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PubMed1982

Do phenoxy herbicides cause cancer in man?

Two Swedish case-control studies have shown an increased risk of soft-tissue sarcomas in men exposed to phenoxy herbicides and chlorophenols during their application. A high incidence of soft-tissue sarcomas has also been observed among workers employed in the manufacture of these products in the U.S.A. Other studies have failed to demonstrate this association. A third case-control study in Sweden suggests that phenoxy acids and chlorophenols may also predispose to Hodgkin's disease and non-Hodgkin's lymphoma, but as yet there is little support for this theory from other sources. Further research is urgently needed to confirm or refute these associations, to define the extent of the risk (if any), and to identify the carcinogen(s).

2,4,5-Trichlorophenoxyacetic Acid↗
PubMed1999

Estimation of .OH radical reaction rate constants for phenol and chlorinated phenols using UV/H2O2 photo-oxidation.

A detailed investigation on UV/H2O2 photooxidation has been carried out in order to determine the kinetics of the oxidative degradation of phenol and 2- and 4-chlorophenols in dilute aqueous solutions. Effects of different process parameters, such as initial substrate and H2O2 concentrations, substrate to H2O2 ratio on the degradation kinetics of the phenolic substrates, have been studied. Degradation rates of phenol and chlorophenols are insignificantly small with ultraviolet radiation only and also with hydrogen peroxide (in the absence of UV radiation), but the synergistic effect of UV/H2O2 results in a marked enhancement of the rates of degradation. A mechanistic model for UV/H2O2 photooxidation has been developed. Room temperature (27 degrees C) rate constants for the reaction of .OH radical (formed by absorption of photons) with the substrates have been estimated by using the model equation. The calculated rate constants are of the same order of magnitude as reported for other similar aromatic compounds.

Absorption↗
PubMed2003

Oxidative transformation of triclosan and chlorophene by manganese oxides.

The antibacterial agents triclosan (5-chloro-2-(2,4-dichlorophenoxy)phenol) and chlorophene (4-chloro-2-(phenylmethyl)phenol) show similar susceptibility to rapid oxidation by manganese oxides (delta-MnO2 and MnOOH) yielding Mn(II) ions. Both the initial reaction rate and adsorption of triclosan to oxide surfaces increase as pH decreases. The reactions are first-order with respect to the antibacterial agent and MnO2. The apparent reaction orders to H+ were determined to be 0.46 +/- 0.03 and 0.50 +/- 0.03 for triclosan and chlorophene, respectively. Dissolved metal ions (Mn(II), Zn(II), and Ca(II)) and natural organic matter decrease the reaction rate by competitively adsorbing and reacting with MnO2. Product identification indicates that triclosan and chlorophene oxidation occurs at their phenol moieties and yields primarily coupling and p-(hydro)quinone products. A trace amount of 2,4-dichlorophenol is also produced in triclosan oxidation, suggesting bond-breaking of the ether linkage. The experimental results support the mechanism that after formation of a surface precursor complex of the antibacterial agent and the surface-bound Mn(IV), triclosan and chlorophene are oxidized to phenoxy radicals followed by radical coupling and further oxidation to form the end products. Compared to several structurally related substituted phenols (i.e., 2-methyl-4-chlorophenol, 2,4-dichlorophenol, 3-chlorophenol, and phenol), triclosan and chlorophene exhibit comparable or higher reactivities toward oxidation by manganese oxides. The higher reactivities are likely affected by factors including electronic and steric effects of substituents and compound hydrophobicity. Once released into the environment, partitioning of triclosan and chlorophene to soils and sediments is expected because of their relatively hydrophobic nature. Results of this study indicate that manganese oxides in soils will facilitate transformation of these antibacterial agents.

Anti-Infective Agents, Local↗
PubMed2006

Partitioning of CPs, PCDEs, and PCDD/Fs between particulate and experimentally enhanced dissolved natural organic matter in a contaminated soil.

We determined the distribution of hydrophobic organic contaminants (HOCs) to fractions of natural organic matter in a soil contaminated by chlorophenol wood preservatives more than 30 years ago. The concentration of dissolved organic matter (DOM) was enhanced in soil suspensions by raising pH to 6.8-9.1. After 48 h of desorption/equilibration, the DOM fraction was separated from the particulate organic matter (POM) of the soil by filtration. In the next step, DOM was flocculated by Al-nitrate, and free concentrations of HOCs were determined in the aqueous phase. The HOCs associated with DOM and POM were extracted with toluene. No significant differences in gross carbon chemistry were detected between DOM and POM, using X-ray photoelectron spectroscopy (XPS). Normalized to organic C, chlorophenols (CPs) showed a similar degree of partitioning between DOM and POM, whereas the partitioning of polychlorinated diphenyl ethers (PCDEs), polychlorinated dibenzo-p-dioxins, and furans (PCDD/Fs) was highly shifted toward POM. The partitioning to POM, relative to DOM, increased in the order PCDE < PCDF < PCDD, reflecting the hydrophobicity of the compounds.

