Base de dados : MEDLINE
Pesquisa : D02.455.526.368.200 [Categoria DeCS]
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  1 / 92 MEDLINE  
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[PMID]:16337879
[Au] Autor:Guéraud F; Peiro G; Bernard H; Alary J; Créminon C; Debrauwer L; Rathahao E; Drumare MF; Canlet C; Wal JM; Bories G
[Ad] Endereço:Institut National de la Recherche Agronomique, UMR-1089 Xénobiotiques, INRA/ENVT, BP 3, 180 chemin de Tournefeuille, 31931 Toulouse Cedex 9, France. fgueraud@toulouse.inra.fr
[Ti] Título:Enzyme immunoassay for a urinary metabolite of 4-hydroxynonenal as a marker of lipid peroxidation.
[So] Source:Free Radic Biol Med;40(1):54-62, 2006 Jan 01.
[Is] ISSN:0891-5849
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Free radical reactions are involved in the pathogenesis of numerous diseases, so there is a real need to develop biomarkers that reflect these reactions in vivo. 4-Hydroxy-2-nonenal (HNE) is a major product of the lipid peroxidation process that is a consequence of free radical reactions. We present here the development and validation of an enzyme immunoassay (EIA) of the major urinary metabolite of HNE, namely 1,4-dihydroxynonane-mercapturic acid (DHN-MA). EIA allowed direct measurement of DHN-MA in rat urine with good sensitivity (0.02 ng/ml) and precision (intraassay CV = 5.7%). Recovery was complete (99-102%). Cross-reactivity was very low with 1,4-dihydroxynonene and with different mercapturic acids except with one other HNE urinary metabolite. Good correlation (EIA = 0.79 x LC/MS + 14.03, r = 0.877, p < 10(-8)) was obtained between EIA and liquid chromatography/mass spectrometry (LC/MS) quantitation when analyzing urine samples of rats with different oxidative status, due to treatment with either BrCCl(3) or trinitrobenzene sulfonic acid, which are known to induce hepatic lipid peroxidation or colon inflammation, respectively.
[Mh] Termos MeSH primário: Acetilcisteína/análogos & derivados
Aldeídos/urina
Biomarcadores/urina
Peroxidação de Lipídeos
[Mh] Termos MeSH secundário: Acetilcisteína/imunologia
Acetilcisteína/urina
Alcenos/metabolismo
Animais
Bromotriclorometano/farmacologia
Cromatografia Líquida
Reações Cruzadas
Radicais Livres
Técnicas Imunoenzimáticas
Masculino
Coelhos
Ratos
Ratos Wistar
Sensibilidade e Especificidade
Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz
Ácido Trinitrobenzenossulfônico/farmacologia
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (1,4-dihydroxy-2-nonene); 0 (1,4-dihydroxynonene mercapturic acid); 0 (Aldehydes); 0 (Alkenes); 0 (Biomarkers); 0 (Free Radicals); 8T3HQG2ZC4 (Trinitrobenzenesulfonic Acid); IKJ30QXM63 (Bromotrichloromethane); K1CVM13F96 (4-hydroxy-2-nonenal); WYQ7N0BPYC (Acetylcysteine)
[Em] Mês de entrada:0603
[Cu] Atualização por classe:161124
[Lr] Data última revisão:
161124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:051213
[St] Status:MEDLINE


  2 / 92 MEDLINE  
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[PMID]:16403967
[Au] Autor:Peiro G; Alary J; Cravedi JP; Rathahao E; Steghens JP; Guéraud F
[Ad] Endereço:UMR 1089-Xénobiotiques, INRA/ENVT, BP 3, 31931, Toulouse Cedex 9, France.
[Ti] Título:Dihydroxynonene mercapturic acid, a urinary metabolite of 4-hydroxynonenal, as a biomarker of lipid peroxidation.
[So] Source:Biofactors;24(1-4):89-96, 2005.
