| Name | cytochrome P450 (protein family or complex) |
|---|---|
| Synonyms | cytochrome P450; cytochrome P 450; CYP450; CYP 450 |
| Name | pentachlorophenol |
|---|---|
| CAS | 2,3,4,5,6-pentachlorophenol |
| PubMed | Abstract | RScore(About this table) | |
|---|---|---|---|
| 3729973 | Stewart FP, Smith AG: Metabolism of the "mixed" cytochrome P-450 inducer hexachlorobenzene by rat liver microsomes. Biochem Pharmacol. 1986 Jul 1;35(13):2163-70. Hexachlorobenzene (HCB) was metabolised by phenobarbital-induced liver microsomes from male rats to pentachlorobenzene, pentachlorophenol, tetrachloro-1,2-benzenediol and tetrachloro- (1:88:2:9). |
1(0,0,0,1) | Details |
| 9212788 | Randerath K, Zhou GD, Randerath E, Safe SH, Donnelly KC: Comparative 32P-postlabeling analysis of exogenous and endogenous DNA adducts in mouse skin exposed to a wood-preserving waste extract, a complex mixture of polycyclic and polychlorinated chemicals. Environ Mol Mutagen. 1997;29(4):372-8. This effect was explained by the presence of cytochrome P450 inducers in the extract. |
1(0,0,0,1) | Details |
| 10670822 | Bostrom M, Becedas L, DePierre JW: Conjugation of 1-naphthol in primary cell cultures of rat ovarian cells. Chem Biol Interact. 2000 Jan 15;124(2):103-18. Pentachlorophenol (PCP), a commonly used inhibitor of P-SULT, inhibited 1-naphthol conjugation 50% in cell cultures, as well as in microsomal preparations. alpha-Naphthoflavone (ANF) and ellipticine (ELP), both cytochrome P450 (CYP) inhibitors, affected the conjugation of 1-naphthol in different ways; ANF did not affect P-UGT activity in microsomal preparations, but inhibited 1-naphthol conjugation in cell cultures by as much as 90%. |
0(0,0,0,0) | Details |
| 2789443 | van Ommen B, Hendriks W, Bessems JG, Geesink G, Muller F, van Bladeren PJ: The relation between the oxidative biotransformation of hexachlorobenzene and its porphyrinogenic activity. Toxicol Appl Pharmacol. 1989 Sep 15;100(3):517-28. This modulation was achieved by selective in vivo inhibition of the major cytochrome P450 isoenzyme involved in both the hydroxylation of hexachlorobenzene and its primary oxidative metabolite, pentachlorophenol. |
113(1,2,2,3) | Details |
| 8157216 | Hasheminejad G, Caldwell J: Genotoxicity of the alkenylbenzenes alpha- and beta-asarone, myristicin and elimicin as determined by the UDS assay in cultured rat hepatocytes. Food Chem Toxicol. 1994 Mar;32(3):223-31. The genotoxicity of the asarones is inhibited by the cytochrome P-450 inhibitor cimetidine but the sulfotransferase inhibitor pentachlorophenol (PCP) is without effect. |
32(0,1,1,2) | Details |
| 7728907 | Connors MS, Malfatti MA, Felton JS: The metabolism and DNA binding of the cooked-food mutagen, 2-amino-1-methyl-6-phenylimidazo [4,5-b] (PhIP) in precision-cut rat liver slices. Chem Biol Interact. 1995 May 19;96(2):185-202. The acetyltransferase and sulfotransferase inhibitors, pentachlorophenol (PCP) and 2,6-dichloro- (DCNP), and the cytochrome P450 inhibitor, alpha-naphthoflavone (ANF), were used to modulate PhIP metabolism and DNA and protein adduct formation. |
31(0,1,1,1) | Details |
| 317704 | Vizethum W, Goerz G: Induction of the hepatic microsomal and nuclear cytochrome P-450 system by hexachlorobenzene, pentachlorophenol and trichlorophenol. Chem Biol Interact. 1979 Dec;28(2-3):291-9. |
15(0,0,2,5) | Details |