Carbon↗
PubMed2002

Biological monitoring of 2,4,5-trichlorophenol (II): evaluation of an enzyme-linked immunosorbent assay for the analysis of water, urine, and serum samples.

Chlorophenols are frequently found in the urine of the population as consequence of the widespread use of chlorophenols and other organochlorinated compounds. An immunoassay for 2,4,5-trichlorophenol (2,4,5-TCP) has been evaluated as a tool to assess risk exposure of the population to these substances. The immunoassay is stable in media with pH values ranging from 6.6 to 10.5 units and ionic strength values varying within 20 and 80 mS cm(-)(1). Considering these parameters, the optimized immunoassay shows a limit of detection of 0.05 microg L(-)(1) and the dynamic range is placed between 0.09 and 0.72 microg L(-)(1). It shows a good accuracy and the coefficients of variation within and between assays are around 12% or lower. However, matrix effects can diminish the efficiency and detectability of the immunochemical methods. In this paper, the effect of water and complex biological sample matrices, such as serum and urine, on the immunoassay for 2,4,5-TCP has been evaluated. Simple sample treatment procedures have been developed for the analysis of these matrices. The final analytical protocols allow straightforward immunochemical determination of 2,4,5-TCP in natural waters, urine, and serum with detection limits of 0.07, 0.26, and 0.8 microg L(-)(1), respectively.

Binding, Competitive↗
PubMed1997

Bioprotection of microbial communities from toxic phenol mixtures by a genetically designed pseudomonad.

Pseudomonas sp. B13 SN45RE is a genetically engineered microorganism (GEM) that is able to simultaneously degrade mixtures of chloro- and methylaromatics ordinarily toxic for microbial communities via a designed novel ortho-cleavage pathway. The utility of the GEM was investigated in a laboratory scale sewage plant fed with mixtures of either 4-chlorophenol and 4-methyphenol or 3-chlorophenol and 4-methylphenol. In the model system the GEM significantly increased the rate and extent of degradation of the phenol mixtures. In the absence of the GEM, shock loads of the phenol mixtures (1 mM of each compound) reduced the numbers of culturable bacteria by three orders of magnitude, completely eliminated protozoa and metazoa, and caused a drastic decrease in oxygen consumption, whereas the presence of the GEM protected the indigenous microbial community and assured continued functioning of the sewage plant.

Biodegradation, Environmental↗
PubMed2003

An improved model for the binding of lidocaine and structurally related local anaesthetics to fast-inactivated voltage-operated sodium channels, showing evidence of cooperativity.

1. The interaction of lidocaine-like local anaesthetics with voltage-operated sodium channels is traditionally assumed to be characterized by tighter binding of the drugs to depolarized channels. As inactivated and drug-bound channels are both unavailable on depolarization, an indirect approach is required to yield estimates for the dissociation constants from channels in inactivated states. The established model, originally described by Bean et al., describes the difference in affinity between resting and inactivated states in terms of the concentration dependence of the voltage shift in the availability curve. We have tested the hypothesis that this model, which assumes a simple Langmuir relationship, could be improved by introducing a Hill-type exponent, which would take into account potential sources of cooperativity. 2. Steady-state block by lidocaine was studied in heterologously (HEK 293) expressed human skeletal muscle sodium channels and compared with experimental data previously obtained for 2,6-dimethylphenol, 3,5-dimethyl-4-chlorophenol, and 4-chlorophenol. Cells were clamped to membrane potentials from -150 to -5 mV, and a subsequent test pulse was used to assess the number of channels available to open. 3. All compounds shifted the voltage dependence of channel availability in the direction of negative prepulse potentials. Prediction of the concentration dependence of the voltage shift in the availability curve was improved by the modified model, as shown by a marked reduction in the residual sum of squares. 4. For all compounds, the Hill-type exponent was significantly greater than one. These results could be interpreted in the light of the contemporary hypothesis that lidocaine functions as an allosteric gating effector to enhance sodium channel inactivation by strengthening the latch mechanism of inactivation, which is considered to be a particle-binding process allosterically coupled to activation. Alternatively, they could be interpreted by postulating additional binding sites for lidocaine on fast-inactivated sodium channels.

