Simultaneous enantioselective separation of polychlorinated biphenyls and their methyl sulfone metabolites by heart-cut MDGC: Determination of enantiomeric fractions in fish oils and cow liver samples

Chirality

Volumn 24, Issue 7, 2012, Pages 577-583

  Pérez Ferńandez, Virginia ^a,b   Castro Puyana, María ^a   González, María José ^a   Marina, María Luisa ^b   García, María Ángeles ^b   Gómara, Belén ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b UNIVERSITY OF ALCALÁ   (Spain)

Author keywords

Food samples; MeSO2 PCBs; Metabolites; Multidimensional GC; PCBs

Indexed keywords

DIMETHYL SULFONE; FISH OIL; POLYCHLORINATED BIPHENYL;

ARTICLE; COW; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; LIVER; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; BETA-CYCLODEXTRINS; CATTLE; CHROMATOGRAPHY, GAS; DIMETHYL SULFOXIDE; FISH OILS; LIVER; POLYCHLORINATED BIPHENYLS; STEREOISOMERISM; SULFONES; TEMPERATURE;

EID: 84862834505     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22062     Document Type: Article

References (28)

1. Schecter A, Stanley J, Boggess K, Masuda Y, Mes J, Wolff M, Fürst P, Fürst C, Wilson-Yang K, Chisholm B. Polychlorinated biphenyl levels in the tissues of exposed and nonexposed humans. Environ Health Perspect Suppl 1994;102:149-158. (Pubitemid 24083116)
2. Letcher RJ, Klasson-Wehlere E, Bergman A. The handbook of environmental chemistry. Berlin: Springer; 2000. p 315-359.
3. Safe S. Toxicology, structure-function relationship, and human and environmental health impacts of polychlorinated biphenyls: progress and problems. Health Perspect 1992;100:259-268. (Pubitemid 23197104)
4. Norén K, Weistrand C, Karpe F. Distribution of PCB congeners, DDE, hexachlorobenzene, and methylsulfonyl metabolites of PCB and DDE among various fractions of human blood plasma. Arch Environ Contam Toxicol 1999;37:408-414. (Pubitemid 29461449)
5. Troisi GM, Haraguchi K, Simmonds MP, Mason CF. Methyl sulphone metabolites of polychlorinated biphenyls (PCBs) in cetaceans from the Irish and the Aegean Seas. Arch Environ Contam Toxicol 1998;35:121-128. (Pubitemid 28275499)
6. Chu S, Covaci A, Haraguchi K, Voorspoels S, Van De Vijver K, Das K, Bouquegneau JM, De Coen W, Blust R, Schepens P. Levels and enantiomeric signatures of methyl sulfonyl PCB and DDE metabolites in livers of harbor porpoises (Phocoena phocoena) from the southern North Sea. Environ Sci Technol 2003;37:4573-4578. (Pubitemid 37270590)
7. Linderholm L, Park JS, Kocan A, Trnovec T, Athanasiadou M, Bergman Å, Hertz-Picciotto I. Maternal and cord serum exposure to PCB and DDE methyl sulfone metabolites in eastern Slovakia. Chemosphere 2007;69:403-410. (Pubitemid 47248678)
8. Guvenius DM, Hassanzadeh P, Bergman Å, Norén K. Metabolites of polychlorinated biphenyls in human liver and adipose tissue. Environ Toxicol Chem 2002;21:2264-2269. (Pubitemid 35155118)
9. Montie EW, Reddy CM, Gebbink WA, Touhey KE, Hahn ME, Letcher RJ. Organohalogen contaminants and metabolites in cerebrospinal fluid and cerebellum gray matter in short-beaked common dolphins and Atlantic white-sided dolphins from the western North Atlantic. Environ Pollut 2009;157:2345-2358.
10. Hoekstra P, Letcher RJ, O'Hara TM, Backus SM, Soloman KR, Muir DCG. Hydroxylated and methylsulfone-containing metabolites of polychlorinated biphenyls in the plasma and blubber of bowhead whales (Balaena mysticetus). Environ Toxicol Chem 2003;22:2650-2658. (Pubitemid 37214749)
11. Lundén K, Pettersson Å, Bergman Å. Methylsulfonyl metabolites of PCBs and DDE in human milk in Sweden, 1972-1992. Environ Health Perspect 1996;104:766-772. (Pubitemid 26285316)