[Is] ISSN:0951-6433
[Cp] País de publicação:Netherlands
[La] Idioma:eng
[Ab] Resumo:The objective of our study was to compare the information obtained through the use of three different urinary biomarkers of lipoperoxidation during the time course of a bromotrichloromethane (BrCCl3) induced oxidative stress in rats. These biomarkers were malondialdehyde (MDA) measured by LC/MS after derivatization, the isoprostane 8-iso-PGF2alpha measured by enzyme immunoassay and 1,4-dihydroxynonene mercapturic acid (DHN-MA), the major 4-hydroxynonenal urinary metabolite [1], measured by LC-MS. Male Wistar rats received a single dose of 100 microL/kg BrCCl3 per os and lipid peroxidation was estimated every day for a 4-day-period after treatment. MDA, 8-iso-PGF2alpha and DHN-MA significantly increased in response to BrCCl3 treatment for this period of time, and DHN-MA showed the main increase during the 24-48 h period after treatment.
[Mh] Termos MeSH primário: Acetilcisteína/análogos & derivados
Aldeídos/urina
Biomarcadores/urina
Peroxidação de Lipídeos
[Mh] Termos MeSH secundário: Acetilcisteína/urina
Animais
Bromotriclorometano/administração & dosagem
Cromatografia Líquida
Dinoprosta/análogos & derivados
Dinoprosta/urina
Cinética
Masculino
Malondialdeído/urina
Espectrometria de Massas
Estresse Oxidativo
Ratos
Ratos Wistar
[Pt] Tipo de publicação:JOURNAL ARTICLE
[Nm] Nome de substância:
0 (1,4-dihydroxynonene mercapturic acid); 0 (Aldehydes); 0 (Biomarkers); 27415-26-5 (8-epi-prostaglandin F2alpha); 4Y8F71G49Q (Malondialdehyde); B7IN85G1HY (Dinoprost); IKJ30QXM63 (Bromotrichloromethane); K1CVM13F96 (4-hydroxy-2-nonenal); WYQ7N0BPYC (Acetylcysteine)
[Em] Mês de entrada:0605
[Cu] Atualização por classe:161124
[Lr] Data última revisão:
161124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:060113
[St] Status:MEDLINE


  3 / 92 MEDLINE  
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[PMID]:12106824
[Au] Autor:Pirlich M; Müller C; Sandig G; Jakstadt M; Sitte N; Lochs H; Grune T
[Ad] Endereço:Department of Gastroenterology and Hepatology, University Hospital Charité, Humboldt-University Berlin, Germany.
[Ti] Título:Increased proteolysis after single-dose exposure with hepatotoxins in HepG2 cells.
[So] Source:Free Radic Biol Med;33(2):283-91, 2002 Jul 15.
[Is] ISSN:0891-5849
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Chronic ethanol consumption is associated with increased protein oxidation and decreased proteolysis in the liver. We tested the hypothesis that even single-dose treatment with ethanol or bromotrichloromethane causes increased protein oxidation and a distinct proteolytic response in cultured hepatocytes. HepG2 cells were treated for 30 min with ethanol, H(2)O(2) and bromotrichloromethane at various nontoxic concentrations. Protein degradation was measured in living cells using [35S]-methionine labeling. Protein oxidation, and 20S proteasome activity were measured in cell lysates. Oxidized proteins increased immediately after ethanol, H(2)O(2), and bromotrichloromethane exposure, but a further significant increase 24-h after exposure was observed only following ethanol and bromotrichloromethane treatment. All three reagents caused a significant increase of the overall intracellular proteolysis at rather low concentrations, which could be suppressed by the proteasome inhibitor lactacystin. A decline of proteolysis observed at higher-subtoxic-concentrations was not related to decreased proteasome activity. Preincubation with ketoconazole or 4-methylpyrazole completely prevented the ethanol- and bromotrichloromethane-induced but not the H(2)O(2)-induced protein oxidation and proteolysis, suggesting strongly an enzyme-mediated generation of reactive oxygen species. In conclusion single-dose exposure with ethanol or haloalkanes causes increased protein oxidation followed by an increased proteasome-dependent protein degradation in human liver cells.