| 12227954 | Qiao GL, Riviere JE: Systemic uptake and cutaneous disposition of pentachlorophenol in a sequential exposure scenario: effects of skin preexposure to benzo [a] pyrene. J Toxicol Environ Health A. 2002 Sep 27;65(18):1307-31. To assess sequential chemical exposure effect on chemical cutaneous disposition and systemic uptake of a toxicant, [(14) C] pentachlorophenol (PCP) was topically administered in three porcine skin models (in vivo, ex vivo, and in vitro) at 40 micro g/cm (2) with or without skin preexposure to benzo [a] pyrene (BaP), a known human carcinogen and cutaneous cytochrome P-450 (CYP450) inducer. |
7(0,0,1,2) | Details |
| 12704435 | : NTP Toxicology and Carcinogenesis Studies of Two Pentachlorophenol Technical-Grade Mixtures (CAS No. 87-86-5) in B6C3F1 Mice (Feed Studies). Natl Toxicol Program Tech Rep Ser. 1989 Mar;349:1-265. All grades of pentachlorophenol also resulted in a dose-related induction of aryl hydrocarbon hydroxylase and an increase in cytochrome P450. |
6(0,0,1,1) | Details |
| 1688520 | Wierckx FC, Wedzinga R, Meerman JH, Mulder GJ: Bioactivation of 2-nitrofluorene to reactive intermediates that bind covalently to DNA, RNA and protein in vitro and in vivo in the rat. Carcinogenesis. 1990 Jan;11(1):27-32. In vitro, such binding was catalyzed by the hepatic microsomal fraction, was dependent and could be inhibited by SKF 525A, an inhibitor of cytochrome P450. Pentachlorophenol, a selective sulfation inhibitor, did not influence the covalent binding of 2-NF; therefore, the reactive intermediate is not formed by sulfation of N--2-acetylaminofluorene, which could be a metabolite of 2-NF. |
4(0,0,0,4) | Details |
| 8199301 | Malfatti MA, Buonarati MH, Turteltaub KW, Shen NH, Felton JS: The role of sulfation and/or acetylation in the metabolism of the cooked-food mutagen 2-amino-1-methyl-6-phenylimidazo [4,5-b] in Salmonella typhimurium and isolated rat hepatocytes. Chem Res Toxicol. 1994 Mar-Apr;7(2):139-47. Mutagenic activity of the cooked-food mutagen/carcinogen 2-amino-1-methyl-6-phenylimidazo-[4,5-b] (PhIP) is highly dependent upon cytochrome P450 activation to the N-hydroxylated intermediate. In the Ames/S. typhimurium assay, the acetyltransferase and sulfotransferase enzyme inhibitors pentachlorophenol (PCP) and 2,6-dichloro- (DCNP) were used to modulate mutagenicity. |
2(0,0,0,2) | Details |
| 2273443 | Kato Y, Konishi S, Yamada S, Kimura R: Effects of -containing metabolites of hexachlorobenzene on the heme metabolic enzymes in rat liver. J Pharmacobiodyn. 1990 May;13(5):278-84. A single injection of HCB caused the increase in activities of (ALA) synthetase and heme oxygenase, and contents of cytochrome P-450 and total heme. |
2(0,0,0,2) | Details |
| 3768314 | Takazawa RS, Strobel HW: Cytochrome P-450 mediated reductive dehalogenation of the perhalogenated aromatic compound hexachlorobenzene. Biochemistry. 1986 Aug 26;25(17):4804-9. Trace levels of pentachlorophenol (PCP) and an unidentified metabolite are also observed. |
2(0,0,0,2) | Details |
| 1530660 | Yamazaki H, Shimada T: Activation of 6-aminochrysene to genotoxic products by different forms of rat liver cytochrome P450 in an O-acetyltransferase-overexpressing Salmonella typhimurium strain (NM2009). Biochem Pharmacol. 1992 Sep 1;44(5):913-20. We also found that the microsomal activation of 6-aminochrysene was catalyzed more effectively in an acetyltransferase-overexpressing strain (NM2009) than in the original TA1535/pSK1002 strain and that these activities could be inhibited by an acetyltransferase inhibitor, pentachlorophenol, in liver microsomes from PB-treated rats, but not in those from BNF-treated rats. |
