Disease relevance of pentachlorophenol

• Aplastic anemia due to pentachlorophenol [1].
• Urticaria from contact with pentachlorophenate [2].
• The pathway for degradation of the xenobiotic pesticide pentachlorophenol in Sphingomonas chlorophenolica probably evolved in the past few decades by the recruitment of enzymes from two other catabolic pathways [3].
• Pentachlorophenol pancreatitis [4].
• The crystal structure of Escherichia coli nitrate reductase A (NarGHI) in complex with pentachlorophenol has been determined to 2.0 A of resolution [5].

High impact information on pentachlorophenol

• Exposure to chlorophenols gave an odds ratio of 4.8 (2.7-8.8) with pentachlorophenol being the most common type [6].
• We have shown that pentachlorophenol is a potent inhibitor of quinol:nitrate oxidoreductase activity and that it also perturbs the EPR spectrum of one of the hemes located in the membrane anchoring subunit (NarI) [5].
• The metal-independent production of hydroxyl radicals (*OH) from H(2)O(2) and tetrachloro-1,4-benzoquinone (TCBQ), a carcinogenic metabolite of the widely used wood-preservative pentachlorophenol, was studied by electron spin resonance methods [7].
• We conclude that an H2DIDS and PCP inhibitable system, probably the Cl/HCO3 exchanger, is at least partially responsible for keeping intracellular pH above electrochemical equilibrium in HL60 cells under resting conditions [8].
• Furthermore, pentachlorophenol, an inhibitor of SULT1A1, strongly reduced the mutagenic effect of aristolochic acids in V79-hCYP2E1-hSULT1A1 cells [9].

Chemical compound and disease context of pentachlorophenol

• Tetrachlorohydroquinone dehalogenase is found in Sphingomonas chlorophenolica, a soil bacterium that degrades pentachlorophenol, a widely used wood preservative [10].
• Evidence that pcpA encodes 2,6-dichlorohydroquinone dioxygenase, the ring cleavage enzyme required for pentachlorophenol degradation in Sphingomonas chlorophenolica strain ATCC 39723 [11].
• An enzyme that catalyzes an Fe2+-dependent reaction of 2, 6-dichlorohydroquinone with O2 has been isolated from Sphingomonas chlorophenolica sp. strain ATCC 39723, a soil microorganism capable of complete mineralization of pentachlorophenol [11].
• Injection of 0.04 mumol/g body weight of pentachlorophenol (PCP) 45 min before the dose of N-hydroxy-AAF decreased the number of adducts in the DNA by 90% and the average number of hepatomas per liver by 80-90% [12].
• Stronger associations for non-Hodgkin lymphoma and kidney cancer incidence were observed with pentachlorophenol than with total chlorophenol; no association was observed with tetrachlorophenol [13].

Biological context of pentachlorophenol

• It was also apparent that there are two pathways of metabolic activation of tamoxifen, one being sensitive and the other resistant to pentachlorophenol [14].
• DNA damage induced by tetrachlorohydroquinone (Cl(4)HQ), the quinonoid metabolite of pentachlorophenol (PCP), was investigated in human HeLa S3 tumor cells [15].
• Inhibition of bacterial transport by uncouplers of oxidative phosphorylation. Effects of pentachlorophenol and analogues in Bacillus subtilis [16].
• We explored the potential preventive effects of green tea against the promoting action of pentachlorophenol (PCP) in mouse hepatocarcinogenesis, examining whether drinking green tea prevents the down-regulation of GJIC inhibition in the liver caused by tumorigenic doses of PCP [17].
• Control experiments with another uncoupler, pentachlorophenol, showed that the inhibitory effect of CCCP was not the result of a decrease in membrane potential [18].

Anatomical context of pentachlorophenol

• Electrical conductivity induced in thin lipid bilayer membranes by pentachlorophenol has been studied [19].
• DNA damage induced by quinoid metabolites of pentachlorophenol (PCP), i.e. tetrachloro-1,4-benzoquinone (Cl(4)BQ) and tetrachlorohydroquinone (Cl(4)HQ), was investigated in calf thymus DNA [20].
• Effect of pentachlorophenol on calcium accumulation in barnacle muscle cells [21].
• 1. The effect of extracellularly applied pentachlorophenol (PCP) was studied on the membrane potential (Vm) and Ca2+ uptake in isolated single skeletal muscle cells of Balanus nubilus [21].
• Highly cooperative inhibition of acetylcholinesterase by pentachlorophenol in human erythrocytes [22].

Associations of pentachlorophenol with other chemical compounds

• Pretreatment with pentachlorophenol, a known inhibitor of sulphotransferases, inhibited the binding of safrole to mouse-liver DNA, providing further evidence that the metabolic activation of the allylbenzenes proceeds by the formation of 1'-hydroxy derivatives as proximate carcinogens and 1'-sulphoöxy derivatives as ultimate carcinogens [23].
• In order to explore a possibility that the custom of drinking green tea infusion is efficacious for reducing the carcinogenic risk of environmental exposure to pentachlorophenol (PCP), we examined the effects in a hepato- and cholangiocarcinogenesis model in mice exposed to diethylnitrosamine (DEN) [24].
• Increase of cholesterol content increases pentachlorophenol induced conductivity in all membranes and shifts the conductivity toward lower pH [19].
• Two HCB main metabolites, pentachlorophenol (PCP) and pentachlorobenzenethiol (PCBT), were detected in 51% and 54% of feces samples, respectively [25].
• Latvian men demonstrated higher plasma levels of DDE and DDT but lower levels of [sigman]PCB and PCP than did Swedish men [26].

Gene context of pentachlorophenol

• The tested products fell into four major groups: a first group with pentachlorophenol, identified as a CYP3A inducer; a second group containing the methylcholanthrene-type inducers that increase CYP1A-related activities; a third class represented by dieldrin, a PB-type inducer; a fourth group including inert compounds or weak inducers [27].
• Neuregulin 1-Beta Cytoprotective Role in AML 12 Mouse Hepatocytes Exposed to Pentachlorophenol [28].
• CYP1a1, HSP70, P53, and c-fos expression in human liver carcinoma cells (HepG2) exposed to pentachlorophenol [29].
• Hexachlorocyclohexane reduced [3H]5 alpha-DHT binding to hSHBG by 20%, but the stereospecific effects observed with ABP did not occur. o,p'-DDT and pentachlorophenol resulted in a statistically significant 20% inhibition of [3H]5 alpha-DHT binding to hSHBG [30].
• Human lymphocyte reactivity after in vitro exposure to technical and analytical grade pentachlorophenol [31].

Analytical, diagnostic and therapeutic context of pentachlorophenol

• The RDE/ CE system was capable of separation and determination of pentachlorophenol in contaminated soils, and the result obtained agreed well with conventional liquid chromatography, an EPA recommended procedure [32].
• Typical detection limits of the HPLC/TOF-MS method were 5 pg/g ww (1-2 pg injected) for HO-PCBs and PCP and 20 pg/g ww (3 pg injected) for TBBPA [33].
• The cyclodextrin-mediated capillary electrophoresis system was also applicable for separating and quantifying the level of pentachlorophenol in contaminated soil samples [34].
• Anaerobic biodegradation of pentachlorophenol (PCP) was studied in rotative bioreactors containing 200 g of PCP-contaminated soil and 250 ml of liquid medium [35].
• Bioassays were carried out to assess the toxicity of 3,5-dichlorophenol (3,5-DCP), pentachlorophenol (PCP), copper and zinc [36].

References