced cells followed time courses that reflected simultaneous desorption and biodegradation of pyrene, ultimately causing a quasi-steady-state concentration of dissolved pyrene balancing desorptive inputs and biodegradation removals. The increasing concentrations of (14)CO(2) in these suspensions, as determined with liquid scintillation, evidenced the strong impact of sorption to BC-rich sediments on the biodegradation rate. Using the best-fit parameter values, we integrated oxygen and sorption effects and showed that oxygen tensions far below saturation levels in water are sufficient to enable significant decreases in the steady-state concentrations of aqueous-phase pyrene. These findings may be relevant for bioaccumulation scenarios that consider the effect of sediment resuspension events on exposure to water column and sediment pore water, as well as the direct uptake of PAHs from sediments.

Evaluation of soil pH and moisture content on in-situ ozonation of pyrene in soils.

PubMed

Luster-Teasley, S; Ubaka-Blackmoore, N; Masten, S J

2009-08-15

In this study, pyrene spiked soil (300 ppm) was ozonated at pH levels of 2, 6, and 8 and three moisture contents. It was found that soil pH and moisture content impacted the effectiveness of PAH oxidation in unsaturated soils. In air-dried soils, as pH increased, removal increased, such that pyrene removal efficiencies at pH 6 and pH 8 reached 95-97% at a dose of 2.22 mg O(3)/mg pyrene. Ozonation at 16.2+/-0.45 mg O(3)/ppm pyrene in soil resulted in 81-98% removal of pyrene at all pH levels tested. Saturated soils were tested at dry, 5% or 10% moisture conditions. The removal of pyrene was slower in moisturized soils, with the efficiency decreasing as the moisture content increased. Increasing the pH of the soil having a moisture content of 5% resulted in improved pyrene removals. On the contrary, in the soil having a moisture content of 10%, as the pH increased, pyrene removal decreased. Contaminated PAH soils were stored for 6 months to compare the efficiency of PAH removal in freshly contaminated soil and aged soils. PAH adsorption to soil was found to increase with longer exposure times; thus requiring much higher doses of ozone to effectively oxidize pyrene.

Influence of algal and bacterial particulate organic matter on benzo[a]pyrene bioaccumulation in Daphnia magna.

PubMed

Gourlay, Catherine; Mouchel, Jean-Marie; Tusseau-Vuillemin, Marie-Hélène; Garric, Jeanne

2005-06-15

In order to better asses the influence of organic matter on the bioavailability of hydrophobic organic contaminants, the effect of algae and POM of bacterial origin on the bioaccumulation of benzo[a]pyrene in Daphnia magna was evaluated. The bioaccumulation was monitored with increasing concentrations of particulate organic matter (POM) and dissolved organic matter (DOM). In all experiments, the presence of POM greatly reduced the bioaccumulation of benzo[a]pyrene. The reduction was more pronounced in the presence of algae, for which we observed a 99%-reduction effect in the presence of 6 x10 (5) cell/mL (equivalent to 5.3 mg C/L). The bioaccumulation of benzo[a]pyrene was decreased by 49% by organic matter of bacterial origin at 4.7 mg C/L. Assuming that benzo[a]pyrene was partitioned between water, DOM and POM and supposing that D. magna accumulated free benzo[a]pyrene via respiration and POM-bond benzo[a]pyrene via ingestion, bioaccumulation data allowed to estimate the dietary uptake rate of benzo[a]pyrene as well as partitioning coefficients K(POC) and K(DOC). Despite the ingestion of contaminated particles, we could not observe any dietary uptake of benzo[a]pyrene in daphnids. We verified, as usually supposed, that the bioaccumulation of benzo[a]pyrene to D. magna occurs mainly via direct contact. Very high partitioning coefficients (log K(POC) between 5.2 and 6.2) were estimated. This study pointed out the great influence of biogenic organic matter on the fate and the bioavailability of benzo[a]pyrene in aquatic ecosystems.

Biochemical response of anthracene and benzo [a] pyrene in milkfish Chanos chanos.

PubMed

Palanikumar, L; Kumaraguru, A K; Ramakritinan, C M; Anand, M

2012-01-01

Polycyclic aromatic hydrocarbons (PAHs) are common toxic pollutants found in the aquatic environment, and the assessment of their impact on biota is of considerable concern. The aim of the present research was to study the acute toxicity, bioaccumulation and biochemical response of milkfish Chanos chanos (Forsskal) to two selected PAHs: anthracene and benzo [a] pyrene. Acute toxicity test results were evaluated by the Probit analysis method and 96h LC(50) values for C. chanos exposed to anthracene was 0.030mgl(-1) and 0.014mgl(-1) for benzo [a] pyrene. Bioaccumulation concentration of anthracene was high when compared to benzo [a] pyrene. Biomarkers indicative of neurotoxicity (acetylcholinesterase, AchE), oxidative stress (lipid peroxidation, LPO and catalase, CAT) and phase II biotransformation of xenobiotics (glutathione S transferase, GST and reduced glutathione, GSH) were measured to assess effects of selected PAHs. Anthracene and benzo [a] pyrene increase LPO and CAT level of C. chanos suggesting that these PAHs may induce oxidative stress. Both the PAHs inhibited AchE indicating that they have at least one mechanism of neurotoxicity in common: the disruption of cholinergic transmission by inhibition of AChE. An induction of C. chanos glutathione S-transferase (GST) activity was found in fish exposed to benzo [a] pyrene, while an inhibition was observed after exposure to anthracene. These results suggest that GST is involved in the detoxification of benzo [a] pyrene, but not of anthracene. Copyright © 2011 Elsevier Inc. All rights reserved.

Using a Differential Scanning Calorimeter to Teach Phase Equilibria to Students of Igneous and Metamorphic Petrology

ERIC Educational Resources Information Center

Maria, Anton H.; Millam, Evan L.; Wright, Carrie L.

2011-01-01

As an aid for teaching phase equilibria to undergraduate students of igneous and metamorphic petrology, we have designed a laboratory exercise that allows them to create a phase diagram from data produced by differential scanning calorimetry. By preparing and analyzing samples of naphthalene and phenanthrene, students acquire hands-on insight into…

Oxidation of Naphthenoaromatic and Methyl-Substituted Aromatic Compounds by Naphthalene 1,2-Dioxygenase

PubMed Central

Selifonov, S. A.; Grifoll, M.; Eaton, R. W.; Chapman, P. J.

1996-01-01

Oxidation of acenaphthene, acenaphthylene, and fluorene was examined with recombinant strain Pseudomonas aeruginosa PAO1(pRE695) expressing naphthalene dioxygenase genes cloned from plasmid NAH7. Acenaphthene underwent monooxygenation to 1-acenaphthenol with subsequent conversion to 1-acenaphthenone and cis- and trans-acenaphthene-1,2-diols, while acenaphthylene was dioxygenated to give cis-acenaphthene-1,2-diol. Nonspecific dehydrogenase activities present in the host strain led to the conversion of both of the acenaphthene-1,2-diols to 1,2-acenaphthoquinone. The latter was oxidized spontaneously to naphthalene-1,8-dicarboxylic acid. No aromatic ring dioxygenation products were detected from acenaphthene and acenaphthylene. Mixed monooxygenase and dioxygenase actions of naphthalene dioxygenase on fluorene yielded products of benzylic 9-monooxygenation, aromatic ring dioxygenation, or both. The action of naphthalene dioxygenase on a variety of methyl-substituted aromatic compounds, including 1,2,4-trimethylbenzene and isomers of dimethylnaphthalene, resulted in the formation of benzylic alcohols, i.e., methyl group monooxygenation products, which were subsequently converted to the corresponding carboxylic acids by dehydrogenase(s) in the host strain. Benzylic monooxygenation of methyl groups was strongly predominant over aromatic ring dioxygenation and essentially nonspecific with respect to the substitution pattern of the aromatic substrates. In addition to monooxygenating benzylic methyl and methylene groups, naphthalene dioxygenase behaved as a sulfoxygenase, catalyzing monooxygenation of the sulfur heteroatom of 3-methylbenzothiophene. PMID:16535238

Naphthalene and benzene degradation under Fe(III)-reducing conditions in petroleum-contaminated aquifers

USGS Publications Warehouse

Anderson, Robert T.; Lovely, Derek R.

1999-01-01

Naphthalene was oxidized anaerobically to CO2 in sediments collected from a petroleum-contaminated aquifer in Bemidji, Minnesota in which Fe(III) reduction was the terminal electron-accepting process. Naphthalene was not oxidized in sediments from the methanogenic zone at Bemidji or in sediments from the Fe(III)-reducing zone of other petroleum-contaminated aquifers studied. In a profile across the Fe(III)-reducing zone of the Bemidji aquifer, rates of naphthalene oxidation were fastest in sediments with the highest proportion of Fe(III), which was also the zone of the most rapid degradation of benzene, toluene, and acetate. The comparative studies attempted to elucidate factors that might account for the fact that unsubstituted aromatic hydrocarbons such as benzene and naphthalene were degraded under Fe(III)-reducing conditions at Bemidji, but not at the other aquifers examined. These studies indicated that the ability of Fe(III)-reducing microorganisms to degrade benzene and naphthalene at the Bemidji site cannot be attributed to groundwater components that make Fe(III) more available for reduction or other potential factors that were evaluated. However, unlike the other aquifers evaluated, uncontaminated sediments at the Bemidji site could be adapted for anaerobic benzene degradation merely with the addition of benzene. These findings indicate that Bemidji sediments naturally contain Fe(III) reducers capable of degradation of unsubstituted aromatic hydrocarbons.

Energetic costs of pyrene metabolism in isolated hepatocytes of rainbow trout, Oncorhynchus mykiss.

PubMed

Bains, Onkar S; Kennedy, Christopher J

2004-04-28

The respiratory costs of pyrene exposure and biotransformation were examined in isolated hepatocytes of adult rainbow trout, Oncorhynchus mykiss. Baseline oxygen consumption rates measured at an acclimation temperature of 7.5 degrees C and during an acute temperature increase to 15 degrees C were 10.1 +/- 0.1 and 22.6 +/- 0.4 ng O(2)/min/mg cells, respectively. Hepatocytes exposed to pyrene at 1, 5 and 10 microg/ml exhibited concentration-dependent increases in oxygen consumption. Respiration rates of cells exposed to these concentrations at their acclimation temperature were 12.5 +/- 0.1, 14.7 +/- 0.1 and 17.1 +/- 0.2 ng O(2)/min/mg cells, respectively. Exposure of cells to pyrene at 15 degrees C also elevated oxygen consumption to a maximum of 34.4 +/- 0.3 ng O(2)/min/mg cells, however, the relationship with pyrene concentration was biphasic. The major metabolite identified through a series of solvent extractions, acid hydrolysis, and synchronous fluorometric spectroscopy was conjugated 1-hydroxypyrene. At 7.5 degrees C, increased pyrene metabolism correlated with increased hepatocyte respiration rates. At 15 degrees C, however, pyrene metabolism reached a maximum at 5 microg/ml, suggesting saturation of detoxification enzymes, which correlated with maximum respiration rates at this concentration. Measures of respiration by isolated mitochondria indicated that changes in hepatocyte oxygen consumption were not through direct effects of pyrene on mitochondria. This study indicates that significant respiratory costs may be accrued by teleost hepatocytes actively metabolizing and secreting xenobiotic compounds.

Diversity of organotrophic bacteria, activity of dehydrogenases and urease as well as seed germination and root growth Lepidium sativum, Sorghum saccharatum and Sinapis alba under the influence of polycyclic aromatic hydrocarbons.

PubMed

Lipińska, Aneta; Wyszkowska, Jadwiga; Kucharski, Jan

2015-12-01

Polycyclic aromatic hydrocarbons are organic compounds with highly toxic, carcinogenic, and mutagenic properties, which adversely affect the basic biological parameters of the soil, including the count of microorganisms, and the enzymatic activity. In addition to disturbances to the biological activity of the soil, PAHs may also exhibit toxic effects on plants. In view of the above, the study involved testing aimed at the determination of the effects of polycyclic aromatic hydrocarbons in a form of naphthalene, phenanthrene, anthracene and pyrene on the count, colony development (CD) index, ecophysiological (EP) diversity index of organotrophic bacteria, and the activity of soil dehydrogenases and soil urease. Moreover, an attempt was made to determine the soil's resistance based on the activity of the above-listed enzymes, and the effect of polycyclic aromatic hydrocarbons on seed germination and root growth was assessed by Lepidium sativum, Sorghum saccharatum, and Sinapis alba. In addition, the species of bacteria found in a soil subjected to strong pressure of polycyclic aromatic hydrocarbons were isolated. The experiment was performed in a laboratory on samples of loamy sand. Polycyclic aromatic hydrocarbons were introduced into the soil in an amount of 0, 1000, 2000, and 4000 mg kg(-1) of soil dry matter. Germination and growth of cress (L. sativum), white mustard (S. alba), and sweet sorghum (S. saccharatum) were determined using Phytotoxkit tests. It was found that the tested PAHs increased the average colony counts of organotrophic soil bacteria; pyrene did so to the greatest extent (2.2-fold relative to non-contaminated soil), phenanthrene to the smallest extent (1.4-fold relative to non-contaminated soil). None of the PAHs changed the value of the bacterial colony development (CD) index, while anthracene and pyrene increased the value of the eco-physiological (EP) diversity indicator. PAHs lowered the activity of the tested enzymes. The activity of

Optical nonlinearity and charge transfer analysis of pyrene adsorbed on silver: Computational and experimental investigations

NASA Astrophysics Data System (ADS)

Reeta Felscia, U.; Rajkumar, Beulah J. M.; Sankar, Pranitha; Philip, Reji; Briget Mary, M.

2017-09-01

The interaction of pyrene on silver has been investigated using both experimental and computational methods. Hyperpolarizabilities computed theoretically together with experimental nonlinear absorption from open aperture Z-scan measurements, point towards a possible use of pyrene adsorbed on silver in the rational design of NLO devices. Presence of a red shift in both simulated and experimental UV-Vis spectra confirms the adsorption on silver, which is due to the electrostatic interaction between silver and pyrene, inducing variations in the structural parameters of pyrene. Fukui calculations along with MEP plot predict the electrophilic nature of the silver cluster in the presence of pyrene, with NBO analysis revealing that the adsorption causes charge redistribution from the first three rings of pyrene towards the fourth ring, from where the 2p orbitals of carbon interact with the valence 5s orbitals of the cluster. This is further confirmed by the downshifting of ring breathing modes in both the experimental and theoretical Raman spectra.

Effect of red clover on the microbial transformation of phenanthrene and octadecane in the soil

NASA Astrophysics Data System (ADS)

Nazarov, A. V.; Shestakova, E. A.; Anan'yina, L. N.

2017-08-01

The influence of red clover ( Trifolium pratense L.) plants on the decomposition of phenanthrene and octadecane in the soil has been studied. Effect of plant root mass on the abundance of hydrocarbondegrading bacteria, the composition of their communities, and the degradation of hydrocarbons in the soil has been revealed. Changes in the taxonomic composition of hydrocarbon-degrading bacteria under the effect of red clover are characterized by an increase in the abundance of species from the genera Acinetobacter, Kaistia, Novosphingobium, Pseudomonas, and Xanthomonas. A positive effect of the studied microbial-plant association on the degradation of octadecane and especially phenanthrene in the soil has been revealed.

Microbial community structure and biodegradation activity of particle-associated bacteria in a coal tar contaminated creek

DOE Office of Scientific and Technical Information (OSTI.GOV)

Jennifer M. DeBruyn; Gary S. Sayler

The Chattanooga Creek Superfund site (Chattanooga, TN) is one of the most polluted waterways in the southeastern U.S. with high polycyclic aromatic hydrocarbon (PAH) concentrations in the sediments. PAHs associate with suspended solids in the water column, and may be redeposited onto the floodplain. These suspended particles represent an interesting but understudied environment for PAH-degrading microbial communities. This study tested the hypotheses that particle-associated bacterial (PAB) communities have genotypic potential (PAH-dioxygenase genes) and activity (naphthalene and pyrene mineralization), and can contribute to natural attenuation of PAHs in Chattanooga Creek. Upstream of the Superfund site, mineralization ranged from 0.2 to 2.0%more » of added {sup 14}C-naphthalene and 0 to 0.1% {sup 14}C-pyrene (after 40 h), with first order biodegradation rate constants (k{sub 1}) ranging from 1.09 to 9.18 x 10{sup -5} h{sup -1} and 0 to 1.13 x 10{sup -6} h{sup -1}, respectively. Mineralization was significantly greater in PAB communities within the contaminated zone, with 11.8 to 31.2% {sup 14}C-naphthalene (k{sup 1} 5.34 to 14.2 x 10-4 h{sup -1}) and 1.3 to 6.6% {sup 14}C-pyrene mineralized (k{sub 1} 2.89 to 15.0 x 10{sup -5} h{sup -1}). Abundances of nagAc (naphthalene dioxygenase) and nidA (pyrene dioxygenase) genes indicated that PAB communities harbored populations with genetic potential for both low- and high-molecular weight PAH degradation, and quantification of Mycobacterium 16S rDNA genes indicated that PAH-degrading mycobacteria are also prevalent in this environment. Phylogenetic comparisons (T-RFLPs) between PAB and sediments indicated these microbial communities were taxonomically distinct, but shared some functional similarities, namely PAH catabolic genotypes, mineralization capabilities, and community structuring along a contamination gradient. 38 refs., 4 figs., 2 tabs.« less

40 CFR 721.10045 - Diazotized substituted heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel...

Code of Federal Regulations, 2014 CFR

2014-07-01

... coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (generic). 721.10045... derivative, nickel complex, alkaline salt (generic). (a) Chemical substance and significant new uses subject... heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (PMN P-02-737) is...

40 CFR 721.10045 - Diazotized substituted heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel...

Code of Federal Regulations, 2011 CFR

2011-07-01

... coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (generic). 721.10045... derivative, nickel complex, alkaline salt (generic). (a) Chemical substance and significant new uses subject... heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (PMN P-02-737) is...

40 CFR 721.10045 - Diazotized substituted heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel...

Code of Federal Regulations, 2013 CFR

2013-07-01

... coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (generic). 721.10045... derivative, nickel complex, alkaline salt (generic). (a) Chemical substance and significant new uses subject... heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (PMN P-02-737) is...

40 CFR 721.10045 - Diazotized substituted heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel...

Code of Federal Regulations, 2010 CFR

2010-07-01

... coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (generic). 721.10045... derivative, nickel complex, alkaline salt (generic). (a) Chemical substance and significant new uses subject... heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (PMN P-02-737) is...

40 CFR 721.10045 - Diazotized substituted heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel...

Code of Federal Regulations, 2012 CFR

2012-07-01

... coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (generic). 721.10045... derivative, nickel complex, alkaline salt (generic). (a) Chemical substance and significant new uses subject... heteromonocycle coupled with naphthalene sulfonic acid derivative, nickel complex, alkaline salt (PMN P-02-737) is...

Native Fluorescence Detection Methods and Detectors for Naphthalene and/or Other Volatile Organic Compound Vapors

NASA Technical Reports Server (NTRS)

Hug, William F. (Inventor); Bhartia, Rohit (Inventor); Reid, Ray D. (Inventor); Lane, Arthur L. (Inventor)

2014-01-01

Naphthalene, benzene, toluene, xylene, and other volatile organic compounds have been identified as serious health hazards. This is especially true for personnel working with JP8 jet fuel and other fuels containing naphthalene as well as other hazardous volatile organic compounds (VOCs). Embodiments of the invention are directed to methods and apparatus for near-real-time in-situ detection and accumulated dose measurement of exposure to naphthalene vapor and other hazardous gaseous VOCs. The methods and apparatus employ excitation of fluorophors native or endogenous to compounds of interest using light sources emitting in the ultraviolet below 300 nm and measurement of native fluorescence emissions in distinct wavebands above the excitation wavelength. The apparatus of some embodiments are cell-phone-sized sensor/dosimeter "badges" to be worn by personnel potentially exposed to naphthalene or other hazardous VOCs. The badge sensor of some embodiments provides both real time detection and data logging of exposure to naphthalene or other VOCs of interest from which both instantaneous and accumulated dose can be determined. The badges employ a new native fluorescence based detection method to identify and differentiate VOCs. The particular focus of some embodiments are the detection and identification of naphthalene while other embodiments are directed to detection and identification of other VOCs like aromatic hydrocarbons such as benzene, toluene, and xylene.

Metal oxides, clay minerals and charcoal determine the composition of microbial communities in matured artificial soils and their response to phenanthrene.

PubMed

Babin, Doreen; Ding, Guo-Chun; Pronk, Geertje Johanna; Heister, Katja; Kögel-Knabner, Ingrid; Smalla, Kornelia

2013-10-01

Microbial communities in soil reside in a highly heterogeneous habitat where diverse mineral surfaces, complex organic matter and microorganisms interact with each other. This study aimed to elucidate the long-term effect of the soil mineral composition and charcoal on the microbial community composition established in matured artificial soils and their response to phenanthrene. One year after adding sterile manure to different artificial soils and inoculating microorganisms from a Cambisol, the matured soils were spiked with phenanthrene or not and incubated for another 70 days. 16S rRNA gene and internal transcribed spacer fragments amplified from total community DNA were analyzed by denaturing gradient gel electrophoresis. Metal oxides and clay minerals and to a lesser extent charcoal influenced the microbial community composition. Changes in the bacterial community composition in response to phenanthrene differed depending on the mineral composition and presence of charcoal, while no shifts in the fungal community composition were observed. The abundance of ring-hydroxylating dioxygenase genes was increased in phenanthrene-spiked soils except for charcoal-containing soils. Here we show that the formation of biogeochemical interfaces in soil is an ongoing process and that different properties present in artificial soils influenced the bacterial response to the phenanthrene spike. © 2012 Federation of European Microbiological Societies. Published by Blackwell Publishing Ltd. All rights reserved.

MUTATIONS INDUCED BY BENZO[ A ]PYRENE AND DIBENZO[ A,L ]PYRENE IN LACI TRANSGENIC B6C3F1 MOUSE LUNG RESULT FROM STABLE DNA ADDUCTS

EPA Science Inventory

Dibenzo[a,l]pyrene (DB[a,l]P) and benzo[a]pyrene (B[a]P) are carcinogenic polycyclic aromatic hydrocarbons (PAH) that are each capable of forming a variety of covalent adducts with DNA, some of which spontaneously depurinate, producing apurinic (AP) si...

