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PubMed1994

Patterns of sensitivity to cadmium and pentachlorophenol among nematode species from different taxonomic and ecological groups.

The variation of acute toxicity data among nematode species belonging to different taxonomic and ecological groups was investigated. Twelve different nematode species were extracted from the soil and directly exposed to cadmium and pentachlorophenol. LC50-values were estimated after 24, 48, 72, and 96 h of exposure in aqueous solutions. The species exhibited large differences in sensitivity. LC50-values (72 h) for pentachlorophenol ranged from 0.5 to more than 34.5 mumol/L and for cadmium from 29 to more than 800 mumol/L. These toxicity data could be described by a log-logistic distribution function. LC50-values for cadmium were not correlated with those for pentachlorophenol. Species of the subphylum Secernentia were less sensitive to pentachlorophenol than species of the subphylum Penetrantia, while no differences were observed for cadmium. In addition, no relationship was found between toxicity data and life-history strategies. Slow colonizers (K-strategists, sensu lato) were not more sensitive to cadmium and pentachlorophenol than opportunistic species (r-strategists, sensu lato). Nematodes appeared to be as sensitive to pentachlorophenol as other soil invertebrates. Nematodes were generally tolerant to cadmium.

Animals↗
PubMed1978

Metabolism of pentachlorophenol in vivo and in vitro.

Pentachlorophenol has earlier been shown to be metabolized in mammals to tetrachloro-p-hydroquinone. The metabolite possesses pronounced inhibitory activity on bacterial beta-glucuronidase but not on beta-glucuronidase from liver. Indirect evidence for the occurrence of both pentachlorophenol and tetrachloro-p-hydroquinone as conjugates with glucuronic acid in the urine from pentachlorophenol-treated rats is now presented. Bovine liver beta-glucuronidase has been utlizied to split the conjugates present. The in vivo metabolism of pentachlorophenol has also been studied in rats treated with phenobarbital and beta-diethylaminoethylidiphenyl propylacetate (SKF 525-A). In vitro metabolism has been studied using liver microsomes from rats pretreated with pehnobarbital. Quantitative analysis of the compounds occurring in extracts of urine or extracts from the microsomal incubates was performed by means of mass fragmentography. Pretreatment with phenobarbital increased the metabolism of pentachlorophenol to tetrachloro-p-hydroquinone both in vivo and in vitro. SKF 525-A, however, inhibited the metabolism in vitro but enhanced the metabolism in vivo when given less frequently than every 6th h. Dechlorination of pentachlorophenol is mediated by microsomal enzymes that can be induced by phenobarbital. SKF 525-A does not inhibit the dechlorination in vivo but does so in vitro.

Animals↗
PubMedDate not supplied

Determining pentachlorophenol in body fluids by gas chromatography after acetylation.

A sensitive, precise, and accurate method for rapidly analyzing body fluids for pentachlorophenol has been developed. The method includes acidification and extraction of the fluid with hexane. The extract is reacted with acetic anhydride, washed with buffer, and injected into a gas chromatograph fitted with an electron capture detector. Quantitation of the pentachlorophenol is based on the ratio of the peak height of pentachlorophenyl acetate to an internal standard, tribromophenyl acetate. The lower detection limit in urine or serum is 1-2 parts per billion. The method was applied to workers in pentachlorophenol formulating plants and to residents of pentachlorophenol treated log houses. Hydrolysis increased the yield of determined urinary pentachlorophenol by a factor of approximately 1.8. Serum levels of pentachlorophenol were 2-3 time higher than the corresponding whole blood levels.

Acetylation↗
PubMed1993

[The place of pentachlorophenol in general medicinal practice].

Pentachlorophenol is a substance whose widespread use has led to substantial environmental contamination. Causing local irritations the pentachlorophenol can be absorbed into the body by all the routes of occupational exposure. The acute pentachlorophenol intoxication is dangerous for the life: its quick diagnose and adequate therapy is very important. Chronic high pentachlorophenol exposure may increase the incidence of several diseases, eg. immunodeficiency, blood disorders, hepatic lesions and malignancies. The prevalence of alcoholism in working places applying pentachlorophenol is between 6 and 10 per cent, so the general practitioner of these workers should take precautions to distinguish between of drunkenness and acute pentachlorophenol intoxication.

