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PubMed1984

Influence of food on the absorption of the p-chlorophenolic ester of chlorophenoxyisobutyric acid in man.

A study was designed to investigate the effect of a fatty meal on the absorption of chlorophenoxyisobutyric acid (CPIB) in six healthy adult volunteers after oral administration of the p-chlorophenolic (PCP) ester of CPIB. Plasma concentrations of CPIB when administered with food were higher than those observed in the fasting state. The Cmax in the former case was 24.0 +/- 4.6 mg l-1 as against a value of 15.2 +/- 6.9 mg l-1 in the latter (P less than 0.01). The pharmacokinetic parameters measured were found to be linear with the dose administered. This could be due to low plasma concentrations of CPIB unable to cause a saturation of the plasma protein binding of this drug. It is concluded that a fatty meal enhances the absorption of this hypolipidaemic drug.

Adult↗
PubMed1993

Adaptation of Pseudomonas aeruginosa to 2,2'-methylenebis (4-chlorophenol).

A culture of Pseudomonas aeruginosa, isolated from a cooling water system, was grown in the presence of sub-inhibitory concentrations of 2,2'-methylenebis(4-chlorophenol) (MBC). It adapted to increasing concentrations from an initial minimum inhibitory concentration of 36 micrograms ml-1 to the highest, 80 micrograms ml-1. Resistant cultures exhibited a higher survival rate when exposed to 320 micrograms ml-1 than did the original strain. Lipopolysaccharide and outer membrane protein profiles were determined by SDS PAGE. No changes were detected in lipopolysaccharide profiles. The quantity of OprP, the phosphate uptake protein in the outer membrane, decreased to a low level correlating with decreased phosphate (P(i)) uptake during growth. It is proposed that OprP is the place of entry for MBC and that the cell can adapt by decreasing the level of OprP in the outer membrane.

Adaptation, Physiological↗
PubMed1994

Comparison of reactors for oxygen-sensitive reactions: reductive dechlorination of chlorophenols by vitamin b(12s).

Serum bottles are frequently used for studies of reductive dechlorination by vitamin B(12), but reducing conditions can be maintained only for several days. This time period is inadequate for evaluating the reductive dechlorination of some slow-reacting aromatic compounds. Sealed glass ampoules maintain reducing conditions for many months, but this method has the disadvantage of disallowing subsampling of the reaction mixture. A glass serum tube was modified for these experiments which not only maintained anoxic conditions for several days but also allowed subsamples to be removed during experiments. The modification was a restriction placed in the middle of the tube by heating in a flame, creating two chambers separated by a narrow neck. The lower chamber contained the oxygen-sensitive reaction mixture. The upper chamber, sealed with a septum and screw cap, was purged with purified nitrogen or argon introduced and vented through fused silica capillaries. Reductive dechlorination of chlorophenols by vitamin B(12) reduced with Ti(III) citrate was monitored in all three reactor types. Sealed ampoules maintained reducing conditions for up to 12 months. The two-chambered reactor maintained reducing conditions longer than the serum vials when frequent samples were taken.

Journal Article↗
PubMed1996

Straw compost and bioremediated soil as inocula for the bioremediation of chlorophenol-contaminated soil.

We evaluated the use of straw compost and remediated soil as inocula for bioremediation of chlorophenol-contaminated soil. The in situ biotransformation of pentachlorophenol (PCP) and mineralization of radiolabeled [U-(sup14)C]PCP by straw compost and remediated soil were studied under field-simulating conditions before and after 3 months of adaptation with PCP in a percolator. After PCP adaptation, the straw compost mineralized up to 56% of the [(sup14)C]PCP. No partial dechlorination of PCP was found. The native straw compost did not mineralize PCP, but partial dechlorination of PCP occurred (i) at pH 8 under near-thermophilic conditions (45(deg)C) and (ii) at pH 7 under aerobic and mesophilic conditions. No biotransformation reactions occurred at room temperature (25(deg)C) at pH 8. Enrichment in the percolator enhanced the mineralization rate of remediated soil to 56% compared with that of the native remediated soil, which mineralized 24% of [(sup14)C]PCP added. Trace amounts of chloroanisoles as the only biotransformation products were detected in PCP-adapted remediated soil. Both inoculants studied here showed effective mineralization of PCP when they were adapted to PCP in the percolator. No harmful side reactions, such as extensive methylation, were observed.