Effect of Bacillus subtilis and NTA-APG on pyrene dissipation in phytoremediation of nickel co-contaminated wetlands by Scirpus triqueter.

PubMed

Liu, Xiaoyan; Hu, Xiaoxin; Zhang, Xinying; Chen, Xueping; Chen, Jing; Yuan, Xiaoyu

2018-06-15

A complex mix of organic pollutants and heavy metal made the remediation of contaminated wetlands more difficult. Few research focus on the remediation for pyrene enhanced by chemical reagents and pyrene degrading bacteria in the nickel co-contaminated soil. In this paper, the effect of chemical reagents (nitrilotriacetic acid and alkyl polyglucoside) and Bacillus subtilis on pyrene dissipation in phytoremediation of nickel co-contaminated soil by Scirpus triqueter was investigated. Similar seedlings of Scirpus triqueter were moved to uncontaminated soil and pyrene-nickel co-contaminated soil. The pots (14.8 cm diameter and 8.8 cm height) were set up in greenhouse and treated in different ways. After 60 days, plant biomass, radial oxygen loss (ROL), soil dehydrogenase activity (DHA) and pyrene concentration in soil were determined. Results showed that ROL rate and DHA in different groups was positively correlated with pyrene dissipation from soil. In the process of remediation, chemical reagents might have an indirect slight effect on pyrene dissipation (pyrene dissipation increased 21%) by affecting DHA firstly and redistributing pyrene fractions in the presence of pyrene degrading bacteria. Pyrene degrading bacteria were likely to affect pyrene dissipation by impacting ROL rate and DHA and played a more vital role in contributing to pyrene dissipation (pyrene dissipation increased 45%) from wetland. This study demonstrated that phytoremediation for pyrene in nickel co-contaminated soil by Scirpus triqueter can be enhanced by the application of NTA-APG and pyrene degrading bacteria and they could be reasonably restore the ecological environment of PAH-contaminated wetlands. Copyright © 2018 Elsevier Inc. All rights reserved.

The influence of smoking in traditional conditions on content of polycyclic aromatic hydrocarbons in Petrovská klobása

NASA Astrophysics Data System (ADS)

Škaljac, S.; Petrović, Lj; Jokanović, M.; Tomović, V.; Tasić, T.; Ivić, M.; Šojić, B.; Ikonić, P.; Džinić, N.

2017-09-01

The aim of this study was to determine the content of 13 polycyclic aromatic hydrocarbons (acenaphthylene, fluorene, phenanthrene, anthracene, pyrene, benz[a]anthracene, chrysene, benzo[b]fluoranthene, benzo[k]fluoranthene, benzo[a]pyrene, indeno[1,2,3-cd]pyrene, dibenz[a,h]anthracene and benzo[ghi]perylene) the from Environmental Protection Agency list (US-EPA PAH) in traditional dry fermented sausage Petrovská klobása. Sausages were smoked in traditional conditions and samples for analyses were taken on day 0 of production (0), at the end of drying (T1) and at the end of the storage period (T2). The highest total content of 13 US-EPA PAHs was determined in sausages at the end of the storage period (73.5 μg/kg). Phenanthrene was the most abundant of the PAHs in all examined sausage samples (0-4.90 μg/kg T1-18.0 μg/kg and T2-26.3 μg/kg). Benzo[a]pyrene, with a maximum allowed content in smoked meat products of 2 µg/kg (EC No. 835/2011), was below the limit of detection in all examined samples. Also, PAH4 (the total content of benz[a]anthracene, chrysene, benzo[b]fluoranthene and benzo[a]pyrene) with a maximum allowed content in smoked meat products of 12 µg/kg (EC No. 835/2011), was below the limit of detection in all examined sausage samples. According to the results obtained in this study, and in regard to the European regulation on PAHs content, the dry fermented sausage Petrovská klobása, smoked in traditional conditions, was safe for consumers.

Comment on: Negative ions, molecular electron affinity and orbital structure of cata-condensed polycyclic aromatic hydrocarbons by Rustem V. Khatymov, Mars V. Muftakhov and Pavel V. Shchukin.

PubMed

Chen, Edward S; Chen, Edward C M

2018-02-15

The anion mass spectral lifetimes for several aromatic hydrocarbons reported in the subject article were related to significantly different electron affinities. The different values are rationalized using negative ion mass spectral data. Electron affinities for polycyclic aromatic hydrocarbons are reported from the temperature dependence of unpublished electron capture detector data. These are compared with published values and the largest values are assigned to the ground state. The ground state adiabatic electron affinities: (eV) pentacene, 1.41 (3); tetracene, 1.058 (5); benz(a)pyrene, 0.82 (4); benz(a) anthracene, 0.69 (2) anthracene, 0.68 (2); and pyrene, 0.59 (1) are used to assign excited state adiabatic electron affinities: (eV) tetracene: 0.88 (4); anthracene 0.53 (1); pyrene, 0.41 (1); benz(a)anthracene, 0.39 (10); chrysene, 0.32 (1); and phenanthrene, 0.12 (2) and ground state adiabatic electron affinities: (eV) dibenz(a,j)anthracene, 0.69 (3); dibenz(a,h)anthracene, 0.68 (3); benz(e)pyrene, 0.60 (3); and picene, 0.59 (3) from experimental data. The lifetime of benz(a)pyrene is predicted to be larger than 150 μs and for benzo(c)phenanthrene and picene about 40 μs, from ground state adiabatic electron affinities. The assignments of adiabatic electron affinities of aromatic hydrocarbons determined from electron capture detector and mass spectrometric data to ground and excited states are supported by constant electronegativities. A set of consistent ground state adiabatic electron affinities for 15 polycyclic aromatic hydrocarbons is related to lifetimes from the subject article. Copyright © 2017 John Wiley & Sons, Ltd.

Topological, functional, and dynamic properties of the protein interaction networks rewired by benzo(a)pyrene

DOE Office of Scientific and Technical Information (OSTI.GOV)

Ba, Qian; Key Laboratory of Food Safety Risk Assessment, Ministry of Health, Beijing; Li, Junyang

2015-03-01

Benzo(a)pyrene is a common environmental and foodborne pollutant that has been identified as a human carcinogen. Although the carcinogenicity of benzo(a)pyrene has been extensively reported, its precise molecular mechanisms and the influence on system-level protein networks are not well understood. To investigate the system-level influence of benzo(a)pyrene on protein interactions and regulatory networks, a benzo(a)pyrene-rewired protein interaction network was constructed based on 769 key proteins derived from more than 500 literature reports. The protein interaction network rewired by benzo(a)pyrene was a scale-free, highly-connected biological system. Ten modules were identified, and 25 signaling pathways were enriched, most of which belong tomore » the human diseases category, especially cancer and infectious disease. In addition, two lung-specific and two liver-specific pathways were identified. Three pathways were specific in short and medium-term networks (< 48 h), and five pathways were enriched only in the medium-term network (6 h–48 h). Finally, the expression of linker genes in the network was validated by Western blotting. These findings establish the overall, tissue- and time-specific benzo(a)pyrene-rewired protein interaction networks and provide insights into the biological effects and molecular mechanisms of action of benzo(a)pyrene. - Highlights: • Benzo(a)pyrene induced scale-free, highly-connected protein interaction networks. • 25 signaling pathways were enriched through modular analysis. • Tissue- and time-specific pathways were identified.« less

Circularly Polarized Luminescence from a Pyrene-Cyclodextrin Supra-Dendron.

PubMed

Zhang, Yuening; Yang, Dong; Han, Jianlei; Zhou, Jin; Jin, Qingxian; Liu, Minghua; Duan, Pengfei

2018-05-22

Soft nanomaterials with circularly polarized luminescence (CPL) have been currently attracting great interest. Here, we report a pyrene-containing π-peptide dendron hydrogel, which shows 1D and 2D nanostructures with varied CPL activities. It was found that the individual dendrons formed hydrogels in a wide pH range (3-12) and self-assembled into helices with pH-tuned pitches. Through chirality transfer, the pyrene unit could show CPL originated from both the monomer and excimer bands. When cyclodextrin was introduced, different supra-dendrons were obtained with β-cyclodextrin (PGAc@β-CD) and γ-cyclodextrin (PGAc@γ-CD) through host-guest interactions, respectively. Interestingly, the PGAc@β-CD and PGAc@γ-CD supra-dendrons self-assembled into 2D nanosheet and entangled nanofibers, respectively, showing cyclodextrin induced circularly polarized emission from both the monomer and excimer bands of the pyrene moiety. Thus, through a simple host-guest interaction, both the nanostructures and the chiroptical activities could be modulated.

Di-epoxides of the three isomeric dicyclopenta-fused pyrenes: ultimate mutagenic active agents.

PubMed

Otero-Lobato, María José; Kaats-Richters, Veronica E M; Havenith, Remco W A; Jenneskens, Leonardus W; Seinen, Willem

2004-11-14

To rationalize the high bacterial mutagenic response recently found for the (di-) cyclopenta-fused pyrene congeners, viz. cyclopenta[cd]-(1), dicyclopenta[cd,mn]-(2), dicyclopenta[cd,fg]-(3) and dicyclopenta[cd,jk]pyrene (4), in the presence of a metabolic activation mixture (S9-mix), their (di-)epoxides at the externally fused unsaturated five-membered rings were previously proposed as the ultimate mutagenic active forms. In this study, cyclopenta[cd]pyrene-3,4-epoxide (5) and the novel dicyclopenta[cd,mn]pyrene-1,2,4,5-di-epoxide (6), dicyclopenta[cd,fg]pyrene-5,6,7,8-di-epoxide (7) and dicyclopenta[cd,jk]pyrene-1,2,6,7-di-epoxide (8) were synthesised from 1 to 4, respectively, and subsequently assayed for bacterial mutagenicity in the standard microsomal/histidine reverse mutation assay (Ames-assay with Salmonella typhimurium strain TA98). The di-epoxides 6-8 are present as a mixture of their cis- and trans-stereo-isomers in a close to 1:1 ratio ((1)H NMR spectroscopy and ab initio IGLO/III//RHF/6-31G** calculations). The direct-acting mutagenic activity and the strong cytotoxicity exerted by 5-8 both in the absence or presence of an exogenous metabolic activation system (+/-S9-mix) demonstrate that the ultimate mutagenic active forms are the proposed (di-)epoxides of 1-4.

Community structure and PAH ring-hydroxylating dioxygenase genes of a marine pyrene-degrading microbial consortium.

PubMed

Gallego, Sara; Vila, Joaquim; Tauler, Margalida; Nieto, José María; Breugelmans, Philip; Springael, Dirk; Grifoll, Magdalena

2014-07-01

Marine microbial consortium UBF, enriched from a beach polluted by the Prestige oil spill and highly efficient in degrading this heavy fuel, was subcultured in pyrene minimal medium. The pyrene-degrading subpopulation (UBF-Py) mineralized 31 % of pyrene without accumulation of partially oxidized intermediates indicating the cooperation of different microbial components in substrate mineralization. The microbial community composition was characterized by culture dependent and PCR based methods (PCR-DGGE and clone libraries). Molecular analyses showed a highly stable community composed by Alphaproteobacteria (84 %, Breoghania, Thalassospira, Paracoccus, and Martelella) and Actinobacteria (16 %, Gordonia). The members of Thalasosspira and Gordonia were not recovered as pure cultures, but five additional strains, not detected in the molecular analysis, that classified within the genera Novosphingobium, Sphingopyxis, Aurantimonas (Alphaproteobacteria), Alcanivorax (Gammaproteobacteria) and Micrococcus (Actinobacteria), were isolated. None of the isolates degraded pyrene or other PAHs in pure culture. PCR amplification of Gram-positive and Gram-negative dioxygenase genes did not produce results with any of the cultured strains. However, sequences related to the NidA3 pyrene dioxygenase present in mycobacterial strains were detected in UBF-Py consortium, suggesting the representative of Gordonia as the key pyrene degrader, which is consistent with a preeminent role of actinobacteria in pyrene removal in coastal environments affected by marine oil spills.

Toxicological effects of benzo[a]pyrene on DNA methylation of whole genome in ICR mice.

PubMed

Zhao, L; Zhang, S; An, X; Tan, W; Pang, D; Ouyang, H

2015-10-30

It has been well known that alterations in DNA methylation - an important regulator of gene transcription - lead to cancer. Therefore a change in the level of DNA methylation of whole genome has been considered as a biomarker of carcinogenesis. Previously, a large number of experimental results in genetic toxicology have showed that benzo[a]pyrene could cause DNA mutation and fragmentation. However, there was little to no studies on alterations in DNA methylation of genome directly result from exposure to benzo[a]pyrene. In this paper, possible mechanisms of alterations in whole genomic DNA methylation by benzo[a]pyrene were investigated using ICR mice after benzo[a]pyrene exposure. The blood, liver, pancreas, skin, lung and bladder of ICR mice were removed and checked after a fixed time interval (6 hours) of benzo[a]pyrene exposure, and whole genomic DNA methylation level was determined by high performance liquid chromatography (HPLC). The results exhibited tissue specificity, that is, the level of whole genomic DNA methylation decreases significantly in blood and liver, rather than pancreas, lung, skin and bladder of ICR mice. This study investigated the direct relationship between aberrant DNA methylation level and benzo[a]pyrene exposure, which might be helpful to clarify the toxicological mechanism of benzo[a]pyrene in epigenetic perspectives.

Toxicity and metabolism of methylnaphthalenes: Comparison with naphthalene and 1-nitronaphthalene

PubMed Central

Lin, Ching Yu; Wheelock, Åsa M.; Morin, Dexter; Baldwin, R. Michael; Lee, Myong Gong; Taff, Aysha; Plopper, Charles; Buckpitt, Alan; Rohde, Arlean

2009-01-01

Naphthalene and close structural analogues have been shown to cause necrosis of bronchiolar epithelial cells in mice by both inhalation exposure and by systemic administration. Cancer bioassays of naphthalene in mice have demonstrated a slight increase in bronchiolar/alveolar adenomas in female mice, and in inflammation and metaplasia of the olfactory epithelium in the nasal cavity. Similar work in rats demonstrated a significant, and concentration-dependent increase in the incidence of respiratory epithelial adenomas and neuroblastomas in the nasal epithelium of both male and female rats. Although the studies on the acute toxicity of the methylnaphthalene derivatives are more limited, it appears that the species selective toxicity associated with naphthalene administration also is observed with methylnaphthalenes. Chronic administration of the methylnaphthalenes, however, failed to demonstrate the same oncogenic potential as that observed with naphthalene. The information available on the isopropylnaphthalene derivatives suggests that they are not cytotoxic. Like the methylnaphthalenes, 1-nitronaphthalene causes lesions in both Clara and ciliated cells. However, the species selective lung toxicity observed in the mouse with both naphthalene and the methylnaphthalenes is not seen with 1-nitronaphthalene. With 1-nitronaphthalene, the rat is far more susceptible to parenteral administration of the compound than mice. The wide-spread distribution of these compounds in the environment and the high potential for low level exposure to humans supports a need for further work on the mechanisms of toxicity in animal models with attention to whether these processes are applicable to humans. Although it is tempting to suppose that the toxicity and mechanisms of toxicity of the alkylnaphthalenes and nitronaphthalenes are similar to naphthalene, there is sufficient published literature to suggest that this may not be the case. Certainly the enzymes involved in the metabolic

Mutations Induced by Benzo[a]pyrene and Dibenzo[a,l]pyrene in lacI Transgenic B6C3F1 Mouse Lung Result from Stable DNA Adducts

EPA Science Inventory

Dibenzo[a,l]pyrene (DB[a,l]P) and benzo[a]pyrene (B[a]P) are carcinogenic polycyclic aromatic hydrocarbons (PAH) that are each capable of forming a variety of covalent adducts with DNA. Some of the DNA adducts formed by these PAHs have been demonstrated to spontaneously depurina...

Surface tailored organobentonite enhances bacterial proliferation and phenanthrene biodegradation under cadmium co-contamination.

PubMed

Mandal, Asit; Biswas, Bhabananda; Sarkar, Binoy; Patra, Ashok K; Naidu, Ravi

2016-04-15

Co-contamination of soil and water with polycyclic aromatic hydrocarbon (PAH) and heavy metals makes biodegradation of the former extremely challenging. Modified clay-modulated microbial degradation provides a novel insight in addressing this issue. This study was conducted to evaluate the growth and phenanthrene degradation performance of Mycobacterium gilvum VF1 in the presence of a palmitic acid (PA)-grafted Arquad® 2HT-75-based organobentonite in cadmium (Cd)-phenanthrene co-contaminated water. The PA-grafted organobentonite (ABP) adsorbed a slightly greater quantity of Cd than bentonite at up to 30mgL(-1) metal concentration, but its highly negative surface charge imparted by carboxylic groups indicated the potential of being a significantly superior adsorbent of Cd at higher metal concentrations. In systems co-contained with Cd (5 and 10mgL(-1)), the Arquad® 2HT-75-modified bentonite (AB) and PA-grafted organobentonite (ABP) resulted in a significantly higher (72-78%) degradation of phenanthrene than bentonite (62%) by the bacterium. The growth and proliferation of bacteria were supported by ABP which not only eliminated Cd toxicity through adsorption but also created a congenial microenvironment for bacterial survival. The macromolecules produced during ABP-bacteria interaction could form a stable clay-bacterial cluster by overcoming the electrostatic repulsion among individual components. Findings of this study provide new insights for designing clay modulated PAH bioremediation technologies in mixed-contaminated water and soil. Copyright © 2016 Elsevier B.V. All rights reserved.

40 CFR 464.31 - Specialized definitions.

Code of Federal Regulations, 2013 CFR

2013-07-01

... § 464.31 Specialized definitions. For the purpose of this subpart: (a) Total Toxic Organics (TTO). TTO... comprised of a discrete list of toxic organic pollutants for each process segment where it is regulated, as...-benzanthracene) 76. chrysene 77. acenaphthylene 78. anthracene 80. fluorene 81. phenanthrene 84. pyrene (5) Mold...

Development of Naphthalene PLIF for Visualizing Ablation Products From a Space Capsule Heat Shield

NASA Technical Reports Server (NTRS)

Combs, C. S.; Clemens, N. T.; Danehy, P. M.

2014-01-01

The Orion Multi-Purpose Crew Vehicle (MPCV) will use an ablative heat shield. To better design this heat shield and others that will undergo planetary entry, an improved understanding of the ablation process would be beneficial. Here, a technique developed at The University of Texas at Austin that uses planar laser-induced fluorescence (PLIF) of a low-temperature sublimating ablator (naphthalene) to enable visualization of the ablation products in a hypersonic flow is applied. Although high-temperature ablation is difficult and expensive to recreate in a laboratory environment, low-temperature sublimation creates a limited physics problem that can be used to explore ablation-product transport in a hypersonic flow-field. In the current work, a subscale capsule reentry vehicle model with a solid naphthalene heat shield has been tested in a Mach 5 wind tunnel. The PLIF technique provides images of the spatial distribution of sublimated naphthalene in the heat-shield boundary layer, separated shear layer, and backshell recirculation region. Visualizations of the capsule shear layer using both naphthalene PLIF and Schlieren imaging compared favorably. PLIF images have shown high concentrations of naphthalene in the capsule separated flow region, intermittent turbulent structures on the heat shield surface, and interesting details of the capsule shear layer structure. It was shown that, in general, the capsule shear layer appears to be more unsteady at lower angels of attack. The PLIF images demonstrated that during a wind tunnel run, as the model heated up, the rate of naphthalene ablation increased, since the PLIF signal increased steadily over the course of a run. Additionally, the shear layer became increasingly unsteady over the course of a wind tunnel run, likely because of increased surface roughness but also possibly because of the increased blowing. Regions with a relatively low concentration of naphthalene were also identified in the capsule backshell

Benzene and Naphthalene Degrading Bacterial Communities in an Oil Sands Tailings Pond

PubMed Central

Rochman, Fauziah F.; Sheremet, Andriy; Tamas, Ivica; Saidi-Mehrabad, Alireza; Kim, Joong-Jae; Dong, Xiaoli; Sensen, Christoph W.; Gieg, Lisa M.; Dunfield, Peter F.

2017-01-01

Oil sands process-affected water (OSPW), produced by surface-mining of oil sands in Canada, is alkaline and contains high concentrations of salts, metals, naphthenic acids, and polycyclic aromatic compounds (PAHs). Residual hydrocarbon biodegradation occurs naturally, but little is known about the hydrocarbon-degrading microbial communities present in OSPW. In this study, aerobic oxidation of benzene and naphthalene in the surface layer of an oil sands tailings pond were measured. The potential oxidation rates were 4.3 μmol L−1 OSPW d−1 for benzene and 21.4 μmol L−1 OSPW d−1 for naphthalene. To identify benzene and naphthalene-degrading microbial communities, metagenomics was combined with stable isotope probing (SIP), high-throughput sequencing of 16S rRNA gene amplicons, and isolation of microbial strains. SIP using 13C-benzene and 13C-naphthalene detected strains of the genera Methyloversatilis and Zavarzinia as the main benzene degraders, while strains belonging to the family Chromatiaceae and the genus Thauera were the main naphthalene degraders. Metagenomic analysis revealed a diversity of genes encoding oxygenases active against aromatic compounds. Although these genes apparently belonged to many phylogenetically diverse taxa, only a few of these taxa were predominant in the SIP experiments. This suggested that many members of the community are adapted to consuming other aromatic compounds, or are active only under specific conditions. 16S rRNA gene sequence datasets have been submitted to the Sequence Read Archive (SRA) under accession number SRP109130. The Gold Study and Project submission ID number in Joint Genome Institute IMG/M for the metagenome is Gs0047444 and Gp0055765. PMID:29033909

Impact of kerogen heterogeneity on sorption of organic pollutants. 2. Sorption equilibria

DOE Office of Scientific and Technical Information (OSTI.GOV)

Yang, C.; Yu, Z.Q.; Xiao, B.H.

