Analytical strategies for successful enantioselective separation of atropisomeric polybrominated biphenyls 132 and 149 in environmental samples

Götsch, Arntraut; Mariussen, Espen; Recke, Roland von der; Herzke, Dorte; Berger, Urs; Vetter, Walter

doi:10.1016/j.chroma.2004.11.059

Cited by 15 publications

(9 citation statements)

References 15 publications

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“…However, due to their more bulky bromine substituents, it can be assumed that more than 19 atropisomeric forms (like the ones for PCBs) exist at ambient temperature. Up to now, few atropisomers have been identified [79,80] and separated by GC or HPLC. To our knowledge, no method has been developed till now for the chiral separation of PBBs atropisomers by CE, constituting other research line to be explored.…”

Section: Chiral Analysis Of Other Pollutantsmentioning

confidence: 99%

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Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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Chiral analysis of pollutants and their metabolites by capillary electromigration methodsChiral separation of enantiomers is one of the most challenging tasks for any analytical technique including CE. Since the first report in 1985 showing the great possibilities of CE for the separation of chiral compounds, the amount of publications concerning this topic has quickly increased. Although chiral electromigration methods have mainly been used for enantioseparation of drugs and pharmaceuticals, they have also been applied to analyze chiral pollutants. This article intends to provide an updated overview, including works published till January 2005, on the principal applications of CE to the chiral analysis of pollutants and their metabolites, with especial emphasis on articles published in the last 10 years. The main advantages and drawbacks regarding the use of CE for chiral separation of pollutants are addressed including some discussion on the foreseen trends of electromigration procedures applied to chiral analysis of contaminants. IntroductionSeparation of chiral compounds is an interesting and challenging topic of research in many analytical chemistry areas, especially in the biomedical, pharmaceutical, and environmental fields where pure enantiomeric forms are widely required. It is already well-known that enantiomers, in spite of their very similar structure, when exposed to an identical biological environment can show very different biological activity. Furthermore, as a general rule, when the toxicological effect of an active substance is directly related to its desired biological activity, the most active isomer is usually the most toxic one Abbreviations: Allyl-TER, 1-allylterguride; ANDSA, 7-aminonaphthalene-1,3-disulfonic acid; ANSA, 5-aminonaphthalene-1-sulfonic acid; ANTS, 8-aminonaphthalene-1,3,6-trisulfonic acid; CA, chrysanthemic acid; CM-ª-CD, carboxymethylated-g-CD; CMBA, 2-(4-chlorophenyl)-3-methylbutanoic acid; 2,2-CPPA, 2-(2-chlorophenoxy)-propionic acid; 2,3-CPPA, 2-(3-chlorophenoxy)-propionic acid; 2,4-CPPA, 2-(4-chlorophenoxy)-propionic acid; â-CD-NH 2 , 6-monodeoxy-6-monoamino-b-CD; â-CD- (NH 3 )

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Section: Chiral Analysis Of Other Pollutantsmentioning

confidence: 99%

“…Likewise their chlorinated analogs (PCBs) they exist in a theoretical variety of 209 congeners [79] and they can show atropisomery too. However, due to their more bulky bromine substituents, it can be assumed that more than 19 atropisomeric forms (like the ones for PCBs) exist at ambient temperature.…”

Section: Chiral Analysis Of Other Pollutantsmentioning

confidence: 99%

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

et al. 2005

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“…DecaBB is highly non-volatile and a very short capillary column and higher carrier gas velocity increases the analysis speed and reduces possible degradation at high temperatures in the GC oven. Enantiomeric pairs of PBB congeners can occur in the environment, and these pairs may be separated using enantioselective GC columns (Götsch et al, 2005).…”

Section: Methods Of Analysismentioning

confidence: 99%

Scientific Opinion on Polybrominated Biphenyls (PBBs) in Food

2010

EFSA Journal

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EFSA was asked by the European Commission to deliver a scientific opinion on polybrominated biphenyls (PBBs) in food. PBBs are additive flame retardants which were applied in synthetic fibres and polymers. PBBs are present in the environment at low concentrations and likewise in biota and in food and feed. Data from the analysis of 16 PBB congeners in 794 food samples were provided to EFSA by 6 Member States, covering the period from 2003 to 2009. Toxicity studies were carried out with technical PBB mixtures of which the exact congener composition is not known. Main targets were the liver, thyroid hormone homeostasis and the reproductive, nervous and immune systems. PBBs are not directly genotoxic. The Panel on Contaminants in the Food Chain (CONTAM Panel) selected the hepatic carcinogenic effects as the critical effect, with a no‐observed‐effect level (NOEL) of 0.15 mg/kg body weight (b.w.). Since this NOEL was obtained in a study with a technical PBB mixture, the congener profile of which differs from that currently found in food, the CONTAM Panel concluded that it was inappropriate to use this NOEL to derive a health based guidance value. The intake of PBBs by high and frequent consumers of fatty fish, the subgroup with the highest dietary exposure, was approximately 6 orders of magnitude less than this NOEL. Exposure for high consuming breast‐fed infants is 5 orders of magnitude less than this NOEL. Therefore the CONTAM Panel concluded that the risk to the European population from exposure to PBBs through the diet is of no concern. Since PBBs are no longer produced or used in Europe and taking into account low and declining environmental concentrations, the CONTAM Panel concluded that PBBs are a low priority for further research or monitoring efforts.

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“…This advancement opens the opportunity for development of chiral GC-APCI-MS/MS methods for NBFRs. Also (Gotsch et al, 2005), enantioseparated 7 PBBs pairs were using HPLC sample preparation followed by chiral GC-EI-MS-MS (QQQ) (see Table 1). Nevertheless, for large molecules like HBCDs and most likely HCDBCO, the chiral GC analysis methods are not at all suitable due to instability and high boiling points of compounds and LC methods must be used.…”

Section: Spectrometric Parametersmentioning

confidence: 99%

Advances in enantioselective analysis of chiral brominated flame retardants. Current status, limitations and future perspectives

Badea

Niculescu

Ionete

et al. 2016

Science of The Total Environment

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Analytical strategies for successful enantioselective separation of atropisomeric polybrominated biphenyls 132 and 149 in environmental samples

Cited by 15 publications

References 15 publications

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Chiral analysis of pollutants and their metabolites by capillary electromigration methods

Scientific Opinion on Polybrominated Biphenyls (PBBs) in Food

Advances in enantioselective analysis of chiral brominated flame retardants. Current status, limitations and future perspectives

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