Journal Article↗
PubMed1996

Effect of added heavy metal ions on biotransformation and biodegradation of 2-chlorophenol and 3-chlorobenzoate in anaerobic bacterial consortia.

The effect of added Cd(II), Cu(II), Cr(VI), or Hg(II) at 0.01 to 100 ppm on metabolism in anaerobic bacterial consortia which degrade 2-chlorophenol (2CP), 3-chlorobenzoate (3CB), phenol, and benzoate was examined. Three effects were observed, including extended acclimation periods (0.1 to 2.0 ppm), reduced dechlorination or biodegradation rates (0.1 to 2.0 ppm), and failure to dechlorinate or biodegrade the target compound (0.5 to 5.0 ppm). 3CB biodegradation was most sensitive to Cd(II) and Cr(VI). Biodegradation of benzoate and phenol was most sensitive to Cu(II) and Hg(II), respectively. Adding Cr(VI) at 0.01 ppm increased biodegradation rates of phenol (177%) and benzoate (169%), while Cd(II) and Cu(II) at 0.01 ppm enhanced biodegradation rates of benzoate (185%) and 2CP (168%), respectively. Interestingly, with Hg(II) at 1.0 to 2.0 ppm, 2CP and 3CB were biodegraded 133 to 154% faster than controls after an extended acclimation period, suggesting adaptation to Hg(II). Metal ions were added at inhibitory, but sublethal, concentrations to investigate effects on metabolic intermediates and end products. Phenol accumulated to concentrations higher than those in controls only in the 2CP consortium with added Cu(II) at 1.2 ppm but was subsequently degraded. There was no effect on benzoate, and little effect on acetate intermediates was observed. In most cases, methane yields were reduced by 23 to 97%. Thus, dehalogenation, aromatic degradation, and methanogenesis in these anaerobic consortia showed differential sensitivities to the heavy metal ions added. These data indicate that the presence of heavy metals can affect the outcome of anaerobic bioremediation of aromatic pollutants. In addition, a potential exists to use combinations of anaerobic bacterial species to bioremediate sites contaminated with both heavy metals and aromatic pollutants.

Journal Article↗
PubMed1997

Degradation of 4-Chlorophenol via the meta Cleavage Pathway by Comamonas testosteroni JH5.

Comamonas testosteroni JH5 used 4-chlorophenol (4-CP) as its sole source of energy and carbon up to a concentration of 1.8 mM, accompanied by the stoichiometric release of chloride. The degradation of 4-CP mixed with the isomeric 2-CP by resting cells led to the accumulation of 3-chlorocatechol (3-CC), which inactivated the catechol 2,3-dioxygenase. As a result, further 4-CP breakdown was inhibited and 4-CC accumulated as a metabolite. In the crude extract of 4-CP-grown cells, catechol 1,2-dioxygenase and muconate cycloisomerase activities were not detected, whereas the activities of catechol 2,3-dioxygenase, 2-hydroxymuconic semialdehyde dehydrogenase, 2-hydroxymuconic semialdehyde hydrolase, and 2-oxopent-4-enoate hydratase were detected. These enzymes of the meta cleavage pathway showed activity with 4-CC and with 5-chloro-2-hydroxymuconic semialdehyde. The activities of the dioxygenase and semialdehyde dehydrogenase were constitutive. Two key metabolites of the meta cleavage pathway, the meta cleavage product (5-chloro-2-hydroxymuconic semialdehyde) and 5-chloro-2-hydroxymuconic acid, were detected. Thus, our previous postulation that C. testosteroni JH5 uses the meta cleavage pathway for the complete mineralization of 4-CP was confirmed.

Journal Article↗
PubMed1973

Biodegradation of o-benzyl-p-chlorophenol.

