Differential potency of atropisomers of polychlorinated biphenyls on cytochrome P450 induction and uroporphyrin accumulation in the chick embryo hepatocyte culture

Rodman, Larry E.; Shedlofsky, Steven I.; Mannschreck, Albrecht; Püttmann, Michael; Swim, Alice T.; Robertson, Larry W.

doi:10.1016/0006-2952(91)90196-c

Cited by 83 publications

(59 citation statements)

References 30 publications

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“…27 The chiral chemicals could interact with different enzymes or endogenous compounds. 39,40 It was reported that rat CYP2B1 preferentially biotransformed the second-eluting enantiomers of CBs 45 and 95 at substrate concentrations lower than 15 μM. 39 However, it remains unclear whether CYPs or other enzymes would metabolize or bind with HBCD enantiomers differently in adult chickens and hatchling chickens, which is of great importance for HBCD toxicological studies in avian species.…”

Section: ■ Discussionmentioning

confidence: 99%

Alteration of Diastereoisomeric and Enantiomeric Profiles of Hexabromocyclododecanes (HBCDs) in Adult Chicken Tissues, Eggs, and Hatchling Chickens

Zheng

Qiao

Sun

et al. 2017

Environ. Sci. Technol.

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ABSTRACT:The concentrations and enantiomer fractions (EFs) of α-, β-, and γ-hexabromocyclododecanes (HBCDs) were measured in chicken diet sources (soil and chicken feed), home-raised adult chicken (Gallus domesticus) tissues, eggs during incubation, and hatchling chicken tissues. HBCD concentrations were not detected−0.69 ng/g dry weight (dw) and 25.6−48.4 ng/g dw in chicken feed and soil, respectively. HBCDs were detected in all adult chicken tissues, except the brain, at median levels of 13.1−44.0 ng/g lipid weight (lw). The proportions of α-HBCD in total HBCDs increased from 51% in soil to more than 87% in adult chicken tissues. The accumulation ratios (ARs) of α-HBCD from diet to adult chicken tissues were 4.27 for liver, 11.2 for fat, and 7.64−12.9 for other tissues, respectively. The AR and carry-over rate (COR) of α-HBCD from diet to eggs were 22.4 and 0.226, respectively. The concentrations of α-HBCD in hatchling chicken liver (median: 35.4 ng/g lw) were significantly lower than those in hatchling chicken pectoral muscle (median: 130 ng/g lw).The EFs of α-HBCD decreased from soil to adult chicken tissues and from eggs to hatchling chicken liver. Meanwhile, the EFs of γ-HBCD increased from soil to adult chicken tissues. These results indicate the preferential enrichment of (−)-α-HBCD and (+)-γ-HBCD in chickens. The alteration of diastereoisomeric and enantiomeric patterns of HBCDs might be influenced by the different absorption and elimination rates of the six HBCD enantiomers as well as variations in HBCD metabolism in chickens.

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Section: ■ Discussionmentioning

confidence: 99%

Alteration of Diastereoisomeric and Enantiomeric Profiles of Hexabromocyclododecanes (HBCDs) in Adult Chicken Tissues, Eggs, and Hatchling Chickens

Zheng

Qiao

Sun

et al. 2017

Environ. Sci. Technol.

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“…Many studies were performed to evaluate the congener's toxicity andror to look for the optimum separation w x condition for them by chromatography 2, 4 . Recently, several studies showed that the chirality of atropermic PCBs plays an important role in the w x enzyme induction and shows different potency 5,6 . The separation of enantiomeric PCBs is then getting more interesting.…”

Section: Introductionmentioning

confidence: 99%

Separation of atropisomeric polychlorinated biphenyls by cyclodextrin modified micellar electrokinetic chromatography

1999

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“…The (+)-and (−)-enantiomers of PCB 84 had a significantly different effect on protein kinase C translocation as determined by [ 3 H]-phorbol ester binding in cerebellar granule cells, with (−)-PCB 84 being slightly more potent; however, (+)-and (−)-PCB 84 did not have a significantly different effect on calcium regulation in microsomes isolated from adult rat cerebellum, another important neurochemical measure. PCB atropisomers have also been shown to have differential potencies in their abilities to induce various liver enzymes in chick embryo hepatocytes (8) and rats (9,10).…”

Section: Introductionmentioning

confidence: 99%

Distribution of Chiral PCBs in Selected Tissues in the Laboratory Rat

Kania-Korwel

Garrison

Avants

et al. 2006

Environ. Sci. Technol.

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The enantiomeric enrichment of polychlorinated biphenyl (PCB) atropisomers has been reported in both wildlife and in humans. The biological processes causing this enrichment are only poorly investigated, a fact that limits the use of enantiomeric fractions (EFs) as a tool to study various processes of environmental relevance. To further understand these enantioselective processes, this study investigates the tissue distribution and EFs of some PCB atropisomers after administration of PCB mixtures to immature male Sprague-Dawley rats. The mixtures selected for this study, Aroclor 1254 and an environmental mixture extracted from Chlorofen-contaminated soil, are qualitatively different and are known to induce different groups of hepatic enzymes. Animals were sacrificed six days after dosing, PCBs were extracted, and, whenever possible, the EFs of PCBs 84, 91, 95, 149, 174 and 176 were determined by chiral gas chromatography. The EFs of PCB 95 (adipose tissue, liver and skin) and PCB 149 (adipose tissue, liver, skin and blood) in tissues from Aroclor 1254-treated animals differed significantly from EFs in the Aroclor standard, while only EFs of PCB 95 (blood) and PCB 174 (adipose tissue) in tissues from soil extract-treated animals were different from those of the Chlorofen soil extract. PCB 149 in tissues from soil extract-treated animals underwent no statistically significant enantiomeric enrichment. These differences in the EFs clearly suggest that the enantioselective enrichment of PCB atropisomers may correlate with exposure history, and with the induction of hepatic enzymes, and that EFs may be useful chemical markers of physiologic and biochemical changes following exposure to PCBs.

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Differential potency of atropisomers of polychlorinated biphenyls on cytochrome P450 induction and uroporphyrin accumulation in the chick embryo hepatocyte culture

Cited by 83 publications

References 30 publications

Alteration of Diastereoisomeric and Enantiomeric Profiles of Hexabromocyclododecanes (HBCDs) in Adult Chicken Tissues, Eggs, and Hatchling Chickens

Alteration of Diastereoisomeric and Enantiomeric Profiles of Hexabromocyclododecanes (HBCDs) in Adult Chicken Tissues, Eggs, and Hatchling Chickens

Separation of atropisomeric polychlorinated biphenyls by cyclodextrin modified micellar electrokinetic chromatography

Distribution of Chiral PCBs in Selected Tissues in the Laboratory Rat

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