Transformations of pentachlorophenol

Cytotoxic effects of pentachlorophenol (PCP) and its metabolite tetrachlorohydroquinone (TCHQ) on liver cells are modulated by antioxidants

“…PCP is extensively used as a biocide and wood preservative. Additionally, it has been shown that several environmental chemicals, such as lindane, pentachloronitrobenzene, and pentachlorobenzene, can be metabolized to PCP in animals and plants (Koss and Koransky 1978;van Ommen et al 1985;Renner and Mücke 1986;WHO 2003). Due to its worldwide distribution, PCP levels in the range of 0.01-0.09 μM in groundwater have been reported (WHO 1987) although, for example, extreme levels of >700 μM PCP have been found due to an industrial point source for chlorophenols (Lampi et al 1990).…”

Investigating the Bioaccumulation Potential of Anionic Organic Compounds Using a Permanent Rainbow Trout Liver Cell Line

“…Thus, RTL-W1 cells express enzymes that are involved in phase I (addition of functional group) and II (conjugation) of biotransformation. DCF and PCP are known to biotransform in rainbow trout (Kobayashi et al, 1976;Kobayashi, 1979;McKim et al, 1986;Renner and Mücke, 1986;Stehly and Hayton, 1989;Oikari and Kunnamo-Ojala, 1987;Frankovic et al, 1995;Cravedi et al, 1999;Mehinto et al, 2010;Kallio et al, 2010;Lahti et al, 2011), while there is no information available on the biotransformation of BHPP and TT in fish. PCP was found to be biotransformed in rainbow trout to dechlorinated congeners (Frankovic et al, 1995) and its glucuronide and sulfate conjugates (Kobayashi et al, 1976;Kobayashi, 1979;Renner and Mücke, 1986;Stehly and Hayton, 1989;Cravedi et al, 1999), while DCF was biotransformed to hydroxylated DCF isomers and a variety of their conjugate isoforms, such as glucuronide, sulfate and glutathione conjugates (Kallio et al, 2010;Lahti et al, 2011;Fu et al, 2020;Kosfeld et al, 2020).…”

“…DCF and PCP are known to biotransform in rainbow trout (Kobayashi et al, 1976;Kobayashi, 1979;McKim et al, 1986;Renner and Mücke, 1986;Stehly and Hayton, 1989;Oikari and Kunnamo-Ojala, 1987;Frankovic et al, 1995;Cravedi et al, 1999;Mehinto et al, 2010;Kallio et al, 2010;Lahti et al, 2011), while there is no information available on the biotransformation of BHPP and TT in fish. PCP was found to be biotransformed in rainbow trout to dechlorinated congeners (Frankovic et al, 1995) and its glucuronide and sulfate conjugates (Kobayashi et al, 1976;Kobayashi, 1979;Renner and Mücke, 1986;Stehly and Hayton, 1989;Cravedi et al, 1999), while DCF was biotransformed to hydroxylated DCF isomers and a variety of their conjugate isoforms, such as glucuronide, sulfate and glutathione conjugates (Kallio et al, 2010;Lahti et al, 2011;Fu et al, 2020;Kosfeld et al, 2020). However, in vitro clearance of DCF in different assays, which used rainbow trout liver tissue, was relatively low (but significantly different from controls) (Connors et al, 2013;Baron et al, 2017;Kosfeld et al, 2020) and we could not detect the formation of DCF BTPs in RTL-W1 cells.…”