Hepatic arachidonic acid metabolism is disrupted after hexachlorobenzene treatment
Hexaclorobenzene (HCB), one of the most persistent environmental pollutants, can cause a wide range of toxic effects including cancer in animals, and hepatotoxicity and porphyria both in humans and animals. In the present study, liver microsomal cytochrome P450 (CYP)-dependent arachidonic acid (AA)...
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2005
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| LEADER | 17169caa a22013697a 4500 | ||
|---|---|---|---|
| 001 | PAPER-4152 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203340.0 | ||
| 008 | 190411s2005 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-15944389919 | |
| 024 | 7 | |2 cas |a aminopyrine n demethylase, 9037-69-8; arachidonic acid, 506-32-1, 6610-25-9, 7771-44-0; cytochrome P450, 9035-51-2; ethoxyresorufin deethylase, 59793-97-4; hexachlorobenzene, 118-74-1, 55600-34-5; phospholipase A2, 9001-84-7; prostaglandin E, 11042-70-9 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a TXAPA | ||
| 100 | 1 | |a Billi De Catabbi, S.C. | |
| 245 | 1 | 0 | |a Hepatic arachidonic acid metabolism is disrupted after hexachlorobenzene treatment |
| 260 | |b Academic Press Inc. |c 2005 | ||
| 270 | 1 | 0 | |m Cochón, A.C.; Fac. de Ciencias Exactas Y Naturales, Depto. de Quím. Biol., Pabellón II, 1428 Buenos Aires, Argentina; email: adcris@qb.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a (1998) Toxicological Profile for Chlorinated Dibenzo-p-Dioxins, , Agency for Toxic Substances and Disease Registry (ATSDR) U.S. Public Health Services, U.S. Department of Health and Human Services Atlanta, GA | ||
| 504 | |a (2002) Toxicological Profile for Hexachlorobenzene, , Agency for Toxic Substances and Disease Registry (ATSDR) U.S. Public Health Services, U.S. Department of Health and Human Services Atlanta, GA | ||
| 504 | |a Billi De Catabbi, S., Sterin-Speziale, N., Fernandez, M.C., Minutolo, C., Aldonatti, C., San Martin De Viale, L.C., Time course of hexachlorobenzene-induced alterations of lipid metabolism and their relation to porphyria (1997) Int. J. Biochem. Cell Biol., 29, pp. 335-344 | ||
| 504 | |a Billi De Catabbi, S.C., Aldonatti, C., San Martín De Viale, L.C., Heme metabolism after discontinued hexachlorobenzene administration in rats: Possible irreversible changes and biomarker for hexachlorobenzene persistence (2000) Comp. Biochem. Physiol., C: Toxicol. Pharmacol., 127, pp. 165-175 | ||
| 504 | |a Billi De Catabbi, S.C., Setton-Advruj, C.P., Sterin-Spezziale, N., San Martin De Viale, L.C., Cochón, A.C., Hexachlorobenzene-induced alterations on neutral and acidic sphingomyelinases and serine palmitoyltransferase activities. A time course study in two strains of rats (2000) Toxicology, 149, pp. 89-100 | ||
| 504 | |a Cantoni, L., Rizzardini, M., Tacconi, M.T., Graziani, A., Comparison of hexachlorobenzene-induced alterations of microsomal membrane composition and monooxygenase activity in male and female rats (1987) Toxicology, 45, pp. 291-305 | ||
| 504 | |a Capdevila, J.H., Karara, A., Waxman, D.J., Martin, M.V., Falck, J.R., Guenguerich, F.P., Cytochrome P-450 enzyme-specific control of the regio- and enantiofacial selectivity of the microsomal arachidonic acid epoxygenase (1990) J. Biol. Chem., 265, pp. 10865-10871 | ||