2009-08-15

Phenanthrene and naphthalene sorption isotherms were measured for three different series of kerogen materials using completely mixed batch reactors. Sorption isotherms were nonlinear for each sorbate-sorbent system, and the Freundlich isotherm equation fit the sorption data well. The Freundlich isotherm linearity parameter n ranged from 0.192 to 0.729 for phenanthrene and from 0.389 to 0.731 for naphthalene. The n values correlated linearly with rigidity and aromaticity of the kerogen matrix, but the single-point, organic carbon-normalized distribution coefficients varied dramatically among the tested sorbents. A dual-mode sorption equation consisting of a linear partitioning domain and a Langmuir adsorption domain adequately quantifiedmore » the overall sorption equilibrium for each sorbent-sorbate system. Both models fit the data well, with r{sup 2} values of 0.965 to 0.996 for the Freundlich model and 0.963 to 0.997 for the dual-mode model for the phenanthrene sorption isotherms. The dual-mode model fitting results showed that as the rigidity and aromaticity of the kerogen matrix increased, the contribution of the linear partitioning domain to the overall sorption equilibrium decreased, whereas the contribution of the Langmuir adsorption domain increased. The present study suggested that kerogen materials found in soils and sediments should not be treated as a single, unified, carbonaceous sorbent phase.« less

Theoretical Study of the Electronic Spectra of a Polycyclic Aromatic Hydrocarbon, Naphthalene, and its Derivatives

NASA Technical Reports Server (NTRS)

Du, Ping; Salama, Farid; Loew, Gilda H.

1993-01-01

In order to preselect possible candidates for the origin of diffuse interstellar bands observed, semiempirical quantum mechanical method INDO/S was applied to the optical spectra of neutral, cationic, and anionic states of naphthalene and its hydrogen abstraction and addition derivatives. Comparison with experiment shows that the spectra of naphthalene and its ions were reliably predicted. The configuration interaction calculations with single-electron excitations provided reasonable excited state wavefunctions compared to ab initio calculations that included higher excitations. The degree of similarity of the predicted spectra of the hydrogen abstraction and derivatives to those of naphthalene and ions depends largely on the similarity of the it electron configurations. For the hydrogen addition derivatives, very little resemblance of the predicted spectra to naphthalene was found because of the disruption of the aromatic conjugation system. The relevance of these calculations to astrophysical issues is discussed within the context of these polycyclic aromatic hydrocarbon models. Comparing the calculated electronic energies to the Diffuse Interstellar Bands (DIBs), a list of possible candidates of naphthalene derivatives is established which provides selected candidates for a definitive test through laboratory studies.

Purification and characteristics of an inducible by polycyclic aromatic hydrocarbons NADP(+)-dependent naphthalenediol dehydrogenase (NDD) in Mucor circinelloides YR-1.

PubMed

Camacho-Morales, Reyna Lucero; Zazueta-Novoa, Vanesa; Casillas, Juana Lizbeth González; Ballesteros, Elizabeth Aranda; Bote, Juan Antonio Ocampo; Zazueta-Sandoval, Roberto

2014-05-01

We detected NADP(+)-dependent dihydrodiol dehydrogenase (DD) activity in a cell-free extract from Mucor circinelloides YR-1, after high-speed centrifugation. We analyzed the enzymatic activity in the cytosolic fraction by zymograms, as described previously, and eight different DD activity bands were revealed. Five constitutive DD activities (DD1-5) were present when glucose was used as carbon source and three inducible activities (NDD, PDD1 and PDD2) when aromatic hydrocarbon compounds were used. NDD activity was induced all of the aromatic hydrocarbon compounds. The highest DD activity inducer was naphthalene and the lowest was pyrene. One of the enzymes showed higher activity with cis-naphthalene-diol rather than with trans-nahthalenediol as a substrate. We purified this particular enzyme to homogeneity and found that it had an isoelectric point of 4.6. The molecular weight for the native protein was 197.4kDa and 49.03±0.5kDa for the monomer that conforms it, suggesting a homotetrameric structure for the complete enzyme. Polyclonal antibodies were raised against it and obtained. NDD activity was almost totally inhibited when antibodies were used at low concentrations, and in native immunoblots only one band, which corresponds to the activity band detected in the zymograms, could be detected. In denaturing PAGE immunoblots only one band was detected. This band corresponds to the purified protein band of 49kDa detected in SDS-PAGE gels. The other two inducible enzymes PDD1 and PDD2 were present only when phenanthrene was used as sole carbon source in the culture media. Copyright © 2014 Elsevier Inc. All rights reserved.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Walton, B.T.

In the present study, acute and chronic toxicities of five PAHs (naphthalene, anthracene, benz(a)anthracene, pyrene, and benzo(a)pyrene) and an oxygenated PAH derivative (anthrone) were determined in a terrestrial insect, Acheta domesticus (L.), with emphasis on the influence of route of entry on toxicity. Hexamethylphosphoric triamide (hempa) was included in the chronic tests since this chemosterilant is a useful reference compound for investigations of reproductive effects of chemicals in insects.

[Phenanthrene constituents from rhizome of Arundina graminifolia].

PubMed

Liu, Mei-feng; Ding, Yi; Zhang, Dong-ming

2005-03-01

To isolate and elucidate the constituents from rhizome of Arundina graminifolia. Theconstituents were extracted with 95% alcohol and isolated by chromatography on silica gel, Sephedax LH-20. The structures were determined by UV, IR, NMR and MS spectral analysis. Five phenanthrene constituents were identified as 7-hydroxy-2, 4-dimethoxy-9, 10-dihydrophenanthrene( I ), 4, 7-dihydroxy-2-methoxy-9, 10-dihydrophenanthrene ( II ), 2, 7-dihydroxy-4-methoxy-9, 10-dihydrophenanthrene ( III ), 7-hydroxy-2-methoxyphenanthrene-1,4-dione ( IV ), 7-hydroxy-2-methoxy-9, 10-dihydrophenanthrene-1,4-dione (V), respectively. All compounds were isolated from rhizome of A. graminifolia for the first time.

Influence of tea saponin on enhancing accessibility of pyrene and cadmium phytoremediated with Lolium multiflorum in co-contaminated soils.

PubMed

Wang, Qian; Liu, Xiaoyan; Zhang, Xinying; Hou, Yunyun; Hu, Xiaoxin; Liang, Xia; Chen, Xueping

2016-03-01

Tea saponin (TS), a kind of biodegradable surfactant, was chosen to improve the accessible solubilization of pyrene and cadmium (Cd) in co-contaminated soils cultivated Lolium multiflorum. TS obviously improved the accessibility of pyrene and Cd for L. multiflorum to accelerate the process of accumulation and elimination of the pollutants. The chemical forms of Cd was transformed from Fe-Mn oxides and associated to carbonates fractions into exchangeable fractions by adding TS in single Cd and pyrene-Cd contaminated soils. Moreover, the chemical forms of pyrene were transformed from associated fraction into bioaccessible fraction by adding TS in pyrene and pyrene-Cd contaminated soils. In pyrene-Cd contaminated soil, the exchangeable fraction of Cd was hindered in the existence of pyrene, and bioaccessible fraction of pyrene was promoted by the cadmium. Besides, in the process of the pyrene degradation and Cd accumulation, the effect could be improved by the elongation of roots with adding TS, and the microorganism activity was stimulated by TS to accelerate the removal of pollutions. Therefore, Planting L. multiflorum combined with adding TS would be an effective method on the phytoremediation of organics and heavy metals co-contaminated soils.

Naphthalene emissions from moth repellents or toilet deodorant blocks determined using head-space and small-chamber tests.

PubMed

Jo, Wan-Kuen; Lee, Jong-Hyo; Lim, Ho-Jin; Jeong, Woo-Sik

2008-01-01

The present study investigated the emissions of naphthalene and other compounds from several different moth repellents (MRs) and one toilet deodorant block (TDB) currently sold in Korea, using a headspace analysis. The emission factors and emission rates of naphthalene were studied using a small-scale environmental chamber. Paper-type products emitted a higher concentration of the total volatile organic compounds (VOCs) (normalized to the weight of test piece) than ball-type products, which in turn emitted higher concentration than a gel-type product. In contrast, naphthalene was either the most or the second highest abundant compound for the four ball products, whereas for paper and gel products it was not detected or was detected at much lower levels. The abundance of naphthalene ranged between 18.4% and 37.3% for ball products. The results showed that the lower the air changes per hour (ACH) level was, the higher the naphthalene concentrations became. In general, a low ACH level suggests a low ventilation rate. The emission factor for naphthalene was nearly 100 times higher for a ball MR than for a gel or a paper MR. For the ball MR, the lower ACH level resulted in higher emission rate.

Behavioural alterations from exposure to Cu, phenanthrene, and Cu-phenanthrene mixtures: linking behaviour to acute toxic mechanisms in the aquatic amphipod, Hyalella azteca.

PubMed

Gauthier, Patrick T; Norwood, Warren P; Prepas, Ellie E; Pyle, Greg G

2016-01-01

Phenanthrene (PHE) and Cu are two contaminants commonly co-occurring in marine and freshwater environments. Mixtures of PHE and Cu have been reported to induce more-than-additive lethality in the amphipod, Hyalella azteca, a keystone aquatic invertebrate, yet little is understood regarding the interactive toxic mechanisms that mediate more-than-additive toxicity. Understanding the interactions among toxic mechanisms among Cu and PHE will allow for better predictive power in assessing the ecological risks of Cu-PHE mixtures in aquatic environments. Here we use behavioural impairment to help understand the toxic mechanisms of Cu, PHE, and Cu-PHE mixture toxicity in the aquatic amphipod crustacean, Hyalella azteca. Our principal objective was to link alterations in activity and ventilation with respiratory rates, oxidative stress, and neurotoxicity in adult H. azteca. Adult amphipods were used for all toxicity tests. Amphipods were tested at sublethal exposures of 91.8- and 195-μgL(-1) Cu and PHE, respectively, and a Cu-PHE mixture at the same concentrations for 24h. Neurotoxicity was measured as acetylcholinesterase (AChE) activity, where malathion was used as a positive control. Oxidative stress was measured as reactive oxygen species (ROS) production. Phenanthrene-exposed amphipods exhibited severe behavioural impairment, being hyperstimulated to the extent that they were incapable of coordinating muscle movements. In addition, respiration and AChE activity in PHE-exposed amphipods were increased and reduced by 51% and 23% respectively. However, ROS did not increase following exposure to phenanthrene. In contrast, Cu had no effect on amphipod behaviour, respiration or AChE activity, but did lead to an increase in ROS. However, co-exposure to Cu antagonized the PHE-induced reduction in ventilation and negated any increase in respiration. The results suggest that PHE acts like an organophosphate pesticide (e.g., malathion) in H. azteca following 24h sublethal

Profile distribution of polycyclic aromatic hydrocarbons in soils of drained peatlands after wildfires (Moscow region, Russia)

NASA Astrophysics Data System (ADS)

Tsibart, Anna; Gennadiev, Alexander; Koshovskii, Timur; Kovach, Roman

2014-05-01

Polycyclic aromatic compounds (PAHs) are formed in different natural and anthropogenic processes and could be found in many landscape components. These compounds are carcinogenic and belong to the group of persistent organic pollutants. The anthropogenic sources of PAHs are well-studied, but insufficient data are available on the hightemperature production of PAHs in natural processes. For example, natural fires are frequently related to the PAHs sources in landscapes, but very little factual data are on this topic. The soils of drained peatlands affected by catastrophic wildfires of 2010 and 2002 were studied in the Eastern part of Moscow Region (Russia). A total of 14 profiles of histosols and histic podsols were investigated. These series included soils of plots subjected to fires of different intensities and age, as well as soils of the background plots. Soil samples were taken from genetic horizons and from every 10 cm. The samples were analyzed for the contents of 14 prevailing individual compounds: fluorene, naphthalene, phenanthrene, chrysene, pyrene, anthracene, tetraphene, benz[a]pyrene, benzo[ghi]perylene, benzo[e]pyrene, coronene, dibenztiophene, triphenilene, benz(k)fluorantene. Morfological properties of soils after wildfires on drained peatlands were changed dramatically, the horizons of ash and char instead of organic layers were formed. These new horizons differ in the capability of PAHs accumulation. The char horizons have the highest concentrations of PAHs - up to 300 ng/g because of incomplete burning of organic matter in this sites, and the ash horizons, where the complete burning occured, contain only 10 ng/g PAHs. The highest concentrations of PAHs in soil profiles were detected after recent fires, and in cases of thick peat layers. After the combustion of peat chrysene, benz[a]pyrene, benz[e]pyrene, benzo[ghi]perylene, benz(k)fluorantene and tetraphene accumulated in soils. This is mainly the group of 4-6-nuclear compounds. The formation of

Changes in oxygen consumption and respiratory enzymes as stress indicators in an estuarine edible crab Scylla serrata exposed to naphthalene.

PubMed

Vijayavel, K; Balasubramanian, M P

2006-06-01

The sublethal effect of naphthalene was studied on the physiology of a mud crab Scylla serrata. The 96 h acute toxicity of naphthalene was determined and found to be 28 mg 1(-1) (LC100), 18 mg 1(-1) (LC50), 10 mg 1(-1) (LC0) respectively. The 30 days sublethal effect (LC0) 9 mg 1(-1), 8 mg 1(-1), 10 mg 1(-1), of naphthalene was investigated in the crab S. serrata with reference to oxygen consumption and changes in the activity of respiratory enzymes. The results indicated that naphthalene caused disturbance in the normal physiology of the crab. The bioaccumulation of naphthalene was also investigated in gills, hepatopancreas, haemolymph and ovary. The consumption of oxygen increased in the naphthalene medium when compared with that of the crabs exposed to naphthalene free medium. A decreased trend in the activity of respiratory enzymes such as lactate dehydrogenase (LDH), isocitrate dehydrogenase (ICDH), succinate dehydrogenase (SDH), malate dehydrogenase (MDH), alpha-ketoglutarate dehydrogenase (alpha-KDH) and glutathione (GSH) were recorded in the hepatopancreas, ovary and gills of S. serrata for all the tested concentrations of naphthalene and the results were analyzed for their significance.

Laboratory studies to characterize the efficacy of sand capping a coal tar-contaminated sediment.

PubMed

Hyun, Seunghun; Jafvert, Chad T; Lee, Linda S; Rao, P Suresh C

2006-06-01

Placement of a microbial active sand cap on a coal tar-contaminated river sediment has been suggested as a cost effective remediation strategy. This approach assumes that the flux of contaminants from the sediment is sufficiently balanced by oxygen and nutrient fluxes into the sand layer such that microbial activity will reduce contaminant concentrations within the new benthic zone and reduce the contaminant flux to the water column. The dynamics of such a system were evaluated using batch and column studies with microbial communities from tar-contaminated sediment under different aeration and nutrient inputs. In a 30-d batch degradation study on aqueous extracts of coal tar sediment, oxygen and nutrient concentrations were found to be key parameters controlling the degradation rates of polycyclic aromatic hydrocarbons (PAHs). For the five PAHs monitored (naphthalene, fluorene, phenanthrene, anthracene, and pyrene), degradation rates were inversely proportional to molecular size. For the column studies, where three columns were packed with a 20-cm sand layer on the top of a 5 cm of sediment layer, flow was established to sand layers with (1) aerated water, (2) N(2) sparged water, or (3) HgCl(2)-sterilized N(2) sparged water. After steady-state conditions, PAH concentrations in effluents were the lowest in the aerated column, except for pyrene, whose concentration was invariant with all effluents. These laboratory scale studies support that if sufficient aeration can be achieved in the field through either active and passive means, the resulting microbially active sand layer can improve the water quality of the benthic zone and reduce the flux of many, but not all, PAHs to the water column.

High-Capacity and Photoregenerable Composite Material for Efficient Adsorption and Degradation of Phenanthrene in Water.

PubMed

Liu, Wen; Cai, Zhengqing; Zhao, Xiao; Wang, Ting; Li, Fan; Zhao, Dongye

2016-10-18

We report a novel composite material, referred to as activated charcoal supported titanate nanotubes (TNTs@AC), for highly efficient adsorption and photodegradation of a representative polycyclic aromatic hydrocarbon (PAH), phenanthrene. TNTs@AC was prepared through a one-step hydrothermal method, and is composed of an activated charcoal core and a shell of carbon-coated titanate nanotubes. TNTs@AC offered a maximum Langmuir adsorption capacity of 12.1 mg/g for phenanthrene (a model PAH), which is ∼11 times higher than the parent activated charcoal. Phenanthrene was rapidly concentrated onto TNTs@AC, and subsequently completely photodegraded under UV light within 2 h. The photoregenerated TNTs@AC can then be reused for another adsorption-photodegradation cycle without significant capacity or activity loss. TNTs@AC performed well over a wide range of pH, ionic strength, and dissolved organic matter. Mechanistically, the enhanced adsorption capacity is attributed to the formation of carbon-coated ink-bottle pores of the titanate nanotubes, which are conducive to capillary condensation; in addition, the modified microcarbon facilitates transfer of excited electrons, thereby inhibiting recombination of the electron-hole pairs, resulting in high photocatalytic activity. The combined high adsorption capacity, photocatalytic activity, and regenerability/reusability merit TNTs@AC a very attractive material for concentrating and degrading a host of micropollutants in the environment.

Distribution and sources of bioaccumulative air pollutants at Mezquital Valley, Mexico, as reflected by the atmospheric plant Tillandsia recurvata L.

NASA Astrophysics Data System (ADS)

Zambrano García, A.; Medina Coyotzin, C.; Rojas Amaro, A.; López Veneroni, D.; Martínez, L. Chang; Sosa Iglesias, G.

2009-03-01

Mezquital Valley (MV), a Mexican wastewater-based agricultural and industrial region, is a ''hot spot'' of regulated air pollutants emissions, but the concurrent unregulated ones, like hazardous metals and polycyclic aromatic hydrocarbons (PAH), remain undocumented. A biomonitoring survey with the epiphytic Tillandsia recurvata was conducted there to detect spatial patterns and potential sources of 20 airborne elements and 15 PAH. The natural δ13C and δ15N ratios of this plant helped in source identification. The regional mean concentrations of most elements was two (Cr) to over 40 times (Ni, Pb, V) higher than reported for Tillandsia in other countries. Eleven elements, pyrene and chrysene had 18-214% higher mean concentration at the industrial south than at the agricultural north of MV. The total quantified PAH (mean, 572 ng g-1; range, 142.6-2568) were composed by medium (65%, phenanthrene to chrysene), low (28%, naphthalene to fluorene) and high molecular weight compounds (7%, Benzo(b)fluoranthene to indeno(1,2,3-cd)pyrene). The δ13C (mean, -14.6‰; range, -5.7 to -13.7‰) was lower (<-15‰) near the major petroleum combustion sources. The δ15N (mean, -3.0‰; range, -9.9 to 3.3‰) varied from positive at agriculture/industrial areas to negative at rural sites. Factor analysis provided a five-factor solution for 74% of the data variance: (1) crustal rocks, 39.5% (Al, Ba, Cu, Fe, Sr, Ti); (2) soils, 11.3%, contrasting contributions from natural (Mg, Mn, Zn) and saline agriculture soils (Na); (3) cement production and fossil fuel combustion, 9.8% (Ca, Ni, V, chrysene, pyrene); (4) probable agricultural biomass burning, 8.1% (K and benzo(g,h,i)perylene), and (5) agriculture with wastewater, 5.2% (δ15N and P). These results indicated high deposition of bioaccumulative air pollutants at MV, especially at the industrial area. Since T. recurvata reflected the regional differences in exposition, it is recommended as a biomonitor for comparisons within and

40 CFR 464.21 - Specialized definitions.

Code of Federal Regulations, 2013 CFR

2013-07-01

... § 464.21 Specialized definitions. For the purpose of this subpart: (a) Total Toxic Organics (TTO). TTO... comprised of a discrete list of toxic organic pollutants for each process segment where it is regulated, as.... chrysene 77. acenaphthylene 78. anthracene 81. phenanthrene 84. pyrene (5) Mold Cooling (§ 464.25(g) and...

Adsorption of polycyclic aromatic hydrocarbons by graphene and graphene oxide nanosheets.

PubMed

Wang, Jun; Chen, Zaiming; Chen, Baoliang

2014-05-06

The adsorption of naphthalene, phenanthrene, and pyrene onto graphene (GNS) and graphene oxide (GO) nanosheets was investigated to probe the potential adsorptive sites and molecular mechanisms. The microstructure and morphology of GNS and GO were characterized by elemental analysis, XPS, FTIR, Raman, SEM, and TEM. Graphene displayed high affinity to the polycyclic aromatic hydrocarbons (PAHs), whereas GO adsorption was significantly reduced after oxygen-containing groups were attached to GNS surfaces. An unexpected peak was found in the curve of adsorption coefficients (Kd) with the PAH equilibrium concentrations. The hydrophobic properties and molecular sizes of the PAHs affected the adsorption of G and GO. The high affinities of the PAHs to GNS are dominated by π-π interactions to the flat surface and the sieving effect of the powerful groove regions formed by wrinkles on GNS surfaces. In contrast, the adsorptive sites of GO changed to the carboxyl groups attaching to the edges of GO because the groove regions disappeared and the polar nanosheet surfaces limited the π-π interactions. The TEM and SEM images initially revealed that after loading with PAH, the conformation and aggregation of GNS and GO nanosheets dramatically changed, which explained the observations that the potential adsorption sites of GNS and GO were unusually altered during the adsorption process.

Gas chromatographic retention behavior of polycyclic aromatic hydrocarbons (PAHs) and alkyl-substituted PAHs on two stationary phases of different selectivity.