[Mh] Termos MeSH primário: Bromotriclorometano/toxicidade
Cisteína Endopeptidases/metabolismo
Etanol/toxicidade
Hepatócitos/efeitos dos fármacos
Peróxido de Hidrogênio/toxicidade
Complexos Multienzimáticos/metabolismo
Proteínas/metabolismo
[Mh] Termos MeSH secundário: Sobrevivência Celular/efeitos dos fármacos
Células Cultivadas
Sistema Enzimático do Citocromo P-450/metabolismo
Primers do DNA/química
Relação Dose-Resposta a Droga
Inibidores Enzimáticos/farmacologia
Hepatócitos/metabolismo
Seres Humanos
Oxirredução
Estresse Oxidativo
Reação em Cadeia da Polimerase
Complexo de Endopeptidases do Proteassoma
RNA/metabolismo
Espécies Reativas de Oxigênio
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (DNA Primers); 0 (Enzyme Inhibitors); 0 (Multienzyme Complexes); 0 (Proteins); 0 (Reactive Oxygen Species); 3K9958V90M (Ethanol); 63231-63-0 (RNA); 9035-51-2 (Cytochrome P-450 Enzyme System); BBX060AN9V (Hydrogen Peroxide); EC 3.4.22.- (Cysteine Endopeptidases); EC 3.4.25.1 (Proteasome Endopeptidase Complex); IKJ30QXM63 (Bromotrichloromethane)
[Em] Mês de entrada:0301
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:020711
[St] Status:MEDLINE


  4 / 92 MEDLINE  
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[PMID]:10762731
[Au] Autor:Wang YF; Hu ML
[Ad] Endereço:Department of Food Science, National Chung-Hsing University, 250 Kuo-Kuang Road, Taichung, Taiwan.
[Ti] Título:Use of rat liver slices for the study of oxidative DNA damage in comparison with isolated rat liver nuclei and HepG2 human hepatoma cells.
[So] Source:Food Chem Toxicol;38(5):451-8, 2000 May.
[Is] ISSN:0278-6915
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Tissue slices are a useful biological system for lipid peroxidation studies but their use for DNA damage studies is not well characterized. Hence, the present study investigates DNA damage in rat liver slices, in comparison with isolated rat liver nuclei and HepG2 human hepatoma cells, incubated with ferric nitrilotriacetate (Fe(III)-NTA), bromotrichloromethane (BrCCl(3)), bromobenzene (BrB) or 2-nitropropane (2-NP) at 37 degrees C for 2 hr. DNA damage was measured in slices, cells or nuclei after centrifugation as formation of as 8-hydroxy-2'-deoxyguanosine (8-OH-dGu) and loss of double-stranded (dsDNA) due to strand breakage using a fluorometric analysis of DNA unwinding (FADU). Lipid peroxidation was measured as thiobarbituric acid-reactive substances (TBARS) released into the medium. The results show that in liver slices and isolated nuclei, Fe/NTA (1 mM/4 mM) induced high levels of TBARS but low levels of 8-OH-dGu, whereas the oxidant induced low levels of TBARS and no formation of 8-OH-dGu in HepG2 cells. In all three systems, inclusion of ascorbate caused dose-dependent formation of 8-OH-dGu, and the levels were similar between liver slices and HepG2 cells but were far higher in isolated nuclei. In liver slices the FADU assay was not applicable due to limited solubilization of DNA from the slice, whereas the assay detected significant loss of dsDNA in HepG2 cells and slight loss in isolated nuclei induced by Fe/NTA with or without ascorbate. Liver slices incubated with 1 mm BrCCl(3), BrB or 2-NP had elevated TBARS but had little or no formation of 8-OH-dGu; none of these oxidants induced lipid peroxidation or DNA damage in HepG2 cells. When liver slices obtained from rats injected with diethylmaleate (to deplete GSH) were incubated with BrCCl(3), BrB or 2-NP, levels of TBARS and 8-OH-dGu increased markedly. Similarly, HepG2 cells with decreased GSH showed marked elevation of TBARS and loss of dsDNA induced by these oxidants, although no formation of 8-OH-dGu was detected. The present study demonstrates the usefulness and limitations of liver slices for DNA damage studies and the importance of cellular GSH in the protection of DNA against environmental toxicants.
