Pentachlorophenol metabolism

Topp, E., Crawford, R. D. Hanson, R. S. (1988). Influence of readily metabolizable carbon on pentachlorophenol metabolism by a pentachlorophenol-degrading Flavobacterium sp. Applied and Environmental Microbiology, 54, 2452-9-... 

The metabolic activity of other white-rot fungi including Phanerochaete chrysosporium and Pleurotus ostreacus has been discussed in the context of polycyclic aromatic hydrocarbons. For example, the mineralization potential of the manganese peroxide system fmmNematolomafrowardii for a number of substrates has been demonstrated (Hofrichter et al. 1998) the formation of CO2 from labeled substrates ranged from 7% (pyrene) to 36% (pentachlorophenol), 42% (2-amino-4, 6-dinitrotoluene), and 49% (catechol). 

Roy S, O Hanninen (1994) Pentachlorophenol uptake/elimination kinetics and metabolism in an aquatic plant Eichhornia crassipes. Environ Toxicol Chem 13 763-773. 

Schafer W, H Sandermann (1988) Metabolism of pentachlorophenol in cell suspension cultures of wheat (Triticum aestivum L.). Tetrachlorocatecol as a primary product. J Agric Food Chem 36 370-377. 

The tolerance of the strains to high concentrations of pentachlorophenol—S. chlorophenolica appears to be less sensitive than M. chlorophenolicus (Miethling and Karlson 1996). This may be attribnted to the ability of the cells to adapt their metabolism to avoid synthesis of toxic concentrations of chlorinated hydroquinones, and is consistent with the low levels of these metabolites measnred in the cytoplasm of cells metabolizing pentachlorophenol (McCarthy et al. 1997). Inocnla have also been immobilized on polyurethane that, in addition, ameliorates the toxicity of chlorophenols (Valo et al. 1990). 

Rawlings, N.C., S.J. Cook, and D. Waldbillig. 1998. Effects of the pesticides carbofuran, chlorpyrifos, dimethoate, lindane, triallate, trifluralin, 2,4-D, and pentachlorophenol on the metabolic endocrine and reproductive endocrine system in ewes. Jour. Toxicol. Environ. Health 54A 21-36. 

Pentachlorophenol in terrestrial ecosystems clears rapidly (Haque et al. 1988). In one case, a terrestrial ecosystem was given a single surface application of radiolabeled PCP equivalent to 5 kg sodium pentachlorophenate/ha. PCP residues on foliage decreased rapidly, with 50% metabolized within 15 days. After 131 days (autumn), most of the remaining PCP was in the topsoil and plant litter. After 222 days (winter), 39% of the radiocarbon remained. There was little bioconcentration in the resident fauna, due to rapid metabolism and excretion (Haque et al. 1988). 

Pentachlorophenol was most toxic and most rapidly metabolized in aquatic environments at elevated temperatures and reduced pH. Adverse effects on growth, survival, and reproduction of representative sensitive species of aquatic organisms occurred at PCP concentrations of about 8 to 80 pg/L for algae and macrophytes, about 3 to 100 pg/L for invertebrates (especially molluscs), and <1 to 68 pg/L for fishes, especially salmonids. Fatal PCP doses for birds were 380 to 504 mg/kg BW (acute oral), >3850 mg/kg in diets, and >285 mg/kg in nesting materials. Adverse sublethal effects were noted at dietary levels as low as 1.0 mg/kg ration. Residues (mg/kg fresh weight) in birds found dead from PCP poisoning were >11 in brain, >20 in kidney, >46 in liver, and 50 to 100 in egg. 

Pentachlorophenol applied to beech forest soils every 2 months for 2 years at the rate of 1.0 g/m2 markedly reduced populations of soil organisms. At 5.0 g/m2, it drastically reduced most of the soil animal species and also the microflora (Zietz et al. 1987). Reduction of the soil metabolism by PCP retards decomposition and affects the overall nutrient balance of forest ecosystems (Zietz et al. 1987). Pentachlorophenol is more toxic to earthworms in soils with comparatively low levels of organic materials. The LC50 (14-day) value for Lumbricus rubellus was 1094 mg PCP/kg DW soils with 6.1% organic matter, and 883 mg/kg DW soils with 3.7% organic matter (Van Gestel and Ma 1988). The earthworm Eisenia fetida andrei is more sensitive than Lumbricus rubellus ... 