PubMed

Nalin, Federica; Sander, Lane C; Wilson, Walter B; Wise, Stephen A

2018-01-01

Retention indices (I) for 45 polycyclic aromatic hydrocarbons (PAHs) and 63 methyl-substituted PAHs were determined by gas chromatography - mass spectrometry (GC-MS) using two different stationary phases: a Rxi-PAH phase (a "higher phenyl-content stationary phase") and a 50% (mole fraction) liquid crystalline dimethylpolysiloxane phase. Retention data were obtained for parent PAHs from molecular mass (MM) 128 g/mol (naphthalene) to 328 g/mol (benzo[c]picene) and for 12 sets of methyl-PAHs (methylfluorenes, methylanthracenes, methylphenanthrenes, methylfluoranthenes, methylpyrenes, methylbenz[a]anthracenes, methylbenzo[c]phenanthrenes, methylchrysenes, methyltriphenylenes, methylbenzo[a]pyrenes, methylperylenes, and methylpicenes). Molecular shape descriptors such as length-to-breath ratio (L/B) and thickness (T) were determined for all the PAHs studied. Correlation between I and L/B ratio was evaluated for both stationary phases with a better correlation observed for the 50% liquid crystalline phase (correlation coefficients ranging from 0.22 to 1.00). Graphical Abstract GC separation of six methylchrysene isomers (m/z 242) on two different stationary phases: 50 % phenyl-like methylpolysiloxane phase and 50 % liquid crystalline phase. Retention indices (I) are plotted as a function of L/B for both phases. The data marker numbers identify each isomer based on methyl-substitution position.

Passive dosing of polycyclic aromatic hydrocarbon (PAH) mixtures to terrestrial springtails: linking mixture toxicity to chemical activities, equilibrium lipid concentrations, and toxic units.

PubMed

Schmidt, Stine N; Holmstrup, Martin; Smith, Kilian E C; Mayer, Philipp

2013-07-02

A 7-day mixture toxicity experiment with the terrestrial springtail Folsomia candida was conducted, and the effects were linked to three different mixture exposure parameters. Passive dosing from silicone was applied to tightly control exposure levels and compositions of 12 mixture treatments, containing the polycyclic aromatic hydrocarbons (PAHs) naphthalene, phenanthrene, and pyrene. Springtail lethality was then linked to sum chemical activities (∑a), sum equilibrium lipid concentrations (∑C(lipid eq.)), and sum toxic units (∑TU). In each case, the effects of all 12 mixture treatments could be fitted to one sigmoidal exposure-response relationship. The effective lethal chemical activity (La50) of 0.027 was well within the expected range for baseline toxicity of 0.01-0.1. Linking the effects to the lipid-based exposure parameter yielded an effective lethal concentration (LC(lipid eq 50)) of 133 mmol kg(-1) lipid in good correspondence with the lethal membrane burden for baseline toxicity (40-160 mmol kg(-1) lipid). Finally, the effective lethal toxic unit (LTU50) of 1.20 was rather close to the expected value of 1. Altogether, passive dosing provided tightly controlled mixture exposure in terms of both level and composition, while ∑a, ∑C(lipid eq.), and ∑TU allowed baseline toxicity to be linked to mixture exposure.

Effect of humic acid on pyrene removal from water by polycation-clay mineral composites and activated carbon.

PubMed

Radian, Adi; Mishael, Yael

2012-06-05

Pyrene removal by polycation-montmorillonite (MMT) composites and granulated activated carbon (GAC) in the presence of humic acid (HA) was examined. Pyrene, HA, and sorbent interactions were characterized by FTIR, fluorescence and zeta measurements, adsorption, and column filtration experiments. Pyrene binding coefficients to the macromolecules were in the order of PVPcoS (poly-4-vinylpiridine-co-styrene) > HA > PDADMAC (poly diallyl-dimethyl-ammonium-chloride), correlating to pyrene-macromolecules compatibility. Electrostatic interactions explained the high adsorption of HA to both composites (∼100%), whereas HA adsorption by GAC was low. Pyrene removal by the composites, unlike GAC, was enhanced in the presence of HA; removal by PDADMAC-MMT increased from ∼50 (k(d) = 2.2 × 10(3) kg/L) to ∼70% (k(d) = 2.4 × 10(3) kg/L) in the presence of HA. This improvement was attributed to the adsorption of pyrene-HA complexes. PVPcoS-MMT was most efficient in removing pyrene (k(d) = 1.1 × 10(4) kg/L, >95% removal) which was explained in terms of specific π donor-π acceptor interactions. Pyrene uptake by column filters of GAC reached ∼50% and decreased to ∼30% in the presence of HA. Pyrene removal by the PVPcoS-MMT filter was significantly higher (100-85% removal), exhibiting only a small decrease in the presence of HA. The utilization of HA as an enhancing agent in pollutant removal is novel and of major importance in water treatment.

Biodegradation of polycyclic aromatic hydrocarbons (PAHs) by laccase from Trametes versicolor covalently immobilized on amino-functionalized SBA-15.

PubMed

Bautista, Luis Fernando; Morales, Gabriel; Sanz, Raquel

2015-10-01

A covalent immobilization method based on glutaraldehyde and amino-functionalized SBA-15 supports has been successfully applied to covalently and stably immobilize laccase from Trametes versicolor. The resultant biocatalysts displayed high incorporation yields of enzyme and led to excellent biodegradation rates of selected HPAs models, i.e. naphthalene, phenanthrene and anthracene, in water. The nature of the hydrocarbon chain accompanying the amino group has been shown as determinant for the immobilization as well as for the activity and reusability of the materials. Thus, alkyl moieties displayed higher enzyme loadings than phenyl moieties, being more adequate the larger n-butyl tethering residue likely due to its higher mobility. Using the aminobutyl-based laccase-SBA-15, 82%, 73%, and 55% conversion of naphthalene, phenanthrene and anthracene, respectively, were achieved after 48 h, very close to the values obtained with free laccase under the same reaction conditions. On the other hand, aminopropyl-based laccase-SBA-15 biocatalysts displayed the best reusability properties, retaining higher activity after four repeated uses than the corresponding aminobutyl-based materials. Copyright © 2015 Elsevier Ltd. All rights reserved.

Turbulent Coagulation of Particles Smaller Than the Length Scales of Turbulence and Equilibrium Sorption of Phenanthrene to Clay: Implications for Pollutant Transport in the Estuarine Water Column

DTIC Science & Technology

1997-05-01

estuaries was modeled using phenanthrene, bacterial extracellular polymer and kaolinite clay as surrogates for a hydrophobic organic pollutant...coefficients obtained for phenanthrene sorption to kaolinite and bentonite in the presence of varying amounts of DOM represented by alginic acid and tannic...acid. 333 Table B.3: Literature values for sorption between phenanthrene, humic acid and kaolinite for [DOM]a = 10 mg/L 334 Table E.1: Sample output data

Measurement of Biologically Available Naphthalene in Gas and Aqueous Phases by Use of a Pseudomonas putida Biosensor

PubMed Central

Werlen, Christoph; Jaspers, Marco C. M.; van der Meer, Jan Roelof

2004-01-01

Genetically constructed microbial biosensors for measuring organic pollutants are mostly applied in aqueous samples. Unfortunately, the detection limit of most biosensors is insufficient to detect pollutants at low but environmentally relevant concentrations. However, organic pollutants with low levels of water solubility often have significant gas-water partitioning coefficients, which in principle makes it possible to measure such compounds in the gas rather than the aqueous phase. Here we describe the first use of a microbial biosensor for measuring organic pollutants directly in the gas phase. For this purpose, we reconstructed a bioluminescent Pseudomonas putida naphthalene biosensor strain to carry the NAH7 plasmid and a chromosomally inserted gene fusion between the sal promoter and the luxAB genes. Specific calibration studies were performed with suspended and filter-immobilized biosensor cells, in aqueous solution and in the gas phase. Gas phase measurements with filter-immobilized biosensor cells in closed flasks, with a naphthalene-contaminated aqueous phase, showed that the biosensor cells can measure naphthalene effectively. The biosensor cells on the filter responded with increasing light output proportional to the naphthalene concentration added to the water phase, even though only a small proportion of the naphthalene was present in the gas phase. In fact, the biosensor cells could concentrate a larger proportion of naphthalene through the gas phase than in the aqueous suspension, probably due to faster transport of naphthalene to the cells in the gas phase. This led to a 10-fold lower detectable aqueous naphthalene concentration (50 nM instead of 0.5 μM). Thus, the use of bacterial biosensors for measuring organic pollutants in the gas phase is a valid method for increasing the sensitivity of these valuable biological devices. PMID:14711624

Adsorption of naphthalene and ozone on atmospheric air/ice interfaces coated with surfactants: a molecular simulation study.

PubMed

Liyana-Arachchi, Thilanga P; Valsaraj, Kalliat T; Hung, Francisco R

2012-03-15

The adsorption of gas-phase naphthalene and ozone molecules onto air/ice interfaces coated with different surfactant species (1-octanol, 1-hexadecanol, or 1-octanal) was investigated using classical molecular dynamics (MD) simulations. Naphthalene and ozone exhibit a strong preference to be adsorbed at the surfactant-coated air/ice interfaces, as opposed to either being dissolved into the bulk of the quasi-liquid layer (QLL) or being incorporated into the ice crystals. The QLL becomes thinner when the air/ice interface is coated with surfactant molecules. The adsorption of both naphthalene and ozone onto surfactant-coated air/ice interfaces is enhanced when compared to bare air/ice interface. Both naphthalene and ozone tend to stay dissolved in the surfactant layer and close to the QLL, rather than adsorbing on top of the surfactant molecules and close to the air region of our systems. Surfactants prefer to orient at a tilted angle with respect to the air/ice interface; the angular distribution and the most preferred angle vary depending on the hydrophilic end group, the length of the hydrophobic tail, and the surfactant concentration at the air/ice interface. Naphthalene prefers to have a flat orientation on the surfactant coated air/ice interface, except at high concentrations of 1-hexadecanol at the air/ice interface; the angular distribution of naphthalene depends on the specific surfactant and its concentration at the air/ice interface. The dynamics of naphthalene molecules at the surfactant-coated air/ice interface slow down as compared to those observed at bare air/ice interfaces. The presence of surfactants does not seem to affect the self-association of naphthalene molecules at the air/ice interface, at least for the specific surfactants and the range of concentrations considered in this study.

[Characteristics of natural strains of naphthalene-utilizing bacteria of the genus Pseudomonas].

PubMed

Levchuk, A A; Vasilenko, S L; Bulyga, I M; Titok, M A; Thomas, K M

2005-01-01

Sixty-three strains of bacteria capable of utilizing naphthalene as the sole source of carbon and energy were isolated from 137 samples of soil taken in different sites in Belarus. All isolated bacteria contained extrachromosomal genetic elements of 45 to 150 kb in length. It was found that bacteria of 31 strains contained the IncP-9 incompatibility group plasmids, bacteria of one strain carried a plasmid containing replicons IncP-9 and IncP-7, and bacteria of 31 strains contained unidentified plasmids. Primary identification showed that the hosts of plasmids of naphthalene biodegradation are fluorescent bacteria of the genus Pseudomonas (P. putida and P. aeruginosa; a total of 47 strains) and unidentified nonfluorescent microorganisms (a total of 16 strains). In addition to the ability to utilize naphthalene, some strains exhibited the ability to stimulate the growth and development of the root system of Secale cereale.

Indeno[1,2,3-cd]pyrene

Integrated Risk Information System (IRIS)

Indeno [ 1,2,3 - cd ] pyrene ; CASRN 193 - 39 - 5 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Nonc

Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4.

PubMed

Gibson, D T; Resnick, S M; Lee, K; Brand, J M; Torok, D S; Wackett, L P; Schocken, M J; Haigler, B E

1995-05-01

The stereospecific oxidation of indan and indene was examined with mutant and recombinant strains expressing naphthalene dioxygenase of Pseudomonas sp. strain 9816-4. Pseudomonas sp. strain 9816/11 and Escherichia coli JM109(DE3)[pDTG141] oxidized indan to (+)-(1S)-indanol, (+)-cis-(1R,2S)-indandiol, (+)-(1S)-indenol, and 1-indanone. The same strains oxidized indene to (+)-cis-(1R,2S)-indandiol and (+)-(1S)-indenol. Purified naphthalene dioxygenase oxidized indan to the same four products formed by strains 9816/11 and JM109(DE3)[pDTG141]. In addition, indene was identified as an intermediate in indan oxidation. The major products formed from indene by purified naphthalene dioxygenase were (+)-(1S)-indenol and (+)-(1R,2S)-indandiol. The results show that naphthalene dioxygenase catalyzes the enantiospecific monooxygenation of indan to (+)-(1S)-indanol and the desaturation of indan to indene, which then serves as a substrate for the formation of (+)-(1R,2S)-indandiol and (+)-(1S)-indenol. The relationship of the desaturase, monooxygenase, and dioxygenase activities of naphthalene dioxygenase is discussed with reference to reactions catalyzed by toluene dioxygenase, plant desaturases, cytochrome P-450, methane monooxygenase, and other bacterial monooxygenases.

Desaturation, dioxygenation, and monooxygenation reactions catalyzed by naphthalene dioxygenase from Pseudomonas sp. strain 9816-4.

PubMed Central

Gibson, D T; Resnick, S M; Lee, K; Brand, J M; Torok, D S; Wackett, L P; Schocken, M J; Haigler, B E

1995-01-01

The stereospecific oxidation of indan and indene was examined with mutant and recombinant strains expressing naphthalene dioxygenase of Pseudomonas sp. strain 9816-4. Pseudomonas sp. strain 9816/11 and Escherichia coli JM109(DE3)[pDTG141] oxidized indan to (+)-(1S)-indanol, (+)-cis-(1R,2S)-indandiol, (+)-(1S)-indenol, and 1-indanone. The same strains oxidized indene to (+)-cis-(1R,2S)-indandiol and (+)-(1S)-indenol. Purified naphthalene dioxygenase oxidized indan to the same four products formed by strains 9816/11 and JM109(DE3)[pDTG141]. In addition, indene was identified as an intermediate in indan oxidation. The major products formed from indene by purified naphthalene dioxygenase were (+)-(1S)-indenol and (+)-(1R,2S)-indandiol. The results show that naphthalene dioxygenase catalyzes the enantiospecific monooxygenation of indan to (+)-(1S)-indanol and the desaturation of indan to indene, which then serves as a substrate for the formation of (+)-(1R,2S)-indandiol and (+)-(1S)-indenol. The relationship of the desaturase, monooxygenase, and dioxygenase activities of naphthalene dioxygenase is discussed with reference to reactions catalyzed by toluene dioxygenase, plant desaturases, cytochrome P-450, methane monooxygenase, and other bacterial monooxygenases. PMID:7751268

CeO2 nanoparticles induce no changes in phenanthrene toxicity to the soil organisms Porcellionides pruinosus and Folsomia candida.

PubMed

Tourinho, Paula S; Waalewijn-Kool, Pauline L; Zantkuijl, Irene; Jurkschat, Kerstin; Svendsen, Claus; Soares, Amadeu M V M; Loureiro, Susana; van Gestel, Cornelis A M

2015-03-01

Cerium oxide nanoparticles (CeO2 NPs) are used as diesel fuel additives to catalyze oxidation. Phenanthrene is a major component of diesel exhaust particles and one of the most common pollutants in the environment. This study aimed at determining the effect of CeO2 NPs on the toxicity of phenanthrene in Lufa 2.2 standard soil for the isopod Porcellionides pruinosus and the springtail Folsomia candida. Toxicity tests were performed in the presence of CeO2 concentrations of 10, 100 or 1000mg Ce/kg dry soil and compared with results in the absence of CeO2 NPs. CeO2 NPs had no adverse effects on isopod survival and growth or springtail survival and reproduction. For the isopods, LC50s for the effect of phenanthrene ranged from 110 to 143mg/kg dry soil, and EC50s from 17.6 to 31.6mg/kg dry soil. For the springtails, LC50s ranged between 61.5 and 88.3mg/kg dry soil and EC50s from 52.2 to 76.7mg/kg dry soil. From this study it may be concluded that CeO2 NPs have a low toxicity and do not affect toxicity of phenanthrene to isopods and springtails. Copyright © 2014 Elsevier Inc. All rights reserved.

Comparative Metabolism of Hydrazine and Naphthalene.

DTIC Science & Technology

1980-09-01

compounds and chemicals like those in cigarette smoke. Another question of considerable importance to the Air Force is whether animal species currently...the pulmonary cytochrome P-450 monooxygenases differ between species or that enzymes responsible for the detoxification of the "toxic" metabolite(s...metabolic steps in the activation and detoxification of a compound like naphthalene are undertaken in animal lung tissue so that such processes can be

The disposition and metabolism of naphthalene in rats.

PubMed

Kilanowicz, A; Czerski, B; Sapota, A

1999-01-01

The aim of this study was to investigate the distribution, excretion and metabolism of naphthalene-[ring-U-3H] in rats. The experiments were performed on 54 male outbred IMP: Wist rats with body weight of 200-220 g. The compound was administered intraperitoneally in olive oil in a single dose of 20 mg/kg (about 540 kBq per animal). 3H radioactivity was traced in selected organs and tissues, blood, urine and faeces, 1-72 h following the administration. The main metabolites were isolated from urine and identified by the GC-MS method. Urine and faeces proved to be the main route of tritium elimination. Over 88% of the compound was excreted during the first 72 hours. Maximum level of tritium in plasma was observed at the 2nd h after administration following a biphasic decline. Half-lifes for phases I and II were 0.8 and 99 h, respectively. In erythrocytes 3H-decline was monophasic with the half-life of about 9 h. In organs and tissues, the highest concentrations during the first hours after administration were detected in the fat, liver and kidneys. Then, gradual decline of tritium was noticed in all examined tissues. In urine of rats the following substances were identified: (1) naphthalene, (2) 1-naphthol, (3) 2-naphthol, (4) 1,2-naphthalenediol-1,2-dihydro, (5) methylthionaphthalenes (two isomers). In conclusion, naphthalene has a relatively rapid turnover rate in the rat organism and does not form considerable deposits in the tissue. The metabolism encompasses ring hydroxylation, hydration and glutathione conjugation.

Determination of polycyclic aromatic hydrocarbons in roasted coffee

PubMed Central

JIMENEZ, ANGELICA; ADISA, AFOLABI; WOODHAM, CARA; SALEH, MAHMOUD

2016-01-01

Polycyclic aromatic hydrocarbons (PAHs) are suspected to be carcinogenic and mutagenic. This study describes the presence of PAHs in light, medium and dark roasted coffee including instant and decaffeinated brands. Total PAHs concentration was related to the degree of roasting with light roasted coffee showing the least and dark roasted coffee showing the highest level. Both instant and decaffeinated coffee brand showed lower levels of PAHs. Naphthalene, acenaphthylene, pyrene and chrysene were the most abundant individual isomers. The concentrations ranged from 0 to 561 ng g−1 for naphthalene, 0 to 512 ng g−1 for acenaphthylene, 60 to 459 ng g−1 for pyrene and 56 to 371 ng g−1 for chrysene. Thus, roasting conditions should be controlled to avoid the formation of PAHs due to their suspected carcinogenic and mutagenic properties. PMID:25190557

PAH concentrations simulated with the AURAMS-PAH chemical transport model over Canada and the USA

NASA Astrophysics Data System (ADS)

Galarneau, E.; Makar, P. A.; Zheng, Q.; Narayan, J.; Zhang, J.; Moran, M. D.; Bari, M. A.; Pathela, S.; Chen, A.; Chlumsky, R.

2013-07-01

The off-line Eulerian AURAMS chemical transport model was adapted to simulate the atmospheric fate of seven PAHs: phenanthrene, anthracene, fluoranthene, pyrene, benz[a]anthracene, chrysene + triphenylene, and benzo[a]pyrene. The model was then run for the year 2002 with hourly output on a~grid covering southern Canada and the continental USA with 42 km horizontal grid spacing. Model predictions were compared to ~ 5000 24 h average PAH measurements from 45 sites, eight of which also provided data on particle/gas partitioning which had been modelled using two alternative schemes. This is the first known regional modelling study for PAHs over a North American domain and the first modelling study at any scale to compare alternative particle/gas partitioning schemes against paired field measurements. Annual average modelled total (gas + particle) concentrations were statistically indistinguishable from measured values for fluoranthene, pyrene and benz[a]anthracene whereas the model underestimated concentrations of phenanthrene, anthracene and chrysene + triphenylene. Significance for benzo[a]pyrene performance was close to the statistical threshold and depended on the particle/gas partitioning scheme employed. On a day-to-day basis, the model simulated total PAH concentrations to the correct order of magnitude the majority of the time. Model performance differed substantially between measurement locations and the limited available evidence suggests that the model spatial resolution was too coarse to capture the distribution of concentrations in densely populated areas. A more detailed analysis of the factors influencing modelled particle/gas partitioning is warranted based on the findings in this study.

Thermal removal of pyrene contamination from soil: basic studies and environmental health implications.

PubMed Central

Saito, H H; Bucalá, V; Howard, J B; Peters, W A

1998-01-01

Effects of temperature (400-1000 degrees C) and rate of heating to 550 degrees C (100, 1000, 5000 degrees C/sec) on reduction of pyrene contamination in a Superfund-related soil and on yields of volatile products (tars, CO, CO2, methane, acetylene, ethylene) have been measured. Fifty (+/- 3)-milligram thin layers (less than or equal to 150 micron) of 63- to 125-micron soil particles, neat (i.e., without exogenous chemicals), or pretreated with 4.75 wt% of pyrene, were heated for about 1 to 6 sec, under 3 psig (pounds per in.(2) gauge) of helium in a 12-liter sealed chamber. Pyrene removal, defined as the difference in weight loss of neat versus contaminated soil, was virtually immune to heating rate but increased strongly with increasing temperature, approaching 100% at about 530 degrees C. However, for pyrenepolluted soil, excess soil weight loss and modified CO yields were observed above about 500 degrees C for a 1000 degrees C/sec heating rate. These observations suggest that soil chemical reactions with pyrene or pyrene decomposition products augment soil volatilization. Consequently at elevated temperatures, the difference in weight loss protocol may overestimate polycyclic aromatic hydrocarbon (PAH) removal from soil. Increasing heating rate caused yields of CO, CO(2), and acetylene from pyrene-polluted soil to pass through maxima. Heating neat or contaminated soil resulted in at least two gaseous products of particular environmental interest:acetylene, a precursor to PAH in thermal synthesis, and CO, a toxin to human hemoglobin. Images Figure 1 Figure 2 PMID:9703498

Effect of mixed soil microbiomes on pyrene removal and the response of the soil microorganisms.