[Mh] Termos MeSH primário: Núcleo Celular/efeitos dos fármacos
Dano ao DNA/efeitos dos fármacos
Neoplasias Hepáticas Experimentais/patologia
Fígado/metabolismo
[Mh] Termos MeSH secundário: Animais
Ácido Ascórbico/farmacologia
Bromobenzenos/toxicidade
Bromotriclorometano/toxicidade
Carcinógenos/toxicidade
Núcleo Celular/ultraestrutura
Desoxiguanosina/análogos & derivados
Desoxiguanosina/toxicidade
Compostos Férricos/farmacologia
Seres Humanos
Peroxidação de Lipídeos/efeitos dos fármacos
Fígado/patologia
Ácido Nitrilotriacético/análogos & derivados
Ácido Nitrilotriacético/farmacologia
Nitroparafinas/toxicidade
Oxirredução
Propano/análogos & derivados
Propano/toxicidade
Ratos
Substâncias Reativas com Ácido Tiobarbitúrico/metabolismo
Células Tumorais Cultivadas
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Bromobenzenes); 0 (Carcinogens); 0 (Ferric Compounds); 0 (Nitroparaffins); 0 (Thiobarbituric Acid Reactive Substances); 88847-89-6 (8-oxo-7-hydrodeoxyguanosine); G9481N71RO (Deoxyguanosine); GKV234L2QH (2-nitropropane); IKJ30QXM63 (Bromotrichloromethane); KA90006V9D (Nitrilotriacetic Acid); PQ6CK8PD0R (Ascorbic Acid); T75W9911L6 (Propane); Z3U5ED15B9 (ferric nitrilotriacetate)
[Em] Mês de entrada:0006
[Cu] Atualização por classe:151119
[Lr] Data última revisão:
151119
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:000414
[St] Status:MEDLINE


  5 / 92 MEDLINE  
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[PMID]:10375406
[Au] Autor:Cameron MD; Aust SD
[Ad] Endereço:Biotechnology Center, Utah State University, Logan, Utah, 84322-4705, USA.
[Ti] Título:Degradation of chemicals by reactive radicals produced by cellobiose dehydrogenase from Phanerochaete chrysosporium.
[So] Source:Arch Biochem Biophys;367(1):115-21, 1999 Jul 01.
[Is] ISSN:0003-9861
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:Phanerochaete chrysosporium, grown on cellulose, produced a cellobiose-dependent dehydrogenase which reduced both ferric iron and molecular oxygen, resulting in the generation of the hydroxyl radical. The hydroxyl radical was detected in reaction mixtures with and without the addition of exogenous H2O2. The purified reductase and the fungus grown under nonligninolytic conditions that promote the production of the reductase were able to depolymerize an insoluble polyacrylate polymer. When oxalate, a secondary metabolite of P. chrysosporium, was used as the iron chelator, it was oxidized by the hydroxyl radical to form the carboxylate anion radical, a strong reductant. Under these reductive conditions, the enzyme was shown to catalyze the reduction of bromotrichloromethane to the trichloromethyl radical. We propose that these oxidative and reductive mechanisms may contribute to the degradation of a wide range of environmental pollutants by fungi which produce this enzyme.
[Mh] Termos MeSH primário: Desidrogenases de Carboidrato/metabolismo
Radicais Livres/metabolismo
Phanerochaete/enzimologia
[Mh] Termos MeSH secundário: Resinas Acrílicas/metabolismo
Ânions/metabolismo
Biodegradação Ambiental
Bromotriclorometano/metabolismo
Tetracloreto de Carbono/análogos & derivados
Tetracloreto de Carbono/metabolismo
Ácidos Carboxílicos/metabolismo
Celobiose/metabolismo
Celulose/metabolismo
Peróxido de Hidrogênio/metabolismo
Radical Hidroxila/metabolismo
Ferro/metabolismo
Quelantes de Ferro/metabolismo
Ácido Oxálico/metabolismo
Oxigênio/metabolismo
Phanerochaete/crescimento & desenvolvimento
Substâncias Redutoras/metabolismo
Solubilidade
Detecção de Spin
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Acrylic Resins); 0 (Anions); 0 (Carboxylic Acids); 0 (Fenton's reagent); 0 (Free Radicals); 0 (Iron Chelating Agents); 0 (Reducing Agents); 16462-44-5 (Cellobiose); 3170-80-7 (trichloromethyl free radical); 3352-57-6 (Hydroxyl Radical); 4Q93RCW27E (carbopol 940); 9004-34-6 (Cellulose); 9E7R5L6H31 (Oxalic Acid); BBX060AN9V (Hydrogen Peroxide); CL2T97X0V0 (Carbon Tetrachloride); E1UOL152H7 (Iron); EC 1.1.- (Carbohydrate Dehydrogenases); EC 1.1.99.18 (cellobiose-quinone oxidoreductase); IKJ30QXM63 (Bromotrichloromethane); S88TT14065 (Oxygen)
[Em] Mês de entrada:9907
[Cu] Atualização por classe:161124
[Lr] Data última revisão:
161124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:990622
[St] Status:MEDLINE


  6 / 92 MEDLINE  
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[PMID]:9485440
[Au] Autor:Wilks A; Medzihradszky KF; Ortiz de Montellano PR
[Ad] Endereço:Department of Pharmaceutical Chemistry, School of Pharmacy, and Liver Center, University of California, San Francisco, California 94143-0446, USA.
