Literature DB >> 18760792

Gas chromatographic separation of methoxylated polychlorinated biphenyl atropisomers.

Izabela Kania-Korwel1, Sandhya M Vyas, Yang Song, Hans-Joachim Lehmler.   

Abstract

Several polychlorinated biphenyls (PCBs) and their hydroxylated metabolites display axial chirality. Here we describe an enantioselective, gas chromatographic separation of methylated derivatives of hydroxylated (OH-)PCB atropisomers (MeO-PCB) using a chemically bonded beta-cyclodextrin column (Chirasil-Dex). The atropisomers of several MeO-PCBs could be separated on this column with resolutions ranging from 0.42 to 0.87 under isothermal or temperature-programmed conditions. In addition, the enantiomeric fraction of OH-PCB 136 metabolites was determined in male and female rats treated with racemic PCB 136. The methylated derivatives of two OH-PCB 136 metabolites showed an enantiomeric enrichment in liver tissue, whereas PCB 136 itself was near racemic.

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Year:  2008        PMID： 18760792      PMCID： PMC2579784          DOI： 10.1016/j.chroma.2008.08.044

Source DB:  PubMed          Journal:  J Chromatogr A        ISSN： 0021-9673            Impact factor:   4.759


  30 in total

1.  2,2',3,3',6,6'-hexachlorobiphenyl hydroxylation by active site mutants of cytochrome P450 2B1 and 2B11.

Authors:  S C Waller; Y A He; G R Harlow; Y Q He; E A Mash; J R Halpert
Journal:  Chem Res Toxicol       Date:  1999-08       Impact factor: 3.739

2.  Enantioselective formation of methyl sulfone metabolites of 2,2',3,3',4,6'-hexachlorobiphenyl in rat.

Authors:  Karin Norstrom; Johan Eriksson; Johanna Haglund; Virginia Silvari; Ake Bergman
Journal:  Environ Sci Technol       Date:  2006-12-15       Impact factor: 9.028

3.  Dose-dependent enantiomeric enrichment of 2,2',3,3',6,6'-hexachlorobiphenyl in female mice.

Authors:  Izabela Kania-Korwel; Keri C Hornbuckle; Larry W Robertson; Hans-Joachim Lehmler
Journal:  Environ Toxicol Chem       Date:  2008-02       Impact factor: 3.742

4.  Distribution of chiral PCBs in selected tissues in the laboratory rat.

Authors:  Izabela Kania-Korwel; A Wayne Garrison; Jimmy K Avants; Keri C Hornbuckle; Larry W Robertson; Wieslaw W Sulkowski; Hans-Joachim Lehmler
Journal:  Environ Sci Technol       Date:  2006-06-15       Impact factor: 9.028

5.  Enantioselective semipreparative HPLC separation of PCB metabolites and their absolute structure elucidation using electronic and vibrational circular dichroism.

Authors:  Hai Pham-Tuan; Christina Larsson; Frank Hoffmann; Ake Bergman; Michael Fröba; Heinrich Hühnerfuss
Journal:  Chirality       Date:  2005-05-15       Impact factor: 2.437

6.  Enantiomer separation of polychlorinated biphenyl atropisomers and polychlorinated biphenyl retention behavior on modified cyclodextrin capillary gas chromatography columns.

Authors:  C S Wong; A W Garrison
Journal:  J Chromatogr A       Date:  2000-01-14       Impact factor: 4.759

7.  The effect of dietary glycine on the hepatic tumor promoting activity of polychlorinated biphenyls (PCBs) in rats.

Authors:  Rodica Petruta Bunaciu; Job C Tharappel; Hans-Joachim Lehmler; Izabela Kania-Korwel; Larry W Robertson; Cidambi Srinivasan; Brett T Spear; Howard P Glauert
Journal:  Toxicology       Date:  2007-07-07       Impact factor: 4.221

8.  Chiral effects in the induction of drug-metabolizing enzymes using synthetic atropisomers of polychlorinated biphenyls (PCBs).

Authors:  M Püttmann; A Mannschreck; F Oesch; L Robertson
Journal:  Biochem Pharmacol       Date:  1989-04-15       Impact factor: 5.858

9.  Enantioselective gas chromatography/mass spectrometry of methylsulfonyl PCBs with application to arctic marine mammals.