Air Pollutants, Occupational↗
PubMed1999

The role of the Sphingomonas species UG30 pentachlorophenol-4-monooxygenase in p-nitrophenol degradation.

Pentachlorophenol-4-monooxygenase is an aromatic flavoprotein monooxygenase which hydroxylates pentachlorophenol and a wide range of polyhalogenated phenols at their para position. The PCP-degrading Sphingomonas species UG30 was recently shown to mineralize p-nitrophenol. In this study, the UG30 pcpB gene encoding the pentachlorophenol-4-monooxygenase gene was cloned for use to study its potential role in p-nitrophenol degradation. The UG30 pcpB gene consists of 1614 bp with a predicted translational product of 538 amino acids and a molecular mass of 59,933 Da. The primary sequence of pentachlorophenol-4-monooxygenase contained a highly conserved FAD binding site at its N-terminus associated with a beta alpha beta fold. UG30 has been shown previously to convert p-nitrophenol to 4-nitrocatechol. We observed that pentachlorophenol-4-monooxygenase catalyzed the hydroxylation of 4-nitrocatechol to 1,2,4-benzenetriol. About 31.2% of the nitro substituent of 4-nitrocatechol (initial concentration of 200 microM) was cleaved to yield nitrite over 2 h, indicating that the enzyme may be involved in the second step of p-nitrophenol degradation. The enzyme also hydroxylated p-nitrophenol at the para position, but only to a very slight extent. Our results confirm that pentachlorophenol-4-monooxygenase is not the primary enzyme in the initial step of p-nitrophenol metabolism by UG30.

Biodegradation, Environmental↗
PubMed2003

Application of microscopic fungi isolated from polluted industrial areas for polycyclic aromatic hydrocarbons and pentachlorophenol reduction.

The growth abilities of fifteen fungal strains isolated from contaminated areas, in the presence of xenobiotics compounds mixture (overworked cutting fluid, crude and waste oil) were examined. Strains with the richest growth were chosen for anthracene, phenanthrene and pentachlorophenol biodegradation in Sabouraud medium (with initial xenobiotic concentration 250 mg/l in cultures with polycyclic aromatic hydrocarbons and 10 mg/l for the chlorinated substrate). Strains IM 1063 and IM 6325 were able to attack phenanthrene forming its derivative 9-phenanthrenol with the yields 5.22 mg/l and 2.82 mg/l, respectively. Strain IM 1063 and IM 6325 transformed pentachlorophenol to an intermediate compound--pentachloromethoxybenzene. Final content of pentachloromethoxybenzene reached 3.46 mg/l and 3.2 mg/l, respectively. Strain IM 6203 (contrary to other strains) released an intermediate product of pentachlorophenol metabolism--2,3,5,6-tetrachlorohydroquinone (8.73 mg/l substrate remaining and 1.2 mg/l 2,3,5,6-tetrachlorohydroquinone forming). The IM 6203 strain was identified as Mucor ramosissimus. The chlorinated pesticide degradation by M. ramosissimus was improved significantly on a medium with overworked oil. Only 8.3% of pentachlorophenol and 4.3% of 2,3,5,6-tetrachlorohydroquinone in relation to the introduced substrate (10 mg/l) were found, after 7 days of incubation. The growth of M. ramosissimus on medium with overworked oil in pentachlorophenol presence was associated with oil emulgation, which enhanced fungal growth and the pesticide degradation.

Biodegradation, Environmental↗
PubMedDate not supplied

Impaired in-vitro lymphocyte responses in patients with elevated pentachlorophenol (PCP) blood levels.