| 504 | |a Capdevila, J.H., Falck, J.R., Harris, R.C., Cytochrome P450 and arachidonic acid bioactivation: Molecular and functional properties of the arachidonate monooxygenase (2000) J. Lipid Res., 41, pp. 163-181 | ||
| 504 | |a Courtney, K.D., Hexachlorobenzene (HCB): A review (1979) Environ. Res., 20, pp. 225-266 | ||
| 504 | |a Elder, G.H., Porphyria cutanea tarda (1998) Semin. Liver Dis., 18, pp. 67-75 | ||
| 504 | |a Ertel, W., Morrison, M.H., Ayala, A., Chaudry, I.H., Chloroquine attenuates hemorrhagic shock-induced suppression of Kupffer cell antigen presentation and major histocompatibility complex class II antigen expression through blockade of tumor necrosis factor and prostaglandin release (1991) Blood, 78, pp. 1781-1788 | ||
| 504 | |a Faletti, A., Perez Martinez, S., Perotti, C., Gimeno, M.A., Activity of ovarian nitric oxide synthase (NOs) during ovulatory process in the rat: Relationship with prostaglandins (PGs) production (1999) Nitric Oxide, 3, pp. 340-347 | ||
| 504 | |a Fernandez-Tomé, M., Del, C., Speziale, E.H., Sterin-Speziale, N.B., Phospholipase C inhibitors and prostaglandins differentially regulate phosphatidylcholine synthesis in rat renal papilla. Evidence of compartmental regulation of CTP:phosphocholine cytidylyltransferase and CDP-choline:1,2- diacylglycerolcholinephosphotransferase (2002) Biochim. Biophys. Acta, 1583, pp. 185-194 | ||
| 504 | |a Franchi, A.M., Motta, A., Gimeno, A.L., Gimeno, M.A.F., Relationship between factors influencing Na+-K +-ATPase activity and eicosanoid production from 14C- arachidonic acid in spayed rat uterus (1993) Prostaglandins Leukot. Essent. Fat. Acids, 48, pp. 273-275 | ||
| 504 | |a Gijón, M.A., Leslie, C.C., Phospholipases A2 (1997) Semin. Cell Dev. Biol., 8, pp. 297-303 | ||
| 504 | |a Gorman, N., Ross, K.L., Walton, H.S., Bement, W.J., Szakacs, J.G., Gerhard, G.S., Dalton, T.P., Sinclair, P.R., Uroporphyria in mice: Thresholds for hepatic CYP 1A2 and iron (2002) Hepatology, 35, pp. 912-921 | ||
| 504 | |a Karara, A., Dishman, E., Falck, J.R., Capdevila, J.H., Endogenous epoxyeicosatrienoyl-phospholipids. A novel class of cellular glycerolipids containing epoxidized arachidonate moieties (1991) J. Biol. Chem., 266, pp. 7561-7569 | ||
| 504 | |a Klotz, A.V., Stegeman, J.J., Walsh, C., An alternative 7-ethoxyresorufin O-deethylase activity assay: A continuous visible spectrophotometric method for measurement of cytochrome P-450 monooxygenase activity (1984) Anal. Biochem., 140, pp. 138-145 | ||
| 504 | |a Kószó, F., Horváth, L.I., Simon, N., Siklosi, Cs., Kiss, M., The role of possible membrane damage in porphyria cutanea tarda: A spin label study of rat liver cell membranes (1982) Biochem. Pharmacol., 31, pp. 11-17 | ||
| 504 | |a Laethem, R.M., Laethem, C.L., Koop, D.R., Purification and properties of a cytochrome P450 arachidonic acid epoxygenase from rabbit renal cortex (1992) J. Biol. Chem., 267, pp. 5552-5559 | ||
| 504 | |a Lake, B.G., Preparation and characterization of microsomal fractions for studies on xenobiotic metabolism (1987) Biochemical Toxicology: A Practical Approach, pp. 183-213. , K. Snell B. Mullocck IRL Press Oxford, Washington, DC | ||
| 504 | |a Lee, C.A., Lawrence, B.P., Kerkvliet, N.I., Rifkind, A.B., 2,3,7,8-Tetrachlorodibenzo-p-dioxin induction of cytochrome P450-dependent arachidonic acid metabolism in mouse liver microsomes: Evidence for species-specific differences in responses (1998) Toxicol. Appl. Pharmacol., 153, pp. 1-11 | ||
