Relationship between liquid and gas chromatographic retention behavior and calculated molecular surface area of selected polyhalogenated biphenyls

Hoefler, Frank; Melzer, H.; Moeckel, H.; Robertson, Larry W.; Anklam, Elke

doi:10.1021/jf00083a016

Cited by 29 publications

(6 citation statements)

References 8 publications

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“…3,3′,4,4′-Tetrachlorobiphenyl (PCB-77), 2′,3,3′,4,5,-pentachlorobiphenyl (PCB-122), 3,3′,4,4′,5-pentachlorobiphenyl (PCB-126), 3,3′, 4,4′-tetrabromobiphenyl (PBB-77), 3,3′,5,5′-tetrabromobiphenyl (PBB-80), and 3,3′,4,4′,5,5,′-hexabromobiphenyl (PBB-169) were synthesized as previously described [ 13 , 14 ]. 2,2′,3,3′,5,5′-Hexachlorobiphenyl (PCB-133) was prepared via a multistep synthesis involving the chlorination of 2,2′,5,5′-tetrachlorobenzidine with N-chlorosuccinimide and subsequent deamination with hypophosphorous acid, as described by Kubiczak et al [ 15 ].…”

Section: Methodsmentioning

confidence: 99%

Suppression of Peroxisomal Enzyme Activities and Cytochrome P450 4A Isozyme Expression by Congeneric Polybrominated and Polychlorinated Biphenyls

et al. 2007

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The purpose of this study was to determine the effects of PCBs and PBBs on peroxisome proliferator-activated receptor-α-(PPARα-) associated enzyme activities or protein levels. Male Sprague-Dawley rats were administered a single IP injection (150 μ mol/kg) of either 3,3′,4,4′-tetrabromobiphenyl, 3,3′,4,4′-tetrachlorobiphenyl, 3,3′,5,5′-tetrabromobiphenyl, 2′,3,3′,4,5-pentachlorobiphenyl, 3,3′,4,4′,5-pentachlorobiphenyl, 2,2′,3,3′,5,5′-hexachlorobiphenyl, or 3,3′,4,4′,5,5′-hexabromobiphenyl in corn oil (10 ml/kg). One week later, the activities of catalase, peroxisomal fatty acyl-CoA oxidase, and peroxisomal beta-oxidation as well as cytochrome P450 4A (CYP4A) protein content were determined in subcellular liver fractions. None of the peroxisomal enzyme activities were significantly increased by any of the halogenated biphenyl congeners tested. Except for minor (approx. 25%) increases in the total CYP4A content following treatment with 2,2′,3,3′,5,5′-hexachlorobiphenyl and 3,3′,5,5′-tetrabromobiphenyl, CYP4A protein contents were not increased by any treatment. The two Ah receptor agonists, 3,3′,4,4′-tetrabromobiphenyl and 3,3′,4,4′,5-pentachlorobiphenyl, significantly diminished the liver content of CYP4A proteins and activities of the peroxisomal enzymes studied. Since a range of congeners with different biologic and toxicologic activities were selected for this study, it may be concluded that the polyhalogenated biphenyls do not induce peroxisome proliferation in the male rat, but rather certain members of this class of compounds down regulate peroxisome-associated enzymes. Since PCBs and PBBs do not increase enzyme activities and expression of proteins associated with PPARα, these agents are therefore exerting their carcinogenic and promoting activities by some other mechanism.

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Section: Methodsmentioning

confidence: 99%

Suppression of Peroxisomal Enzyme Activities and Cytochrome P450 4A Isozyme Expression by Congeneric Polybrominated and Polychlorinated Biphenyls

et al. 2007

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“…PCB 3 and PCB 12 were synthesized by the Cadogan coupling [16–18]. PCB 77 and PCB 153 were synthesized from the corresponding chlorinated benzidines by the Sandmeyer reaction [19,20].…”

