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At least 811 records · Page 45Linked to original sources
PubMed2002

Persistent organic pollutants in Detroit River suspended sediments: polychlorinated dibenzo-p-dioxins and dibenzofurans, dioxin-like polychlorinated biphenyls and polychlorinated naphthalenes.

Suspended sediments from the Detroit River were collected in 1999 and 2000 using sediment traps at sites ranging from western Lake Erie to southern Lake St. Clair and analyzed to determine the spatial distributions of contaminants including polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDDs/PCDFs), dioxin-like PCBs (DLPCBs) and polychlorinated naphthalenes (PCNs). Concentrations of all three contaminant classes were clearly elevated at sites in the lower reaches of the river in the Trenton Channel. The potential influence of the Trenton Channel as a source of contamination to western Lake Erie was further evidenced by PCDD/PCDF homologue profiles, which indicated a contribution from chemical manufacturing in addition to the normal background combustion profile. Toxic equivalents (TEQs) for PCDDs/PCDFs generally exceeded those for DLPCBs; combined total TEQs in July 2000 for these two compound classes ranged from 2.30 pg/g in southern Lake St. Clair to 306 pg/g at a station just downstream of the outflow of Monguagon Creek in the Trenton Channel. The spatial distribution of PCN contamination was similar to that of PCDDs/PCDFs and DLPCBs, with the highest level of total PCNs (8200 ng/g) detected at a site in the Trenton Channel near Elizabeth Park; TEQs for PCNs in the Trenton Channel ranged from 73 to 3300 pg/g. The data indicate that PCNs represent a significant contribution to dioxin-like biological activity in Detroit River suspended sediments.

Benzofurans↗
PubMed2003

Interlaboratory study for the polychlorinated naphthalenes (PCNs): phase 1 results.

An interlaboratory study was initiated to investigate consistency in reported concentrations of polychlorinated naphthalenes (PCNs). Results are reported from the first phase of a study that examined the variability associated with different quantification methodologies, instrumentation and standards. Nine participating labs from seven countries quantified individual homolog groups, summation operator PCN (the sum of 2-8 chlorinated homologs), and selected congeners in two test solutions derived from Halowax 1014. The means of the reported summation operator PCN values were within less than 15% of the known concentrations of the two test solutions and the relative standard deviation among laboratories was 11%. However, the among laboratory variability was in the range 20-40% for individual PCN homologs and individual PCN congeners. These results suggest the need for additional interlaboratory studies and for the development of reference materials for PCN analysis. Future PCN interlaboratory comparison exercises are discussed that will utilize control materials and unknowns consisting of suitable environmental matrices.

Chlorine Compounds↗
PubMed1999

Polychlorinated naphthalenes in sediments from the Venice and Orbetello lagoons, Italy.

The purpose of this study was to evaluate the contamination caused by polychlorinated naphthalenes in two polluted Mediterranean lagoons. Surface sediment samples from Venice and Orbetello lagoons were analysed using HRGC-HRMS. The levels of the sum of mono- to octa-CN ranged from 0.03 to 1.51 ng/g. Differences in PCN levels were observed as a function of the sampling site, with levels at the industrial sites exceeding those at the control sites. Although the PCN patterns and profiles resembled one another in different sediment samples, they differed considerably when compared with those in the technical PCN formulation Halowax 1014.

Environmental Monitoring↗
PubMed1997

Concentrations and biomagnification of polychlorinated naphthalenes in black cormorants Phalacrocorax carbo sinensis from the Gulf of Gdańsk, Baltic Sea.

Black cormorants, Phalacrocorax carbo sinensis (the breast muscles and liver) originating from the colony near Katy Rybackie on the south coast of the Gulf of Gdańsk, Baltic Sea, were collected in 1992 and analysed for polychlorinated naphthalenes. PCNs were determined employing a multi-residue procedure including a non-destructive wide-bore open-tube extraction step, cleanup using semipermeable polyethylene membrane, HPLC fractionation of planar compounds on activated carbon column and final separation and identification and quantification with HRGC/HRMS. Tetra- to hepta-CNs were found in all samples examined, and penta- and next tetra-CNs were dominating homologue groups. Dominating members in the fingerprint of PCNs in black cormorants were 1,3,5,7-T4CN (no. 42); 1,2,3,5,7-/1,2,4,6,7-P5CN (no. 52/60); 1,2,4,6,8-P5CN (no. 61); 1,2,3,4,6,7-/1,2,3,5,6,7-H6CN (no. 66/67); 1,2,4,6-/1,2,4,7-/1,2,5,7-T4CN (no. 33/34); 1,2,4,5,7-P5CN (no. 58); and 1,2,4,7,8-P5CN (no. 62). When related to potential food items, black cormorants biomagnify in their body many PCNs and the congeners no. 42 and 66/67 show highest biomagnification factor (BMF) values.