Immune parameters were examined in 188 patients who were exposed for more than 6 mo to pentachlorophenol-containing pesticides. Blood levels of pentachlorophenol, lymphocyte subpopulations, in-vitro responses to mitogenic and allogeneic stimulation, plasma neopterin levels, and plasma cytokine and cytokine receptor levels were determined. Impaired in-vitro lymphocyte stimulation responses were impaired in 65% of the patients. The likelihood of impaired lymphocyte stimulation increased significantly with levels of pentachlorophenol that exceeded 10 microliters/l (p < .05). Patients who had high blood levels of pentachlorophenol and abnormal lymphocyte stimulation also had increased proportions of blood monocytes in blood (p < .05), as well as increased IL-8 serum levels (p < .02). Eleven patients who had abnormal mitogen stimulation experienced decreased CD4/CD8 ratios of < 1.0; 5 of these patients had decreased CD4+ lymphocyte counts of < 500/microliters, and 3 patients had increased plasma neopterin of > 15 nmol/l. These results indicate that increased levels of pentachlorophenol in blood can lead to severe T lymphocyte dysfunction.

Adolescent↗
PubMed1994

Strong intensification of mouse hepatic tamoxifen DNA adduct formation by pretreatment with the sulfotransferase inhibitor and ubiquitous environmental pollutant pentachlorophenol.

Although negative in assays for mutagenicity, the clinically important antiestrogen tamoxifen induces hepatic DNA adduct formation in mice, rats and hamsters, as indicated by 32P-postlabeling, and is a potent hepatocarcinogen in rats. Both phenolic and alcoholic metabolites of tamoxifen have been reported. As these metabolites are potential candidates for sulfate conjugation, we examined whether the sulfotransferase inhibitor pentachlorophenol, a ubiquitous environmental contaminant, modulates hepatic tamoxifen adduct formation in vivo. Female ICR mice were given tamoxifen (45 mg/kg) daily per os for up to 4 days, with and without i.p. pretreatment with pentachlorophenol (20 mg/kg) 1 h before dosing with tamoxifen. At days 1, 2 and 4, liver DNA was analyzed 5 h after tamoxifen administration by a modified monophosphate version of the 32P-postlabeling assay. At day 4, pentachlorophenol pretreatment led to a large increase (13- to 17-fold) of the levels of four tamoxifen adduct fractions, while two adducts appeared unaffected, resulting in an approximately 7-fold enhancement of overall adduct formation. Significant pentachlorophenol related increases were also observed at day 1 and day 2. The mechanism of this effect has not yet been determined, but may involve the inhibition of sulfation of a tamoxifen metabolite(s) involved in the detoxication of the drug to nonelectrophilic derivatives. It was also apparent that there are two pathways of metabolic activation of tamoxifen, one being sensitive and the other resistant to pentachlorophenol.

Animals↗
PubMed1976

Dinitrophenol, dicoumarol and pentachlorophenol as inhibitors and parasite substrates in the ATP phosphoribosyltransferase reaction.

Adenosine-triphosphate phosphoribosyltransferase from Escherichia coli is inhibited by dicoumarol and pentachlorophenol in competition with ATP. Ki was approximately 60 muM for dicoumarol and 50 muM for pentachlorophenol. Carbonylcyanide m-chlorphenylhydrazine did not seem to have any kinetic effect. Dicoumarol is bound to the extent of 6 sites per enzyme hexamer with a dissociation constant Kd of 50 muM. Dicoumarol and pentachlorophenol partly prevent the binding of ATP and AMP to the transferase. The reverse reaction is inhibited by dicoumarol and pentachlorophenol without changes in [s]0.5 for phosphoribostladenosine trophosphate. Dicumarol, dinitrophenol and pentachlorophenol diminish the yield of phosphoribosyladenosine triphosphate in the transferase reaction apparently by acting as parasite substrates; carbonylcyanide m-chlorophenylhydrazone had no effect.

ATP Phosphoribosyltransferase↗
PubMed1992

Reductive dechlorination of chlorophenols by a pentachlorophenol- acclimated methanogenic consortium.