[Ti] Título:Heme oxygenase active-site residues identified by heme-protein cross-linking during reduction of CBrCl3.
[So] Source:Biochemistry;37(9):2889-96, 1998 Mar 03.
[Is] ISSN:0006-2960
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:The reduction of CBrCl3 by the heme-heme oxygenase complex forms dissociable and covalently bound heme products. No such products are formed with mesoheme in which the heme vinyl substituents are replaced by ethyl groups. The dissociable heme products are chromatographically similar but not identical to those obtained in the analogous reaction with myoglobin. Tryptic digestion of the heme-protein adduct and Edman sequencing and mass spectrometric analysis of the heme-linked peptide identify His-25, the proximal iron ligand, as the alkylated residue. Reaction of CBrCl3 with the heme complexes of the T135V mutant and a Delta221 C-terminal truncated protein yields heme-linked peptides in addition to that from the wild-type reaction. The sequence of the principal labeled peptide from the T135V reaction, 205TAFLLNIQLFEELQELLTHDTK226 , and the lability of the adduct suggest the heme is attached to one of the carboxylic acid residues. A carboxylic acid residue is probably also labeled in the modified peptide 49LVMASLYHIYVALEEEIER67 from the Delta221 truncated protein. Thus, addition of the reductively generated trichloromethyl radical to a heme vinyl group produces a species that alkylates active-site residues. The changes in the alkylated residue caused by the Thr-135 mutation or truncation of the protein places residues in the sequences 49-67 and 205-226 within the active site. Furthermore, this is the first demonstration that heme oxygenase, like cytochrome P450, may catalyze the reductive metabolism of halocarbons and thus contribute to the toxicity of these agents.
[Mh] Termos MeSH primário: Bromotriclorometano/metabolismo
Heme Oxigenase (Desciclizante)/metabolismo
Heme/metabolismo
[Mh] Termos MeSH secundário: Sequência de Aminoácidos
Animais
Sítios de Ligação
Bromotriclorometano/química
Catálise
Cromatografia Líquida de Alta Pressão
Reagentes para Ligações Cruzadas
Heme/química
Heme Oxigenase (Desciclizante)/química
Dados de Sequência Molecular
Coelhos
Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, U.S. GOV'T, P.H.S.
[Nm] Nome de substância:
0 (Cross-Linking Reagents); 42VZT0U6YR (Heme); EC 1.14.14.18 (Heme Oxygenase (Decyclizing)); IKJ30QXM63 (Bromotrichloromethane)
[Em] Mês de entrada:9804
[Cu] Atualização por classe:161124
[Lr] Data última revisão:
161124
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:980416
[St] Status:MEDLINE


  7 / 92 MEDLINE  
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[PMID]:8548861
[Au] Autor:Fanelli SL; Castro GD; Castro JA
[Ad] Endereço:Centro de Investigaciones Toxicológicas (CEITOX) CITEFA/CONICET, Pcia. de Buenos Aires, Argentina.
[Ti] Título:Cholesterol interaction with free radicals produced from carbon tetrachloride or bromotrichloromethane by either catalytic decomposition or via liver microsomal activation.
[So] Source:Chem Biol Interact;98(3):223-36, 1995 Dec 22.