The extent of biodegradation of o-benzyl-p-chlorophenol, marketed as a germicide under the name Santophen((R)) 1 (Monsanto Co.), in river water, sewage, and activated sludge was determined. Biodegradation was assessed by use of a colorimetric procedure for phenolic materials, carbon analysis, and CO(2) evolution. In unacclimated river water, 0.1 mg of Santophen 1 per liter was degraded within 6 days. In sewage, 0.5 and 1.0 mg/liter levels of Santophen 1 were degraded in 1 day. Acclimated activated sludge achieved 80% biodegradation of 1.0 mg/liter Santophen 1 in 8 h and 100% in 24 h. When effluent from a semicontinuous activated sludge unit, acclimated to 20 mg of Santophen 1 per liter was used as the inoculum for the CO(2) evolution procedure, 60% of the total theoretical CO(2) was evolved from Santophen 1. Based on the results of these studies, indicating Santophen 1 to be readily biodegraded in at least four biological systems, the continued use of present levels of Santophen 1 should present no significant environmental problems.

Alkanesulfonates↗
PubMed2000

Assessment of genotoxicity of dental antiseptics: ability of phenol, guaiacol, p-phenolsulfonic acid, sodium hypochlorite, p-chlorophenol, m-cresol or formaldehyde to induce unscheduled DNA synthesis in cultured Syrian hamster embryo cells.

To assess the genotoxicity of seven dental antiseptics, the ability of these agents to induce unscheduled DNA synthesis (UDS) was examined using Syrian hamster embryo (SHE) cells. Treatment of SHE cells with phenol or formaldehyde induced UDS in a concentration-dependent manner as determined by direct scintillation counting of [3H]thymidine incorporated into DNA during repair synthesis. Guaiacol or m-cresol induced UDS only in the presence of exogenous metabolic activation. p-Phenolsulfonic acid, sodium hypochlorite and p-chlorophenol failed to induce UDS in the presence or absence of exogenous metabolic activation. Our results suggest that phenol, guaiacol, m-cresol and formaldehyde are genotoxic to mammalian cells.

Animals↗
PubMed1997

Biodegradation of the mixture of 2,4,6-trichlorophenol, 4-chlorophenol, and phenol by a defined mixed culture.

Two new strains, Pseudomonas sp. TCP114 degrading 2,4,6-trichlorophenol (TCP) and Arthrobacter sp. CPR706 degrading 4-chlorophenol (4-CP), were isolated through a selective enrichment procedure. Both strains could also degrade phenol. The degradability of one component by a pure culture was strongly affected by the presence of other compounds in the medium. For example, when all three components (TCP, 4-CP, and phenol) were present in the medium, a pure culture of CPR706 could not degrade any of the components present. This restriction on degradability could be overcome by employing a defined mixed culture of the two strains. The mixed culture could degrade all three components in the mixture through cooperative activity. It was also demonstrated that the mixed culture could be immobilized by using calcium alginate for the semi-continuous degradation of the three-component mixture. Immobilization not only accelerates the degradation rate, but also enables reuse of the cell mass several times without losing the cells' degrading capabilities.

Journal Article↗
PubMed2002

Reversed flow injection spectrophotometric determination of low residuals of chlorine dioxide in water using chlorophenol red.

A novel, simple, rapid, sensitive and highly selective flow injection procedure for the spectrophotometric determination of chlorine dioxide in the presence of other chlorine species, viz, free chlorine, chlorite, chlorate and hypochlorite, is developed. The method is based on the discoloration reaction between chlorine dioxide and chlorophenol red and can overcome the shortcomings existed in direct spectrophotometric determination for chlorine dioxide owing to the serious interference of free and combined chlorine. The procedure gave a linear calibration graph over the range 0-0.71 mg/L of chlorine dioxide. With a detection limit of 0.024 mg/L and a sample throughput of 60 samples/h.

Chlorine Compounds↗
PubMed2004

[Study on the solid phase extraction spectrophotometric determination of mercury in water with 5-(2-hydroxy-4-sulfo-5-chlorophenol-1-azo)-thiorhodanine].