Anaerobic digester sludge fed 5,300 mg of acetate per liter, 3.4 microM pentachlorophenol, and nutrients for 10 days biotransformed pentachlorophenol by sequential ortho dechlorinations to produce 2,3,4,5-tetrachlorophenol and 3,4,5-trichlorophenol. Upon acclimation to 3.4 microM pentachlorophenol for 6 months, the methanogenic consortium removed chlorines from the ortho, meta, and para positions of pentachlorophenol and its reductive dechlorination products. Pentachlorophenol was degraded to produce 2,3,4,5-tetrachlorophenol, 2,3,4,6-tetrachlorophenol, and 2,3,5,6-tetrachlorophenol. Dechlorination of 2,3,4,5-tetrachlorophenol produced 3,4,5-trichlorophenol, which was subsequently degraded to produce 3,4-dichlorophenol and 3,5-dichlorophenol. 2,3,4,6-Tetrachlorophenol was dechlorinated at the ortho and meta positions to produce 2,4,6-trichlorophenol and 2,4,5-trichlorophenol. 2,3,5,6-Tetrachlorophenol yielded 2,3,5-trichlorophenol, followed by production of 3,5-dichlorophenol. 2,4,6-Trichlorophenol was degraded to form 2,4-dichlorophenol, and 2,4,5-trichlorophenol was dechlorinated at two positions to form 2,4-dichlorophenol and 3,4-dichlorophenol. Of the three dichlorophenols produced (2,4-dichlorophenol, 3,4-dichlorophenol, and 3,5-dichlorophenol), only 2,4-dichlorophenol was degraded significantly within 3 weeks, to produce 4-chlorophenol.

Adaptation, Physiological↗
PubMed2001

Effects of Cu2+, Ni2+, Pb2+, Zn2+ and pentachlorophenol on photosynthesis and motility in Chlamydomonas reinhardtii in short-term exposure experiments.

BACKGROUND: Heavy metals, especially copper, nickel, lead and zinc, have adverse effects on terrestrial and in aquatic environments. However, their impact can vary depending on the nature of organisms. Taking into account the ability of heavy metals to accumulate in sediments, extended knowledge of their effects on aquatic biota is needed. In this context the use of model organisms (often unicellular), which allows for rapid assessment of pollutants in freshwater, can be of advantage. Pentachlorophenol has been extensively used for decades as a bleaching agent by pulp- and paper industry. Pentachlorophenol tends to accumulate in the nature. We aim to determine if photosynthesis and motility can be used as sensitive physiological parameters in toxicological studies of Chlamydomonas reinhardtii, a motile green unicellular alga. It is discussed if photosynthesis and motility can be used as sensitive physiological parameters in toxicological studies. RESULTS: The concentrations studied ranged from 0.1 to 2.0 mg l-1 for copper, nickel, lead and zinc, and from 0.1 to 10.0 mg l-1 for pentachlorophenol. Exposure time was set to 24 h. Copper and pentachlorophenol turned out to be especially toxic for photosynthetic efficiency (PE) in C. reinhardtii. CONCLUSION: Copper and pentachlorophenol turned out to be especially toxic for PE in C. reinhardtii. Zinc has been concluded to be moderately toxic while nickel and lead had stimulatory effects on the PE. Because of high variance, motility was not considered a reliable physiological parameter when assessing toxicity of the substances using C. reinhardtii.

Animals↗
PubMed1999

Reproductive and endocrine function in rams exposed to the organochlorine pesticides lindane and pentachlorophenol from conception.