[Is] ISSN:0009-2797
[Cp] País de publicação:Ireland
[La] Idioma:eng
[Ab] Resumo:The reaction between cholesterol (Ch) and trichloromethyl or trichloromethyl peroxyl radicals was studied. The latter were generated from CCl4 either by benzoyl peroxide (BP) catalysis or via thermal activation or by liver microsomal NADPH-dependent biotransformation of CBrCl3. The structure of the products formed was elucidated by gas chromatography-mass spectrometry (GC/MS). Under aerobic conditions and using thermal activation of CCl4, the formation of 6 products was observed. Two (I and II) were dehydrated Ch derivatives (one also having a third double bond) (I). Another product was a delta(5)-3 ketone derivative of Ch (III). Two additional reaction products were determined as ketocholesterols (IV and V). One chloro Ch was also formed (VI). At low concentrations of BP, reaction was more extensive than under thermal activation, and the formation of peaks I to IV was also observed. When the reaction was conducted anaerobically and using thermal activation of CCl4 to generate radicals, only products I and II were formed in low yield. Under anaerobic conditions, but using catalyst, compounds I and III were produced plus two new isomeric ketocholesterol derivatives (VIII and IX) and also a compound having an extra hydroxyl group on the Ch structure (X). In order to check whether similar reactions are observable under biological experimental conditions, we used activation of CBrCl3 by liver microsomes. The incubation using only microsomes (without CBrCl3 or NADPH) showed two ketocholesterol peaks (A and B). In the presence of CBrCl3 we could detect peak B and hydroxycholesterol (C) and two others, ketocholesterols (D and E). D was the only peak showing close similarity (spectrum and retention time) to one of those observed in the chemical reaction system (V). The reaction of CBrCl3 in the presence of NADPH showed peaks B, C, D and E, in low abundance and a 7-ketocholesterol (F). If some of the reaction products reported here were formed during the intoxication with these haloalkanes, significant biological consequences might be expected.
[Mh] Termos MeSH primário: Bromotriclorometano/metabolismo
Tetracloreto de Carbono/análogos & derivados
Tetracloreto de Carbono/metabolismo
Colesterol/metabolismo
[Mh] Termos MeSH secundário: Aerobiose
Anaerobiose
Animais
Biotransformação
Tetracloreto de Carbono/química
Colesterol/química
Radicais Livres/metabolismo
Masculino
Espectrometria de Massas
Microssomos Hepáticos/metabolismo
Ratos
Ratos Sprague-Dawley
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, U.S. GOV'T, P.H.S.
[Nm] Nome de substância:
0 (Free Radicals); 3170-80-7 (trichloromethyl free radical); 97C5T2UQ7J (Cholesterol); CL2T97X0V0 (Carbon Tetrachloride); IKJ30QXM63 (Bromotrichloromethane)
[Em] Mês de entrada:9602
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:951222
[St] Status:MEDLINE


  8 / 92 MEDLINE  
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[PMID]:7624875
[Au] Autor:Manno M; Tolando R; Ferrara R; Rezzadore M; Cazzaro S
[Ad] Endereço:Institute of Occupational Medicine, University of Padua Medical School, Italy.
[Ti] Título:Suicidal inactivation of haemoproteins by reductive metabolites of halomethanes: a structure-activity relationship study.
[So] Source:Toxicology;100(1-3):175-83, 1995 Jun 26.
