A unique approach to the synthesis of 2,3,4,5-substituted polybrominated biphenyls: quantitation in FireMaster FF-1 and FireMaster BP-6

Kubiczak, Gerhard A.; Oesch, Franz; Borlakoglu, Juergen T.; Kunz, H. H.; Robertson, Larry W.

doi:10.1021/jf00088a075

Cited by 15 publications

(10 citation statements)

References 24 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 ]. The synthetic polyhalogenated biphenyl congeners were purified by Florisil (Macherey-Nagel, Duren, Germany) and Alumina (Aluminiumoxid 90, Merck, Darmstadt, Germany) chromatography and recrystallization from methanol.…”

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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“…First, 4,4′‐dichlorobiphenyl was prepared by chlorination of biphenyl in glacial acetic acid with chlorine gas. Selective nitration of 4,4′‐dichlorobiphenyl with nitric acid in glacial acetic acid produced 4,4′‐dichloro‐2‐nitro‐biphenyl [21,22], which, after reduction with iron powder, produced 4,4′‐dichloro‐2‐amino‐biphenyl [23,24]. In the final step, PCB 28 was obtained from the 4,4′‐dichloro‐2‐amino‐biphenyl by a Sandmeyer reaction [19].…”

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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“…3 To further decrease the reaction time with NBS as the reagent, solvents with higher boiling points were employed. Acetonitrile had successfully been used in the literature, 25 but this solvent also proved to be unsuitable in the case of 1c. Use of acetic acid at reflux temperature gave rise to conversion of 1c but much slower than with TFA.…”

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confidence: 99%

Sixfold Peripheral Halogenation of Tribenzotriquinacenes: An Alternative Access to Useful TBTQ Building Blocks

et al. 2017

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Sixfold electrophilic bromination and iodination of the molecular periphery of the bridgehead-tetramethylated tribenzotriquinacene (TBTQ) with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively, under various conditions was studied to develop an alternative preparative approach to the classical Lewis acid catalyzed bromination. Running these reactions in trifluoroacetic acid either in pure form or with chloroform as a co-solvent at elevated temperatures, or under sonication or microwave irradiation was found to give increasingly fast and efficient conversion of TBTQ to the target hexahalogenated TBTQ derivatives in excellent yields. NIS was found to be markedly more reactive than NBS, whereas N-chlorosuccimide reacted hardly. The new method was applied to the sixfold functionalization of the 4b,8b,12b-tripropyl-12d-methyl-TBTQ analogue to give the corresponding hexabromo and hexaiodo derivatives. Some sixfold C–C cross-coupling reactions of hexahalo derivatives of TBTQ were carried out in excellent yields to enlarge the three spatially orthogonal indane wings of the TBTQ core.

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A unique approach to the synthesis of 2,3,4,5-substituted polybrominated biphenyls: quantitation in FireMaster FF-1 and FireMaster BP-6

Cited by 15 publications

References 24 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

Sixfold Peripheral Halogenation of Tribenzotriquinacenes: An Alternative Access to Useful TBTQ Building Blocks

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