12. Newsome WH, Davies D. Determination of PCB metabolites in Canadian human milk. Chemosphere 1996;33:559-565. (Pubitemid 26193425)
13. Chu S, Covaci A, Jacobs W, Haraguchi K, Schepens P. Distribution of methyl sulfone metabolites of polychlorinated biphenyls and p,p-DDE in human tissues. Environ Health Perspect 2003;1111:1222-1227. (Pubitemid 36939405)
14. Kaiser KLE. Optical-activity of polychlorinated biphenyls. Environ Pollut 1974;7:93-101.
15. Buser HR, Muller MD, Rappe C. Enantioselective determination of chlordane components using chiral high-resolution gas-chromatography mass-spectrometry with application to environmental-samples. Environ Sci Technol 1992;26:1533-1540.
16. Püttmann M, Mannschreck A, Oesch F, Robertson L. Chiral effects in the induction of drug-metabolizing-enzymes using synthetic atropisomers of polychlorinated biphenyls (PCBs). Biochem Pharmacol 1989;38:1345-1352. (Pubitemid 19101965)
17. Lehmler HJ, Harrad SJ, Hühnerfuss H, Kania-Korwel I, Lee CM, Lu Z, Wong CS. Chiral polychlorinated biphenyl transport, metabolism, and distribution: a review. Environ Sci Technol 2010;44:2757-2766.
18. Marriott PJ, Haglund P, Ong RCY. A review of environmental toxicant analysis by using multidimensional gas chromatography and comprehensive GC. Clin Chim Acta 2003;328:1-19. (Pubitemid 36138811)
19. Deans DR. Use of heart cutting in gas-chromatography - a review. J Chromatogr 1981;203:19-28.
20. Wong CS, Garrison AW. Enantiomer separation of polychlorinated biphenyl atropisomers and polychlorinated biphenyl retention behavior on modified cyclodextrin capillary gas chromatography columns. J Chromatogr A 2000;866:213-220.
21. Magnusson J, Blomberg LG, Claude S, Tabacchi R, Saxer A, Schürch S. Gas chromatographic enantiomer separation of atropisomeric PCBs using modified cyclodextrins as chiral phases. J High Resolut Chrom 2000;23:619-627.
22. Ellerichmann T, Bergman Å, Franke S, Hhnerfuss H, Jakobsson E, Knig W, Larsson C. Gas chromatographic enantiomer separations of chiral PCB methyl sulfons and identification of selectively retained enantiomers in human liver. Fresenius Environ Bull 1998;7:244-257. (Pubitemid 28195188)
23. Wiberg K, Letcher R, Sandau C, Duffe J, Norstrom R, Haglund P, Bidleman T. Enantioselective gas chromatography mass spectrometry of methylsulfonyl PCBs with application to arctic marine mammals. Anal Chem 1998;70:3845-3852.
24. Ballschmiter K, Zell AM. Analysis of polychlorinated-biphenyls (PCB) by glass-capillary gas-chromatography - composition of technical aroclor-PCB and clophen - PCB mixtures. Fresenius Z Anal Chem 1980;302:20-31.
25. Hovander L, Linderholm L, Athanasiadou M, Athanassiadis I, Bignert A, Fängström B, Kocan A, Petrik J, Trnovec T, Bergman Å. Levels of PCBs and their metabolites in the serum of residents of a highly contaminated area in eastern Slovakia. Environ Sci Technol 2006;40:3696-3703. (Pubitemid 43902363)
26. Harner T, Wiberg K, Norstrom R. Enantiomer fractions are preferred to enantiomer ratios for describing chiral signatures in environmental analysis. Environ Sci Technol 2000;34:218-220. (Pubitemid 30030755)
27. Bordajandi LR, Korytár P, De Boer J, González MJ. Enantiomeric separation of chiral polychlorinated biphenyls on beta-cyclodextrin capillary columns by means of heart-cut multidimensional gas chromatography and comprehensive two-dimensional gas chromatography. Application to food samples. J Sep Sci 2005;28:163-171. (Pubitemid 40360926)
28. Gómara B, González MJ. Enantiomeric fractions and congener specific determination of polychlorinated biphenyls in eggs of predatory birds from Donana National Park (Spain). Chemosphere 2006;63:662-669.