[Is] ISSN:0300-483X
[Cp] País de publicação:Ireland
[La] Idioma:eng
[Ab] Resumo:Human haemoglobin (Hb), methaemalbumin (MHA) or rat liver microsomal cytochrome P-450 (P-450) were incubated anaerobically at microM concentrations with 1 mM carbon tetrachloride (CCl4), trichlorobromomethane (CCl3Br), chloroform (CHCl3) or methylene chloride (CH2Cl2) in presence of 1 mM sodium dithionite as the reducing agent. At the end of a 5-min incubation, haem was measured by various methods, i.e. binding spectrum with CO, pyridine-haemochromogen haem assay and porphyrin fluorescence, and compared for the four analogues. Statistically significant losses were observed, with all three haemo-protein systems, for CCi3Br, CCl4 and CHCl3, but not CH2Cl2. For Hb, the loss was greater with CCl3Br (haem assay, 63%; porphyrin fluorescence, 48%; CO binding, 24%) than with CCl4 (haem assay, 31%) or CHCl3 (haem assay, 13%). On the other hand, with MHA, CCl4 gave a dramatic loss (haem assay, 88%; porphyrin fluorescence, 83%; CO binding, 67%), which was greater than that observed with CCl3Br (haem assay, 49%; porphyrin fluorescence, 38%; CO binding, 25%). No loss was found with CHCl3. Finally, with microsomes, the inactivation was larger with CCl4 (CO binding, 58%; haem assay, 50%; porphyrin fluorescence, 33%) than with CCl3Br (CO binding, 33%; haem assay, 10%) or CHCl3 (haem assay, 9%; CO binding, 6%). In a separate set of similar experiments, an ion-pairing reverse phase HPLC method showed the formation of substrate-dependent hae-derived products during incubation of CCl3Br with Hb or microsomes, and of CCl4 with Hb. A correlation between potential for free radical formation (CCl3Br > CCl4 > CHCl3 > CH2Cl2) and extent of haem inactivation was observed with all methods for Hb, but not for microsomal P-450 or MHA. The results indicate that these halomethanes may be activated differently by different haemoproteins and suggest that their potential ability to undergo reductive metabolism may not be the only critical factor involved in P-450 haem inactivation by these chemicals.
[Mh] Termos MeSH primário: Sistema Enzimático do Citocromo P-450/efeitos dos fármacos
Hemoglobinas/efeitos dos fármacos
Hidrocarbonetos Halogenados/toxicidade
Metemoglobina/efeitos dos fármacos
Microssomos Hepáticos/efeitos dos fármacos
[Mh] Termos MeSH secundário: Animais
Ligação Competitiva
Bromotriclorometano/metabolismo
Bromotriclorometano/toxicidade
Tetracloreto de Carbono/toxicidade
Clorofórmio/metabolismo
Clorofórmio/toxicidade
Cromatografia Líquida de Alta Pressão
Sistema Enzimático do Citocromo P-450/metabolismo
Ditionita/química
Hemoglobinas/metabolismo
Seres Humanos
Metemoglobina/metabolismo
Cloreto de Metileno/metabolismo
Cloreto de Metileno/toxicidade
Microssomos Hepáticos/enzimologia
Oxirredução
Ratos
Relação Estrutura-Atividade
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, NON-U.S. GOV'T
[Nm] Nome de substância:
0 (Hemoglobins); 0 (Hydrocarbons, Halogenated); 14844-07-6 (Dithionite); 588X2YUY0A (Methylene Chloride); 7V31YC746X (Chloroform); 9008-37-1 (Methemoglobin); 9035-51-2 (Cytochrome P-450 Enzyme System); CL2T97X0V0 (Carbon Tetrachloride); IKJ30QXM63 (Bromotrichloromethane)
[Em] Mês de entrada:9508
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:950626
[St] Status:MEDLINE


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[PMID]:7581826
[Au] Autor:Castro GD; Stamato CJ; Castro JA
[Ad] Endereço:Centro de Investigaciones Toxicológicas (CEITOX) CITEFA/CONICET Zufriategui, Buenos Aires, Argentina.
[Ti] Título:Reaction of bromotrichloromethane derived free radicals with uracil in a model system. Structures of products formed.
[So] Source:Free Radic Res;23(5):431-42, 1995 Nov.
[Is] ISSN:1071-5762
[Cp] País de publicação:England
[La] Idioma:eng
[Ab] Resumo:Free radicals generated by benzoyl peroxide-mediated catalytic decomposition of bromotrichloromethane (eg. trichloromethyl) were allowed to react under nitrogen or under air with uracil. Under nitrogen two reaction products were formed, one was identified as 5-chlorouracil and the other as a 5-bromouracil. Under air, besides the above two products other nine were also formed: 5,6-dihydrouracil; 5-hydroxyuracil; a chlorohydroxy adduct of uracil; a bromohydroxy derivative of uracil having the 5,6 bond in the saturated form; other bromohydroxy derivative of uracil having the double bond intact; 5,6-dihydroxyuracil; two dihalogenated hydroxylated uracil derivatives and one peak we were not able to descipher its structure. No single reaction product formed had carbon centered radicals (eg. trichloromethyl) added from CBrCl3 and consequently would be missed in 'in vivo' covalent binding studies where 14C haloalkane (CBrCl3 or carbon tetrachloride) were employed. If similar reaction products resulted during interaction of CBrCl3 reactive metabolites with uracil in RNAs, significant deleterious effects in their function would be expected. That possibility, however, remains to be established.