Algorithms↗
PubMed1978

Inhibition of bacterial transport by uncouplers of oxidative phosphorylation. Effects of pentachlorophenol and analogues in Bacillus subtilis.

Analogues of the potent uncoupler of oxidative phosphorylation pentachlorophenol were tested as inhibitors of proline and glycine transport by Bacillus subtilis. These analogues included less highly substituted chlorophenols and pentachlorothiophenol. Like pentachlorophenol, they are non-competitive inhibitors of proline transport and uncompetitive inhibitors of glycine transport. However, the less highly substituted chlorophenols are weaker acids than pentachlorophenol and also weaker inhibitors. Analysis indicated that the anionic form of the uncouplers is the inhibiting species. Pentachlorothiophenol, a water-insoluble anion, is also a potent inhibitor. These results support previous studies that concluded that uncouplers of oxidative phosphorylation inhibit amino acid transport by binding at specific sites on proteins, the free energy of interaction stabilizing 'unproductive' conformations. Such specific interactions of uncoupler with protein are probably commonplace.

Bacillus subtilis↗
PubMed2000

Anaphylaxis to chlorhexidine. Case report. Implication of immunoglobulin E antibodies and identification of an allergenic determinant.

BACKGROUND: There are many reports of allergic reactions, including anaphylaxis, following exposure to chlorhexidine. Reactions may occur via contact with the skin and mucous membranes or from catheters treated with the antibacterial agent. Apart from implicating chlorguanide in immunoglobulin (Ig) E antibody-binding studies on serum from an anaphylactic patient, little work has been done on the molecular basis of recognition of the agent in sensitive subjects. OBJECTIVES: The molecular basis of IgE-binding to chlorhexidine was closely examined with the view of defining its fine structural recognition features by antibodies from a subject who experienced anaphylaxis following contact with the antiseptic. METHODS: Tryptase determinations, different drug-solid phases, immunoassays and quantitative hapten inhibition studies with chlorhexidine and selected structural analogues were employed together with serum from the anaphylactic patient. Results were analysed to define the complete drug allergenic determinant and to identify the important structural features complementary to the IgE antibody combining sites. RESULTS: The subject's serum tryptase levels sampled after the reaction were elevated and employment of a chlorhexidine-EA Sepharose solid phase showed the presence of serum IgE antibodies to the drug. Lack of inhibition by 4-chlorophenol and other selected substituted phenyl compounds showed that the terminal groups at each end of the chlorhexidine molecule, alone, did not account for antibody recognition of the antibacterial agent. Although chlorguanide and alexidine, the structures of which each comprise part of the chlorhexidine molecule, showed significant inhibition of the binding of IgE antibodies to chlorhexidine, neither compound was as potent an inhibitor as chlorhexidine itself. Two molecules of chlorguanide make up the symmetrical molecule of chlorhexidine while the interior structure of alexidine (that is excluding the terminal 2-ethylhexyl groups) is identical to part of the chlorhexidine molecule. CONCLUSIONS: Taken together, for this patient, these results lead to the conclusion that the whole chlorhexidine molecule is complementary to the IgE antibody combining sites and that the 4-chlorophenol, biguanide and hexamethylene structures together comprise the allergenic determinant. Hence, like one of the trimethoprim determinants identified, but unlike most drug allergenic determinants identified so far, the chlorhexidine allergenic determinant identified here encompasses the entire molecule.

Aged↗
PubMed1983

The determination of pentachlorophenol and tetrachlorophenols in wadden sediment and clams (Mya arenaria) using triethylsulfonium hydroxide for extraction and pyrolytic ethylation.

A method to determine the concentration of pentachlorophenol and tetrachlorophenols in wadden sediments and clams is described. This method involves the extraction of lyophilized specimens with toluene under acidic conditions and the back extraction of the chlorophenols into a methanol/water solution of triethylsulfonium hydroxide. Upon injection of the methanol/water phase into the gaschromatograph a pyrolytic ethylation is performed and the ethylethers of pentachlorophenol and tetrachlorophenols formed thereby are separated in quartz capillary columns and detected by an electron capture detector. Using tribromophenol as internal standard the recovery rates for the chlorophenols were within the range of 76.7 and 98.8%. The method described does not require any evaporation or chromatographic clean-up steps. The detection limit was found to be 2 nmol/kg (approximately 500 ng/kg) for sediment and 0.1 mumol/kg (approximately 25 micrograms/kg) for clams. Its accuracy was verified by gaschromatography-mass spectrometry experiments.

