Methylsulfonyl Metabolites of PCBs and DDE in Human Tissues

Weistrand, Cecilia; Norén, Koidu

doi:10.2307/3433610

Cited by 10 publications

(18 citation statements)

References 19 publications

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“…The adrenocorticolytic activity of MeSO 2 -DDE has been characterized in subcellular adrenal fractions, cultured adrenal cells, and intact experimental animals. As shown by these studies, there are major differences in toxic potency between species, mice being highly sensitive whereas rats appear insensitive (4,11,36,38,41 (8,9), a risk evaluation of possible human toxicity is called for.…”

Section: Discussionmentioning

confidence: 99%

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Irreversible Binding and Adrenocorticolytic Activity of the DDT Metabolite 3-Methylsulfonyl-DDE Examined in Tissue-Slice Culture

Lindhe¹,

Lund²,

Bergman³

et al. 2001

Environ Health Perspect

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Section: Discussionmentioning

confidence: 99%

“…These persistent chemicals subsequently have been found in human breast milk, blood, and adipose tissue, as well as in adipose tissue of arctic polar bears (7)(8)(9). Several of these aryl methyl sulfones are characterized by their cell-and tissue-specific distribution patterns in the body.…”

mentioning

confidence: 99%

Irreversible Binding and Adrenocorticolytic Activity of the DDT Metabolite 3-Methylsulfonyl-DDE Examined in Tissue-Slice Culture

Lindhe¹,

Lund²,

Bergman³

et al. 2001

Environ Health Perspect

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“…The initial shorthand notation used for MeSO 2 -PCBs assigned the methyl sulfonyl group based on a higher numbering priority on the biphenyl system than for chlorine atoms, and thus the position of methyl sulfonyl substitution was not primed (Letcher et al 1995;Weistrand and Norén 1997). For example, using this initial numbering approach, a methyl sulfonyl group in a meta-position would always be assigned to position 3.…”

Section: Nomenclature Of Meso 2 -Pcbsmentioning

confidence: 99%

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

Maervoet

Covaci

Schepens

et al. 2004

Environ Health Perspect

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Polychlorinated biphenyls (PCBs) are a widespread class of persistent organic chemicals that accumulate in the environment and humans and are associated with a broad spectrum of health effects. PCB biotransformation has been shown to lead to two classes of PCB metabolites that are present as contaminant residues in the tissues of selected biota: hydroxylated (HO) and methyl sulfone (MeSO2) PCBs. Although these two types of metabolites are related structures, different rules for abbreviation of both classes have emerged. It is important that a standardized nomenclature for the notation of PCB metabolites be universally agreed upon. We suggest that the full chemical name of the PCB metabolite and a shorthand notation should be adopted using the International Union of Pure and Applied Chemistry's chemical name/original Ballschmiter and Zell number of the parent congener, followed by the assignment of the phenyl ring position number of the MeSO2- or HO-substituent. This nomenclature provides a clear, unequivocal set of rules in naming and abbreviating the PCB metabolite structure. Furthermore, this unified PCB metabolite nomenclature approach can be extended to the naming and abbreviation of potential metabolites of structurally analogous contaminants such as HO-polybrominated biphenyls and HO-polybrominated diphenyl ethers.

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“…It was found that these contaminants are ubiquitous and bioaccumulate in the environment (5)(6)(7)(8)(9)(10). However, there is only little information available on the distribution of MeSO2-PCBs and -DDE metabolites in marine mammals.…”

Section: Introductionmentioning

confidence: 99%

Levels and Enantiomeric Signatures of Methyl Sulfonyl PCB and DDE Metabolites in Livers of Harbor Porpoises (Phocoena phocoena) from the Southern North Sea

Chu

Covaci

Haraguchi

et al. 2003

Environ. Sci. Technol.

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The concentration of 26 methyl sulfonyl metabolites of polychlorinated biphenyls (MeSO 2 -PCBs) and of p,p′-DDE (MeSO 2 -DDE) were determined in 19 liver samples from harbor porpoises (Phocoena phocoena) stranded between 1997 and 2000 on the Belgian and French North Sea Coasts. The total concentration of MeSO 2 -PCBs ranged from 39 to 4221 ng/g lipid weight (lw) and were generally higher in adults (age >2 yr, range 969-4 221 ng/g lw) than in juveniles (age <2 yr, range 39-1815 ng/g lw). The concentrations of MeSO 2 -DDE were generally also higher in adults (21-96 ng/g lw) than in juveniles (0.5-60 ng/g lw). Congeners 3-and 4-MeSO 2 -CB101 were the dominating metabolites in all samples. Due to their preferential retention in the liver, the MeSO 2 -PCB congeners could be divided into two groups. The first group was dominated by the 3-MeSO 2 -PCB congeners and consisted of MeSO 2 -CB31, -CB49, -CB52, -CB87, and -CB101, which all have a 2,5-chlorine substitution in the phenyl ring containing the methyl sulfonyl group. The second group was dominated by the 4-MeSO 2 -PCB congeners and consisted of MeSO 2 -CB64, -CB91, -CB110, and -CB132, which all have a 2,3,6-chlorine substitution. The ratios of sum of PCBs/sum of MeSO 2 -PCBs and p,p′-DDE/MeSO 2 -DDE differed greatly between individual subjects and ranged from 15 to 419 and from 17 to 1088, respectively. The ratio between the precursor PCB congeners and their corresponding metabolites ranged from 0.6 (CB49) to 175 (CB174). Enantiomeric fractions (EFs) for MeSO 2 -PCB atropisomers, which include 3-MeSO 2 -CB132, 3-MeSO 2 -CB149, 4-MeSO 2 -CB149, 3-MeSO 2 -CB174, and 4-MeSO 2 -CB174, were also measured in 8 out of the 19 subjects. High enantiomeric excess (EF > 0.73 or EF < 0.23) for the measured chiral MeSO 2 -PCB congeners was found in all samples. This result may suggest that one atropisomer may be preferentially formed in harbor porpoises or that the atropisomers are retained in a highly selective manner.

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Methylsulfonyl Metabolites of PCBs and DDE in Human Tissues

Cited by 10 publications

References 19 publications

Irreversible Binding and Adrenocorticolytic Activity of the DDT Metabolite 3-Methylsulfonyl-DDE Examined in Tissue-Slice Culture

Irreversible Binding and Adrenocorticolytic Activity of the DDT Metabolite 3-Methylsulfonyl-DDE Examined in Tissue-Slice Culture

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

Levels and Enantiomeric Signatures of Methyl Sulfonyl PCB and DDE Metabolites in Livers of Harbor Porpoises (Phocoena phocoena) from the Southern North Sea

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