| 504 | |a Llambías, E.B.C., Aldonatti, C., San Martín De Viale, L.C., Tryptophan metabolism via serotonin in rats with hexachlorobenzene experimental porphyria (2003) Biochem. Pharmacol., 66, pp. 35-42 | ||
| 504 | |a Loffler, B.M., Bohn, E., Hesse, B., Kunze, H., Effects of antimalarial drugs on phospholipase a and lysophospholipase activities in plasma membrane, mitochondrial, microsomal and cytosolic subcellular fractions of rat liver (1985) Biochim. Biophys. Acta, 835, pp. 448-455 | ||
| 504 | |a Lowry, O.H., Rosebrough, A., Farr, L., Randall, R.S., Protein measurement with the folin phenol reagent (1951) J. Biol. Chem., 249, pp. 265-275 | ||
| 504 | |a Mylchreest, E., Charbonneau, M., Studies on the mechanism of uroporphyrinogen decarboxylase inhibition in hexachlorobenzene-induced porphyria in the female rat (1997) Toxicol. Appl. Pharmacol., 145, pp. 23-33 | ||
| 504 | |a Nakai, K., Ward, A.M., Gannon, M., Rifkind, A.B., β-Naphthoflavone induction of a cytochrome P-450 arachidonic acid epoxygenase in chick embryo liver distinct from the aryl hydrocarbon hydroxylase and from phenobarbital-induced arachidonate epoxygenase (1992) J. Biol. Chem., 267, pp. 19503-19512 | ||
| 504 | |a Nordmann, Y., Puy, H., Human hereditary hepatic porphyries (2002) Clin. Chim. Acta, 325, pp. 17-37 | ||
| 504 | |a Nosál, R., Jančinová, V., Cationic amphiphilic drugs and platelet phospholipase A2 (cPLA2) (2002) Thromb. Res., 105, pp. 339-345 | ||
| 504 | |a Puga, A., Hoffer, A., Zhou, S., Bohm, J.M., Leikauf, G.D., Shertzer, H.G., Sustained increase in intracellular free calcium and activation of cyclooxygenase-2 expression in mouse hepatoma cells treated with dioxin (1997) Biochem. Pharmacol., 54, pp. 1287-1296 | ||
| 504 | |a Ramana, K.V., Kohli, K.K., Purification and characterization of the hepatic CYP2C and 3A isozymes from phenobarbitone pretreated rhesus monkey (1999) Mol. Cell. Biochem., 198, pp. 79-88 | ||
| 504 | |a Randi, A.S., Sancovich, H.A., Ferramola De Sancovich, A.M., Loaiza, A., Krawiek, L., Kleiman De Pisarev, D.L., Hexachlorobenzene-induced alterations of rat hepatic microsomal membrane function (1998) Toxicology, 125, pp. 83-94 | ||
| 504 | |a Rifkind, A.B., Gannon, M., Gross, S.S., Arachidonic acid metabolism by dioxin-induced cytochrome P-450: A new hypothesis on the role of P-450 in dioxin toxicity (1990) Biochem. Biophys. Res. Commun., 172, pp. 1180-1188 | ||
| 504 | |a San Martin De Viale, L.C., Viale, A., Nacht, S., Grinstein, M., Experimental porphyria induced in rats by hexachlorobenzene. A study of the porphyrin excreted by urine (1970) Clin. Chim. Acta, 28, pp. 13-23 | ||
| 504 | |a San Martín De Viale, L.C., Ríos De Molina, M., Del, C., Wainstok De Calmanovici, R., Tomio, J.M., Porphyrins and porphyrinogen carboxy-lyase in hexachlorobenzene-induced porphyria (1977) Biochem. J., 168, pp. 393-400 | ||
| 504 | |a Sharma, S., Sharma, S.C., An update on eicosanoids and inhibitors of cyclooxygenase enzyme systems (1997) Indian J. Exp. Biol., 35, pp. 1025-1031 | ||
| 504 | |a Sinclair, P.R., Gorman, N., Dalton, T., Walton, H.S., Bement, W.J., Sinclair, J.F., Smith, A.G., Nebert, W., Uroporphyria produced in mice by iron and 5-aminolevulinic acid does not occur in Cyp1a2(-/-) null mutant mice (1998) Biochem. J., 330, pp. 149-153 | ||