Animals↗
PubMed2003

Dechlorination of chlorinated phenols by zero valent zinc.

Reductive dechlorination of chlorophenols (Pentachlorophenol, three tetrachlorophenols (TeCPs), six trichlorophenols (TCPs)) with zero valent zinc was examined through batch experiments. Zinc showed much higher reactivity towards PCP than iron and amended iron indicating that zero valent zinc can be a good candidate for reductive dechlorination of chlorinated phenols. Chlorophenols were sequentially dechlorinated and less chlorinated phenols were identified as reduction products. The mass balance was not complete, indicating that by-products are important and/or that products being measured were lost by unknown pathways. The dechlorination rate of the chlorinated phenols usually followed the order: PCP > TeCPs > TCPs. Among the TeCP and TCP isomers, the reactivity was in the order of 2,3,4,5-TeCP > 2,3,4,6-TeCP > 2,3,5,6-TeCP and 2,3,4-TCP > 2,3,6-TCP > 2,3,5-TCP > 2,4,6-TCP > 2,4,5-TCP > 3,4,5-TCP. The first order reaction rates varied by one order of magnitude or more, depending on the chlorines positions on a phenol ring. A regioselectivity was observed and daughter compound distributions could be rationalized by a mechanism in which radical intermediates were more stabilized by chlorine and hydroxyl groups than by hydrogen; positions alpha to the radical were found to be the most important in stabilization, followed by beta-positions.

Chlorine↗
PubMed2006

Photocatalytic degradation of water-soluble organic pollutants on TiO2 modified with gold nanoparticles.

Well characterised novel catalysts consisting of TiO2 modified with very small amounts of gold nanoparticles have been applied to the photocatalytic degradation of two important pollutants, methyl tert-butyl ether (MTBE) and 4-chlorophenol, in dilute aqueous solution using a fixed bed flow-through photocatalytic reactor. Although the thermal processing that was necessary for coating the reactor walls with the photocatalysts did lead to some loss of performance, the net gains in activity relative to unmodified TiO2 were nevertheless substantial and in excess of anything previously reported. Improvements in reaction rate by 50% and 100% for the removal of 4-chlorophenol and MTBE, respectively, were achieved. It was also found that effective removal of both pollutants could be achieved at water flow rates that are relevant to field applications involving the photocatalytic clean-up of contaminated groundwater. Due to their very small Au content, the cost of these materials is compatible with large scale use.

Catalysis↗
PubMed1986

Industrial hygiene, chemical and biological assessments of exposures to a chlorinated phenolic sapstain control agent.

A two-year study of the occupational exposure of workers in a lumber mill to a wood preservative containing chlorophenol has been conducted. The methods were biological (urine) monitoring, industrial hygiene assessment and a questionnaire related to worker-perceived health effects. Approximately 40 workers exposed to the wood preservative and 40 unexposed controls working in other locations of the plant participated in the study. Evaluation of work conditions, assessment of urinary levels of tetra- and pentachlorophenol, and administration of a medical questionnaire were performed at a six-month intervals over a two-year period. Industrial hygiene ratings of exposures and adequacy of protection were evaluated in relation to the results of biological monitoring. Workers who came into contact with freshly treated and still wet wood had consistently higher urinary levels of tetrachlorophenol. Workers stationed adjacent to the spray applicator also had higher tetrachlorophenol levels. There was no statistically significant relationship between the subjective ratings by the industrial hygienist of exposure and adequacy of worker protection with the urinary levels of tetrachlorophenol. Nor was there a consistent pattern linking exposure ratings with adequacy of protection. The short half-life of tetrachlorophenol in the urine makes this a good indicator of only the most recent exposure. The differences in urinary levels between controls and exposed workers were large, with averages of 240.4 ppb for exposed workers and 14.6 for controls. Traditional industrial hygiene evaluation techniques, in conjunction with biological monitoring, proved to be the most effective method of assessing both exposure and work practices. Exposed workers reported a statistically significant increase of positive answers to known signs and symptoms of chlorophenol exposure compared with the controls. There was no statistically significant relationship between the number of these health problems reported and the mean urinary levels of tetra- or pentachlorophenol for the exposed group; however, for certain variables (heavy vs. light exposure, inadequate vs. adequate protection, greater than 100 ppb urinary tetrachlorophenol vs. less than 100 ppb), those with heavier exposure, inadequate protection or higher urinary tetrachlorophenol reported on the average more health problems over the two-year period. Firm statistical conclusions could not be drawn because of the small size of the study population.

