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PubMedDate not supplied

Validation of a terrestrial food chain model.

An increasingly important topic in risk assessment is the estimation of human exposure to environmental pollutants through pathways other than inhalation. The Environmental Protection Agency (EPA) has recently developed a computerized methodology (EPA, 1990) to estimate indirect exposure to toxic pollutants from Municipal Waste Combuster emissions. This methodology estimates health risks from exposure to toxic pollutants from the terrestrial food chain (TFC), soil ingestion, drinking water ingestion, fish ingestion, and dermal absorption via soil and water. Of these, one of the most difficult to estimate is exposure through the food chain. This paper estimates the accuracy of the EPA methodology for estimating food chain contamination. To our knowledge, no data exist on measured concentrations of pollutants in food grown around Municipal Waste Incinerators, and few field-scale studies have been performed on the uptake of pollutants in the food chain. Therefore, to evaluate the EPA methodology, we compare actual measurements of background contaminant levels in food with estimates made using EPA's computerized methodology. Background levels of contaminants in air, water, and soil were used as input to the EPA food chain model to predict background levels of contaminants in food. These predicted values were then compared with the measured background contaminant levels. Comparisons were performed for dioxin, pentachlorophenol, polychlorinated biphenyls, benzene, benzo(a)pyrene, mercury, and lead.

Air Pollutants↗
PubMed2004

Chlorophenols identification in water using an electronic nose and ANNs (artificial neural networks) classification.

Electronic artificial noses are being developed as systems for the automated detection and classification of odours, vapors and gases. In the food industry, such devices are used as aids for quality control or process-monitoring tools. An electronic nose (EN) is generally composed of a chemical sensing system and a pattern recognition system (e.g. artificial neural network). An EN based on a non-specific conducting polymer array was used to monitor chlorophenols in water samples. Operational parameters for the EN were optimized by a Plackett-Burman factorial design. The experimental parameters studied were: sample volume, platen temperature, sample equilibration time, loop fill time, sample pressurization time and injection time. Optimal experimental conditions were applied to chlorophenols determination and differentiation in ultrapure water samples spiked with the EPA listed chlorophenols. Data analysis was carried out using principal component analysis (PCA) and artificial neural networks (ANNs) to predict the chlorophenols presence in water samples. The obtained results showed that it was possible to differentiate the five chlorophenol groups: monochlorophenol, dichlorophenol, trichlorophenol, tetrachlorophenol and pentachlorophenol. Differentiation of chlorophenol groups was based on Mahalanobis distance between the formed clusters. This Mahalanobis distance is designated by the Quality Factor, a value >2 for this quality factor means a good differentiation between the clusters.

Automation↗
PubMedDate not supplied

[Peroxidase oxidation of phenols].

Partially purified preparations of horseradish peroxidase were able to catalyze the effective transformation of such phenol compounds as phenol, o-chlorophenol, 2,4,6-trichlorophenol, pentachlorophenol (giving rise to the formation of polymer products insoluble in water), resorcinol, and thymol (giving rise to the formation of low-molecular-weight products). The following conditions were found to be optimal for peroxidase oxidation and provide the maximum extent of elimination of phenol compounds: temperature, 15-25 and 25-30 degrees C for phenol and chlorophenol compounds, respectively; molar ratio H2O2/phenol, 1:1; and transformation time, 1-3 h. Although effective transformation was observed within a broad range of pH, the efficiency of the process slightly increased at a pH from 6.0 to 7.5. It was suggested to carry out multiple peroxidase oxidations of phenols using partially purified peroxidase enclosed in a dialysis membrane bag placed into a solution of a phenol compound containing hydrogen peroxide.

Catalysis↗
PubMed2005

Quantitative structure-activity relationships for the toxicity of substituted benzenes to Cyprinus carpio.