Authors:  K Wiberg; R Letcher; C Sandau; J Duffe; R Norstrom; P Haglund; T Bidleman
Journal:  Anal Chem       Date:  1998-09-15       Impact factor: 6.986

10.  A reassessment of the nomenclature of polychlorinated biphenyl (PCB) metabolites.

Authors:  Johan Maervoet; Adrian Covaci; Paul Schepens; Courtney D Sandau; Robert J Letcher
Journal:  Environ Health Perspect       Date:  2004-03       Impact factor: 9.031
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  24 in total

1.  Gas chromatographic analysis with chiral cyclodextrin phases reveals the enantioselective formation of hydroxylated polychlorinated biphenyls by rat liver microsomes.

Authors:  Izabela Kania-Korwel; Michael W Duffel; Hans-Joachim Lehmler
Journal:  Environ Sci Technol       Date:  2011-10-19       Impact factor: 9.028

2.  Effect of pregnancy on the disposition of 2,2',3,5',6-pentachlorobiphenyl (PCB 95) atropisomers and their hydroxylated metabolites in female mice.

Authors:  Izabela Kania-Korwel; Christopher D Barnhart; Pamela J Lein; Hans-Joachim Lehmler
Journal:  Chem Res Toxicol       Date:  2015-08-13       Impact factor: 3.739

3.  Human Liver Microsomes Atropselectively Metabolize 2,2',3,4',6-Pentachlorobiphenyl (PCB 91) to a 1,2-Shift Product as the Major Metabolite.

Authors:  Eric Uwimana; Xueshu Li; Hans-Joachim Lehmler
Journal:  Environ Sci Technol       Date:  2018-04-27       Impact factor: 9.028

4.  2,2',3,5',6-Pentachlorobiphenyl (PCB 95) and its hydroxylated metabolites are enantiomerically enriched in female mice.

Authors:  Izabela Kania-Korwel; Christopher D Barnhart; Marianna Stamou; Kim M Truong; Mohammed H M E El-Komy; Pamela J Lein; Peter Veng-Pedersen; Hans-Joachim Lehmler
Journal:  Environ Sci Technol       Date:  2012-09-28       Impact factor: 9.028

Review 5.  Toxicokinetics of chiral polychlorinated biphenyls across different species--a review.

Authors:  Izabela Kania-Korwel; Hans-Joachim Lehmler
Journal:  Environ Sci Pollut Res Int       Date:  2015-04-01       Impact factor: 4.223

Review 6.  Chiral polychlorinated biphenyl transport, metabolism, and distribution: a review.

Authors:  Hans-Joachim Lehmler; Stuart J Harrad; Heinrich Hühnerfuss; Izabela Kania-Korwel; Cindy M Lee; Zhe Lu; Charles S Wong
Journal:  Environ Sci Technol       Date:  2010-04-15       Impact factor: 9.028

7.  Editor's Highlight: Congener-Specific Disposition of Chiral Polychlorinated Biphenyls in Lactating Mice and Their Offspring: Implications for PCB Developmental Neurotoxicity.

Authors:  Izabela Kania-Korwel; Tracy Lukasiewicz; Christopher D Barnhart; Marianna Stamou; Haeun Chung; Kevin M Kelly; Stelvio Bandiera; Pamela J Lein; Hans-Joachim Lehmler
Journal:  Toxicol Sci       Date:  2017-07-01       Impact factor: 4.849

8.  Metabolism of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) atropisomers in tissue slices from phenobarbital or dexamethasone-induced rats is sex-dependent.

Authors:  Xianai Wu; Izabela Kania-Korwel; Hao Chen; Marianna Stamou; Karigowda J Dammanahalli; Michael Duffel; Pamela J Lein; Hans-Joachim Lehmler
Journal:  Xenobiotica       Date:  2013-04-12       Impact factor: 1.908

9.  Biological and tumor-promoting effects of dioxin-like and non-dioxin-like polychlorinated biphenyls in mouse liver after single or combined treatment.

Authors:  Benjamin Rignall; Konstanze Grote; Alina Gavrilov; Marc Weimer; Annette Kopp-Schneider; Eberhard Krause; Klaus E Appel; Albrecht Buchmann; Larry W Robertson; Hans-Joachim Lehmler; Izabela Kania-Korwel; Ibrahim Chahoud; Michael Schwarz
Journal:  Toxicol Sci       Date:  2013-03-01       Impact factor: 4.849

10.  Effects of thiol antioxidants on the atropselective oxidation of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) by rat liver microsomes.

Authors:  Xianai Wu; Hans-Joachim Lehmler
Journal:  Environ Sci Pollut Res Int       Date:  2015-07-09       Impact factor: 4.223
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