[Mh] Termos MeSH primário: Bromotriclorometano/química
Uracila/química
[Mh] Termos MeSH secundário: Aerobiose
Anaerobiose
Radicais Livres
Cromatografia Gasosa-Espectrometria de Massas
Modelos Teóricos
[Pt] Tipo de publicação:COMPARATIVE STUDY; JOURNAL ARTICLE; RESEARCH SUPPORT, U.S. GOV'T, P.H.S.
[Nm] Nome de substância:
0 (Free Radicals); 56HH86ZVCT (Uracil); IKJ30QXM63 (Bromotrichloromethane)
[Em] Mês de entrada:9512
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:951101
[St] Status:MEDLINE


  10 / 92 MEDLINE  
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Fotocópia
[PMID]:8195191
[Au] Autor:Osawa Y; Fellows CS; Meyer CA; Woods A; Castoro JA; Cotter RJ; Wilkins CL; Highet RJ
[Ad] Endereço:Laboratories of Chemical Pharmacology, NHLBI, National Institutes of Health, Bethesda, Maryland 20892.
[Ti] Título:Structure of the novel heme adduct formed during the reaction of human hemoglobin with BrCCl3 in red cell lysates.
[So] Source:J Biol Chem;269(22):15481-7, 1994 Jun 03.
[Is] ISSN:0021-9258
[Cp] País de publicação:United States
[La] Idioma:eng
[Ab] Resumo:It was previously shown that the reductive debromination of BrCCl3 to trichloromethyl radical by human hemoglobin leads to formation of dissociable altered heme products, two of which are identical to those formed from myoglobin and one which is novel. In this study, we have elucidated the structure of this novel adduct with the use of mass spectrometry, as well as 1H and 13C NMR as a substitution product of a -C(Cl) = CCl2 moiety for a beta-hydrogen atom on the prosthetic heme's ring I vinyl group. From studies with the use of 13C-enriched BrCCl3, it was determined that the added carbon atoms were derived from 2 eq of BrCCl3. A mechanism that involves multiple reductive events and a radical cation heme intermediate is proposed. Consistent with this mechanism, cellular reductants were found to selectively enhance the amount of this novel dissociable heme adduct. These studies reveal fine differences between myoglobin and hemoglobin in the accessibility of reactive intermediates to the ring I vinyl group, as well as the potential importance of cellular reductants on the course of heme alteration.
[Mh] Termos MeSH primário: Bromotriclorometano/sangue
Eritrócitos/metabolismo
Heme/metabolismo
Hemoglobinas/metabolismo
[Mh] Termos MeSH secundário: Ácido Ascórbico/farmacologia
Sítios de Ligação
Bromotriclorometano/metabolismo
Isótopos de Carbono
Glutationa/farmacologia
Heme/química
Hemoglobinas/química
Hemoglobinas/efeitos dos fármacos
Hemólise
Seres Humanos
Cinética
Espectroscopia de Ressonância Magnética
Estrutura Molecular
Mioglobina/metabolismo
[Pt] Tipo de publicação:JOURNAL ARTICLE; RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.; RESEARCH SUPPORT, U.S. GOV'T, P.H.S.
[Nm] Nome de substância:
0 (Carbon Isotopes); 0 (Hemoglobins); 0 (Myoglobin); 42VZT0U6YR (Heme); GAN16C9B8O (Glutathione); IKJ30QXM63 (Bromotrichloromethane); PQ6CK8PD0R (Ascorbic Acid)
[Em] Mês de entrada:9406
[Cu] Atualização por classe:131121
[Lr] Data última revisão:
131121
[Sb] Subgrupo de revista:IM
[Da] Data de entrada para processamento:940603
[St] Status:MEDLINE



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