Animals↗
PubMed2003

Anguilla anguilla L. liver ethoxyresorufin O-deethylation, glutathione S-transferase, erythrocytic nuclear abnormalities, and endocrine responses to naphthalene and beta-naphthoflavone.

The effects of naphthalene (NAP) and beta-naphthoflavone (BNF) on phase I biotransformation and genotoxicity in Anguilla anguilla L. were evaluated. Phase II biotransformation and cortisol levels were also assessed in NAP-treated fish. Two groups of eels were exposed to either a NAP or a BNF concentration range (0.1-2.7 microM) for different exposure periods (2-72 h). An early significant ethoxyresorufin O-deethylation (EROD) activity inhibition was observed, especially for the highest NAP concentrations at 2-6 h exposure and for BNF at 2h exposure. However, a significant EROD activity increase was detected from 16 to 72 h exposure for NAP and from 4 to 72 h exposure for BNF. The cytochrome P450 (P450) content was not dose related. However, with regard to BNF exposure, P450 was the first biomarker to respond. Liver alanine transaminase (ALT) activity was measured as an indicator of hepatic health condition. ALT results demonstrated that the EROD activity decrease, previously described for NAP, was not related to tissue damage. Nevertheless, the highest BNF concentrations were demonstrated to induce liver damage and to impair the EROD activity response. An increased genotoxic response, measured as erythrocytic nuclear abnormalities (ENA), was observed during the first 8h NAP exposure. However, for exposures longer than 8 h, ENA frequency returned to the control levels. This response profile may reflect a considerable DNA repair capacity and/or a metabolic adaptation providing an efficient NAP biotransformation and consequent detoxification. BNF revealed no ENA alterations for all concentrations and exposure lengths. In the NAP experiment a causal relationship between immature erythrocytes (IE) and ENA frequency disappearance was not found. BNF results with regard to IE frequency revealed an ability to alter the balance between erythropoiesis and removal of erythrocytes. Liver glutathione S-transferase activity was significantly induced after 2 and 48 h NAP exposure. A cortisol-impaired response seems to occur from 4 to 24 h NAP exposure, demonstrating an endocrine disruption. However, an adaptation process seems to occur after 48 h, since the plasma cortisol had a tendency to increase. The present findings confirm the usefulness of the adopted biomarkers. The ecological risk associated with aquatic contamination by NAP was also confirmed by the present data.

Anguilla↗
PubMed2002

Naphthalene and beta-naphthoflavone effects on Anguilla anguilla L. hepatic metabolism and erythrocytic nuclear abnormalities.

The effects of a polycyclic aromatic hydrocarbon (PAH) such as naphthalene (NAP)--an environmental contaminant--and beta-naphthoflavone (BNF)--a model substance (PAH-like compound)--were investigated in European eel (Anguilla anguilla L.) over 3-, 6-, and 9-day exposure (0.1-2.7 microM). Both xenobiotics revealed to be strong biotransformation (phase I) inducers. After 3-day exposure, liver ethoxyresorufin O-deethylase (EROD) activity was significantly increased by all NAP and BNF tested concentrations. At 6 and 9 days, liver EROD activity was significantly induced mainly by the highest NAP and BNF concentrations. Liver cytochrome P450 content was significantly induced after 3-day exposure to 0.9 and 2.7 microM BNF and 9-day exposure to 0.1, 0.3 and 0.9 microM NAP. Liver alanine transaminase (ALT) activity was measured as an indicator of hepatic health condition, revealing a significant decrease after 6-day exposure to 0.9 microM BNF. Genotoxicity measured as erythrocytic nuclear abnormalities (ENA) was detected in all BNF treated fish on day 6, whereas on day 9, ENA frequencies returned to control levels, significantly decreasing at 0.9 microM BNF exposure. Immature erythrocytes (IE) frequency demonstrated a decreasing tendency along the BNF experiment and concomitantly with the above ENA response. The present experimental results elect EROD activity in A. anguilla as a useful short- to medium-term biomarker of exposure to both PAH and PAH-like compounds. However, some problems can emerge in the presence of high xenobiotic concentrations. Concerning genotoxicity, it is hypothesized that ENA response depends on different factors such as the exhaustion of the detoxification process, the balance erythropoiesis/erythrocytic catabolism and the DNA repairing capacity.