OBJECTIVE: To measure the 96h-LC50 values of 32 substituted benzenes to the carp and to study the relationship between quantitative structure-activity and structural parameters of chemicals. METHODS: The acute toxicity values of 32 substituted benzenes to the carp were determined in a semistatic test. The energy of the lowest unoccupied molecular orbital, and the highest occupied molecular orbital, the dipole moment and the molecular weight of substituted benzenes were calculated by the quantum chemical method MOPAC6.0. RESULTS: The range of the toxicity of studied compounds was broad, and the most toxic compound was pentachlorophenol, while the least toxic compound was 4-methylaniline. By the stepwise regression analyses, a series of Quantitative structure-activity relationships (QSAR) equations were derived from all compounds and subclasses. The equation log1/LC5o=0.759logP + 2.222 (R2 (adj)=0.818) was found to fit well and the average predicted percentage error was 6.16%. CONCLUSION: The toxicity of anilines and phenols to the carp could be modeled well by logP alone, whereas the toxicity of the halogenated benzenes and nitrobenznes not containing hydroxyl or amino group can be controlled by hydrophobic and electronic factors.

1-Octanol↗
PubMed2005

Simultaneous anaerobic-aerobic biodegradation of halogenated phenolic compound under oxygen-limited conditions.

The successful application of co-immobilized aerobic-anaerobic biomass under limited aeration in wastewater treatment systems would eliminate the problems associated with the intermediates mono-chlorophenol (MCP) and di-chlorophenol(DCP) accumulations. With low initial pentachlorophenol (PCP) concentration, all PCP could be completely removed under oxygen-limited strict anaerobic conditions, and the removal efficiencies with different initial headspace oxygen percentage (IHOP) were not obviously different from each other. While at high initial PCP concentration, under strictly anaerobic conditions PCP and their intermediates were clearly higher than that under other conditions, and produced obvious accumulation, the highest PCP reduction was achieved by the system receiving 30 IHOP, oxygen-limited system also exhibited lower residual TOC concentration and lower concentration of metabolic intermediates MCP and DCP. These results suggested that under strictly anaerobic condition the reductive dechlorination of low chlorinated compounds became rate limiting in the reductive dechlorination pathway, less chlorinated compounds be more amenable to aerobic degradation, and the aerobes of outer layers could function under limited oxygen. The co-immobilized aerobic-anaerobic biomass for methanogenesis under limited-aeration for chlorophenol degradation might be an attractive and efficient alternative for the sequential anaerobic/aerobic system to achieve mineralization of a broad range of recalcitrance highly chlorinated organics and low final TOC concentrations.

Anaerobiosis↗
PubMed2004

Removal of phenol and chlorophenols from water by coir pith carbon: equilibrium and rate studies.

Batch mode studies were conducted to study the removal of phenol, 2,4,6-Trichlorophenol (TCP) and Pentachlorophenol (PCP) from aqueous solution on coir pith carbon by adsorption process under varying experimental conditions such as agitation time, adsorbent dose, pH and temperature. Kinetics of adsorption obeyed second order rate equation and the rate constant was found to be in the range 0.0098-0.0672, 0.0949-0.8801 and 0.172-0.305 g/mg/min for phenol, TCP and PCP respectively. Equilibrium adsorption data follow Langmuir isotherm for phenol and PCP and the adsorption capacities were found to be 48.3 mg and 3.7 mg/g, respectively. For TCP, adsorption followed Freundlich isotherm only. Acidic pH was favorable for the adsorption of all the chlorophenols. Studies on pH effect and desorption show that chemisorption seems to play a major rule in the adsorption process. The positive values of H0 24.99, 18.69, and 8.907 kJ/mol for phenol, TCP and PCP respectively, confirm the endothermic nature of adsorption.

Adsorption↗
PubMed1990

[Organic-chemical air pollutants indoors--aspects of environmental toxicologic evaluation].

Indoor air pollution is characterized by a wide range of concentrations of many, mainly organic substances. To avoid adverse health effects it is necessary to develop indoor air quality standards. Standards should reflect the way and time of exposure and the fact that health risks might be possible especially to sensitive people. The toxicological basis for regulating indoor air quality is discussed. Special attention is given to organic substances with a cancerogenic and accumulating potential. An approach in setting standards of indoor air quality for frequent organic substances like toluene, xylene, styrene, dichloromethane, 1.1.1-trichloroethane, trichloroethene, tetrachloroethene, pentachlorophenol and PCB is presented, incorporating adequate protection margins. The results of this approach are compared with the WHO air quality guidelines and the German MIK values.