PubMed

Wang, Beibei; Teng, Ying; Xu, Yongfeng; Chen, Wei; Ren, Wenjie; Li, Yan; Christie, Peter; Luo, Yongming

2018-05-28

Mixed soil microbiomes were established by introducing aliquots of a paddy soil into a red soil. The new mixed microbiomes effectively metabolized high-molecular-weight polycyclic aromatic hydrocarbons (PAHs, pyrene) in the soil mixtures. The pyrene removal efficiencies were 19% and 98%, respectively, in the original red soil and the paddy soil. The pyrene removal effectiveness by the mixed microbial community was enhanced by increasing the amount of paddy soil inoculant and the pyrene removal rates were 93%, 58% and 27% in paddy soil/red soil mixtures of 1:1, 3:7 and 1:9 (w/w), respectively. Supplementation with sterile paddy soil and nutrients changed the soil environment but the pyrene removal efficiency was not enhanced, indicating that the microbial composition largely determined the extent of pyrene removal. Moreover, the pyrene removal rate was positively related to the pyrene dioxygenase gene (nidA) abundance. The greater the percentage of the paddy soil in the soil mixture the greater the similarity of the mixed microbiome to that of the original paddy soil itself. The community of the inoculated sterile paddy soil was similar to that of the red soil and the community diverged from those of the red soil and the paddy soil with increasing culture time. After culture for 42 days, some enriched genera were responsible for PAH degradation, notably Nevskia, Ralstonia, Gemmatimonas and Lysobacter, while some genera have no clear classification information or category name at the genus level, such as f__Acidobacteriaceae and o__JG30-KF-AS9. This study is very important in recognizing the role of natural soil in the formation of a mixed microbiome to stimulate the degradation of PAHs in a soil with low intrinsic PAH degradation capability. Copyright © 2018 Elsevier B.V. All rights reserved.

HISTORICAL MONITORING OF BIOMARKERS OF EXPOSURE OF BROWN BULLHEAD

EPA Science Inventory

Biomarkers of exposure to chemical contamination, benzo(a)pyrene (BAP) and naphthalene (NAPH) type metabolites were measured in brown bullhead from a heavily polycyclic aromatic hydrocarbon (PAH) contaminated section of the Black River, Ohio during and immediately after remedial ...

Isolation of a naphthalene-degrading strain from activated sludge and bioaugmentation with it in a MBR treating coal gasification wastewater.

PubMed

Xu, Peng; Ma, Wencheng; Han, Hongjun; Jia, Shengyong; Hou, Baolin

2015-03-01

A highly effective naphthalene-degrading bacterial strain was isolated from acclimated activated sludge from a coal gasification wastewater plant, and identified as a Streptomyces sp., designated as strain QWE-35. The optimal pH and temperature for naphthalene degradation were 7.0 and 35°C. The presence of additional glucose and methanol significantly increased the degradation efficiency of naphthalene. The strain showed tolerance to the toxicity of naphthalene at a concentration as great as 200 mg/L. The Andrews mode could be fitted to the degradation kinetics data well over a wide range of initial naphthalene concentrations (10-200 mg/L), with kinetic values q max = 0.84 h(-1), K s = 40.39 mg/L, and K i = 193.76 mg/L. Metabolic intermediates were identified by gas chromatography and mass spectrometry, allowing a new degradation pathway for naphthalene to be proposed for the first time. Strain QWE-35 was added into a membrane bioreactor (MBR) to enhance the treatment of real coal gasification wastewater. The results showed that the removal of chemical oxygen demand and total nitrogen were similar between bioaugmented and non-bioaugmented MBRs, however, significant removal of naphthalene was obtained in the bioaugmented reactor. The findings suggest a potential bioremediation role of Streptomyces sp. QWE-35 in the removal of naphthalene from wastewaters.

Effect of multi-walled carbon nanotubes on phytotoxicity of sediments contaminated by phenanthrene and cadmium.

PubMed

Song, Biao; Zeng, Guangming; Gong, Jilai; Zhang, Peng; Deng, Jiaqin; Deng, Canhui; Yan, Jin; Xu, Piao; Lai, Cui; Zhang, Chen; Cheng, Min

2017-04-01

To implement effective control and abatement programs for contaminants accumulating in sediments, strategies are needed for evaluating the quality of amended sediments. In this study, phytotoxicity of the sediments contaminated by cadmium and phenanthrene was evaluated after in situ remediation with multi-walled carbon nanotubes (MWCNTs) as adsorbents. Adsorption experiments and measurement of aqueous concentrations of the contaminants in overlying water were used to investigate the remediation effectiveness from physical and chemical aspects. The results indicated that MWCNTs showed a much better adsorption performance towards phenanthrene and Cd(II) compared with the sediments. The in situ remediation with MWCNTs could distinctly decrease the aqueous concentrations of phenanthrene and Cd(II) released from the sediments, reducing environmental risk towards overlying water. Influences of MWCNTs dose, MWCNTs diameter, and contact time on phtotoxicity of the contaminated sediments were studied. No significant inhibition of the amended sediments on germination of the test species was observed in the experiments, while the root growth was more sensitive than biomass production to the changes of contaminant concentrations. The analysis of Pearson correlation coefficients between evaluation indicators and associated remediation parameters suggested that phytotoxicity of sediments might inaccurately indicate the changes of pollutant content, but it was significant in reflecting the ecotoxicity of sediments after remediation. Copyright © 2017 Elsevier Ltd. All rights reserved.

Research Needs Related to Naphthalene Assessment (2005, Workshop)

EPA Science Inventory

EPA has announced the release of the final report from the 2005 peer consultation workshop which sought expert opinion on research needs related to the mode of action of the inhalation carcinogenicity of naphthalene. This report is a summary of the main points of presentations an...

Infrared spectroscopy of polycyclic aromatic hydrocarbon cations. 1: Matrix-isolated naphthalene and perdeuterated naphthalene

NASA Technical Reports Server (NTRS)

Hudgins, D. M.; Sandford, S. A.; Allamandola, Louis J.

1994-01-01

Ionized polycyclic aromatic hydrocarbons (PAHs) are thought to constitute an important component of the interstellar medium. Despite this fact, the infrared spectroscopic properties of ionized PAHs are almost unknown. The results we present here derive from our ongoing spectroscopic study of matrix isolated PAH ions and include the spectra of the naphthalene cation, C10H8(+), and its fully deuterated analog, C10D8(+), between 4000 and 200/cm. Ions are generated by in situ Lyman-alpha photoionization of the neutral precursor. Bands of the C10H8(+) ion are observed at 1525.7, 1518.8, 1400.9, 1218.0, 1216.9, 1214.9, 1023.2, and 758.7/cm. Positions and relative intensities of these bands agree well with those in the available literature. The 758.7/cm band has not previously been reported. C10D8(+) ion bands appear at 1466.2, 1463.8, 1379.4, 1373.8, 1077.3, 1075.4, and 1063.1/cm. Compared to the analogous modes in the neutral molecule, the intensities of the cation's CC modes are enhanced by an order of magnitude, while CH modes are depressed by this same factor. Integrated absorption intensities are calculated for the strongest bands of C10H8 and for the observed bands of C10H8(+). Absolute intensities derived for the naphthalene cation differ from earlier experimental results by a factor of approximately 50, and from theoretical predictions by a factor of approximately 300. Reasons for these discrepancies and from the astronomical implications of PAH cation spectra are discussed.

Pyrene fate affected by humic acid amendment in soil slurry systems.

PubMed

Liang, Yanna; Sorensen, Darwin L; McLean, Joan E; Sims, Ronald C

2008-09-10

Humic acid (HA) has been found to affect the solubility, mineralization, and bound residue formation of polycyclic aromatic hydrocarbons (PAHs). However, most of the studies on the interaction between HA and PAH concentrated on one or two of the three phases. Few studies have provided a simple protocol to demonstrate the overall effects of HA on PAH distribution in soil systems for all three phases. In this study, three doses of standard Elliott soil HA (ESHA), 15, 187.5, and 1,875 mug ESHA/g soil slurry, were amended to soil slurry systems. 14C-pyrene was added to the systems along with non-radiolabeled pyrene; 14C and 14CO2 were monitored for each system for a period of 120 days. The highest amendment dose significantly increased the 14C fraction in the aqueous phase within 24 h, but not after that time. Pyrene mineralization was significantly inhibited by the highest dose over the 120-day study. While organic solvent extractable 14C decreased with time in all systems, non-extractable or bound 14C was significantly enhanced with the highest dose of ESHA addition. Amendment of the highest dose of ESHA to pyrene contaminated soil was observed to have two major functions. The first was to mitigate CO2 production significantly by reducing 14CO2 from 14C pyrene mineralization. The second was to significantly increase stable bound 14C formation, which may serve as a remediation end point. Overall, this study demonstrated a practical approach for decontamination of PAH contaminated soil. This approach may be applicable to other organic contaminated environments where active bioremediation is taking place.

Does Switching to Reduced Ignition Propensity Cigarettes Alter Smoking Behavior or Exposure to Tobacco Smoke Constituents?

PubMed Central

Rees, Vaughan W.; Norton, Kaila J.; Cummings, K. Michael; Connolly, Gregory N.; Alpert, Hillel R.; Sjödin, Andreas; Romanoff, Lovisa; Li, Zheng; June, Kristie M.; Giovino, Gary A.

2010-01-01

Introduction: Since 2004, several jurisdictions have mandated that cigarettes show reduced ignition propensity (RIP) in laboratory testing. RIP cigarettes may limit fires caused by smoldering cigarettes, reducing fire-related deaths and injury. However, some evidence suggests that RIP cigarettes emit more carbon monoxide and polycyclic aromatic hydrocarbons, and smokers may alter their smoking patterns in response to RIP cigarettes. Both of these could increase smokers’ exposures to harmful constituents in cigarettes. Methods: An 18-day switching study with a comparison group was conducted in Boston, MA (N = 77), and Buffalo, NY (N = 83), in 2006–2007. Current daily smokers completed 4 laboratory visits and two 48-hr field data collections. After a 4-day baseline, Boston participants switched to RIP cigarettes for 14 days, whereas Buffalo participants smoked RIP cigarettes throughout. Outcome measures included cigarettes smoked per day; smoking topography; salivary cotinine; breath CO; and hydroxylated metabolites of pyrene, naphthalene, phenanthrene, and fluorene. Because the groups differed demographically, analyses adjusted for race, age, and sex. Results: We observed no significant changes in smoking topography or CO exposure among participants who switched to RIP cigarettes. Cigarette use decreased significantly in the switched group (37.7 cigarettes/48 hr vs. 32.6 cigarettes/48 hr, p = .031), while hydroxyphenanthrenes increased significantly (555 ng/g creatinine vs. 669 ng/g creatinine, p = .007). No other biomarkers were significantly affected. Discussion: Small increases in exposure to phenanthrene among smokers who switched to RIP versions were observed, while other exposures and smoking topography were not significantly affected. Toxicological implications of these findings are unclear. These findings should be weighed against the potential public health benefits of adopting RIP design standards for cigarette products. PMID:20805292

Rotation and diffusion of naphthalene on Pt(111)

NASA Astrophysics Data System (ADS)

Kolsbjerg, E. L.; Goubert, G.; McBreen, P. H.; Hammer, B.

2018-03-01

The behavior of naphthalene on Pt(111) surfaces is studied by combining insight from scanning tunneling microscopy (STM) and van der Waals enabled density functional theory. Adsorption, diffusion, and rotation are investigated by a series of variable temperature STM experiments revealing naphthalene ability to rotate on-site with ease with a rotational barrier of 0.69 eV. Diffusion to neighbouring sites is found to be more difficult. The experimental results are in good agreement with the theoretical investigations which confirm that the barrier for diffusion is slightly higher than the one for rotation. The theoretical barriers for rotation and translation are found to be 0.75 and 0.78 eV, respectively. An automatic mapping of the possible diffusion pathways reveals very detailed diffusion paths with many small local minima that would have been practically impossible to find manually. This automated procedure provides detailed insight into the preferred diffusion pathways that are important for our understanding of molecule-substrate interactions.

Organization and dynamics of pyrene and pyrene lipids in intact lipid bilayers. Photo-induced charge transfer processes.

PubMed Central

Barenholz, Y; Cohen, T; Korenstein, R; Ottolenghi, M

1991-01-01

The dynamics of fluorescence quenching and the organization of a series of pyrene derivatives anchored in various depths in bilayers of phosphatidylcholine small unilamellar vesicles was studied and compared with their behavior in homogeneous solvent systems. The studies include characterization of the environmental polarity of the pyrene fluorophore based on its vibronic peaks, as well as the interaction with three collisional quenchers: the two membrane-soluble quenchers, diethylaniline and bromobenzene, and the water soluble quencher potassium iodide. The system of diethylaniline-pyrene derivatives in the membrane of phosphatidylcholine vesicles was characterized in detail. The diethylaniline partition coefficient between the lipid bilayers and the buffer is approximately 5,800. Up to a diethylaniline/phospholipid mole ratio of 1:3 the perturbation to membrane structure is minimal so that all photophysical studies were performed below this mole ratio. The quenching reaction, in all cases, was shown to take place in the lipid bilayer interior and the relative quenching efficiencies of the various probe molecules was used to provide information on the distribution of both fluorescent probes and quencher molecules in the lipid bilayer. The quenching efficiency by diethylaniline in the lipid bilayer was found to be essentially independent on the length of the methylene chain of the pyrene moiety. These findings suggest that the quenching process, being a diffusion controlled reaction, is determined by the mobility of the diethylaniline quencher (with an effective diffusion coefficient D approximately 10(-7) cm2 s-1) which appears to be homogeneously distributed throughout the lipid bilayer. The pulsed laser photolysis products of the charge-transfer quenching reaction were examined. No exciplex (excited-complex) formation was observed and the yield of the separated radical ions was shown to be tenfold smaller than in homogenous polar solutions. The decay of the

SENSITIVITY ANALYSIS OF THE APPLICATION OF CHEMICAL EXPOSURE CRITERIA FOR COMPARING SITES AND WATERSHEDS

EPA Science Inventory

A methodology was developed for deriving quantitative exposure criteria useful for comparing a site or watershed to a reference condition. The prototype method used indicators of exposures to oil contamination and combustion by-products, naphthalene and benzo(a)pyrene metabolites...

Electronic absorption spectroscopy of matrix-isolated polycyclic aromatic hydrocarbon cations. II. The phenanthrene cation (C14H10+) and its 1-methyl derivative

NASA Technical Reports Server (NTRS)

Salama, F.; Joblin, C.; Allamandola, L. J.

1994-01-01

The ultraviolet, visible, and near infrared absorption spectra of phenanthrene (C14H10), 1-methylphenanthrene [(CH3)C14H9], and their radical ions [C14H10+; (CH3)C14H9+], formed by vacuum-ultraviolet irradiation, were measured in neon matrices at 4.2 K. The associated vibronic band systems and their spectroscopic assignments are discussed. The oscillator strengths were calculated for the phenanthrene ion and found lower than the theoretical predictions. This study presents the first spectroscopic data for phenanthrene and its methyl derivative trapped in a neon matrix where the perturbation of the isolated species by its environment is minimum; a condition crucial to astrophysical applications.

Public health assessment for Allied Chemical and Ironton Coke, Ironton, Lawrence County, Ohio, Region 5. Cerclis No. OHD043730217. Final report

DOE Office of Scientific and Technical Information (OSTI.GOV)

Not Available

1994-05-16

The Allied Chemical/Ironton Coke site is in the City of Ironton, Lawrence County Ohio. The areas of concern for this public health assessment are the former Coke Plant and Lagoon Area and the Tar Plant. From 1920 to the 1960's, waste was discharged into the lagoon area. Soil samples showed the on-site surface soil to be contaminated with cyanide, phenolics, benzene, naphthalene, and benzo(a)pyrene (a polynuclear aromatic hydrocarbon). Groundwater analysis detected a number of volatile and semi-volatile organic compounds plus cyanide. Sediment samples from Ice Creek, a stream bordering the lagoon area contained low levels of cyanide, phenolics, and naphthalene.more » The site poses a public health hazard because of the potential for long-term exposure to cyanide, benzo(a)pyrene, and naphthalene in on-site soils. The Allied Chemical Coke site also poses an indeterminate public health hazard because of the potential impact on a public water supply. The residents who obtain their drinking water from the Coal Grove well field are potentially at risk of exposure to chemicals originating from the site.« less

Pyrene As a New Detector for Determining the Composition of Silver Nanoparticle Dispersions in Aqueous Solutions

NASA Astrophysics Data System (ADS)

Romanovskaya, G. I.; Kazakova, S. Yu.; Koroleva, M. V.; Zuev, B. K.

2018-03-01

It is proposed that the fluorescence of monomeric molecules of pyrene in solid matrices or in concentrated micellar solutions be used as a detector for determining the compositional homogeneity of silver nanoparticle (NP) dispersions in aqueous solutions synthesized in different ways. It is found that the morphology of silver NPs affects the change in the fluorescence intensity of monomeric molecules of pyrene in a certain (violet or blue) region of the pyrene optical spectrum. The observed phenomenon is attributed to the resonance of electronic transitions in the monomeric molecules of pyrene in regions with plasmon oscillations in silver nanoparticles. A new way of obtaining fluorescent silver NPs is found.

Inoculating wheat (Triticum aestivum L.) with the endophytic bacterium Serratia sp. PW7 to reduce pyrene contamination.

PubMed

Zhu, Xuezhu; Wang, Wanqing; Sun, Kai; Lin, Xianghao; Li, Shuang; Waigi, Michael Gatheru; Ling, Wanting

2017-08-03

This research was conducted to find an optimal inoculation way for a pyrene-degrading endophytic Serratia sp. PW7 to colonize wheat for reducing pyrene contamination. Three inoculation ways, which are soaking seeds in inocula (TS), dipping roots of seedlings in inocula (TR), and spraying inocula on leaves of seedlings (TL), were used in this study. Inoculated seedlings and noninoculated seedlings (CK) were, respectively, cultivated in Hoagland solutions supplemented with pyrene in a growth chamber. The results showed that strain PW7 successfully colonized the inoculated seedlings in high numbers, and significantly promoted the growth of seedlings (TS and TR). More importantly, strain PW7 reduced pyrene levels in the seedlings and the Hoagland solutions. Compared to the noninoculated seedlings, the pyrene contents of the inoculated seedlings were decreased by 35.7-86.3% in the shoots and by 26.8-60.1% in the roots after 8-day cultivation. By comparing the efficiencies of decreasing pyrene residues, it can be concluded that TR was an optimal inoculation way for endophytic strains to colonize the inoculated plants and to reduce the pyrene contamination. Our findings provide an optimized inoculation way to reduce organic contamination in crops by inoculating plants with functional endophytic bacteria.

Decomposition of naphthalene by dc gliding arc gas discharge.

PubMed

Yu, Liang; Li, Xiaodong; Tu, Xin; Wang, Yu; Lu, Shengyong; Yan, Jianhua

2010-01-14

Gliding arc discharge has been proved to be effective in treatment of gas and liquid contaminants. In this study, physical characteristics of dc gliding arc discharge and its application to naphthalene destruction are investigated with different external resistances and carrier gases. The decomposition rate increases with increasing of oxygen concentration and decreases with external resistance. This value can be achieved up to 92.3% at the external resistance of 50 kOmega in the oxygen discharge, while the highest destruction energy efficiency reaches 3.6 g (kW h)(-1) with the external resistance of 93 kOmega. Possible reaction pathways and degradation mechanisms in the plasma with different gases are proposed by qualitative analysis of postdestructed products. In the air and oxygen gliding arc discharges, the naphthalene degradation is mainly governed by reactions with oxygen-derived radicals.

Fluorescence studies on binding of pyrene and its derivatives to humic acid

NASA Astrophysics Data System (ADS)

Nakashima, K.; Maki, M.; Ishikawa, F.; Yoshikawa, T.; Gong, Y.-K.; Miyajima, T.

2007-07-01

Binding of pyrene (PyH) and its derivatives to humic acid (HA) has been studied by fluorescence spectroscopy. The nature of the interaction between HA and pyrene derivatives are extensively investigated by employing three derivatives ranging from anionic to cationic compounds: 1-pyrenebutylic acid (PyA), 1-pyrenemethanol (PyM), and 1-pyrenebutyltrimethylammonium bromide (PyB). Binding constants between HA and PyX (X = H, A, M, B) are obtained by steady-state fluorescence quenching techniques, and it is found that PyB has a markedly large binding constant among the pyrene family. This is attributed to a strong electrostatic interaction between cationic PyB and anionic HA. The result suggests that an electrostatic interaction plays a dominant role in binding of pyrenes to humic acid. The importance of electrostatic interaction was also confirmed by a salt effect on the binding constant. Influence of collisional quenching on the binding constant, which causes overestimation of the binding constant, was examined by time-resolved fluorescence spectroscopy as well as temperature effect in steady-state fluorescence measurements. It is elucidated that collisional quenching does not much bring overestimation into the binding constants.

Uptake of pyrene in a breast-fed child of a mother treated with coal tar.

PubMed

Scheepers, Paul T J; van Houtum, Jeanette L M; Anzion, Rob B M; Harder, Rianne; Bos, Rob P; van der Valk, Pieter G M

2009-01-01

A woman was treated for atopic dermatitis with coal tar containing ointments. Coal tar containing ointments contain genotoxic polycyclic aromatic hydrocarbons. Over a period of 50 days the accumulated dose of different coal tar containing ointments treatments corresponded to 993 mg of pyrene and 464 mg of benz[a]pyrene. During this treatment she gave breast milk to her 3-month-old daughter. Analysis of urine samples from the breast-fed child showed elevated levels of urinary excretion of a metabolite of pyrene (1-hydroxypyrene, 1-OHP). These levels were in the same range as urinary excretion levels of this metabolite observed in the mother's urine. As no pyrene was observed in breast milk at a limit of determination of 0.0035 micromol/L, transfer of pyrene from mother to child via breast milk is not likely. Also, a low level of 1-hydroxypyrene observed in the mother's milk did not account for the observed urinary excretion levels in the child. It must therefore be assumed that pyrene was transferred from mother to child via another route, presumably direct skin-to-skin or skin-to-mouth contact. Dermatologists should inform their patients who receive treatment with coal tar containing ointments of the risk of transfer of polycyclic aromatic hydrocarbons by skin-to-skin or skin-to-mouth contact.

Quantum chemistry and excited states: First investigations on pyrene-like molecules

NASA Technical Reports Server (NTRS)

Parisel, Olivier; Ellinger, Y.