Alanine Transaminase↗
PubMed2001

In vitro response of fish and mammalian cells to complex mixtures of polychlorinated naphthalenes, polychlorinated biphenyls, and polycyclic aromatic hydrocarbons.

In vitro characterization and comparison of responses to different classes of biologically active compounds can increase the utility of bioassays. In this study, the relative potencies (REPs) of mixtures of polychlorinated naphthalenes (PCNs), polychlorinated biphenyls (PCBs), and polycyclic aromatic hydrocarbons (PAHs), to induce in vitro ethoxyresorufin-O-deethylase (EROD) in PLHC-1 fish hepatoma cells, H4IIE wild type (H4IIE-wt) rat hepatoma cells, and recombinant H4IIE cells (H4IIE-EROD) were determined. The mixtures were also analyzed by in vitro luciferase assay with recombinant H4IIE cells (H4IIE-luc). Halowaxes 1051, 1014, and 1013 caused significant induction in all three H4IIE assays at concentrations less than 10 mg/l, but did not elicit a significant response in the PLHC-1 assay. Based on H4IIE results, the Halowaxes were estimated to have relative potencies (REPs) of approximately 10(-6)-10(-8) relative to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). Less than 5 mg/l of Aroclors 1242, 1248, 1254; Clophens A60, T64; and Chlorofen induced significant responses in the H4IIE assays, while only Clophens A60 and T64 caused a significant response in the PLHC-1 assay. The efficacy of the Aroclor mixtures was generally insufficient to allow for quantitative REP estimates, but, based on their responses in the H4IIE assays, Clophen A60 and Chlorofen were estimated to have REPs of approximately 10(-6) and 10(-7), respectively. A mixture of 16 priority PAHs caused significant induction in all four cell types and was estimated to have a REP of approximately 10(-4). Overall, the results of this study add to a growing database on the dioxin-like potency of complex mixtures of xenobiotics, and suggested that H4IIE-based in vitro bioassays were more sensitive than PLHC-1 cells for detecting dioxin-like activity in complex mixtures.

Animals↗
PubMed2003

Sorption and mass fluxes of sulfonated naphthalene formaldehyde condensates in aquifers.

Sulfonated naphthalene formaldehyde condensates (SNFC) and their monomeric analogues were used as superplasticizers for cement suspension injections at two tunnel construction sites that are in direct contact with groundwater. Because in one case the aquifer is an important drinking water resource, the behavior of SNFC in the groundwater was carefully investigated. Chemical analyses showed that SNFC leached to the groundwater in concentrations of up to 58 microg/l of total SNFC at a distance of about 60 m down-gradient from the construction site. Of the individual SNFC components, only monomers and oligomers with up to four units could be detected in the groundwater. Oligomers with more than four units did not leach from the cement paste. The leached oligomers were transported in the groundwater at different velocities, which can be explained by sorption experiments. Mass fluxes of SNFC used at the tunnel construction sites were evaluated. Most SNFC were immobilized in the cement, but 5% (w/w) of the applied SNFC were found to leach into the aquifer. This corresponds to a total amount of leached SNFC of approximately 100 kg, of which about 80% are biodegraded in the aquifer and 20% (20 kg) still remain in the groundwater.

Biodegradation, Environmental↗
PubMed1986

Mothball composition: three simple tests for distinguishing paradichlorobenzene from naphthalene.

We describe three analytical procedures that can be used to distinguish naphthalene from the less toxic mothball component paradichlorobenzene. An initial presumptive identification can be made by noting the characteristic aroma of the two substances. This can be followed by one of the three analytical tests, each of which is simple to perform, gives an answer in seconds to minutes, and is definitive enough to eliminate the need for costly additional testing at an analytical reference laboratory. These tests have as additional advantages that the endpoints are dramatic and the reagents are commonly available.

Chemistry Techniques, Analytical↗
PubMed2002

Polychlorinated naphthalenes and coplanar polychlorinated biphenyls in beluga whale (Delphinapterus leucas) and ringed seal (Phoca hispida) from the eastern Canadian Arctic.

Blubber collected from beluga whales and ringed seals during subsistence hunts in the southern Baffin Island region of the Canadian Arctic were analysed for polychlorinated naphthalenes and eight planar PCB congeners (mono-ortho PCBs: 105, 114, 118 and 156; non-ortho PCBs: 77, 81, 126, 169). SigmaPCN (3-7 Cl) concentrations in blubber ranged from 35.9-383 pg/g (lipid weight; lw) in beluga and 35.4-71.3 pg/g (lw) in ringed seal. These represent the first measurements of PCNs in marine mammals in the Canadian Arctic, mammals which are an important part of the traditional diet of the indigenous population. SigmaCoplPCB concentrations were much higher, ranging from 15.5-317 ng/g (lw) in beluga whale blubber and 16.5-40.9 ng/g (lw) in ringed seal blubber. PCNs and coplanar PCBs both exhibit dioxin-like toxicity. Although average sigmaPCN concentrations were less than 1% of sigmaCoplPCBs, PCNs contribute up to 11% of TEQ relative to the coplanar PCBs based on TEFs determined by H4IIE enzyme assays.

