Polychlorinated biphenyls metabolites

Matta, M.B., Caimcross, C., and Kocan, R.M. (1997). Effect of a polychlorinated biphenyl metabolite on early life stage survival of two species of trout. Bulletin of Environmental Contamination and Toxicology 59, 146-151. 

Fortin PD, AT-F Lo, M-A Haro, SR Kaschabek, W Reineke, LF Eltis (2005) Evolutionarily divergent extra-diol dioxygenases possess higher specificities for polychlorinated biphenyl metabolites. J Bacterial 187 415-421. 

Klasson-Wehler, E., A. Bergman, M. Athanasiodou, J.P. Ludwig, H.J. Auman, K. Kannan, M. Van Den Berg, A.J. Murk, L.A. Feyk, and J.P. Giesy. 1998. Hydroxylated and methylsulfonyl polychlorinated biphenyl metabolites in albatrosses from Midway Atoll, north Pacific Ocean. Environ. Toxicol. Chem. 17 1620-1625. 

Gardner AM, Righter HF, Roach JAG. 1976. Excretion of hydroxylated polychlorinated biphenyl metabolites in cow s milk. J Assoc Off Anal Chem 59(2) 273-277. 

Brandt I, Eund J, Bergman A, et al. 1985. Target cells for the polychlorinated biphenyl metabolite 4,4 -bis(methylsulphonyl)-2,2, 5,5 -tetrachlorobiphenyl in lung and kidney. Drug Metab Dispos 13 490-496. 

Kramer VJ, Helferich WG, Bergman A, et al. 1997. Hydroxylated polychlorinated biphenyl metabolites are anti-estrogenic in a stably transfected human breast adenocarcinoma (MCF7) cell line. Toxicol Appl Pharmacol 144 363-374. 

Egaas E, U Varanasi (1982) Effects of polychlorinated biphenyls and environmental temperature on in vitro formation of benzo[a]pyrene metabolites by liver of trout (Salmo gairdneri). Biochem Pharmacol 31 561-566. 

Fortin PD, GP Horsman, HM Yang, LD Eltis (2006) A glutathione S-transferase catalyzes the debalogenation of inhibitory metabolites of polychlorinated biphenyls. J Bacterial 188 4424-4430. 

Chemicals degraded by WRF include pesticides such as organochlorines DDT and its very toxic metabolite DDE [8, 9] and organophosphate pesticides such as chlorpyrifos, fonofos and terbufos [10] polychlorinated biphenyls (PCBs) of different degrees of chlorine substitution [11-13], some even to mineralization [14, 15] diverse polycyclic aromatic hydrocarbons (PAHs) in liquid media and from contaminated soils or in complex mixtures such as creosote [16-18] components of munition wastes including TNT and its metabolites DNT [19-23], nitroglycerin [24] and RDX [25]. 

Table I. Optical Purity of the Dihydrodiol Metabolites Formed in the Metabolism of Benzo[a]pyrene by Liver Microsomes from Untreated, Phenobarbital (PB)-, 3-Methylcholanthrene (3MC)-, and Polychlorinated Biphenyls (PCBs, Aroclor 1254)-Treated Rats...

Amberlite XAD-2 resin is a suitable adsorbent for polychlorinated biphenyl and chlorinated insecticides (DDT and metabolites, dieldrin) in seawater. These compounds can be suitably eluted from the resin prior to gas chromatography [356,358]. 

Picer and Picer [357] evaluated the application ofXAD-2, XAD-4, and Tenax macroreticular resins for concentrations of chlorinated insecticides and polychlorinated biphenyls in seawater prior to analysis by electron capture gas chromatography. The solvents that were used eluted not only the chlorinated hydrocarbons of interest but also other electron capture sensitive materials, so that eluates had to be purified. The eluates from the Tenax column were combined and the non-polar phase was separated from the polar phase in a glass separating funnel. Then the polar phase was extracted twice with n-pentane. The -pentane extract was dried over anhydrous sodium sulfate, concentrated to 1 ml and cleaned on an alumina column using a modification of the method described by Holden and Marsden. The eluates were placed on a silica gel column for the separation of PCBs from DDT, its metabolites, and dieldrin using a procedure described by Snyder and Reinert [359] and Picer and Abel [360]. 

Buser, H-R. and M.D. Muller. 1986. Methythio metabolites of polychlorinated biphenyls identified in sediment samples from two lakes in Switzerland. Environ. Sci. Technol. 20 730-735. 