Air Pollutants↗
PubMed1985

Ability of several hexachlorobenzene metabolites to induce porphyrin accumulation in chick embryo liver "in ovo".

The present study investigates the ability of several hexachlorobenzene (HCB) metabolites to induce porphyrin accumulation in chick embryo liver cells in ovo, in order to further clarify the role of metabolites in the mechanism of HCB-induced porphyria. HCB per se had no effect on liver porphyrin content, but pretreatment assays with phenobarbital suggested that its metabolic products did. When the direct effect of phenolic, sulfur-containing, and benzenic metabolites of HCB were tested, the following results were obtained. Less chlorinated benzenes (pentachlorobenzene and 1,2,3,4- 1,2,3,5- 1,2,4,5- tetrachlorobenzene) had poor capacity to change the control porphyrin content. On the other hand, the behavior of phenolic metabolites (pentachlorophenol, 2,3,4,5- 2,3,4,6- 2,3,5,6- tetrachlorophenol, 2,3,4- 2,3,5- 2,3,6- 2,4,5- 2,4,6- 3,4,5- trichlorophenol and tetrachlorohydroquinone) as porphyrin inducers was remarkable; the stronger effects were produced by trichlorophenols and tetrachlorohydroquinone. Sulfur containing metabolites produced increases in porphyrin content that were lower than those produced by phenolic compounds and higher than those due to the action of less chlorinated benzenes; only 1-methyl-(2,3,4,5-pentachlorophenyl) sulfoxide was not able to increase porphyrin level. The extent of the effect of the other drugs was pentachlorothiophenol greater than 1-methyl-(2,3,4,5,6-pentachlorophenyl) sulfone greater than tetrachlorothioanisol greater than pentachlorothioanisol. Regarding the mechanism of HCB porphyria, the present results indicate that phenolic metabolites and, in a lower degree, sulfur-containing metabolites, can contribute to the porphyrinogenic ability of HCB.

Animals↗
PubMed1987

Structure-activity studies of the hepatocarcinogenicities of alkenylbenzene derivatives related to estragole and safrole on administration to preweanling male C57BL/6J x C3H/HeJ F1 mice.

Further information on the structure-activity relationships among the synthetic and naturally occurring alkenylbenzene derivatives was obtained by examining their hepatocarcinogenicities for mice following administration of one or a few doses prior to weaning. Under these conditions preweanling male C3H/HeJ mice were more susceptible than male C57BL/6J mice or females of either strain to liver tumor induction by 1'-hydroxyestragole (1'-hydroxy-1-allyl-4-methoxybenzene) and 1'-hydroxysafrole (1'-hydroxy-1-allyl-3,4-methylenedioxybenzene). Male C57BL/6J X C3H/HeJ F1 mice given a single dose of 1'-hydroxyestragole at 12 days of age developed approximately twice as many hepatomas per liver as did those given the same dose per g of body weight at 1 day of age. The acetylenic compounds 1'-hydroxy-2',3'-dehydroestragole and 1'-hydroxy-2',3'-dehydrosafrole were the most potent derivatives studied; they were 5- and 10-fold more potent (based on the average numbers of hepatomas per liver) than the corresponding allylic benzene derivatives. 1'-Acetoxyestragole and 1'-acetoxysafrole had activities similar to those of their respective 1'-hydroxy derivatives; estragole derivatives were consistently 2- to 3-fold more potent than the related safrole derivatives. 1'-Hydroxyelemicin (1'-hydroxy-1-allyl-3,4,5-trimethoxybenzene), its acetic acid ester 1'-oxoestragole, and 3'-bromo-trans-anethole (3'-bromo-1-trans-propenyl-4-methoxybenzene) each had very weak, but statistically significant, hepatocarcinogenic activity. The propenylic derivatives cis-anethole, trans-isosafrole, 1:1 cis,trans-isosafrole, 3'-hydroxy-trans-anethole, piperine, and trans-cinnamaldehyde showed no hepatocarcinogenic activity at the levels examined. In contrast, the propenylic derivatives cis- and trans-asarone (1-propenyl-2,4,5-trimethoxybenzene) were each active; the hepatocarcinogenicities of the asarones were not inhibited by prior administration of pentachlorophenol, a sulfotransferase inhibitor that abolished the hepatocarcinogenicity of estragole under the same conditions. Furthermore, precocene II (6,7-dimethoxy-2,2-dimethyl-2H-1-benzopyran), a cyclic propenylic plant metabolite and asarone analogue, showed strong hepatocarcinogenic activity similar to that of 1'-hydroxy-2',3'-dehydroestragole and 1'-hydroxy-2',3'-dehydrosafrole; precocene I (the 7-methoxy analogue of precocene II) was less active than precocene II but more active than cis-asarone.