Adipose Tissue↗
PubMed2003

Flux estimates and sedimentation of polychlorinated naphthalenes in the northern part of the Baltic Sea.

The concentrations and fluxes of polychlorinated naphthalenes (PCNs) were measured in surface sediments, and settling particulate matter collected in sediment traps, at two coastal and two offshore sampling stations in the Gulf of Bothnia, northern Baltic Sea, Sweden. The PCN concentrations (of tetra- to hepta-chloro congeners) in the surface sediments ranged from 0.27 to 2.8 ng/g dry weight and were of the same order of magnitude as background concentrations reported previously in Europe. The PCN fluxes in the southern basin (0.93 and 0.86 microg/m2/year) of the Gulf of Bothnia were higher than those in the northern basin (0.58 and 0.49 microg/m2/year); they were also higher near the coast than in the open sea. These PCN fluxes are similar to the pre-industrial levels determined from lake sediments in northwest England. The PCN homologue distribution changed from a relatively even distribution in samples collected near the coast, to TeCNs dominating in the samples from the open sea. This indicates that higher chlorinated PCNs are deposited and retained in sediments to a higher degree near the coast. The total annual deposition of PCNs in sediments in the Gulf of Bothnia was estimated to be 91 kg/year.

Geologic Sediments↗
PubMed2000

Identification of four structural genes and two putative promoters necessary for utilization of naphthalene, phenanthrene, fluoranthene by Sphingomonas paucimobilis var. EPA505.

Sphingomonas paucimobilis var. EPA505 utilizes fluoranthene (FLA), naphthalene (NAP), and phenanthrene (PHE) as sole carbon sources for energy and growth. A genetic library of EPA505 was constructed using mini-Tn5 promoter reporter genes encoding for tetracycline resistance (tc(p-)) or luminescence (luxAB(p-)). Out of 2250 Tn5 mutants, ten were deficient in utilization of FLA, NAP, and/or PHE as sole carbon sources. Three classes of Tn5 mutants were defined: classI (nap(-)phe(-)fla(-)), classII (nap(-)phe(-)), and classIII (fla(-)). Four of five mutants in classI did not express dioxygenase function, whereas one classI mutant and all classII and classIII mutants retained dioxygenase activity. In Tn5 tc(p-) classI mutants 200 and 394 (dioxygenase negative) and classII mutant 132 (dioxygenase positive), promoter reporter was expressed when induced with FLA, NAP, PHE, other polycyclic aromatic hydrocarbons (PAHs), and several proposed PAH-derived catabolites. The Tn5 tc(p-) derived classIII mutant 104 was induced only with PAHs and not with PAH-derived catabolites. DNA sequence analysis of cloned regions of classI mutant 200 revealed that Tn5 inserted into a gene that shared (96%) DNA sequence homology with 2,3-dihydroxybiphenyl 1,2-dioxygenase that is designated pbhA. Nucleotide sequences downstream of pbhA shared (84%) homology to a Rieske-type ferredoxin subunit gene of a multicomponent dioxygenase designated pbhB. The Tn5 tc(p-) in classII mutant 132 occurred within sequences that shared (74%) homology with a trans-o-hydroxybenzylidene-pyruvate hydratase-aldolase gene (pbhC). Sequence analysis of the region proximal to this gene revealed a putative promoter that contained a binding site for a LysR transcriptional activator. In classIII mutant 104, the Tn5 tc(p-) resided within a region that shared 94% nucleotide homology to that of a pyruvate phosphate dikinase gene known to be involved in cellular uptake of glucose. The FLA-specific catabolic gene disrupted in mutant 104 was designated phbD. Functional and sequence analyses of promoter probe mutants allowed identification of four genes necessary for the utilization of PAHs that are controlled by at least two promoters that are affected by a wide range of aromatic compounds.

Bacterial Proteins↗
PubMed1990

Determination of 4-amino-1-hydroxybutane-1,1-bisphosphonic acid in urine by automated pre-column derivatization with 2,3-naphthalene dicarboxyaldehyde and high-performance liquid chromatography with fluorescence detection.

