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Bis(4-chlorophenyl) sulfone and PCB methyl sulfone metabolites: Trends and chirality in the Baltic Sea environment
Stockholm University, Faculty of Science, Department of Environmental Chemistry.
2006 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

The Baltic Sea was earlier identified as a highly polluted brackish water body and still is. The high concentrations of polychlorinated biphenyls (PCBs), p,p’-DDT and related compounds led to severe effects on several species in the Baltic region. However, the situation has improved significantly since the 1970’s resulting in lower exposures to a range of pollutants and healthier wildlife populations. Independent of this positive trend there are still new chemicals leaking into the Baltic Sea environment. The objective of this thesis is to improve the knowledge of sulfone containing compounds and pollutant metabolites in wildlife, with special interest in bis(4-chlorophenyl) sulfone (BCPS) distribution, temporal trend and exposure levels, and the methylsulfonyl-PCBs (MeSO2-PCBs). The latter are of particular interest for chiral MeSO2-PCBs. BCPS is used for the production of high temperature polymers and was detected as an environmental contaminant ten years ago. PCBs, p,p’-DDT and related compounds are still of scientific interest.

BCPS is biomagnified and especially in the bird guillemot which has levels of up to 2000 ng BCPS/g fat compared to the grey seal with concentrations of about 60 ng/g fat. The seal levels are similar to the herring, the prey of the bird and seal, with concentrations of 30 ng BCPS/g fat. The guillemot concentration of BCPS has been similar over the last 30 years with a minimal, but significant, annual decline of 1.6%. The reason for the slow decline is not yet understood. Also MeSO2-PCBs and 3-MeSO2-DDE show a small decrease over time in guillemot egg (3 and 9%, respectively), which is less then for the parent compounds. This shows that the sulfone metabolites are more persistent than their precursors in the guillemot. Furthermore, all these sulfone containing compounds showed a specific retention to liver comparing different tissues in grey seal. The atropisomers of the chiral MeSO2-PCB were analysed in both the guillemot and the grey seal and showed to occur in a skewed relationship. This is particularly pronounced in seals where one atropisomer of each chiral congener is very dominating. The dominating atropisomers have been identified with an absolute R configuration, in both grey seal and guillemot. An enantioselective metabolism was indicated to occur when experimentally tested by CB-132 in rat.

This thesis is stressing the high specificity in wildlife for one atropisomer in the pair of chiral PCB methyl sulfones being PCB metabolites, and the high BCPS concentrations in guillemot hatching in the Baltic proper.

Place, publisher, year, edition, pages
Stockholm: Institutionen för miljökemi , 2006. , 69 p.
Keyword [en]
bis(4-chlorophenyl) sulfone, PCB methyl sulfone, Baltic Sea
National Category
Environmental Sciences
Identifiers
URN: urn:nbn:se:su:diva-983ISBN: 91-7155-203-0 (print)OAI: oai:DiVA.org:su-983DiVA: diva2:200775
Public defence
2006-05-12, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 12 A, Stockholm, 10:00 (English)
Opponent
Supervisors
Available from: 2006-04-20 Created: 2006-04-20 Last updated: 2010-01-08Bibliographically approved
List of papers
1. Bis(4-chlorophenyl) sulfone (BCPS) in Swedish marine and fresh water wildlife – a screening study
Open this publication in new window or tab >>Bis(4-chlorophenyl) sulfone (BCPS) in Swedish marine and fresh water wildlife – a screening study
2004 In: Environment International, ISSN 0160-4120, Vol. 30, no 5, 667-674 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-25898 (URN)
Note
Part of urn:nbn:se:su:diva-983Available from: 2006-04-20 Created: 2006-04-20Bibliographically approved
2. Temporal trend of bis(4-chlorophenyl) sulfone, methylsulfonyl-DDE andd -PCB in Baltic guillemot (Uria aalge) egg 1971-2001 - A comparison to 4,4'-DDE and PCB trends
Open this publication in new window or tab >>Temporal trend of bis(4-chlorophenyl) sulfone, methylsulfonyl-DDE andd -PCB in Baltic guillemot (Uria aalge) egg 1971-2001 - A comparison to 4,4'-DDE and PCB trends
Show others...
2006 (English)In: Environmental Pollution, ISSN 0269-7491, Vol. 141, no 2, 226-237 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-25684 (URN)10.1016/j.envpol.2005.08.054 (DOI)
Note
Part of urn:nbn:se:su:diva-8419Available from: 2009-01-15 Created: 2009-01-15 Last updated: 2010-01-08Bibliographically approved
3. Enantiomeric specificity of methylsulfonyl-PCBs and distribution of bis(4-chlorophenyl) sulfone, PCB, and DDE methyl sulfones in grey seal tissues
Open this publication in new window or tab >>Enantiomeric specificity of methylsulfonyl-PCBs and distribution of bis(4-chlorophenyl) sulfone, PCB, and DDE methyl sulfones in grey seal tissues
Show others...
2004 In: Environmental Science and Technology, ISSN 0013-936X, Vol. 38, no 19, 4950-4955 p.Article in journal (Refereed) Published
Identifiers
urn:nbn:se:su:diva-25900 (URN)
Note
Part of urn:nbn:se:su:diva-983Available from: 2006-04-20 Created: 2006-04-20Bibliographically approved
4. Enantioselective metabolism of 2,2’,3,3’,4,6’-hexaCB in rat
Open this publication in new window or tab >>Enantioselective metabolism of 2,2’,3,3’,4,6’-hexaCB in rat
Show others...
Manuscript (Other academic)
Identifiers
urn:nbn:se:su:diva-25901 (URN)
Note
Part of urn:nbn:se:su:diva-983Available from: 2006-04-20 Created: 2006-04-20 Last updated: 2010-01-13Bibliographically approved

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