Age Factors↗
PubMed1987

[Stimulation by quinones of cyanide-resistant respiration in rat liver and heart mitochondria].

It was shown that hydrophilic benzo- and naphthoquinones stimulate the cyanide-resistant respiration in liver and muscle mitochondria when succinate or NADH and glutamate or malate are used as oxidation substrates. The substrate-dependent oxygen uptake in the presence of cyanide is initiated by menadione, vicasol, 1.2-naphthoquinone, coenzyme Q0 and duroquinone. Rotenone and antimycin A do not inhibit the cyanide-resistant respiration. Oxidation of glutamate and malate in the course of CN-resistant respiration is inhibited by ortho- and bathophenanthroline and p-chloromercurybenzoate, whereas succinate oxidation by tenoyltrifluoroacetone, carboxin and pentachlorophenol. Superoxide dismutase, Cu2+ and catalase inhibit the CN-resistant respiration in the presence of quinones. Addition of catalase to the experimental cell causes O2 release.

Animals↗
PubMed1986

Ability of several hexachlorobenzene metabolites to decrease rat-liver porphyrinogen carboxy-lyase and to produce porphyrin accumulation in chick-embryo liver.

Since hexachlorobenzene (HCB) action seems to be mediated through its metabolites, this study aimed to identify the metabolites and account for the HCB action by evaluating the ability of several of them to inhibit normal rat-liver porphyrinogen carboxy-lyase in vitro and to produce porphyrin accumulation in chick-embryo liver in ovo. Only three of the 11 metabolites assayed produced significant inhibitory effects at 10(-3) M concentration, the order being tetrachlorohydroquinone greater than pentachlorophenol much greater than pentachlorothiophenol. At concentrations below 10(-4) M tetrachlorohydroquinone did not inhibit the enzyme. Most of the metabolites assayed produced porphyrin accumulation, in the following order of strength: chlorophenols greater than chlorothiophenols greater than chlorobenzenes. Phenolic metabolites, therefore, not only produce the greatest amounts of porphyrin accumulation in the liver of the chick embryo but are also the strongest of the metabolite inhibitors of porphyrinogen carboxy-lyase in rat liver. It is possible that they decrease enzymatic activity by binding to the enzyme. This paper discusses the implications of these results for the mechanism of HCB porphyria induction.

Animals↗
PubMedDate not supplied

Determination of halogenated phenols in raw and potable water by selected ion gas chromatography-mass spectrometry.

Pentafluorobenzylation and in situ acetylation are compared in the determination of phenol and halogenated phenols in water samples. The latter technique is considered superior to the former for determining phenols at the ng/L level because of less background interference and better recoveries (80% or better except for pentachlorophenol and trichloroguaiacol which had recoveries of about 60%). Further evaluation of the in situ technique by electron capture gas chromatography and gas chromatography-mass spectrometry shows that the latter, in the selected ion monitoring mode, is more suitable because, unlike GC-ECD, it can confirm and quantitate all phenols. In particular, GC-ECD could not detect even high levels of phenol and the monohalogenated phenols. Phenols at 5-473 ng/L were detected in some Canadian drinking water supplies by the in situ acetylation technique combined with GC-MS.