2(0,0,0,2) | Details |
| 9675710 | Umegaki K, Ikegami S: Feeding fish oil to rats accelerates the metabolism of hexachlorobenzene. J Nutr Sci Vitaminol. 1998 Apr;44(2):301-11. The concentrations of HCB and pentachlorophenol (PCP), a major metabolite of HCB, were monitored in the blood for 5 d. The hepatic cytochrome P-450 content in the fish oil group was higher than that in the other groups. |
2(0,0,0,2) | Details |
| 11231299 | Jones JP, O'Hare EJ, Wong LL: Oxidation of polychlorinated benzenes by genetically engineered CYP101 (cytochrome P450 (cam)). Eur J Biochem. 2001 Mar;268(5):1460-7. Increasing the active-site hydrophobicity with the Y96F mutation increased the activity up to 100-fold, and both pentachlorobenzene and hexachlorobenzene were oxidized slowly to pentachlorophenol. |
2(0,0,0,2) | Details |
| 9602860 | Kreis P, Degen GH, Andrae U: Sulfotransferase-mediated genotoxicity of propane 2-nitronate in cultured ovine seminal vesicle cells. Mutat Res. 1998 Feb 23;413(1):69-81. In contrast, the sulfotransferase inhibitor pentachlorophenol strongly reduced genotoxicity. Several metabolic pathways, particularly cytochrome P450-, peroxidase- and sulfotransferase-dependent ones, have been suggested to lead to the formation of DNA-reactive species from 2-NP. |
2(0,0,0,2) | Details |
| 9773498 | Livingstone DR: The fate of organic xenobiotics in aquatic ecosystems: quantitative and qualitative differences in biotransformation by invertebrates and fish. Comp Biochem Physiol A Mol Integr Physiol. 1998 May;120(1):43-9. Use of the same approach showed that fish metabolise pentachlorophenol (PCP) and benzo [a] pyrene (BaP) faster than certain aquatic invertebrates, viz. rates of biotransformation to total metabolites (pmol min-1 g-1 wet wt.) at a tissue parent compound concentration of 10 nmol g-1 were, respectively, 19.2 +/- 3.7 (Carassius auratus) and 4.8 +/- 6.6 (molluscan species) (PCP), and 19.1 +/- 6.3 (fish species) and 2.1 +/- 0.2 (crustacean species) (BaP). The higher rate of biotransformation of BaP in fish is consistent with higher levels of total cytochrome P450 and inducible cytochrome P4501A (CYP1A) activity. |
2(0,0,0,2) | Details |
| 3802408 | Furlong BB, Weaver RP, Goldstein JA: Covalent binding to DNA and mutagenicity of 2,4-diaminotoluene metabolites produced by isolated hepatocytes and 9000 g supernatant from Fischer 344 rats. Carcinogenesis. 1987 Feb;8(2):247-51. Two inhibitors of sulfation, pentachlorophenol and 2,5-dichloro- also inhibited DNA binding in hepatocytes from both BNF-induced (91 and 85% respectively) and control rats (82 and 41% respectively), indicating that sulfation may also be required. 2,4-DAT was a more potent mutagen than 2,5- or 2,6-DAT in the Ames Salmonella mutagenesis assay using hepatic S9 fractions from F344 rats as an activating system. Both cytochrome P-450 and sulfation appear to be involved in the activation. |
1(0,0,0,1) | Details |
| 3275882 | Holme JA, Brunborg G, Alexander J, Trygg B, Bjornstad C: Modulation of the mutagenic effects of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ) and 2-amino-3,4-dimethylimidazo [4,5-f] quinoline (MeIQ) in bacteria with rat-liver 9000 x g supernatant or monolayers of rat hepatocytes as an activation system. Mutat Res. 1988 Jan;197(1):39-49. No marked effect of pentachlorophenol, an inhibitor of hepatocyte sulfation and bacterial O-acetylation, was seen using hepatocytes as an activation system, while the mutagenic activity of both IQ and MeIQ was reduced by 90% in the S9/Salmonella system. The presence of the cytochrome P450 inhibitors alpha-naphthoflavone and during the pre-incubation period reduced the accumulation of mutagenic metabolites. |