Based on the color reaction of mercurywith 5-(2-hydroxy-4-sulfo-5-chlorophenol-1-azo)-thiorhodanine (HSTC) and the solid phase extraction of the colored complex with C18 cartridge, a new method for the determinations microg x L(-1) level of mercury was studied. In the presence of pH 3.6 HAc-NaAc buffer solution. HSTC reacted with mercury (II) to form a stable 2:1 complex. This complex was enriched by solid phase extraction with C18 cartridge and the retained complex from cartridge was eluted with DMF. An enrichment factor of 80 was achieved. In the measured solution, the molar absorptivity was 6.24 x 10(4) L x moL(-1) x cm(-1) at 545 nm. Beer's law was obeyed in the range of 0-1.5 microg x mL(-1). This method was applied to the determination of mercury in water. The relative standard devitions were 1.8%-2.2% and the recoveries were 93%-106%. The results are satisfactory.

Mercury↗
PubMed1975

Urinary metabolites from gamma- and beta-BHC in the mouse: chlorophenol conjugates.

Metabolites produced from gamma- and beta-BHC in the mouse urine were purified and characterized. Most metabolites from both isomers were not extractable by non-polar organic solvents and were conjugates such as sulfates and glucuronides. After hydrolysis with an appropriate enzyme, the conjugates gave chlorophenols, among which 2,4,6-trichlorophenol existed most abundantly (total, about 25% in the urine metabolites). 2,4-Dichlorophenol also constituted a significant portion.

Animals↗
PubMed1996

Reliability of retrospective chlorophenol exposure estimates over five decades.

For a cohort study of chlorophenate-exposed sawmill workers, historical exposures from the 1940s to the 1980s were estimated by teams of 9-20 employees (each interviewed individually). The mill histories were divided into eras when jobs and exposures were relatively stable. Raters with at least 5 years of work experience in an era were asked to estimate the frequency and duration of exposure for each job in the mill. Reliability measures for these estimates were calculated for each of the 39 mill and time period combinations, using the individual intraclass correlation coefficient (ICCind) to assess agreement between raters and the group intraclass correlation coefficient (ICCgroup) to assess the stability of the mean estimates of exposure. ICCind were low, with means that increased from 0.24 to 0.35 over the five decades. ICCgroup were considerably higher (means increasing from 0.78 to 0.88 over time), indicating that the number of raters used in this study was sufficient to produce stable average estimates of exposure throughout the study period. These data confirm the intuitive expectation that reliability of exposure estimates decreases when reconstruction of conditions in the distant past is required, and therefore that the random component of exposure misclassification is a greater threat to validity in these earlier time periods.

Analysis of Variance↗
PubMed1984

Microbial biodegradation of 2,4,5-trichlorophenoxyacetic acid and chlorophenols.

We have succeeded in isolating a pure culture of Pseudomonas cepacia, AC1100, from a chemostat enrichment culture experiment that is capable of growing on 2,4,5-trichlorophenoxyacetic acid as its sole source of carbon and energy. AC1100 is not only capable of degrading 2,4,5-T but is also able to completely or partially dehalogenate a wide variety of halophenols. The regulation of the dehalogenating ability of AC1100 has been investigated which demonstrates that the enzyme(s) which allow the conversion of 2,4,5-T to 2,4,5-TCP are constitutive, while the enzymes that allow the degradation of 2,4,5-TCP are inducible by 2,4,5-TCP (or some metabolite of 2,4,5-TCP) but not by 2,4,5-T or other halophenols which can serve as substrates. Moreover, the 2,4,5-TCP degradative pathway is repressed by the presence of an abundant alternative carbon source. The detailed pathway of 2,4,5-T degradation by AC1100 is currently under study. Although field tests have yet to be conducted, laboratory experiments have demonstrated rapid and complete degradation of 2,4,5-T from contaminated soil. Soil previously contaminated with as much as 5,000 micrograms of 2,4,5-T/g of soil could be detoxified by AC1100 treatment, allowing the growth of plants sensitive to less than 10 micrograms 2,4,5-T/g of soil. Moreover soil contaminated with as much as 20,000 micrograms of 2,4,5-T/g of soil showed greater than 90% degradation after six weekly AC1100 treatments. After 2,4,5-T has been substantially degraded in contaminated soil the titer of AC1100 rapidly falls to nearly undetectable levels, which indicates that no serious ecological disturbance is likely to result from the application of AC1100. It appears possible that the treatment of contaminated areas with appropriate microorganisms may allow essentially a total restoration of the original soil condition.

2,4,5-Trichlorophenoxyacetic Acid↗