The formation of polar metabolites from nonpolar materials may actually facilitate monitoring programs—in many cases the polar chemicals are highly concentrated in certain body fluids such as bile and urine. On the other hand, materials such as certain cyclodienes and polychlorinated biphenyls, which are very lipid soluble and resistant to metabolism, may accumulate and these chemicals may persist in the environment and may be transferred via the food chain to man. There is also interest in these biotransformation processes in lower organisms since the simplicity of these systems may lead to a better understanding of the phylogenetic development of xenobiotic metabolism. 

Furukawa, K., Tomizuka, N., Deck, B.L. Koystyk, N. (1982). Bacterial degradation of polychlorinated biphenyls (PCB) and their metabolites. Advances in Experimental Medicine and Biology, 136A, 407-18. 

From the selectivity point of view, LC-NMR coupling is especially suited to the analysis of compound classes such as nitroaromatics, phenols, aromatic amines, aromatic carboxylic acids, polyaromatic hydrocarbons (PAHs), polychlorinated biphenyls (PCBs), and azo- and anthraquinone dyes. Another advantage of LC-NMR coupling for the investigation of aromatic compounds in environmental samples is that the position of substituents on the aromatic ring, e.g. in unknown metabolites or degradation products, can best be determined by NMR spectroscopy. 

Milk. Mother s milk is rich in lipids and lipoproteins. Milk thus serves as an ideal route for the elimination of both water-soluble and fat-soluble chemicals from the mother s body. For example, the DDT metabolite DDE, the flame retardant mirex, and the polychlorinated biphenyls (PCBs) often have been detected in mother s... 

Lead, cadmium, mercury, cobalt, uranium, antimony, barium, beryllium, cesium, molybdenum, platinum, thallium, tungsten, organochlorine pesticides, organophospho-rus insecticides (dialkyl phosphate metabolites), (specific metabolites), pyrethroid pesticides, other pesticides (2-isopropoyxyphenol, carbofuranphenol), herbicides, phthalates, phytoestrogens, polycyclic aromatic hydrocarbons, polychlorinated dibenzo-p-dioxins and dibenzofurans, polychlorinated biphenyls, tobacco smoke... 

Troisi, G.M., Haraguchi, K., Simmonds, M.P., Mason, C.F., 1998. Methyl sulphone metabolites of polychlorinated biphenyls (PCBs) in cetaceans from the Irish and Aegean Seas. Arch. Environ. Contam. Toxicol. 35, 121-128. 

The possibility that high estrogen levels may be linked to breast cancer has led to concern that estrogen-mimicking chemicals might also increase the likelihood of breast cancer. Among the possibilities are polychlorinated biphenyls and DDT. Elevated blood serum levels of the DDT metabolite DDE have shown a positive correlation with breast cancer incidence. 

Letcher, R. J. Klasson-Wehler, E. Bergman, A., Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls In The Handbook of Environmental Chemistry, J. Paasivirta,editor, volume 3, Springer-Verlag, 2000, p. 315-359. 

Wong, C.S. Chiral polychlorinated biphenyls and their metabolites In PCBs Human and Environmental Disposition and Toxicity, L.G. Hanson L.W. Robertson, editors. University of Illinois Press Urbana IL, 2008, p. 30-50. 

Chu, S. Covad, A. Van de Vijver, K. De Coen, W. Blust, R. Schepens, P, Enantiomeric signatures of chiral polychlorinated biphenyl atropisomers in livers of harbour porpoises (Phocoena phocoena) from the southern North Sea J. Environ. Monit. 2003, 5, 521-526. Chu, S. Covad, A. Haraguchi, K. Voorspoels, S. Van de Vijver K. Das, K. Bouquegneau, J.-M. De Coen, W. Blust, R. Schepens, R, Levels and enantiomeric signatures of methyl sulfonyl PCB and DDE metabolites in liver of harbor porpoises (Phocoena phocoena) from the southern North Sea Environ. Sci. TechnoL 2003, 37, 4573-4578. 

Warner, N.A. Martin, J.W. Wong, C.S., Chiral polychlorinated biphenyls are biotransformed enantioselectively by mammalian c3tiochrome P-450 isozymes to form hydroxylated metabolites Environ. Sci Technol. 2009, 43, 114—121. 

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