1994-01-01

Although the calculations are expected to be accurate within 10%, it follows then that there cannot be proposed unquestionable one-to-one attribution due to the density of the DIB's (Diffuse Interstellar Bands). Nevertheless, it has been shown that if one is interested in the experimental study of methyl-pyrene cations, for example, then, the most promising candidate is the 1-methyl isomer: this isomer has been investigated by d'Hendecourt and Leger (1993,1994) and their spectrum shows very striking features in very good agreement with both our calculations and a few DIB's. However, 1-methyl-pyrene cation is not the only product susceptible of being formed in this experiment, and further investigations are in progress to give a complete interpretations of the results. This preliminary report on pyrene-like molecules illustrates the role that theoretical calculations can ply in both the design and the interpretation of experiments.

Recovery of Phenanthrene-Degrading Bacteria After Simulated In Situ Persulfate Oxidation in Contaminated Soil

PubMed Central

Richardson, Stephen D.; Lebron, Benjamin L.; Miller, Cass T.; Aitken, Michael D.

2010-01-01

A continuous-flow column study was conducted to investigate the long-term effects of persulfate oxidation on the abundance and activity of the indigenous microbial community and phenanthrene-degrading bacteria in contaminated soil from a former manufactured gas plant (MGP) site. Approximately six pore volumes of a 20 g/L persulfate solution were introduced into the column, followed by simulated groundwater for 500 d. Soil samples were collected from the surface of the soil bed and along the column length immediately before and after persulfate injection and up to 500 d following injection. Exposure to persulfate led to a two- to three-log reduction in total bacterial 16S rRNA genes, severe inhibition of 14C-acetate mineralization (as a measure of general microbial activity), and a decrease in community diversity. However, relatively rapid recovery of both bacterial gene abundance and activity was observed within 30 d after persulfate exposure. Mineralization of 14C-phenanthrene was also inhibited but did not recover until 100 d post-oxidation. Known phenanthrene-degrading bacterial groups decreased to below detection limits throughout the column, with recovery times from 100 d to 500 d after persulfate injection. These findings suggest that coupling biological processes with persulfate oxidation is possible, although recovery of specific contaminant degraders may occur much later than the general microbial community recovers. Furthermore, the use of total bacterial quantity or non-specific measures of activity as a surrogate for the recovery of contaminant degraders may be inappropriate for evaluating the compatibility of chemical treatment with subsequent bioremediation. PMID:21162560

Benzo(a)pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo.

PubMed

Weinstein, I B; Jeffrey, A M; Jennette, K W; Blobstein, S H; Harvey, R G; Harris, C; Autrup, H; Kasai, H; Nakanishi, K

1976-08-13

Evidence has been obtained that a specific isomer of a diol epoxide derivative of benzo(a)pyrene, (+/-)-7 beta,8alpha-dihydroxy-9alpha, 10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene, is an intermediate in the binding of benzo(a)pyrene to RNA in cultured bovine bronchial mucosa. An adduct is formed between position 10 of this derivative and the 2-amino group of guanine.

High-mobility pyrene-based semiconductor for organic thin-film transistors.

PubMed

Cho, Hyunduck; Lee, Sunyoung; Cho, Nam Sung; Jabbour, Ghassan E; Kwak, Jeonghun; Hwang, Do-Hoon; Lee, Changhee

2013-05-01

Numerous conjugated oligoacenes and polythiophenes are being heavily studied in the search for high-mobility organic semiconductors. Although many researchers have designed fused aromatic compounds as organic semiconductors for organic thin-film transistors (OTFTs), pyrene-based organic semiconductors with high mobilities and on-off current ratios have not yet been reported. Here, we introduce a new pyrene-based p-type organic semiconductor showing liquid crystal behavior. The thin film characteristics of this material are investigated by varying the substrate temperature during the deposition and the gate dielectric condition using the surface modification with a self-assembled monolayer, and systematically studied in correlation with the performances of transistor devices with this compound. OTFT fabricated under the optimum deposition conditions of this compound, namely, 1,6-bis(5'-octyl-2,2'-bithiophen-5-yl)pyrene (BOBTP) shows a high-performance transistor behavior with a field-effect mobility of 2.1 cm(2) V(-1) s(-1) and an on-off current ratio of 7.6 × 10(6) and enhanced long-term stability compared to the pentacene thin-film transistor.

Mechanistic investigation into sunlight-facilitated photodegradation of pyrene in seawater with oil dispersants.

PubMed

Fu, Jie; Gong, Yanyan; Cai, Zhengqing; O'Reilly, S E; Zhao, Dongye

2017-01-30

This study investigated the effects of 3 model oil dispersants (Corexit EC9500A, Corexit EC9527A and SPC 1000) on photodegradation of pyrene under simulated sunlight. Both Corexit dispersants enhanced photodegradation of pyrene, while SPC1000 slightly inhibited the reaction. Span 80 and Tween 85 were the key ingredients causing the effects, though the underlying mechanisms differed. Span 80 enriches pyrene in the upper layer of water column, whereas Tween 85 induces a photosensitization process. Two reactive oxygen species, 1 O 2 and O 2 - , were found responsible for pyrene photodegradation, though the presence of EC9500A suppressed the 1 O 2 pathway. In terms of photodegradation products, EC9500A enhanced generation of polyaromatic intermediates, i.e., phenaleno[1,9-cd][1,2]dioxine, 1-hydroxypyrene, and 1,8-pyrenequinone, but did not alter the classical photodegradation pathway. The Corexit dispersants were more prone to photochemical decomposition, with multiple by-products detected. The information aids in our understanding of the effects of dispersants on photochemical weathering of oil compositions. Copyright © 2016 Elsevier Ltd. All rights reserved.

Impact of plant photosystems in the remediation of benzo[a]pyrene and pyrene spiked soils.

PubMed

Sivaram, Anithadevi Kenday; Logeshwaran, Panneerselvan; Lockington, Robin; Naidu, Ravi; Megharaj, Mallavarapu

2018-02-01

The phytoremediation potential of 14 different plant species belonging to C3 and C4 carbon fixation pathway for soils spiked with polycyclic aromatic hydrocarbons (PAHs) such as benzo[a]pyrene (B[a]P) and pyrene (PYR) was investigated. A glasshouse experiment was conducted to measure the changes in morphological, physiological, biochemical parameters and the bioaccumulation and biodegradation ability of the plants in soils spiked with 48 and 194 mg kg -1 of B[a]P and PYR, respectively. The per cent removal efficacy of B[a]P and PYR by the tested plant species over a period of 50 days was from 6 to 26% and 14 to 40% respectively. The maximum removal of both B[a]P and PYR was observed in Sudan grass (C4), vetiver (C4), maize (C4), and sunflower (C3). In terms of accumulation in root and shoot, the concentration of PYR was higher in both C3 and C4 plant species when compared to B[a]P. Overall the results indicated that C4 plants were more efficient than their C3 counterparts in terms of morphological, physiological, biochemical and degradation ability of PAHs. Copyright © 2017 Elsevier Ltd. All rights reserved.

[Influence of Three Low-Molecular-Weight Organic Acids on the Adsorption of Phenanthrene in Purple Soil].

PubMed

Xie, Li; Chen, Ben-shou; Zhang, Jin-zhong; Lu, Song; Jiang, Tao

2016-03-15

The effects of three low-molecular-weight organic acids (citric acid, malic acid and oxalic acid) on the adsorption of phenanthrene in purple soil were studied by static adsorption experiment. The results showed that the adsorption kinetic process of phenanthrene in purple soil could be described by the second-order kinetic model, and the adsorption rate constant would significantly decrease in the presence of the three low-molecular-weight organic acids ( LMWOAs). The adsorption thermodynamic process could be well described by linear adsorption model, which was dominated by distribution role. The three LMWOAs could promote the adsorption of phenantherene in purple soil when their concentrations were less than 5 mmol · L⁻¹, whereas inhibit the adsorption when their concentrations were more than 10 mmol · L⁻¹, and the inhibition would increase with increasing concentrations. Moreover, the inhibitory ability displayed a decreasing order of citric acid, oxalic acid, and malic acid when their concentrations were 20 mmol · L⁻¹, which is related to the molecular structure and acidity of the three LMWOAs. Compared with the control, the content of dissolved organic matter (DOM) released from purple soil showed a trend of first decrease and then increase with increasing LMWOAs concentration, and the adsorption capacity of phenanthrene in purple soil was negatively related to DOM content.

Cancer risk assessment, indicators, and guidelines for polycyclic aromatic hydrocarbons in the ambient air.

PubMed Central

Boström, Carl-Elis; Gerde, Per; Hanberg, Annika; Jernström, Bengt; Johansson, Christer; Kyrklund, Titus; Rannug, Agneta; Törnqvist, Margareta; Victorin, Katarina; Westerholm, Roger

2002-01-01

Polycyclic aromatic hydrocarbons (PAHs) are formed during incomplete combustion. Domestic wood burning and road traffic are the major sources of PAHs in Sweden. In Stockholm, the sum of 14 different PAHs is 100-200 ng/m(3) at the street-level site, the most abundant being phenanthrene. Benzo[a]pyrene (B[a]P) varies between 1 and 2 ng/m(3). Exposure to PAH-containing substances increases the risk of cancer in humans. The carcinogenicity of PAHs is associated with the complexity of the molecule, i.e., increasing number of benzenoid rings, and with metabolic activation to reactive diol epoxide intermediates and their subsequent covalent binding to critical targets in DNA. B[a]P is the main indicator of carcinogenic PAHs. Fluoranthene is an important volatile PAH because it occurs at high concentrations in ambient air and because it is an experimental carcinogen in certain test systems. Thus, fluoranthene is suggested as a complementary indicator to B[a]P. The most carcinogenic PAH identified, dibenzo[a,l]pyrene, is also suggested as an indicator, although it occurs at very low concentrations. Quantitative cancer risk estimates of PAHs as air pollutants are very uncertain because of the lack of useful, good-quality data. According to the World Health Organization Air Quality Guidelines for Europe, the unit risk is 9 X 10(-5) per ng/m(3) of B[a]P as indicator of the total PAH content, namely, lifetime exposure to 0.1 ng/m(3) would theoretically lead to one extra cancer case in 100,000 exposed individuals. This concentration of 0.1 ng/m(3) of B[a]P is suggested as a health-based guideline. Because the carcinogenic potency of fluoranthene has been estimated to be approximately 20 times less than that of B[a]P, a tentative guideline value of 2 ng/m(3) is suggested for fluoranthene. Other significant PAHs are phenanthrene, methylated phenanthrenes/anthracenes and pyrene (high air concentrations), and large-molecule PAHs such as dibenz[a,h]anthracene, benzo

Bioavailable cadmium during the bioremediation of phenanthrene-contaminated soils using the diffusive gradients in thin-film technique.

PubMed

Amezcua-Allieri, M A; Rodríguez-Vázquez, R

2006-03-01

To study the impact of fungal bioremediation of phenanthrene on trace cadmium solid-solution fluxes and solution phase concentration. The bioremediation of phenanthrene in soils was performed using the fungus Penicillium frequentans. Metal behaviour was evaluated by the techniques of diffusive gradient in thin-films (DGT) and filtration. Fluxes of cadmium (Cd) show a significant (P < 0.002) increase after the start of bioremediation, indicating that the bioremediation process itself releases significant amount of Cd into solution from the soil solid-phase. Unlike DGT devices, the solution concentration from filtration shows a clear bimodal distribution. We postulate that the initial action of the fungi is most likely to breakdown the surface of the solid phase to smaller, 'solution-phase' material (<0.45 microm) leading to a peak in Cd concentration in solution. Phenanthrene removal from soils by bioremediation ironically results in the mobilization of another toxic pollutant (Cd). Bioremediation of organic pollutants in contaminated soil will likely lead to large increases in the mobilization of toxic metals, increasing metal bio-uptake and incorporation into the wider food chain. Bioremediation strategies need to account for this behaviour and further research is required both to understand the generality of this behaviour and the operative mechanisms.

Co-effects of pyrene and nitrate on the activity and abundance of soil denitrifiers under anaerobic condition.

PubMed

Zhou, Zhi-Feng; Yao, Yan-Hong; Wang, Ming-Xia; Zuo, Xiao-Hu

2017-10-01

It has previously been confirmed that polycyclic aromatic hydrocarbons (PAHs) could be degraded by soil microbes coupling with denitrification, but the relationships among soil denitrifiers, PAHs, and nitrate under obligate anaerobic condition are still unclear. Here, co-effects of pyrene and nitrate on the activity and abundance of soil denitrifiers were investigated through a 45-day incubation experiment. Two groups of soil treatments with (N 30 ) and without (N 0 ) nitrate (30 mg kg -1 dry soil) amendment were conducted, and each group contained three treatments with different pyrene concentrations (0, 30, and 60 mg kg -1 dry soil denoted as P 0 , P 30 , and P 60 , respectively). The pyrene content, abundances of denitrification concerning genes (narG, periplasmic nitrate reductase gene; nirS, cd 1 -nitrite reductase gene; nirK, copper-containing nitrite reductase gene), and productions of N 2 O and CO 2 were measured at day 3, 14, 28, and 45, and the bacterial community structures in four represented treatments (N 0 P 0 , N 0 P 60 , N 30 P 0 , and N 30 P 60 ) were analyzed at day 45. The results indicated that the treatments with higher pyrene concentration had higher final pyrene removal rates than the treatments with lower pyrene concentration. Additionally, intensive emission of N 2 O was detected in all treatments only at day 3, but a continuous production of CO 2 was measured in each treatment during the incubation. Nitrate amendment could enhance the activity of soil denitrifiers, and be helpful for soil microbes to sustain their activity. While pyrene seemed had no influence on the productions of N 2 O and CO 2 , and amendment with pyrene or nitrate both had no obvious effect on abundances of denitrification concerning genes. Furthermore, it was nitrate but not pyrene had an obvious influence on the community structure of soil bacteria. These results revealed that, under anaerobic condition, the activity and abundance of soil denitrifiers both were

Properties of the low-lying electronic states of phenanthrene: Exact PPP results

DOE Office of Scientific and Technical Information (OSTI.GOV)

Chakrabarti, A.; Ramasesha, S.

1996-10-05

The authors report properties of the exact low-lying states of phenanthrene, its anion and dianion within the Pariser-Parr-Pople (PPP) model. The experimentally known singlet states of the neutral molecule are well reproduced by the model. The intensities for one and two photon absorption to various single states are also in good agreement with experiment. From the bond orders of these states, the authors predict the equilibrium geometries. The relaxation energies of these states, computed from charge-charge correlations and bond orders, are presented. The authors also present results of ring current calculations in the singlet ground state of phenanthrene. The authorsmore » have also reported energies, spin densities, bond orders, and relaxation energies of several triplet states and compared then with experiments as well as with other calculations, where available. The fine structure constants D and E, computed in the lowest triplet state, compare well with those obtained from experiments. These properties are also presented for the anions and the dianions. The PPP model in these cases predicts a low-energy (< 1 eV) dipole excitation. 31 refs., 4 figs., 9 tabs.« less

Distribution of polycyclic aromatic hydrocarbons in riverine waters after Mediterranean forest fires.

PubMed

Olivella, M A; Ribalta, T G; de Febrer, A R; Mollet, J M; de Las Heras, F X C

2006-02-15

Extensive forest fires occurred in Catalonia, northern Spain, in 1994. In our study, concentrations and profiles of 12 parent polycyclic aromatic hydrocarbons (PAHs) were determined in riverine waters, ash and sediment samples at nine sampling sites (W1-W9) and at three sampling dates from Llobregat hydrographic basin: in August, 1994, one month after the extensive forest fires; in September, 1994, after the first heavy autumn rainfalls and in January, 1995, six months after forest fires. In August 1994, the total concentrations of 12 PAHs measured in riverine waters varied from 2 ng/l to 336 ng/l. In September 1994, the total PAH concentrations decreased to 0.2-31 ng/l and in January 1995, from 9 ng/l to 73 ng/l. In August, the composition pattern of PAHs showed a distribution dominated by 4-ring PAHs (pyrene, chrysene+triphenylene, benzo(a)anthracene) at W3-W6, W8 and W9 and 3-ring PAHs (phenanthrene) at W1, W2 and W7. In September, a preference by 3-ring PAHs (phenanthrene) at all sampling sites except W5 was shown and in January was clearly dominated by 4-ring PAHs (chrysene+triphenylene, pyrene, benzo(a)anthracene) at all sampling sites. In ash and sediment samples, the total concentrations of 12 PAHs ranged from 1.3 ng/g to 19 ng/g. The dominant compound was phenanthrene.

Identification of products formed during the heterogeneous nitration and ozonation of polycyclic aromatic hydrocarbons

NASA Astrophysics Data System (ADS)

Cochran, Richard E.; Jeong, Haewoo; Haddadi, Shokouh; Fisseha Derseh, Rebeka; Gowan, Alexandra; Beránek, Josef; Kubátová, Alena

2016-03-01

The 3- and 4-ring polycyclic aromatic hydrocarbons (PAHs) are the most abundant of PAHs in air particulate matter (PM). Thus we have investigated heterogeneous oxidation of 3- and 4-ring PAHs in a small-scale flow reactor using quartz filter as a support. Four representative PAHs, anthracene, phenanthrene, pyrene, and fluoranthene, were exposed to either NO2, O3 or NO2+O3 (NO3/N2O5) with a goal to identify and attempt quantification of major product distribution. A combination of gas chromatography with mass spectrometry (GC-MS) with/without derivatization and liquid chromatography with high resolution MS (LC-HRMS) was used for identification. For the first time, a comprehensive characterization of a broad range of products enabled identifying ketone/diketone, aldehyde, hydroxyl, and carboxylic acid PAH derivatives. Exposure to NO3/N2O5 (formed by reacting NO2 with O3, a more powerful reactant than either O3 or NO2) produced additional compounds not observed with either oxidant alone. Multiple isomers of nitrofluoranthene and, for the first time, nitrophenanthrene were identified. In addition hydroxy-nitro-PAH derivatives were observed for the reaction of anthracene with NO3/N2O5. Monitoring of specific common ions such as those of 176 and 205 m/z attributed to carbonyl phenanthrene and deprotonated phenanthrene ions respectively was shown to be a useful tool for identification of multiple pyrene oxidation products.

Comparison of amphiphilic polyurethane nanoparticles to nonionic surfactants for flushing phenanthrene from soil.

PubMed

Kim, Ju-Young; Shim, Sun-Bo; Shim, Jin-Kie

2004-12-31

Amphiphilic polyurethane (APU) nanoparticles were synthesized through crosslinking polymerization of nano-aggregates of urethane acrylate nonionomer (UAN). The efficiency of in situ extraction of sorbed phenanthrene from aquifer material was tested using soil columns and compared with that of surfactants such as Triton X-100, Brij 30, and Tween 80. The extraction efficiency of those washing materials strongly depended on their concentration, flow rate, and the degree of sorption within soil column. That is, the extraction efficiency increased with the decrease of flow rate and the degree of sorption and the increase of the concentration. Even though the surfactants are superior to APU nanoparticles at solubilizing phenanthrene, at the same flow rate (0.02 mL/min) and concentration (4000 mg/L), the effectiveness of in situ soil washing of APU nanoparticles was about two times higher than those of surfactants. This is because, at the lower flow rates, the degree of sorption of APU nanoparticles was lower than that of surfactants, owing to the chemically crosslinked nature of APU nanoparticles.

Comparative study of bioconcentration and EROD activity induction in the Japanese flounder, red sea bream, and Java medaka exposed to polycyclic aromatic hydrocarbons.

PubMed

Cheikyula, J Orkuma; Koyama, Jiro; Uno, Seiichi

2008-06-01

Japanese flounder (Paralichthys olivaceus), red sea bream (Pagrus major), and Java medaka (Oryzias javanicus) were exposed to water borne polycyclic aromatic hydrocarbons (PAHs) for 10 days to compare PAH bioconcentration and P450 enzyme induction by ethoxyresorufin-O-deethylase (EROD) activity for use in oil spill biomonitoring in Asian waters. Target exposure concentration for phenanthrene, pyrene, and chrysene were 30 microg/L each, while benzo[a]pyrene was 3.0 microg/L. Phenanthrene and pyrene were accumulated in the flounder and red sea bream; chrysene was found only in the livers of the red sea bream, while Java medaka accumulated the high molecular weight benzo[a]pyrene along with the other PAHs. Total PAH concentrations increased with duration of exposure in the red sea bream from 184+/-37 ng/g wet weight (w.w.) in day 2 to 572+/-72 ng/g (w.w.) in day 10; It, however, decreased in the other two species. Among the three fish species, Java medaka had the highest initial total PAH concentration of 388+/-62 ng/g (w.w.); this was, however, reduced to the lowest final concentration of 52.3+/-3 ng/g (w.w.). It also had the highest EROD activity of 4.2+/-2.8 n mol/min/mg protein compared to the lowest of 0.11+/-0.03 n mol/min/mg protein in the Japanese flounder. Java medaka with high EROD activity induction and bioaccumulation of all PAHs will be suitable for PAH biomonitoring in Asian waters. Due to its high PAH bioconcentration red sea bream is also recommended for consideration for biomonitoring and PAH chronic toxicity tests.

Pyrene degradation in forest humus microcosms with or without pine and its mycorrhizal fungus.

PubMed

Koivula, Teija T; Salkinoja-Salonen, Mirja; Peltola, Rainer; Romantschuk, Martin

2004-01-01

The mineralization potential of forest humus and the self-cleaning potential of a boreal coniferous forest environment for polycyclic aromatic hydrocarbon (PAH) compounds was studied using a model ecosystem of acid forest humus (pH = 3.6) and pyrene as the model compound. The matrix was natural humus or humus mixed with oil-polluted soil in the presence and absence of Scots pine (Pinus sylvestris L.) and its mycorrhizal fungus (Paxillus involutus). The rates of pyrene mineralization in the microcosms with humus implants (without pine) were initially insignificant but increased from Day 64 onward to 47 microg kg(-1) d(-1) and further to 144 microg kg(-1) d(-1) after Day 105. In the pine-planted humus microcosms the rate of mineralization also increased, reaching 28 microg kg(-1) d(-1) after Day 105. The 14CO2 emission was already considerable in nonplanted microcosms containing oily soil at Day 21 and the pyrene mineralization continued throughout the study. The pyrene was converted to CO2 at rates of 0.07 and 0.6 microg kg(-1) d(-1) in the oily-soil implanted microcosms with and without pine, respectively. When the probable assimilation of 14CO2 by the pine and ground vegetation was taken into account the most efficient microcosm mineralized 20% of the 91.2 mg kg(-1) pyrene in 180 d. The presence of pine and its mycorrhizal fungus had no statistically significant effect on mineralization yields. The rates of pyrene mineralization observed in this study for forest humus exceeded the total annual deposition rate of PAHs in southern Finland. This indicates that accumulation in forest soil is not to be expected.