| 504 | |a Smith, A.G., De Matteis, R., Drugs and porphyria (1980) Clin. Haematol., 9, pp. 399-425 | ||
| 504 | |a Smith, A.G., Francis, J.E., Green, J.A., Grieg, J.B., Wolf, C.R., Manson, M.M., Sex-linked hepatic uroporphyria and the induction of cytochromes P450IA in rats caused by hexachlorobenzene and polyhalogenated biphenyls (1990) Biochem. Pharmacol., 40, pp. 2059-2068 | ||
| 504 | |a Sternfeld, L., Thévenod, F., Schulz, I., FMLP-induced arachidonic acid release in db-cAMP-differentiated HL-60 cells is independent of phosphatidylinositol-4,5-bisphosphate-specific phospholipase C activation and cytosolic phospholipase A2 activation (2000) Arch. Biochem. Biophys., 378, pp. 246-258 | ||
| 504 | |a Stewart, F.P., Smith, A.G., Metabolism of the "mixed" cytochrome P-450 inducer hexachlorobenzene by rat liver microsomes (1986) Biochem. Pharmacol., 35, pp. 2163-2170 | ||
| 504 | |a Taira, M.C., Mazzetti, M.B., Lelli, S.M., San Martín De Viale, L.C., Glycogen metabolism and glucose transport in experimental porphyria (2004) Toxicology, 197, pp. 165-175 | ||
| 504 | |a Tran, K., Wong, J.T., Lee, E., Chan, A.C., Choy, P.C., Vitamin e potentiates arachidonate release and phospholipase A 2 activity in rat heart myoblastic cells (1996) Biochem. J., 319, pp. 385-391 | ||
| 504 | |a Vogel, C., Schuhmacher, U.S., Degen, G.H., Bolt, H.M., Pineau, T., Abel, J., Modulation of prostaglandin H synthase-2 mRNA expression by 2,3,7,8-tetrachlorodibenzo-p-dioxin in mice (1998) Arch. Biochem. Biophys., 351, pp. 265-271 | ||
| 504 | |a Vogel, C., Boerboom, A.M., Baechle, C., El-Bahay, C., Kahl, R., Degen, G.H., Abel, J., Regulation of prostaglandin endoperoxide H synthase-2 induction by dioxin in rat hepatocytes: Possible c-Src-mediated pathway (2000) Carcinogenesis, 21, pp. 2267-2274 | ||
| 504 | |a Wölfle, D., Marotzki, S., Dartsch, D., Schäfer, W., Marquardt, H., Induction of cyclooxygenase expression and enhancement of malignant cell transformation by 2,3,7,8-tetrachlorodibenzo-p-dioxin (2000) Carcinogenesis, 21, pp. 15-21 | ||
| 504 | |a Yang, H.C., Mosior, M., Johnson, C.A., Chen, Y., Dennis, E.A., Group-specific assays that distinguish between the four major types of mammalian phospholipase A2 (1999) Anal. Biochem., 269, pp. 278-288 | ||
| 504 | |a Zhao, X., Imig, J.D., Kidney CYP450 enzymes: Biological actions beyond drug metabolism (2003) Curr. Drug Metab., 4, pp. 73-84 | ||
| 520 | 3 | |a Hexaclorobenzene (HCB), one of the most persistent environmental pollutants, can cause a wide range of toxic effects including cancer in animals, and hepatotoxicity and porphyria both in humans and animals. In the present study, liver microsomal cytochrome P450 (CYP)-dependent arachidonic acid (AA) metabolism, hepatic PGE production, and cytosolic phospholipase A2 (cPLA2) activity were investigated in an experimental model of porphyria cutanea tarda induced by HCB. Female Wistar rats were treated with a single daily dose of HCB (100 mg kg-1 body weight) for 5 days and were sacrificed 3, 10, 17, and 52 days after the last dose. HCB treatment induced the accumulation of hepatic porhyrins from day 17 and increased the activities of liver ethoxyresorufin O-deethylase (EROD), methoxyresorufin O-demethylase (MROD), and aminopyrine N-demethylase (APND) from day 3 after the last dose. Liver