A sensitive (5 ng/ml) method for the determination of 4-amino-1-hydroxybutane-1,1-bisphosphonic acid in human urine is described. The procedure includes (1) the isolation of the drug from urine by co-precipitation of its calcium salt with endogenous phosphates in the presence of base, (2) a solid-phase anion-exchange sample clean-up and (3) automated pre-column derivatization of the primary amino group with 2,3-naphthalene dicarboxyaldehyde-cyanide reagent followed by fluorescence detection of the N-substituted cyanobenz[f]isoindole derivative. The derivative of the drug was synthesized and its spectral and fluorescence properties were evaluated. The fluorescence quantum efficiency was determined to be 0.82 in the mobile phase used for the assay. The derivative is also capable of accepting energy in an oxalate ester-hydrogen peroxide chemiluminescence system.

Alendronate↗
PubMed1989

Multi-dimensional high-performance liquid chromatography of opioid peptides following pre-column derivatization with naphthalene-2,3-dicarboxaldehyde in the presence of cyanide ion. Preliminary results on the determination of leucine- and methionine-enkephalin-like fluorescence in the striatum region of the rat brain.

The reversed-phase high-performance liquid chromatography of three synthetic opioid peptides, 5leucine-enkephalin, 5methionine-enkephalin and [D-2alanine]-5methionine enkephalin, has been studied after their pre-column fluorogenic derivatization with naphthalene-2,3-dicarboxaldehyde in the presence of cyanide to the corresponding 1-cyanobenz[f]isoindole (CBI) derivatives. The chromatographic properties of the three synthetic CBI-peptides were characterized using three different stationary phases, ODS Hypersil, CPS Hypersil and Spherisorb Phenyl, eluted with mobile phases containing various concentrations of methanol, tetrahydrofuran or acetonitrile in 26 mM trifluoroacetic acid, adjusted to pH 3.5. The data obtained using single chromatographic columns were used to design a multi-dimensional system in which the three synthetic CBI-peptides of interest were transferred as a single fraction from one column to a second. The first column served to separate the peptides from the majority of the material in the samples, and the second column was used to separate the three CBI-peptides from each other. The best separation was achieved in which the first column was Spherisorb Phenyl and the second column was ODS Hypersil. Both columns were eluted with a mobile phase of 45% acetonitrile (v/v) in 26 mM trifluoroacetic acid (pH 3.5) at a flow-rate of 1.0 ml/min. The method has been applied to the determination of leucine- and methionine-enkephalin-like fluorescence in the striatum of the rat brain.

Animals↗
PubMed1997

Selective fluorogenic derivatization of a peptide nucleic acid trimer with naphthalene-2,3-dicarboxaldehyde.

The reversed-phase high-performance liquid chromatography of a Peptide Nucleic Acid (PNA) trimer has been studied after its preseparation fluorogenic derivatization with naphthalene-2,3-dicarboxaldehyde in the presence of cyanide (NDA/CN). Trace levels of the PNA trimer were determined in cell homogenate samples containing the PNA trimer at prederivatization concentrations as low as 48.9 ng ml-1. The sample pretreatment operations included a deproteination step, achieved by ultra-filtration, followed by fluorogenic derivatization (NDA/CN). Subsequently, to achieve adequate selectivity, the fluorescently labeled PNA was subjected to high performance anion exchange chromatography prior to quantitation via fluorescence detection. The various problems encountered during sample pretreatment and separation of derivatized PNA trimer in biological samples are presented and discussed.

Caco-2 Cells↗
PubMed1998

Plasma analysis of alpha-difluoromethylornithine using pre-column derivatization with naphthalene-2,3-dicarboxaldehyde/CN and multidimensional chromatography.

A procedure for the plasma analysis of alpha-difluoromethylornithine (DFMO) has been developed that utilizes pre-column derivatization with naphthalene-2,3-dicarboxaldehyde/cyanide (NDA/CN) in pH 9.2 borate buffer. Selective derivatization of delta-amine of DFMO followed by quenching of the reaction results in the formation of a cyanobenz [f] isoindole (CBI) derivative that is stable for 24 h. Plasma was prepared for derivatization by a single step procedure which resulted in an ultrafiltrate compatible with derivatization and analysis. The DFMO derivative (CBI-DFMO) was separated from plasma interferences by multidimensional chromatography with an analysis time of 28 min. The response for DFMO in plasma was linear over the range of 2.1 x 10(-8) 2.1 x 10(-6) M after derivatization. This procedure encompasses a useful linear range and offers the advantages of minimal sample preparation and production of a stable fluorophor.

Chromatography↗