There is controversy over the potential endocrine modulating influence of pesticides, particularly during sensitive phases of development. In this study, ram lambs were exposed to lindane and pentachlorophenol from conception to necropsy at 28 weeks of age. The rams (and their mothers) were given untreated feed (n = 7) or feed treated with 1 mg kg-1 body weight per day of lindane (n = 12) or pentachlorophenol (n = 5). Semen was collected from 19 weeks onwards and reproductive behaviour was tested at 26 weeks. Serum was collected every 2 weeks and at 27 weeks every 15 min for 6 h during both day and night, and for 1 h before and 5 h after stimulation with GnRH, adrenocorticotrophic hormone and thyroid-stimulating hormone. The pesticides did not affect body weight and ejaculate characteristics, or cause overt toxicity. In pentachlorophenol-treated rams, scrotal circumference was increased. However, seminiferous tubule atrophy was more severe and epididymal sperm density was reduced in comparison with untreated rams at necropsy (P < 0.05). Thyroxine concentrations were lower in pentachlorophenol-treated rams than in untreated rams (P < 0.05). However, after thyroid-stimulating hormone treatment, the thyroxine response was unaltered. Reproductive behaviour was reduced in lindane-treated rams compared with control rams (P < 0.05). Serum LH and oestradiol concentrations during reproductive development, LH pulse frequency at 27 weeks and testosterone secretion after GnRH treatment were lower in lindane-treated rams than in untreated rams (P < 0.05). In summary, the effects of pentachlorophenol on the testis may be linked to a decrease in thyroxine concentrations, and reduced reproductive behaviour in lindane-treated rams may be related to decreased LH, oestradiol and testosterone concentrations.

Animals↗
PubMed2006

[Fluorescence quench of bovine serum albumin by pentachlorophenol].

The interaction between pentachlorophenol and bovine serum albumin (BSA) were studied using fluorescence spectra and ultraviolet-visible light absorption spectra. The results show that the fluorescence of BSA was quenched regularly by the pentachlorophenol, the mechanism of the fluorescence quench was investigated. The binding constants and thermodynamic parameters of pentachlorophenol with BSA were obtained at different temperatures. The hydrophobic interaction force and electrostatic force played a main role in the binding of pentachlorophenol with BSA. The distances of binding site between pentachlorophenol and BSA were also obtained according to the theory of Forster's non-radiative energy transfer.

Animals↗
PubMed1985

Uptake, translocation, and transformation of pentachlorophenol in soybean and spinach plants.

Soybean plants were grown for 90 days and spinach plants for 64 days in a mixture of sterilized greenhouse soil and sand containing 10 ppm pentachlorophenol. All plant parts and soil samples were extracted and separated into nonpolar and polar fractions. Major nonpolar and polar metabolites were identified by gas-liquid chromatography and mass spectrometry. Nonpolar fractions from both soybean and spinach plants were found to contain pentachlorophenol and its metabolites, 2,3,4,6-tetrachlorophenol, methoxytetrachlorophenol, 2,3,4,6-tetrachloroanisole, and pentachloroanisole. Cleavage of polar metabolites from the soybean plants by acid hydrolysis yielded organic solvent-extractable products. These products were identified as pentachlorophenol, 2,3,4,6-tetrachlorophenol, and methoxytetrachlorophenol. Cleavage of polar materials from spinach plants yielded only pentachlorophenol. The polar metabolites from the soybean plants were also subjected to enzymatic cleavage by beta-glucosidase. The conjugates consisted mostly of O-glucosides of the same metabolites released by acid hydrolysis. Failure of hydrolysis by aryl sulfatase indicated that very little or no sulfates were present. The metabolites found in the plants were not detected in soil samples obtained from pots immediately after the plants were harvested.

Biotransformation↗
PubMed2005

Cytotoxic effects in mammalian Vero cells exposed to pentachlorophenol.

The effects of pentachlorophenol have been studied on diverse biological systems both in vivo and in vitro, however the cellular basis of the pronounced cytotoxicity of this organochlorine compound is poorly understood. In this work, morphological and biochemical analyses were carried out to identify the primary targets of pentachlorophenol toxicity in mammalian cells. Our results show that pentachlorophenol is a very potent cytotoxic drug that displays an unusual and interesting mode of action in Vero cells. Although this compound is a powerful uncoupler of oxidative phosphorylation, we present the novel finding that lysosome destabilization is an early cytotoxic response that precedes the mitochondrial dysfunction. In addition, soon after exposure to moderate doses of pentachlorophenol, a significant number of cells initiate an apoptotic death process identified by the condensed and fragmented state of their nuclei. These results demonstrate that there are multiple potential targets of PCP-induced toxicity in mammalian cells, and the need to develop further experimental studies for the risk assessment of this environmental pollutant.