Chapman, G.A. and D.L. Shumway. 1978. Effects of sodium pentachlorophenate on survival and energy metabolism of embryonic and larval steelhead trout. Pages 285-299 in K.R. Rao (ed.). Pentachlorophenol Chemistry, Pharmacology, and Environmental Toxicology. Plenum Press, New York. 

Cravedi, J.P., C. Gillet, and G. Monod. 1995. In vivo metabolism of pentachlorophenol and aniline in Arctic charr (Salvelinus alpinus L.) larvae. Bull. Environ. Contam. Toxicol. 54 711-716. 

Ege, M.K. 1985. The Effect of Pentachlorophenol on the Metabolic Activity of the Eastern Chipmunk (Tamias striatus) During Social Interaction. M.S. thesis. Ohio State University, Columbus, OH. 70 pp. 

Glickman, A.H., C.N. Statham, A. Wu, and J.J. Lech. 1977. Studies on the uptake, metabolism, and disposition of pentachlorophenol and pentachloroanisole in rainbow trout. Toxicol. Appl. Pharmacol. 41 649-658. 

Holmberg, B., S. Jensen, A. Larsson, K. Lewander, and M. Olsson. 1972. Metabolic effects of technical pentachlorophenol (PCP) on the eel Anguilla anguilla L. Comp. Biochem. Physiol. 43B 171-183. 

Huber, W., V. Schubert, and C. Sautter. 1982. Effects of pentachlorophenol on the metabolism of the aquatic macrophyte Lemna minor L. Environ. Pollut. 29A 215-223. 

Nishimura, H. 1984. Effect of pentachlorophenol on hepatic glycogen metabolism in rats. Japan. Jour. Hyg. 39 662-669. 

Peer, M.M., J. Nirmala, and M.N. Kutty. 1983. Effects of pentachlorophenol (Na PCP) on survival, activity and metabolism in Rhinomugil corsula (Hamilton), Cyprinus carpio (Linnaeus) and Tilapia mossambica (Peters). Hydrobiologia 107 19-24. 

Renner, G. and C. Hopfer. 1990. Metabolic studies on pentachlorophenol (PCP) in rats. Xenobiotica 20 573-582. 

Stehly, G.R. and W.L. Hayton. 1989. Disposition of pentachlorophenol in rainbow trout (Salmo gairdneri) effect of inhibition of metabolism. Aquat. Toxicol. 14 131-148. 

However, PCP is the second heaviest used pesticide in the United States, although it has been mostly used for the purpose of wood preservation(1). Under such circumstances, an international symposium on "Pentachlorophenol" convened by K. Ranga Rao(University of West Florida) was held in Pensacola, Florida, June 27-29, 1977, concerning the chemistry, pharmacology, and environmental toxicology of PCP. At the symposium, I presented a paper(2) on the metabolism of PCP in fishes, mostly reviewing the works on the absorption, excretion and detoxification of PCP in fish and shellfish, which were done in our laboratory. 

Covalent protein adducts of quinones are formed through Mchael-type addihon reachon with protein sulfhydryl groups or glutathione. Metabolic activahon of several toxins (e.g., naphthalene, pentachlorophenol, and benzene) into quinones has been shown to result in protein quinone adducts (Lin et al, 1997 Rappaport et al, 1996 Zheng et al., 1997). Conversion of substituted hydroquinones such as p-aminophenol-hydroquinone and 2-bromo-hydroquinone to their respective glutathione S-conjugates must occur to allow bioactivation into nephrotoxic metabolites (Dekant, 1993). Western blot analysis of proteins from the kidneys of rats treated with 2-bromo-hydroquinone has revealed three distinct protein adducts conjugated to quinone-thioethers (Kleiner et al, 1998). 

Kobayashi, H. Metabolism of pentachlorophenol in fish, in Pesticide andXenobiotic Metabolism in Aquatic Organisms, ACS Symposium Series 99 (Washington, DC American Chemical Society, 1979). 

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