microsomes from control and HCB-treated rats generated, in the presence of NADPH, hydroxyeicosatetraenoic acids (HETEs), epoxyeicosatrienoic acids (EETs), 11,12-Di HETE, and ω-OH/ω-1-OH AA. HCB treatment caused an increase in total NADPH CYP-dependent AA metabolism, with a higher response at 3 days after the last HCB dose than at the other time points studied. In addition, HCB treatment markedly enhanced PGE production and release in liver slices. This HCB effect was time dependent and reached its highest level after 10 days. At this time cPLA2 activity was shown to be increased. Unexpectedly, HCB produced a significant decrease in cPLA2 activity on the 17th and 52nd day. Our results demonstrated for the first time that HCB induces both the cyclooxygenase and CYP-dependent AA metabolism. The effects of HCB on AA metabolism were previous to the onset of a marked porphyria and might contribute to different aspects of HCB-induced liver toxicity such as alterations of membrane fluidity and membrane-bound protein function. Observations also suggested that a possible role of cPLA2 in the early increase of AA metabolism cannot be excluded. However, the existence of other pathway(s) for metabolizable AA generation different from cPLA2 activation is also proposed. © 2004 Elsevier Inc. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: National Council for Scientific Research | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: We would like to thank Mrs. C. Aldonatti for her skillful technical assistance. This work was supported by grants from the National Research Council of Argentina (CONICET) and from the University of Buenos Aires. | ||
| 593 | |a Fac. de Ciencias Exactas Y Naturales, Depto. de Quím. Biol., Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a Ctro. Estud. Farmacologicos B., 1414 Buenos Aires, Argentina | ||
| 593 | |a Fac. de Ciencias Exactas Y Naturales, Depto. de Quím. Biol., Pabellón II, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ARACHIDONIC ACID |
| 690 | 1 | 0 | |a CYTOCHROME P450 |
| 690 | 1 | 0 | |a CYTOSOLIC PHOSPHOLIPASE A2 |
| 690 | 1 | 0 | |a HEXACHLOROBENZENE |
| 690 | 1 | 0 | |a PROSTAGLANDIN |
| 690 | 1 | 0 | |a RAT LIVER |
| 690 | 1 | 0 | |a AMINOPYRINE N DEMETHYLASE |
| 690 | 1 | 0 | |a ARACHIDONIC ACID |
| 690 | 1 | 0 | |a CYTOCHROME P450 |
| 690 | 1 | 0 | |a ETHOXYRESORUFIN DEETHYLASE |
| 690 | 1 | 0 | |a HEXACHLOROBENZENE |
| 690 | 1 | 0 | |a PHOSPHOLIPASE A2 |
| 690 | 1 | 0 | |a PROSTAGLANDIN E |
| 690 | 1 | 0 | |a ANIMAL EXPERIMENT |
| 690 | 1 | 0 | |a ANIMAL MODEL |
| 690 | 1 | 0 | |a ANIMAL TISSUE |
| 690 | 1 | 0 | |a ARACHIDONIC ACID METABOLISM |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CLINICAL FEATURE |
| 690 | 1 | 0 | |a CONTROLLED STUDY |
| 690 | 1 | 0 | |a CYTOKINE RELEASE |
| 690 | 1 | 0 | |a ENZYME ACTIVITY |
| 690 | 1 | 0 | |a FEMALE |
| 690 | 1 | 0 | |a LIVER |
| 690 | 1 | 0 | |a LIVER MICROSOME |
| 690 | 1 | 0 | |a LIVER TOXICITY |
| 690 | 1 | 0 | |a MEMBRANE FLUIDITY |
| 690 | 1 | 0 | |a NONHUMAN |
| 690 | 1 | 0 | |a PORPHYRIA CUTANEA TARDA |
| 690 | 1 | 0 | |a PROTEIN FUNCTION |
| 690 | 1 | 0 | |a RAT |
| 690 | 1 | 0 | |a STATISTICAL SIGNIFICANCE |
| 700 | 1 | |a Faletti, A. | |
| 700 | 1 | |a Fuentes, F. | |
| 700 | 1 | |a San Martín De Viale, L.C. | |
| 700 | 1 | |a Cochón, A.C. | |
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