Chlorophenols↗
PubMed2006

p-hydroxylation reactions catalyzed by naphthalene dioxygenase.

In this study, naphthalene dioxygenase is shown to catalyze the oxidation of methylphenols and chlorophenols by p- and/or o-hydroxylation reactions. For instance, m-cresol was oxidized to methylhydroquinone with formation of 3- and 4-methylcatechol as minor products. 2-Chlorophenol was exclusively oxidized to chlorohydroquinone, which is an important building block for pharmaceutical products and other organic compounds. The oxygen incorporated in the p-hydroxylation reaction from m-cresol is derived from water with consumption of O2.

Chlorophenols↗
PubMed1986

Complete reductive dechlorination and mineralization of pentachlorophenol by anaerobic microorganisms.

Anaerobically digested municipal sewage sludge which had been acclimated to monochlorophenol degradation for more than 2 years was shown to degrade pentachlorophenol (PCP). Di-, tri-, and tetrachlorophenols accumulated when PCP was added to the individual acclimated sludges. When the 2-chlorophenol- (2-CP), 3-CP-, and 4-CP-acclimated sludges were mixed in equal volumes, PCP was completely dechlorinated. The same results were obtained in sludge acclimated to the three monochlorophenol isomers simultaneously. With repeated PCP additions, 3,4,5,-trichlorophenol, 3,5-dichlorophenol, and 3-CP accumulated in less than stoichiometric amounts. All chlorinated compounds disappeared after PCP additions were stopped. All chlorinated compounds disappeared after PCP additions were stopped. Incubations with [14C]PCP resulted in 66% of the added 14C being mineralized to 14CO2 and 14CH4. Technical-grade PCP was found to be degraded initially at a rate very similar to that of reagent-grade PCP, but after repeated additions, the technical PCP was degraded more slowly. Pentabromophenol was also rapidly degraded by the mixture of acclimated sludges. These results clearly show the complete reductive dechlorination of PCP by the combined activities of three chlorophenol-degrading populations.

Bacteria, Anaerobic↗
PubMed1987

Effects of pentachlorophenol and some of its known and possible metabolites on different species of bacteria.

The antibacterial activity of pentachlorophenol and 35 of its known or possible metabolites against 30 different species of bacteria was tested. In comparison with pentachlorophenol, no increase of inhibitory activity was found for any of the chlorinated anisoles tested (except for pentachloroanisole against Streptomyces spp.), 2-chlorophenol, 2,6-dichlorophenol, 2,3,6- and 2,4,6-trichlorophenol, 2,3,5,6-tetrachlorophenol, tetrachloro-1,4- and -1,3-benzenediol (except for the 1,3-isomer against Streptomyces spp.), tetrachloro-1,3-dimethoxybenzene, and tetrachloro-1,3-benzenediol diacetate. Two chlorophenols, five dichlorophenols, four trichlorophenols, two tetrachlorophenols, and tetrachloro-1,2-benzenediol were more active than pentachlorophenol against some, but not all, of the strains tested.

Bacteria↗
PubMed1991

Influence of phenols on growth and membrane permeability of free and immobilized Escherichia coli.

The inhibition of the exponential growth of Escherichia coli K-12 by different phenolic compounds was examined. Cells entrapped in calcium alginate showed a greater tolerance than cells grown in suspension. The extent of inhibition of growth of the immobilized cells depended on the period of growth in the gel matrix. After the addition of bacteriostatic concentrations of phenol or 4-chlorophenol, a dose-dependent efflux of metabolites such as ATP and of K+ ions was elicited. Provided that glucose was supplied as an energy substrate, a reaccumulation of K+ ions at low phenol concentrations was observed. The restoration of the membrane gradient for K+ always preceded the continuation of growth in the presence of the toxic compounds. Compared with free cells, those cells immobilized and grown in alginate suffered a smaller loss of cations after the addition of 4-chlorophenol. The reestablishment of gradients was observed at higher concentrations of the pollutants with entrapped cells than with free cells. Corresponding to the increase in tolerance, the membrane damage was reduced in cells grown in immobilized form for longer times. These data offer a mechanistic explanation of the protection of immobilized microorganisms from phenolic solvents. The data point to the membrane as an important cell component in the toxicity of these pollutants.

Adenosine Triphosphate↗