Biodegradation and metabolite transformation of pyrene by basidiomycetes fungal isolate Armillaria sp. F022.

PubMed

Hadibarata, Tony; Kristanti, Risky Ayu

2013-04-01

Armillaria sp. F022 is a white-rot fungus isolated from a tropical rain forest in Indonesia that is capable of utilizing pyrene as a source of carbon and energy. Enzymes production during the degradation process by Armillaria sp. F022 was certainly related to the increase in biomass. In the first week after incubation, the growth rate rapidly increased, but enzyme production decreased. After 7 days of incubation, rapid growth was observed, whereas, the enzymes were produced only after a good amount of biomass was generated. About 63 % of pyrene underwent biodegradation when incubated with this fungus in a liquid medium on a rotary shaker (120 rpm, 25 °C) for 30 days; during this period, pyrene was transformed to five stable metabolic products. These metabolites were extracted in ethyl acetate, isolated by column chromatography, and then identified using thin layer chromatography (TLC) and gas chromatography-mass spectrometry (GC-MS). 1-Hydroxypyrene was directly identified by GC-MS, while 4-phenanthroic acid, 1-hydroxy-2-naphthoic acid, phthalic acid, and protocatechuic acid were identified to be present in their derivatized forms (methylated forms and silylated forms). Protocatechuic acid was the end product of pyrene degradation by Armillaria sp. F022. Dynamic profiles of two key enzymes, namely laccase and 1,2-dioxygenase, were revealed during the degradation process, and the results indicated the presence of a complicated mechanism in the regulation of pyrene-degrading enzymes. In conclusion, Armillaria sp. F022 is a white-rot fungus with potential for application in the degradation of polycyclic aromatic hydrocarbons such as pyrene in the environment.

Bacterial Chemotaxis to Naphthalene and Nitroarene Compounds

DTIC Science & Technology

2008-07-31

Qualitative capillary assays showing chemotaxis of succinate-grown 17 (uninduced) and induced (succinate plus salicylate -grown) Acidovorax sp. JS42...succinate plus 2NT- or succinate plus salicylate -grown) wild-type Acidovorax sp. JS42 cells List of Tables Table 1. Summary of chemotaxis...mM salicylate , or naphthalene crystals. Noble agar (1.8%; Difco) was used to solidify MSB medium for plates. For plasmid selection and maintenance

[Transportation and transformation of 14C-phenanthrene in closed chamber (nutrient solution-lava-plant-air) system].

PubMed

Jiang, X; Ou, Z; Ying, P; Yediler, A; Ketrrup, A

2001-06-01

The transportation and transformation of 14C-phenanthrene in a closed 'plant-lava-nutrient solution-air' chamber system was studied by using radioactivity technology. The results showed that in this closed chamber system, phenanthrene was degraded fast. The radioactivity of 14C left at 23d in the nutrient solution was only 25% of applied. At the end of experiment (46d), the distribution sequence of 14C activity in the components of closed chamber system was root (38.55%) > volatile organic compounds (VOCs, 17.68%) > lava (14.35%) > CO2 (11.42%) > stem (2%). 14C-activities in plant tissue were combined with the tissue, and existed in the forms of lava-bound(root 4.68%; stem and leaves 0.68%) and polar metabolites (root 23.14%; stem 0.78%).

Bioaccumulation of lipophilic substances in fish early life stages

DOE Office of Scientific and Technical Information (OSTI.GOV)

Petersen, G.I.; Kristensen, P.

1998-07-01

Accumulation of {sup 14}C-labeled polycyclic aromatic hydrocarbons, naphthalene, phenanthrene, pyrene, and benzo(a)pyrene and polychlorinated biphenyl (PCB) congeners PCB 31 and PCB 105 with a log octanol/water partition coefficient (K{sub ow}) range from 3.37 to 6.5 was investigated in eggs and larvae of zebra fish (Brachydanio rerio), and in larvae of cod (Gadus morhua), herring (Clupea harengus), and turbot (Scophthalmus maximus). Significant differences in the uptake and elimination rate constants between eggs and larvae of zebra fish were seen. The low rate of uptake and the lower elimination rate of eggs did, however, lead to bioconcentration factors (BCFs) comparable to thosemore » for larvae. As biotransformation of xenobiotics in embryonic and larval stages was indicated to be insignificant compared to juvenile/adult stages, body burdens of readily biotransformed chemicals may be higher in fish early life stages. Because weight and lipid content did not differ much between the investigated species, the main reason for the variability in BCFs between marine species and freshwater species was considered to be caused by differences in exposure temperatures that affect the degree of biotransformation. Due to the smaller size of larvae and thus an increased total surface of the membranes per unit fish weight, steady-state conditions were reached at a faster r/ate in early life stages than in juvenile/adult life stages. The lipid-normalized bioconcentration factors (BCF{sub L}) were linearly related to K{sub ow} but BCF{sub L} was, in general, higher than K{sub ow}, indicating that octanol is not a suitable surrogate for fish lipids. Differences in bioconcentration kinetics between larvae and juvenile/adult life stages are considered to be the main reason for the higher sensitivity, with respect to external effect concentrations, generally obtained for early life stages of fish.« less

Biodegradation of Mixed PAHs by PAH-Degrading Endophytic Bacteria.

PubMed

Zhu, Xuezhu; Ni, Xue; Waigi, Michael Gatheru; Liu, Juan; Sun, Kai; Gao, Yanzheng

2016-08-09

Endophytic bacteria can promote plant growth, induce plant defence mechanisms, and increase plant resistance to organic contaminants. The aims of the present study were to isolate highly PAH-degrading endophytic bacteria from plants growing at PAH-contaminated sites and to evaluate the capabilities of these bacteria to degrade polycyclic aromatic hydrocarbons (PAHs) in vitro, which will be beneficial for re-colonizing target plants and reducing plant PAH residues through the inoculation of plants with endophytic bacteria. Two endophytic bacterial strains P₁ (Stenotrophomonas sp.) and P₃ (Pseudomonas sp.), which degraded more than 90% of phenanthrene (PHE) within 7 days, were isolated from Conyza canadensis and Trifolium pretense L., respectively. Both strains could use naphthalene (NAP), PHE, fluorene (FLR), pyrene (PYR), and benzo(a)pyrene (B(a)P) as the sole sources of carbon and energy. Moreover, these bacteria reduced the contamination of mixed PAHs at high levels after inoculation for 7 days; strain P₁ degraded 98.0% NAP, 83.1% FLR, 87.8% PHE, 14.4% PYR, and 1.6% B(a)P, and strain P₃ degraded 95.3% NAP, 87.9% FLR, 90.4% PHE, 6.9% PYR, and negligible B(a)P. Notably, the biodegradation of PAHs could be promoted through additional carbon and nitrogen nutrients; therein, beef extract was suggested as the optimal co-substrate for the degradation of PAHs by these two strains (99.1% PHE was degraded within 7 days). Compared with strain P₁, strain P₃ has more potential for the use in the removal of PAHs from plant tissues. These results provide a novel perspective in the reduction of plant PAH residues in PAH-contaminated sites through inoculating plants with highly PAH-degrading endophytic bacteria.

Photoinduced Charge Transport Spectra for Porphyrin and Naphthalene Derivative-based Dendrimers

NASA Astrophysics Data System (ADS)

Park, J. H.; Wu, Y.; Parquette, J. R.; Epstein, A. J.

2006-03-01

Dendrimers are important chemical structures for harvesting charge. We prepared model dendrimers using two porphyrin derivatives and a naphthalene derivative. Films of these porphyrin derivatives have a strong Soret band (˜430nm) and four significant Q-bands; the naphthalene derivative has strong absorption at 365 and 383nm. Two kinds of photovoltaic cell structures [ITO/BaytronP/(thick or thin) dendrimer/Al] are constructed to investigate the optical response spectra of dendrimers under electric potential(V) on the cell (range from -1V to 2V). To obtain pure optical responses, incident light is modulated with an optical chopper and a lock-in amplifier is used to measure current (IAC) and phase (θ). For the excitation of the Soret band, IAC and θ do not change substantially with change of sign and amplitude of V. For Q-bands and naphthalene absorption bands, θ nearly follows the polarity of V on the cells and IAC is linear with V. Hence, IAC is nearly ohmic for Q- band although there are shifts due to built-in-potential. IAC for Soret band is almost same for thick and thin active layer cells. In contrast, IAC increases with thickness increase for Q bands. Mechanisms of photogeneration and charge transport will be discussed.

Photochemistry of pyrene with water at low temperature: study of atmospherical and astrochemical interest.

PubMed

Guennoun, Zohra; Aupetit, Christian; Mascetti, Joëlle

2011-03-17

Photochemistry of a polyaromatic hydrocarbon, pyrene C(16)H(10), with water has been investigated at cryogenic temperatures. Photoprocessing of this species, performed at λ > 235 nm, in argon matrices, adsorbed onto amorphous water surfaces, and trapped in solid water, led to the formation of ketonic isomers, C(16)H(10)O, and possibly quinones. These species have been identified for the first time by infrared spectroscopy with the support of isotopic substitution experiments and DFT calculations. These oxidized pyrene-like species, of atmospherical and astrochemical interest, most likely arise from a tautomeric rearrangement of their analogous hydroxylated molecules, these latter being formed by reaction of water with pyrene cations.

Mechanism-based inactivation of benzo(a)pyrene hydroxylase by aryl acetylenes and aryl olefins

DOE Office of Scientific and Technical Information (OSTI.GOV)

Gan, L.S.; Lu, J.Y.L.; Alworth, W.L.

A series of aryl acetylenes and aryl olefins have been examined as substrates and inhibitors of cytochrome P-450 dependent monooxgenases in liver microsomes from 5,6-benzoflavone or phenobarbital pretreated rats. 1-Ethynylpyrene, 3-ethynylperylene, 2-ethynylfluorene, methyl 1-pyrenyl acetylene, cis- and trans-1-(2-bromovinyl)pyrene, and 1-allylpyrene serve as mechanism-based irreversible inactivators (suicide inhibitors) of benzo(a)pyrene hydroxylase, while 1-vinylpyrene and phenyl 1-pyrenyl acetylene do not cause a detectable suicide inhibition of benzo(a)pyrene hydroxylase. The mechanism-based loss of benzo(a)pyrene hydroxylase caused by the aryl acetylenes is not accompanied by a corresponding loss of the P-450 content of the microsomes (suicide destruction). The suicide inhibition by these aryl acetylenesmore » therefore does not involve covalent binding to the heme moiety of the monooxygenase. Nevertheless, in the presence of NADPH, /sup 3/H-labeled 1-ethynylpyrene becomes covalently attached to the cytochrome P-450 protein; the measured stoichiometry of binding is one 1-ethynylpyrene per P-450 heme unit. The authors conclude that the inhibition of benzo(a)pyrene hydroxylase produced by 1-ethynylpyrene may be related to the mechanism of suicide inhibition of P-450 activity by chloramphenicol rather than the mechanism of suicide destruction of P-450 previously described for acetylene and propyne.« less

Priority PAHs in orthodox black tea during manufacturing process.

PubMed

Grover, Inderpreet Singh; Singh, Satnam; Pal, Bonamali

2013-08-01

Orthodox black tea is obtained from fresh leaves followed by withering, rolling, fermentation and drying. The presence of 16 priority polycyclic aromatic hydrocarbons (PAHs) was studied in fresh leaves and at various stages of manufacturing. Benzo(a)pyrene (2A: probable human carcinogen) was found in dried tea leaves only whereas, naphthalene (2B: probable human carcinogen) was present during all the stages of manufacturing. Dry tea leaves showed higher content of total 16 PAHs (∑PAHs) about 3 and 211 times than present in withered and dried leaves, respectively. Chrysene, benzo[g,h,i]perylene, indendo[1,2,3-c,d]pyrene, dibenzo[a,h]pyrene and benzo[a]antracene were not found during manufacturing stages of tea.

Synthesis and characterization of novel pyrene-dendronized porphyrins exhibiting efficient fluorescence resonance energy transfer: optical and photophysical properties.

PubMed

Zaragoza-Galán, Gerardo; Fowler, Michael A; Duhamel, Jean; Rein, Regis; Solladié, Nathalie; Rivera, Ernesto

2012-07-31

A novel series of pyrene dendronized porphyrins bearing two and four pyrenyl groups (Py(2)-TMEG1 and Py(4)-TMEG2) were successfully synthesized. First and second generation Fréchet type dendrons (Py(2)-G1OH and Py(4)-G2OH) were prepared from 1-pyrenylbutanol and 3,5-dihydroxybenzyl alcohol. These compounds were further linked to a trimesitylphenylporphyrin containing a butyric acid spacer via an esterification reaction to obtain the desired products. Dendrons and dendronized porphyrins were fully characterized by FTIR and (1)H NMR spectroscopy and their molecular weights were determined by matrix-assisted laser desorption ionization time of flight mass spectrometry. Their optical and photophysical properties were studied by absorption and fluorescence spectroscopies. The formation of dynamic excimers was detected in the pyrene-labeled dendrons, with more excimer being produced in the higher generation dendron. The fluorescence spectra of the pyrene dendronized porphyrins exhibited a significant decrease in the amount of pyrene monomer and excimer emission, jointly with the appearance of a new emission band at 661 nm characteristic of porphyrin emission, an indication that fluorescence resonance energy transfer (FRET) occurred from one of the excited pyrene species to the porphyrin. The FRET efficiency was found to be almost quantitative ranging between 97% and 99% depending on the construct. Model Free analysis of the fluorescence decays acquired with the pyrene monomer, excimer, and porphyrin core established that only residual pyrene excimer formation in the dendrons could occur before FRET from the excited pyrene monomer to the ground-state porphyrin core.

Noncovalent Interactions of DNA Bases with Naphthalene and Graphene.

PubMed

Cho, Yeonchoo; Min, Seung Kyu; Yun, Jeonghun; Kim, Woo Youn; Tkatchenko, Alexandre; Kim, Kwang S

2013-04-09

The complexes of a DNA base bound to graphitic systems are studied. Considering naphthalene as the simplest graphitic system, DNA base-naphthalene complexes are scrutinized at high levels of ab initio theory including coupled cluster theory with singles, doubles, and perturbative triples excitations [CCSD(T)] at the complete basis set (CBS) limit. The stacked configurations are the most stable, where the CCSD(T)/CBS binding energies of guanine, adenine, thymine, and cytosine are 9.31, 8.48, 8.53, 7.30 kcal/mol, respectively. The energy components are investigated using symmetry-adapted perturbation theory based on density functional theory including the dispersion energy. We compared the CCSD(T)/CBS results with several density functional methods applicable to periodic systems. Considering accuracy and availability, the optB86b nonlocal functional and the Tkatchenko-Scheffler functional are used to study the binding energies of nucleobases on graphene. The predicted values are 18-24 kcal/mol, though many-body effects on screening and energy need to be further considered.

A Semi-Empirical Formula of the Dependence of the Fluorescence Intensity of Naphthalene on Temperature and the Oxygen Concentration

NASA Astrophysics Data System (ADS)

An, B.; Wang, Z.-G.; Yang, L.-C.; Li, X.-P.

2017-09-01

Two-ring aromatics, such as naphthalene, are important fluorescent components of kerosene in the planar laser-induced fluorescent (PLIF) technique. Quantifying measurements of kerosene vapor concentrations by PLIF require a prior knowledge of the fluorescence intensity of naphthalene over a wide temperature and oxygen concentration range. To promote the application of PLIF, a semi-empirical formula based on the collision theory and experimental data at the laser wavelength of 266 nm and a pressure of 0.1 MPa is established to predict the fluorescence intensity of naphthalene at different temperatures and oxygen concentrations. This formula takes vibrational states, temperature, and oxygen quenching into account. Verified by published experimental data, the formula can predict the fluorescence intensity of naphthalene with an error less than 9%.

Pyrene based D-π-A architectures: synthesis, density functional theory, photophysics and electron transfer dynamics.

PubMed

Kathiravan, Arunkumar; Srinivasan, Venkatesan; Khamrang, Themmila; Velusamy, Marappan; Jaccob, Madhavan; Pavithra, Nagaraj; Anandan, Sambandam; Velappan, Kandavelu

2017-01-25

Pyrene derivatives show immense potential as sensitizers for dye-sensitized solar cells (DSCs). Therefore, this work focuses on the impact of π-spacers on the photophysical, electrochemical and photovoltaic properties of pyrene based D-π-A dyes, since the insertion of π-spacers is one of the doable strategies to improve the light harvesting properties of the dye. In this respect, three new pyrene based D-π-A dyes have been synthesized and characterized by 1 H, 13 C NMR, and elemental analyses and EI-MS spectrometry. The selected π-spacers are benzene, thiophene and furan. Compared with a benzene spacer, the introduction of a heterocyclic ring spacer reduces the band gap of the dye and brings about the broadening of the absorption spectra to the longer wavelength region through intramolecular charge-transfer (ICT). Combined experimental and theoretical studies were performed to investigate the ICT process involved in the pyrene derivatives. The profound solvatochromism with increased nonradiative rate constants (k nr ) has been construed in terms of ICT from the pyrene core to rhodanine-3-acetic acid via conjugated π-spacers. Electrochemical data also reveal that the HOMO and LUMO energy levels are fine-tuned by incorporating different π-spacers between pyrene and rhodanine-3-acetic acid. On the basis of the optimized DSC test conditions, the best performance was found for PBRA, in which a benzene group is the conjugated π-spacer. The divergence in the photovoltaic behaviors of these dyes was further explicated by femtosecond fluorescence and electrochemical impedance spectroscopy.

Nitration of naphthalene and remarks on the mechanism of electrophilic aromatic nitration.

PubMed

Olah, G A; Narang, S C; Olah, J A

1981-06-01

Naphthalene was nitrated with a variety of nitrating agents. Comparison of data with Perrin's electrochemical nitration [Perrin, C. L. (1977) J. Am. Chem. Soc. 99, 5516-5518] shows that nitration of naphthalene gives an alpha-nitronaphthalene to beta-nitronaphthalene ratio that varies between 9 and 29 and is thus not constant. Perrin's data, therefore, are considered to be inconclusive evidence for the proposed one-electron transfer mechanism for the nitration of naphthalene and other reactive aromatics. Moodie and Schoefield [Hoggett, J. G., Moodie, R. B., Penton, J. R. & Schoefield, K. (1971) Nitration and Aromatic Reactivity (Cambridge Univ. Press, London)], as well as Perrin, independently concluded that, in the general scheme of nitration of reactive aromatics, there is the necessity to introduce into the classical Ingold mechanism an additional step involving a distinct intermediate preceding the formation of the Wheland intermediate (sigma complexes). This view coincides with our two-step mechanistic picture [Kuhn, S. J. & Olah, G. A. (1961) J. Am. Chem. Soc. 83, 4564-4571] of the nitronium salt nitration of aromatic hydrocarbons (including benzene and toluene), in which low substrate selectivity but high positional selectivity was found, indicating the independence of substrate from positional selectivity.

Nitration of naphthalene and remarks on the mechanism of electrophilic aromatic nitration*

PubMed Central

Olah, George A.; Narang, Subhash C.; Olah, Judith A.

1981-01-01

Naphthalene was nitrated with a variety of nitrating agents. Comparison of data with Perrin's electrochemical nitration [Perrin, C. L. (1977) J. Am. Chem. Soc. 99, 5516-5518] shows that nitration of naphthalene gives an α-nitronaphthalene to β-nitronaphthalene ratio that varies between 9 and 29 and is thus not constant. Perrin's data, therefore, are considered to be inconclusive evidence for the proposed one-electron transfer mechanism for the nitration of naphthalene and other reactive aromatics. Moodie and Schoefield [Hoggett, J. G., Moodie, R. B., Penton, J. R. & Schoefield, K. (1971) Nitration and Aromatic Reactivity (Cambridge Univ. Press, London)], as well as Perrin, independently concluded that, in the general scheme of nitration of reactive aromatics, there is the necessity to introduce into the classical Ingold mechanism an additional step involving a distinct intermediate preceding the formation of the Wheland intermediate (σ complexes). This view coincides with our two-step mechanistic picture [Kuhn, S. J. & Olah, G. A. (1961) J. Am. Chem. Soc. 83, 4564-4571] of the nitronium salt nitration of aromatic hydrocarbons (including benzene and toluene), in which low substrate selectivity but high positional selectivity was found, indicating the independence of substrate from positional selectivity. PMID:16593026

Behavior of 2,6-bis(decyloxy)naphthalene inside lipid bilayer.

PubMed

Kepczynski, Mariusz; Kumorek, Marta; Stepniewski, Michał; Róg, Tomasz; Kozik, Bartłomiej; Jamróz, Dorota; Bednar, Jan; Nowakowska, Maria

2010-12-02

Interactions between small organic molecules and lipid or cell membranes are important because of their role in the distribution of biologically active substances inside the membrane and their permeation through the cell membranes. In the current paper, we have explored the effect of the attachment of long hydrocarbon tails on the behavior of small organic molecule inside the lipid membrane. Naphthalene with two decyloxy groups attached at the opposite sites of the ring (2,6-bis(decyloxy)naphthalene, 3) was synthesized and incorporated into phosphatidylcholine (PC) vesicles. Fluorescence methods as well as molecular dynamic (MD) simulations were used to estimate the position, orientation, and migration of compound 3 in PC bilayer. It was found that the naphthalene ring of compound 3 resides in the upper acyl chain region of the bilayer and the hydrocarbon tails are directed to the center of the bilayer. As was shown with cryotransmission electron microscopy (cryo-TEM), such lipidlike conformation enables compound 3 to be incorporated into liposomes at a very high content without their disintegration. Moreover, compound 3 can migrate from one leaflet to other. The mechanism of this process is, however, different from that characteristic of the flip-flop event of lipid molecules in the membrane. Finally, the possible application of compound 3 as a rotational molecular probe for monitoring fluidity of liposomal membrane in the acyl side chain region was checked by studies of the effect of cholesterol on the fluorescence anisotropy of 3.