Section: Methodsmentioning

confidence: 99%

2,4,4′‐trichlorobiphenyl increases STAT5 transcriptional activity

Oakley

Roe

Blouin

et al. 2001

Molecular Carcinogenesis

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The promoting effects of polychlorinated biphenyls (PCBs) have been studied extensively in a variety of two-stage carcinogenesis models. However, the molecular mechanisms responsible for the promotion effects of PCBs have not been elucidated. We measured the effect of PCBs on DNA-binding proteins involved in cell proliferation and transformation. Male Sprague-Dawley rats were injected intraperitoneally with mono-, di-, tri-, tetra-, or hexachlorobiphenyls (300 micromol/kg/d) each day for 4 d and killed 4 h after the last injection. To detect alterations in nuclear proteins that could explain the tumor-promoter activity of PCBs, liver nuclear extracts were analyzed by electrophoretic mobility shift assays. Electrophoretic mobility shift assay analysis of signal transducers and activators of transcription (STAT)-binding activity to a consensus gamma-interferon-activated sequence (GAS) element was compared in liver nuclear extracts from treated rats. STAT-binding activity was eightfold to tenfold higher in nuclear extracts from animals treated with 2,4,4'-trichloro- (PCB 28) and 2,2',4,4',5,5'-hexachlorobiphenyl (PCB 153). Analysis of the protein complex binding to the GAS element, with antibodies specific for STAT3, STAT5, and STAT6, indicated that the protein complex was made up of STAT5 and STAT6 proteins. HepG2 cells transiently transfected with a luciferase reporter gene construct containing many STAT5 binding sites were treated with PCB 28 and PCB 153. PCB 28 stimulated a greater than 25-fold increase in luciferase activity at the highest concentration tested, 1.0 microg/mL. However, enhanced luciferase activity did not occur with PCB 153 treatment. 4-Chlorobiphenyl (PCB 3), PCB 28, and PCB 153 treatment of Sprague-Dawley rats resulted in a large increase in protein binding to a consensus activated protein-1 (AP-1) element. However, 3,4-dichlorobiphenyl (PCB 12) and 3,3',4,4'-tetrachlorobiphenyl (PCB 77) treatments did not increase AP-1 transcription activity. Further analysis of the proteins binding to the AP-1 consensus sequence with antibodies specific for c-fos, junD, and junB indicated that the protein composition consists of junD proteins. These data showed functional differences between noncoplanar and coplanar PCBs with respect to STAT activation and AP-1-DNA binding.

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“…TBB was synthesized by one of the authors (L.W.R.) as described (19), and structural assignments were confirmed by nuclear magnetic resonance spectrometry and mass spectroscopy. Corn oil (Mazola) was purchased fresh for each experiment.…”

Section: Methodsmentioning

confidence: 99%

3,3′,4,4′-Tetrabromobiphenyl sensitizes rats to the hepatotoxic effects of endotoxin by a mechanism that involves more than tumor necrosis factor

Shedlofsky

1991

Hepatology

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To determine whether the cytokine tumor necrosis factor/cachectin might be a mediator of hepatotoxicity seen after exposure to polyhalogenated aromatic hydrocarbons, rats treated with a single dose of 3,3',4,4'-tetrabromobiphenyl (150 mumol/kg intraperitoneally) or corn oil vehicle were studied. The 3,3',4,4'-tetrabromobiphenyl caused the expected anorexia, alterations in organ weights and changes in cytochromes P-450 over 21 days. Although tumor necrosis factor could not be detected in the serum of rats at any time after 3,3',4,4'-tetrabromobiphenyl treatment alone (from 90 min to 21 days), 3,3',4,4'-tetrabromobiphenyl treatment significantly increased peak serum tumor necrosis factor concentrations after intravenous bacterial endotoxin (lipopolysaccharide, 1 mg/kg). This effect was seen with lipopolysaccharide given 24 hr, 48 hr, and 20 days after 3,3',4,4'-tetrabromobiphenyl treatment and increases in peak serum tumor necrosis factor levels ranged from threefold to eightfold over controls in various experiments with no significant differences between the three time points. However, a synergistic increase in hepatic damage (assessed by serum enzymes and liver histological findings 24 hr after lipopolysaccharide injection) was seen in rats given lipopolysaccharide 24 hr and 48 hr after 3,3',4,4'-tetrabromobiphenyl administration, with 75% and 25% lethality, respectively. There was no lethality with lipopolysaccharide given 20 days after 3,3',4,4'-tetrabromobiphenyl administration or with simultaneous administration. A lower dose of lipopolysaccharide (0.1 mg/kg) given 24 hr after 3,3',4,4'-tetrabromobiphenyl also enhanced hepatotoxicity and serum tumor necrosis factor but without lethality. Lipopolysaccharide decreased cytochromes P-450 concentrations and activities to similar extents at all time points tested in both control and 3,3'4,4'-tetrabromobiphenyl-treated rats.(ABSTRACT TRUNCATED AT 250 WORDS)

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Relationship between liquid and gas chromatographic retention behavior and calculated molecular surface area of selected polyhalogenated biphenyls

Abstract: Vettorazzi, G. "State of the Art of the Toxicological Evaluation Carried Out by the Joint FAO/WHO Expert Committee on Pesticide Residues. III. Miscellaneous Pesticides Used in Agriculture and Public Health". In Residue Reviews•

Cited by 29 publications

References 8 publications

Suppression of Peroxisomal Enzyme Activities and Cytochrome P450 4A Isozyme Expression by Congeneric Polybrominated and Polychlorinated Biphenyls

Suppression of Peroxisomal Enzyme Activities and Cytochrome P450 4A Isozyme Expression by Congeneric Polybrominated and Polychlorinated Biphenyls

2,4,4′‐trichlorobiphenyl increases STAT5 transcriptional activity

3,3′,4,4′-Tetrabromobiphenyl sensitizes rats to the hepatotoxic effects of endotoxin by a mechanism that involves more than tumor necrosis factor

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