Gas Chromatography-Mass Spectrometry↗
PubMedDate not supplied

Halogenated phenols in water at forty Canadian potable water treatment facilities.

Samples of raw and treated water were collected once in each of 3 seasons at 40 potable water treatment plants across Canada and were analyzed for phenol and 33 halogenated phenolic compounds including chlorophenols, bromophenols, bromochlorophenols, and chloroguaiacols. Eighteen of the compounds were not found at any treatment plant; phenol and each of the remaining halogenated phenols were found in at least 1 sample. Pentachlorophenol was the only halogenated phenolic compound found in more than 20% of the raw water samples in the fall and winter samples at levels up to 53 ng/L with mean values of 1.9 and 2.8 ng/L, respectively. No halogenated phenols were detected in raw water summer samples. The halogenated phenols found most frequently in treated water samples were 4-chloro-, 2,4-dichloro-, 2,4,6-trichloro-, and bromodichlorophenols. Mean values were less than 15 ng/L and maximum values seldom exceeded 100 ng/L. Most of the positive values for the treated water samples were found at 8 of the 40 treatment plants but no correlations could be found between halogenated phenol levels and raw water type, treatment process, or chemical dosages.

Canada↗
PubMed1977

Mutants of Bacillus megaterium resistant to uncouplers of oxidative phosphorylation.

Mutants of Bacillus megaterium displaying malate-stimulated ATP synthesis resistant to uncouplers of oxidative phosphorylation were isolated and partially characterized. ATP synthesis in such mutants was resistant to carbonyl cyanide m-chlorophenyl hydrazone as well as to other uncouplers including 2,4-dinitrophenol, pentachlorophenol, and sodium azide. ATP synthesis in the wild type and in resistant mutants was sensitive to N,N'-dicyclohexylcarbodiimide, tributyltin, valinomycin plus potassium, and potassium cyanide. Active transport of glycine and glutamine which are sensitive to uncouplers in the wild type was also uncoupler-sensitive in the mutants.

Adenosine Triphosphate↗
PubMed1979

[Two sites of ubisemiquinone binding in mitochondrial succinate oxidase].

The inhibiting effects of several phenol compounds on electron transfer in the respiratory chain of submitochondrial particles were studied. It was shown that the terminal part of the succinate dehydrogenase complex contains a site, which specifically binds the negatively charged phenols (e. g. pentachlorophenol, 2,4-dibromophenol, 2-methoxy-4,6-dibromophenol). The efficiency of the inhibitor anion binding by this site is increased 12-fold after introduction of a methoxy-group into the o-position of 2,4-dibromophenol. Since this site binds both methoxy- and negatively charged phenol groups, it can also act as a possible site of ubisemiquinone interaction with succinate dehydrogenase. Based on the structural similiarity of the b-c1 complex inhibitors, e. g. antimycin, o-hydroxybenzoic acid amides, 2-hydroxy-3-alkyl-1,4-quinones, and ubisemiquinone, an assumption has been made on possible ubisemiquinone binding between cytochromes b and c1. A structural analysis of phenols inhibiting succinate dehydrogenase and the b-c1 complex revealed that in the region between cytochromes b and c1 there act only the inhimitors which contain: a) a negatively charged phenol group; b) a group comprising a heteroatom with an undepleted electron pair and which can act as a ligand, and c) a hydrophobic residue.

Animals↗
PubMed1980

[Dynamics of hexachlorobenzene residues in meat and eggs from chickens].

In a feeding experiment with poultry a more than twofold cumulation of hexachlorobenzene (HCB) in eggs and in meat and a 7.5-fold cumulation in fat, in comparison with the concentration in the feed, have been demonstrated. With the aid of a combined identification by gas chromatography (before and after a conversion into anisole derivatives) and by thin layer chromatography the presence of pentachlorophenol in the liver, in fat and in muscles after feeding the birds with HCB as well as BHC-isomers has been proved. 2,4,6-trichlorophenol and 2,4-dichlorophenol were found by thin layer chromtography (without derivatisation). While 2,4,6-trichlorophenol was found after feeding with HCB only, 1,2,4,5-tetrachlorobenzene has been demonstrated by gas chromatography after feeding with HCB as well as with BHC-isomers.