Animals↗
PubMed2005

Comparison of enhancement of pentachlorophenol sonolysis at 20 kHz by dual-frequency sonication.

The comparison of enhancement effect of pentachlorophenol sonolysis at 20 kHz by different dual-frequency ultrasonic irradiations has been investigated. Dual-frequency (20 kHz/40 kHz, 20 kHz/530 kHz, 20 kHz/800 kHz and 20 kHz/1040 kHz) ultrasounds have been used. It has been found that the rate of pentachlorophenol degradation at dual-frequency ultrasonic irradiation is the highest compared to mono-frequency ultrasonic systems. The combination of dual-frequency systems has synergistic effect and the enhancement effect of sonochemical degradation of pentachlorophenol at 20 kHz by dual-frequency systems appears to be remarkable frequency sensitive. The order of contribution to the enhancement effect of sonochemical degradation of pentachlorophenol at 20 kHz is as follows: 530 kHz > 800 kHz > 40 kHz > 1040 kHz.

Hot Temperature↗
PubMed2000

Pressurised liquid extraction of pentachlorophenol from dyestuffs and cotton.

Pressurised liquid extraction (PLE) was used to extract pentachlorophenol from cotton and dyestuffs. Five dyes and one dyed cotton were investigated for pentachlorophenol. The dyed cotton was found to have between 5.3 and 5.9 microg g(-1) pentachlorophenol, while the dyes were found to have between 42 and 2569 microg g(-1) pentachlorophenol present. The latter were found to be dye and manufacturing site dependant. Recovery experiments, in all cases, were found to be quantitative indicating appropriate sample work-up and manipulations.

Coloring Agents↗
PubMed1984

Hepatic macromolecular covalent binding of the hepatocarcinogen 2,6-dinitrotoluene and its 2,4-isomer in vivo: modulation by the sulfotransferase inhibitors pentachlorophenol and 2,6-dichloro-4-nitrophenol.

The sulfotransferase inhibitors 2,6-dichloro-4-nitrophenol and pentachlorophenol were used to investigate the role of sulfate ester formation during the in vivo bioactivation of 2,4- and 2,6-dinitrotoluene (DNT). Male F-344 rats were administered one of the sulfotransferase inhibitors (40 mu mol/kg i.p.) 45 min prior to oral administration of 28 mg/kg [ring-14C]-2,4-DNT or [3-3H]-2,6-DNT and killed 12 h later. Pentachlorophenol had no significant effect on the urinary excretion of the benzyl glucuronide or benzoic acid metabolites of 2,6-DNT. The sulfotransferase inhibitors decreased the total hepatic macromolecular covalent binding of 2,4-DNT by 33%, and of 2,6-DNT by 69%. Purification of hepatic DNA by hydroxylapatite chromatography indicated covalent binding of 2,4- and 2,6-DNT at levels of 45 and 94 pmol equivalents/mg DNA, respectively. The sulfotransferase inhibitors decreased the binding of the hepatocarcinogen 2,6-DNT to hepatic DNA by greater than 95%. 2,6-Dichloro-4-nitrophenol decreased the binding of 2,4-DNT to DNA by greater than 84% while the decrease due to pentachlorophenol was 33%. These results suggest that sulfation is important in the biotransformation of 2,4- and 2,6-DNT to reactive metabolites which covalently bind to DNA. 3H2O was detected in the urine of rats administered [3-3H]-2,6-DNT. Pentachlorophenol decreased 3H2O formation to the same extent as it decreased the total hepatic macromolecular covalent binding of 2,6-DNT, suggesting that 3H exchange at the 3 position of 2,6-DNT occurs following sulfate ester formation. These results are consistent with a nitrenium-carbonium ion resonance of the sulfate ester-derived reactive intermediate of 2,6-DNT.

Animals↗