The effect of caffeine on the reactions of the excited singlet state of pyrene in micellar sodium lauryl sulfate

NASA Astrophysics Data System (ADS)

Hashimoto, Shuichi; Thomas, J. Kerry

1984-08-01

The effect of caffeine on a few photo-induced reactions of pyrene in micellar sodium lauryl sulfate (NaLS) has been studied. In these systems caffeine complexes with the pyrene (K asso = 85 ± 10 M -1 and also with the other reactants, e.g. Cu 2+ or TI +. The efficiencies of reactions which involve contact, i.e. pyrene excimer formation, and quenching by TI + ions to give the triplet state of pyrene, are significantly reduced in the presence of caffeine, due to geometric inhibitions formed by the complexation processes. The kinetics of photo-induced electron transfer, e.g. between excited pyrene and Cu 2+, are not affected. However, the subsequent reactions of the products are modified and the yield of ionic products is markedly increased.

Pyrene Molecular Orbital Shuffle-Controlling Excited State and Redox Properties by Changing the Nature of the Frontier Orbitals.

PubMed

Merz, Julia; Fink, Julian; Friedrich, Alexandra; Krummenacher, Ivo; Al Mamari, Hamad H; Lorenzen, Sabine; Haehnel, Martin; Eichhorn, Antonius; Moos, Michael; Holzapfel, Marco; Braunschweig, Holger; Lambert, Christoph; Steffen, Andreas; Ji, Lei; Marder, Todd B

2017-09-21

We show that by judicious choice of substituents at the 2- and 7-positions of pyrene, the frontier orbital order of pyrene can be modified, giving enhanced control over the nature and properties of the photoexcited states and the redox potentials. Specifically, we introduced a julolidine-like moiety and Bmes 2 (mes=2,4,6-Me 3 C 6 H 2 ) as very strong donor (D) and acceptor (A), respectively, giving 2,7-D-π-D- and unsymmetric 2,7-D-π-A-pyrene derivatives, in which the donor destabilizes the HOMO-1 and the acceptor stabilizes the LUMO+1 of the pyrene core. Consequently, for 2,7-substituted pyrene derivatives, unusual properties are obtained. For example, very large bathochromic shifts were observed for all of our compounds, and unprecedented green light emission occurs for the D/D system. In addition, very high radiative rate constants in solution and in the solid state were recorded for the D-π-D- and D-π-A-substituted compounds. All compounds show reversible one-electron oxidations, and Jul 2 Pyr exhibits a second oxidation, with the largest potential splitting (ΔE=440 mV) thus far reported for 2,7-substituted pyrenes. Spectroelectrochemical measurements confirm an unexpectedly strong coupling between the 2,7-substituents in our pyrene derivatives. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Combined remediation of pyrene-contaminated soil with a coupled system of persulfate oxidation and phytoremediation with ryegrass.

PubMed

Chen, Xiao; Li, Hongbing; Liu, Xiaoyan; Zhang, Xinying; Liang, Xia; He, Chiquan; Cao, Liya

2016-10-01

The in situ chemical oxidation technology (ISCO) and phytoremediation for PAHs have been studied respectively, but few focus on the feasibility of combining persulfate with ryegrass. This literature revealed the effect of persulfate oxidation on the growth of ryegrass and the removal ratios of pyrene in the couple system of persulfate oxidation and phytoremediation. The results demonstrated that half of pyrene in test soil was oxidized by persulfate in 7 days and then the residual pyrene concentration was decreased to a lower level by ryegrass in the following 2 months in oxidation treatment and drip washing and plants (OWP) and oxidation treatment and drip washing and plants and fertilization (OWFP) treatment. Ryegrass could grow well after persulfate oxidation with the oxidized soil washed by water. Ryegrass in OWP and OWFP treatments had higher ratios of overground and underground biomass. However, the seeds of ryegrass cannot germinate when drip washing was omitted. Pyrene together with residual persulfate changed soil enzyme activities. Drip washing and the growth of ryegrass made soil enzyme activities tend to returned to normal levels. Persulfate oxidation and phytoremediation were compatible to make contributions to the dissipation of pyrene. Persulfate oxidation activated by heat had higher removal efficiency of PAHs and phytoremediation could further decrease the pyrene concentration in spiked soil.

Optical biosensor for environmental on-line monitoring of naphthalene and salicylate bioavailability with an immobilized bioluminescent catabolic reporter bacterium.

PubMed Central

Heitzer, A; Malachowsky, K; Thonnard, J E; Bienkowski, P R; White, D C; Sayler, G S

1994-01-01

An optical whole-cell biosensor based on a genetically engineered bioluminescent catabolic reporter bacterium was developed for continuous on-line monitoring of naphthalene and salicylate bioavailability and microbial catabolic activity potential in waste streams. The bioluminescent reporter bacterium, Pseudomonas fluorescens HK44, carries a transcriptional nahG-luxCDABE fusion for naphthalene and salicylate catabolism. Exposure to either compound resulted in inducible bioluminescence. The reporter culture was immobilized onto the surface of an optical light guide by using strontium alginate. This biosensor probe was then inserted into a measurement cell which simultaneously received the waste stream solution and a maintenance medium. Exposure under defined conditions to both naphthalene and salicylate resulted in a rapid increase in bioluminescence. The magnitude of the response and the response time were concentration dependent. Good reproducibility of the response was observed during repetitive perturbations with either naphthalene or salicylate. Exposure to other compounds, such as glucose and complex nutrient medium or toluene, resulted in either minor bioluminescence increases after significantly longer response times compared with naphthalene or no response, respectively. The environmental utility of the biosensor was tested by using real pollutant mixtures. A specific bioluminescence response was obtained after exposure to either an aqueous solution saturated with JP-4 jet fuel or an aqueous leachate from a manufactured-gas plant soil, since naphthalene was present in both pollutant mixtures. PMID:8017932

40 CFR 464.31 - Specialized definitions.

Code of Federal Regulations, 2014 CFR

2014-07-01

... (dichloromethane) 55. naphthalene 64. pentachlorophenol 65. phenol 66. bis(2-ethylhexyl)phthalate 67. butyl benzyl phthalate 68. di-n-butyl phthalate 70. diethyl phthalate 71. dimethyl phthalate 72. benzo (a)anthracene (1,2... (dichloromethane) 66. bis (2-ethylhexyl) phthalate 77. acenaphthylene 84. pyrene (4) Melting Furnace Scrubber...

40 CFR 464.31 - Specialized definitions.

Code of Federal Regulations, 2012 CFR

2012-07-01

... (dichloromethane) 55. naphthalene 64. pentachlorophenol 65. phenol 66. bis(2-ethylhexyl)phthalate 67. butyl benzyl phthalate 68. di-n-butyl phthalate 70. diethyl phthalate 71. dimethyl phthalate 72. benzo (a)anthracene (1,2... (dichloromethane) 66. bis (2-ethylhexyl) phthalate 77. acenaphthylene 84. pyrene (4) Melting Furnace Scrubber...

Evaluation of dissipation mechanisms for benzo[a]pyrene in the rhizosphere of tall fescue

DOE Office of Scientific and Technical Information (OSTI.GOV)

Banks, M.K.; Schwab, A.P.; Lee, E.

Although polycyclic aromatic hydrocarbons are common contaminants in soil and are potentially carcinogenic and mutagenic, little is known about their fate in the soil/root environment. The impact of tall fescue (Festuca arundinacea Schreber) on chemical and biological transformations of benzo[a]pyrene in soil was investigated in a greenhouse experiment in which [sup 14]C-benzo[a]pyrene was added to soil and placed in sealed chambers with and without plants. The distribution of [sup 14]C in soil, plant tissue, and CO[sub 2] was quantified. Dissipation due to mineralization and volatilization accounted for <2% of the total [sup 14]C added in both planted and unplanted chambersmore » and was greater in the presence of plants. Plant uptake of [sup 14]C was <0.12%. Residual benzo[a]pyrene was lower in soil with plants than in the absence of plants. The majority of the [sup 14]C label was associated with the soil matrix. The presence of plants enhance the degradation of highly adsorbed, recalcitrant benzo[a]pyrene in soil.« less

Urinary and breast milk biomarkers to assess exposure to naphthalene in pregnant women: an investigation of personal and indoor air sources

PubMed Central

2014-01-01

Background Naphthalene exposures for most non-occupationally exposed individuals occur primarily indoors at home. Residential indoor sources include pest control products (specifically moth balls), incomplete combustion such as cigarette smoke, woodstoves and cooking, some consumer and building products, and emissions from gasoline sources found in attached garages. The study aim was to assess naphthalene exposure in pregnant women from Canada, using air measurements and biomarkers of exposure. Methods Pregnant women residing in Ottawa, Ontario completed personal and indoor air sampling, and questionnaires. During pregnancy, pooled urine voids were collected over two 24-hour periods on a weekday and a weekend day. At 2–3 months post-birth, they provided a spot urine sample and a breast milk sample following the 24-hour air monitoring. Urines were analyzed for 1-naphthol and 2-naphthol and breast milk for naphthalene. Simple linear regression models examined associations between known naphthalene sources, air and biomarker samples. Results Study recruitment rate was 11.2% resulting in 80 eligible women being included. Weekday and weekend samples were highly correlated for both personal (r = 0.83, p < 0.0001) and indoor air naphthalene (r = 0.91, p < 0.0001). Urine specific gravity (SG)-adjusted 2-naphthol concentrations collected on weekdays and weekends (r = 0.78, p < 0.001), and between pregnancy and postpartum samples (r = 0.54, p < 0.001) were correlated. Indoor and personal air naphthalene concentrations were significantly higher post-birth than during pregnancy (p < 0.0001 for signed rank tests); concurrent urine samples were not significantly different. Naphthalene in breast milk was associated with urinary 1-naphthol: a 10% increase in 1-naphthol was associated with a 1.6% increase in breast milk naphthalene (95% CI: 0.2%-3.1%). No significant associations were observed between naphthalene sources reported in self

Dynamics of Bacterial Communities in Two Unpolluted Soils after Spiking with Phenanthrene: Soil Type Specific and Common Responders

PubMed Central

Ding, Guo-Chun; Heuer, Holger; Smalla, Kornelia

2012-01-01

Considering their key role for ecosystem processes, it is important to understand the response of microbial communities in unpolluted soils to pollution with polycyclic aromatic hydrocarbons (PAH). Phenanthrene, a model compound for PAH, was spiked to a Cambisol and a Luvisol soil. Total community DNA from phenanthrene-spiked and control soils collected on days 0, 21, and 63 were analyzed based on PCR-amplified 16S rRNA gene fragments. Denaturing gradient gel electrophoresis (DGGE) fingerprints of bacterial communities increasingly deviated with time between spiked and control soils. In taxon specific DGGE, significant responses of Alphaproteobacteria and Actinobacteria became only detectable after 63 days, while significant effects on Betaproteobacteria were detectable in both soils after 21 days. Comparison of the taxonomic distribution of bacteria in spiked and control soils on day 63 as revealed by pyrosequencing indicated soil type specific negative effects of phenanthrene on several taxa, many of them belonging to the Gamma-, Beta-, or Deltaproteobacteria. Bacterial richness and evenness decreased in spiked soils. Despite the significant differences in the bacterial community structure between both soils on day 0, similar genera increased in relative abundance after PAH spiking, especially Sphingomonas and Polaromonas. However, this did not result in an increased overall similarity of the bacterial communities in both soils. PMID:22934091

[Determination of benzo(alpha)pyrene in food with microwave-assisted extraction].

PubMed

Zhou, Na; Luo, He-Dong; Li, Na; Li, Yao-Qun

2014-03-01

Coupling derivative technique and constant-energy synchronous fluorescence scanning technique, a method of determining benzo[alpha] pyrene in foods by second derivative constant-energy synchronous spectrofluorimetry after microwave-assisted treatment of samples was established using domestic microwave oven. The main factors of influencing the efficiency of microwave extraction were discussed, including the extraction solvent types and amounts, the microwave extraction time, microwave radiation power and cooling time. And the comparison with ultrasonic extraction was made. Low-fat food samples, which were just microwave-extracted with mixed-solvents, could be analyzed immediately by the spectrofluorimetric technique. For high-fat food samples, microwave-assisted saponification and extraction were made at the same time, thus simplifying operation steps and reducing sample analysis time. So the whole sample analysis process could be completed within one hour. This method was simple, rapid and inexpensive. In consequence, it was applied to determine benzo(a)pyrene in food with good reproducibility and the recoveries of benzo(alpha) pyrene ranged from 90.0% to 105.0% for the low fat samples and 83.3% to 94.6% for high-fat samples.

Degradation of polycyclic aromatic hydrocarbons (PAHs) by a mixed culture and its component pure cultures, obtained from PAH-contaminated soil.

PubMed

Trzesicka-Mlynarz, D; Ward, O P

1995-06-01

A mixed culture, isolated from soil contaminated with polycyclic aromatic hydrocarbons (PAHs), grew on and degraded fluoranthene in aqueous media supplemented with glucose, yeast extract, and peptone. Increased complex nitrogen levels in the medium promoted bacterial growth and a greater extent of fluoranthene degradation. Amendment of the media with high glucose levels also diminished specific fluoranthene degradation. The mixed culture was capable of degrading a range of other PAHs, including benzo[a]pyrene, anthracene, phenanthrene, acenaphthene, and fluorene. The mixed culture contained four predominant isolates, all of which were Gram-negative rods, three of which were identified as Pseudomonas putida, Flavobacterium sp., and Pseudomonas aeruginosa. Better degradation of a defined PAH mixture was observed with the mixed culture than with individual isolates. A reconstituted culture, prepared by combining the four individual isolates, manifested a similar PAH biodegradation performance to the original mixed culture. When compared with the mixed culture, individual isolates exhibited a relatively good capacity to remove more water-soluble PAHs (acenaphthene, fluorene, phenanthrene, fluoranthene). In contrast, removal of less water-soluble PAHs (anthracene and pyrene) was low or negligible with isolated cultures compared with the mixed culture.

Reinforced microextraction of polycyclic aromatic hydrocarbons from polluted soil samples using an in-needle coated fiber with polypyrrole/graphene oxide nanocomposite.

PubMed

Behfar, Mina; Ghiasvand, Ali Reza; Yazdankhah, Fatemeh

2017-07-01

The surface of a stainless-steel wire was platinized using electrophoretic deposition method to create a high-surface-area with porous and cohesive substrate. The platinized fiber was coated by the polypyrrole/graphene oxide nanocomposite by electropolymerization and accommodated into a stainless-steel needle to fabricate an in-needle coated fiber. The developed setup was coupled to gas chromatography with flame ionization detection and applied to extract and determine polycyclic aromatic hydrocarbons (naphthalene, fluorene, phenanthrene, fluoranthene, and pyrene) in complicated solid matrices, along with reinforcement of the extraction by cooling the sorbent, using liquid carbon dioxide. To obtain the best extraction efficiency, the important experimental variables including extraction temperature and time, temperature of cooled sorbent, sampling flow rate, and desorption condition were studied. Under the optimal condition, limits of detection for five studied analytes were in the range of 0.2-0.8 pg/g. Linear dynamic ranges for the calibration curves were found to be in the range of 0.001-1000 ng/g. Relative standard deviations obtained for six replicated analyses of 1 ng/g of analytes were 4.9-13.5%. The reinforced in-needle coated fiber method was successfully applied for the analysis of polycyclic aromatic hydrocarbons in contaminated soil samples. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PAHs in leachates from thermal power plant wastes and ash-based construction materials.

PubMed

Irha, Natalya; Reinik, Janek; Jefimova, Jekaterina; Koroljova, Arina; Raado, Lembi-Merike; Hain, Tiina; Uibu, Mai; Kuusik, Rein

2015-08-01

The focus of the current study is to characterise the leaching behaviour of polycyclic aromatic hydrocarbons (PAHs) from oil shale ashes (OSAs) of pulverised firing (PF) and circulating fluidised-bed (CFB) boilers from Estonian Thermal Power Plant (Estonia) as well as from mortars and concrete based on OSAs. The target substances were 16 PAHs from the EPA priority pollutant list. OSA samples and OSA-based mortars were tested for leaching, according to European standard EN 12457-2 (2002). European standard CEN/TC 15862(2012) for monolithic matter was used for OSA-based concrete. Water extracts were analysed by GC-MS for the concentration of PAHs. Naphthalene, acenaphthene, fluorene, phenanthrene, anthracene, fluoranthene and pyrene were detected. Still, the release of PAHs was below the threshold limit value for inert waste. The amount of the finest fraction (particle size <0.045 mm), the content of the Al-Si glass phase and the surface characteristics were the main factors, which could affect the accessibility of PAHs for leaching. The mobility of PAHs from OSA of CFB and PF boilers was 20.2 and 9.9%, respectively. Hardening of OSA-based materials did not lead to the immobilisation of soluble PAHs. Release of PAHs from the monolith samples did not exceed 0.5 μg/m(2). In terms of leaching of PAHs, OSA is safe to be used for construction purposes.

Initial environmental impacts of the Obed Mountain coal mine process water spill into the Athabasca River (Alberta, Canada).

PubMed

Cooke, Colin A; Schwindt, Colin; Davies, Martin; Donahue, William F; Azim, Ekram

2016-07-01

On October 31, 2013, a catastrophic release of approximately 670,000m(3) of coal process water occurred as the result of the failure of the wall of a post-processing settling pond at the Obed Mountain Mine near Hinton, Alberta. A highly turbid plume entered the Athabasca River approximately 20km from the mine, markedly altering the chemical composition of the Athabasca River as it flowed downstream. The released plume traveled approximately 1100km downstream to the Peace-Athabasca Delta in approximately four weeks, and was tracked both visually and using real-time measures of river water turbidity within the Athabasca River. The plume initially contained high concentrations of nutrients (nitrogen and phosphorus), metals, and polycyclic aromatic hydrocarbons (PAHs); some Canadian Council of Ministers of the Environmental (CCME) Guidelines were exceeded in the initial days after the spill. Subsequent characterization of the source material revealed elevated concentrations of both metals (arsenic, lead, mercury, selenium, and zinc) and PAHs (acenaphthene, fluorene, naphthalene, phenanthrene, and pyrene). While toxicity testing using the released material indicated a relatively low or short-lived acute risk to the aquatic environment, some of the water quality and sediment quality variables are known carcinogens and have the potential to exert negative long-term impacts. Copyright © 2016 The Authors. Published by Elsevier B.V. All rights reserved.

Ultra preconcentration of polycyclic aromatic hydrocarbons in smoked bacon by a combination of SPE and DLLME.

PubMed

Liu, Xiaofang; Zhou, Shu; Zhu, Quanfei; Ye, Yong; Chen, Huaixia

2014-09-01

A sample pretreatment method, solid-phase extraction combined with dispersive liquid-liquid microextraction (SPE-DLLME), was established for the sensitive determination of polycyclic aromatic hydrocarbons (PAHs) in smoked bacon samples. In the SPE-DLLME process, three PAHs including naphthalene (Naph), phenanthrene (Phen) and pyrene (Pyr) were extracted from samples and transferred into C18 SPE cartridge. The target analytes were subsequently eluted with 1.2 ml of acetonitrile-dichloromethane (5:1, v/v) mixture solution. The eluent was injected directly into the 5.0 ml ultrapure water in the subsequent DLLME procedure. The sedimented phase was concentrated under a gentle nitrogen flow to 120.0 µl. Finally, the analytes in the extraction solvent were determined by high-performance liquid chromatography with a ultra-violet detector. Some important extraction parameters affecting the performance, such as the sample solution flow rate, breakthrough volume, salt addition as well as the type and volume of the elution solvent were optimized. The developed method provided an ultra enrichment factors for PAHs ranged from 3478 to 3824. The method was applied for the selective extraction and sensitive determination of PAHs in smoked bacon samples. The limits of detection (S/N = 3) were 0.05, 0.01, 0.02 μg kg(-1) for Naph, Phen, Pyr, respectively. © The Author [2013]. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Drift mobility of holes in phenanthrene single crystals

NASA Technical Reports Server (NTRS)

Sonnonstine, T. J.; Hermann, A. M.

1974-01-01

The temperature dependence of drift mobilities of holes in single crystals of phenanthrene was measured in the range from 203 to 353 K in three crystallographic directions. Below the anomaly temperature of 72 C, the mobility temperature dependences are consistent with the Munn and Siebrand slow-phonon hopping process in the b direction and the Munn and Siebrand slow-phonon coherent mode in the a and c prime directions. The drift mobility temperature dependences in crystals that have been cooled through the anomaly temperature in the presence of illumination and an electric field are consistent with the model of Spielberg et al. (1971), in which the hindered vibration of the 4,5 hydrogens introduces a new degree of freedom above 72 C.

New phenanthrene and 9, 10-dihydrophenanthrene derivatives from the stems of Dendrobium officinale with their cytotoxic activities.

PubMed

Zhao, Gui-Yun; Deng, Bo-Wen; Zhang, Chong-Yu; Cui, Yi-Da; Bi, Jia-Yi; Zhang, Guo-Gang

2018-01-01

Two new phenanthrene and 9, 10-dihydrophenanthrene derivatives (1-2) with six known congeners (3-8) were isolated from the extraction of stems of Dendrobium officinale. Compounds 1 and 2 were based on carbon skeleton in which phenanthrene and 9, 10-dihydrophenanthrene moiety were linked with a phenylpropane unit through a dioxane bridge, respectively. Their structures were determined by comprehensive NMR spectroscopic data, the absolute configuration of new compounds were determined by comparing their experimental and calculated ECD for the first time. All the compounds were investigated contains two cancer cell lines (HI-60, THP-1). All the isolates showed cytotoxicity, especially compound 4 showed markedly cytotoxic activities against HI-60 and THP-1 cell lines with IC 50 values of 11.96 and 8.92 μM.

An Overview of the Toxicity of Naphthalene, EDB and Ethanol

EPA Science Inventory