Adipose Tissue↗
PubMed1984

[Experimental porphyria induced by chlorinated hydrocarbons. Studies of porphyrinogen carboxy-lyase in the experimental model of human cutaneous delayed porphyria].

The present work tries to elucidate if the strong decrease of porphyrinogen carboxy-lyase (PCL) observed in the experimental porphyria caused by hexachlorobenzene (HCB) is due to the presence of an inhibitor or to a modification of the protein structure of the enzyme. For this purpose: a) cross-assays and heating ones were performed in order to look for the existence of a compound, that present in porphyric animals, would be responsible for the decrease of PCL activity found in them; b) the effect in vitro of HCB, HCB metabolites and other related compounds was studied to find the inhibitor of PCL activity and to look for a relation structure-inhibitory effect; c) hepatic PCL from porphyric and normal rats was purified, and enzyme properties were comparatively studied looking for structural differences between the enzymes obtained from both animal lots. The results indicate that: a) the heat deproteinized porphyric liver preparation produces an inhibition on the normal preparation, but it is smaller than the decrease produced in vivo by the HCB on this enzyme activity, thus other reasons may explain this behavior of PCL in intoxicated animals; b) the HCB had no effect on PCL activity, the phenolic compounds exhibited inhibitions of variable extent that were increased by the presence of electrophilic substituents on the benzenic ring. Pentachlorophenol, the main HCB metabolite, produced inhibition in the in vitro assays, but at doses that were not physiologically significant; thus, it seems not to be the inhibitor found in the heating assays; c) purification of 110 times for the hepatic PCL of both porphyric and normal rats was obtained. Incubation conditions, the effect of salts and chelating agents, the chromatographic behavior in DEAE-cellulose and Sephadex G-100 columns, were comparatively studied with both enzymatic preparations. The effect of sodium diethyldithiocarbamate, sodium pyrophosphate, dithiothreitol, temperature, pH and O2, as well as the chromatographic behavior, would suggest that structural differences in the PCL of porphyric animals may exist; the presence of a thermostable inhibitor could also contribute to the decrease of PCL activity due to HCB.

Animals↗
PubMed1984

A review of chlorinated phenols.

The chlorinated phenols are a group of 19 isomers composed of phenol with substituted chlorines. These chemicals are readily soluble in organic solvents but only slightly soluble in water, except for the chlorophenate salts. Chlorophenols with less than 3 chlorines are not used extensively except in the production of higher chlorophenols and chlorophenyloxyacetic acid herbicides. Pentachlorophenol and some tetrachlorophenols are used worldwide, primarily as wood preservatives or fungicides. Residues of chlorophenols have been found worldwide in soil, water and air samples, in food products, and in human and animal tissues and body fluids. Environmental contamination with these chemicals occurs from industrial effluents, agricultural runoff, breakdown of chlorophenyloxyacetic acid herbicides and hexachlorobenzene, and from spontaneous formation following chlorination of water for disinfection and deodorization. The acute toxicity of these chemicals is relatively low and little is known concerning their chronic effects. Chlorophenols have not been shown conclusively to be mutagens, teratogens or carcinogens. However, these compounds may act as promotors or cocarcinogens and the immune system is particularly sensitive to their toxic effects. Transplacental exposure to chlorophenols may result in embryotoxicity and abortion. The major mode of toxic action is as uncouplers of oxidative phosphorylation. The toxicity of chlorophenols decreases with decreasing chlorination. These chemicals are mild hepatotoxins and are stored mainly in hepatic and renal tissues. Chlorophenols are readily absorbed from the gastrointestinal tract and excreted fairly rapidly via the urine. The acute oral LD50 in various species of animals ranges from 10-4000 mg/kg. Strict standards for acceptable residues of these chemicals in the environment have not been established.

Animals↗