1(0,0,0,1) | Details |
| 8330339 | Yamazaki H, Mimura M, Oda Y, Inui Y, Shiraga T, Iwasaki K, Guengerich FP, Shimada T: Roles of different forms of cytochrome P450 in the activation of the promutagen 6-aminochrysene to genotoxic metabolites in human liver microsomes. Carcinogenesis. 1993 Jul;14(7):1271-8. Pentachlorophenol, an inhibitor of acetyltransferase activity, suppressed the activation of 6-aminochrysene in liver microsomes from phenobarbital-treated rats and from human samples HL-4, HL-13 and HL-18 but not HL-16. |
1(0,0,0,1) | Details |
| 890838 | Arrhenius E, Renberg L, Johansson L: Subcellular distribution, a factor in risk evaluation of pentachlorophenol. Chem Biol Interact. 1977 Jul;18(1):23-34. This favours flavin mediated oxygenation compared with flavin cytochrome P-450 dependent reactions. |
1(0,0,0,1) | Details |
| 2675838 | den Besten C, Peters MM, van Bladeren PJ: The metabolism of pentachlorobenzene by rat liver microsomes: the nature of the reactive intermediates formed. Biochem Biophys Res Commun. 1989 Sep 29;163(3):1275-81. Metabolism of [14C]-pentachlorobenzene by liver microsomes from dexamethasone-induced rats results in the formation of pentachlorophenol and 2,3,4,6-tetrachlorophenol as major primary metabolites in a ratio of 4:1, with 2,3,4,5- and 2,3,5,6-tetrachlorophenols as minor metabolites. During this cytochrome P450-dependent conversion of pentachlorobenzene, 5-15% of the total amount of metabolites becomes covalently bound to microsomal protein. |
1(0,0,0,1) | Details |
| 2462668 | Negishi C, Yamaizumi Z, Sato S: Nucleic acid binding and mutagenicity of active metabolites of 2-amino-3,8-dimethylimidazo [4,5-f] quinoxaline. Mutat Res. 1989 Jan;210(1):127-34. Pentachlorophenol (PCP) caused a dose-dependent inhibition of this mutagenic effect, but 2,6-dichloro- (DCNP) did not. These results suggest that MeIQx is metabolized to N-OH-MeIQx by microsomal cytochrome P-450 and further activated to an acetylated form that binds efficiently to nucleic acids in rat liver. |
1(0,0,0,1) | Details |
| 736603 | Goerz G, Vizethum W, Bolsen K, Krieg T, Lissner R: [Hexachlorbenzene (HCB) induced porphyria in rats. Arch Dermatol Res. 1978 Nov 10;263(2):189-96. These chlorinated aromatic hydrocarbons produced an increase in the liver cytochrome P-450 content in about the same degree, however, only the application of HCB showed an extremely high rise in the P-450 enzymatic activity expressed in terms of the O-dealkylation of 7-Ethoxycoumarine. |
1(0,0,0,1) | Details |
| 8653696 | Malfatti MA, Connors MS, Mauthe RJ, Felton JS: The capability of rat colon tissue slices to metabolize the cooked-food carcinogen 2-amino-1-methyl-6-phenylimidazo [4,5-b] Cancer Res. 1996 Jun 1;56(11):2550-5. The mutagenic potency of PhIP is highly dependent upon cytochrome P450 N-hydroxylation. In rat colon slice preparations, the sulfotransferase and acetyltransferase inhibitors pentachlorophenol (PCP) and 2,6-dichloro- (DCNP) were used to modulate DNA adduct and metabolite formation. |
1(0,0,0,1) | Details |
| 1600620 | Yamazaki H, Oda Y, Funae Y, Imaoka S, Inui Y, Guengerich FP, Shimada T: Participation of rat liver cytochrome P450 2E1 in the activation of N-nitrosodimethylamine and N-nitrosodiethylamine to products genotoxic in an acetyltransferase-overexpressing Salmonella typhimurium strain (NM2009). Carcinogenesis. 1992 Jun;13(6):979-85. The possible roles of cytochrome P450 (P450) enzymes in the metabolic activation of N-nitrosodimethylamine (NDMA) and N-nitrosodiethylamine (NDEA) by rat liver microsomes have been examined in a system containing the bacterial tester strain Salmonella typhimurium NM2009, a newly developed strain showing high O-acetyltransfer activities. Part of the pathway involved in the activation of nitrosamines is suggested to be acetylation of alkyldiazohydroxides formed by P450 or acetylesterase, because the genotoxic activity of N-nitrosomethylacethoxymethylamine in S.typhimurium NM2009 could be inhibited by the O-acetyltransferase inhibitor pentachlorophenol. |
1(0,0,0,1) | Details |
| 8614014 | Markiewicz KV, Howie LE, Safe SH, Donnelly KC: Mutagenic potential of binary and complex mixtures using different enzyme induction systems. J Toxicol Environ Health. 1996 Apr 5;47(5):443-51. Test samples included benzo [a] pyrene (BaP), pentachlorophenol (PCP), a binary mixture of BaP and PCP, two five-component mixtures, a methylene extract of wood preserving waste-amended soil, and a extract of coal gasification waste. These data demonstrate the relative importance of the various induced cytochrome P-450 isozymes for the metabolism of mutagenic chemicals and complex mixtures. |
1(0,0,0,1) | Details |
| 14587904 | Hoekstra PF, Letcher RJ, O'Hara TM, Backus SM, Solomon KR, Muir DC: Hydroxylated and methylsulfone-containing metabolites of polychlorinated biphenyls in the plasma and blubber of bowhead whales (Balaena mysticetus). Environ Toxicol Chem. 2003 Nov;22(11):2650-8. However, similar ratios of MeSO2-PCB metabolites to parent PCB congeners among marine mammals suggest that cytochrome P450 2B-like biotransformation and other necessary enzyme-mediated processes and mechanisms that influence the formation and clearance of MeSO2-PCBs exist in the bowhead whale. Pentachlorophenol was the most abundant halogenated phenolic compound quantified in bowhead plasma (1.55 +/- 0.19 ng g (-1) wet wt). |
1(0,0,0,1) | Details |
| 3779880 | van Ommen B, Adang A, Muller F, van Bladeren PJ: The microsomal metabolism of pentachlorophenol and its covalent binding to protein and DNA. Chem Biol Interact. 1986 Oct 15;60(1):1-11. There are indications that the 1,2- and 1,4-isomers are produced in different ratio's by various cytochrome P-450 isoenzymes: Microsomes from PB- and HCB-treated rats produced the tetrachloro-1,4- and tetrachloro-1,2- in a ratio of about 2, while microsomes from rats induced with 3 MC and ISF showed a ratio of about 1.3. |
1(0,0,0,1) | Details |
| 18433972 | Jeurissen SM, Punt A, Delatour T, Rietjens IM: Basil extract inhibits the sulfotransferase mediated formation of DNA adducts of the procarcinogen 1'-hydroxyestragole by rat and human liver S9 homogenates and in HepG2 human hepatoma cells. Food Chem Toxicol. 2008 Jun;46(6):2296-302. Epub 2008 Mar 16. Basil was chosen since it contains the procarcinogen estragole that can be metabolized to 1'-hydroxyestragole by cytochrome P450 enzymes. Because the inhibition resembled the inhibition by the sulfotransferase inhibitor pentachlorophenol and since the inhibition was not observed in incubations with the direct electrophile 1'-acetoxyestragole it is concluded that the inhibition occurs at the level of the sulfotransferase mediated bioactivation step. |
1(0,0,0,1) | Details |