Methyl Sulfone and Hydroxylated Metabolites of Polychlorinated Biphenyls

Letcher, Robert J.; Klasson-Wehler, Eva; Bergman, Åke

doi:10.1007/3-540-48915-0_11

Cited by 239 publications

(527 citation statements)

References 156 publications

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“…These are congeners predominantly containing a phenyl group with un-chlorinated meta and para positions (i.e. 2,5-chlorine substitution), which are particularly susceptible to metabolic attack by P450 cytochromes (Letcher et al, 1999). The signature also contained elevated proportions of CB-74, CB-153, CB-138 and CB-180 (Fig.…”

Section: Occupational Exposure To A1260mentioning

confidence: 99%

Can polychlorinated biphenyl (PCB) signatures and enantiomer fractions be used for source identification and to age date occupational exposure?

Megson

Focant

Patterson

et al. 2015

Environment International

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Detailed polychlorinated biphenyl (PCB) signatures and chiral Enantiomer Fractions (EFs) of CB-95, CB-136 and CB-149 were measured for 30 workers at a transformer dismantling plant. This was undertaken to identify sources of exposure and investigate changes to the PCB signature and EFs over different exposure periods. Approximately 1.5 g of serum was extracted and PCB signatures were created through analysis by comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry (GC × GC-TOFMS) and EFs calculated following analysis by gas chromatography with high resolution mass spectrometry (GC-HRMS). A total of 84 PCBs were identified in the serum samples with concentrations of the 7 indicator PCBs ranging from 11-350 ng g −1 of serum (1.2-39 μg g −1 lipid). The PCB signatures were interpreted using principal component analysis (PCA) which was able to distinguish workers with background or recent minimal exposure from those with prolonged occupational exposure. Occupationally exposed individuals had a similar PCB profile to Aroclor A1260. However, individuals with prolonged exposure had depleted proportions of several PCB congeners that are susceptible to metabolism (CB-95, CB-101 and CB-151) and elevated proportions of PCBs that are resistant to metabolism (CB-74, CB-153, CB-138 and CB-180). The results also identified a third group of workers with elevated proportions of CB-28, CB-60, CB-66, CB-74, CB-105 and CB-118 who appeared to have been exposed to an additional source of PCBs. The results show near complete removal of the CB-95 E2 enantiomer in some samples, indicating that bioselective metabolism or preferential excretion of one enantiomer occurs in humans. By considering PCB concentrations along with detailed congener specific signatures it was possible to identify different exposure sources, and gain an insight into both the magnitude and duration of exposure.

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Section: Occupational Exposure To A1260mentioning

confidence: 99%

Can polychlorinated biphenyl (PCB) signatures and enantiomer fractions be used for source identification and to age date occupational exposure?

Megson

Focant

Patterson

et al. 2015

Environment International

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“…The enzyme-mediated biotransformation depends both on the congener structure and on the metabolic capacity of the species. The majority of the persistent and bioaccumulative MeSO2-PCBs are congeners that originate from PCBs possessing 3-7 chlorine atoms and a 2,5-dichloro or a 2,3,6-trichloro substitution pattern on one of the biphenyl rings, while only 2-and 3-MeSO2-DDE have been found in environmental samples until now (1). The initial phase I metabolism is mediated by cytochrome P450 2B-like (CYP2B) isoenzymes (1).…”

Section: Introductionmentioning

confidence: 99%

“…The dehydration and hydrolysis of the glutathionyl-PCB occurs via the mercapturic acid pathway to form a cysteine conjugate, which is converted to a PCB thiol via a biliary excretion into the gastrointestinal tract and further to methylthio-PCB via C-S lyase and S-adenosylmethionine mediation. A following two-step CYP enzyme-mediated oxidation results in persistent 3-or 4-MeSO2-PCBs (1).…”

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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“…Hydroxylated polychlorinated biphenyls (OH-PCBs) are produced in the environment by oxidation of PCBs through a variety of mechanisms, including metabolisms in living organisms, reactions with atmospheric active hydroxyl radicals, and transformations in wastewater treatment plants [3][4][5][6]. In bacteria and higher organisms, including human beings, PCBs are metabolized to OH-PCBs by cytochrome P-450 mono-oxygenases [7,8], which have been found in the blood and tissues of humans and wildlife [9]. A number of OH-PCBs have been identified as endocrine disruptors, therefore, their toxicities may be greater than those of their parent PCBs [10].…”

Section: Introductionmentioning

confidence: 99%

Determination of hydroxylated polychlorinated biphenyls by offline solid-phase extraction-liquid chromatography–tandem mass spectrometry using a molecularly imprinted polymer as a sorbent for sample preconcentration

Liang

Zhao

et al. 2015

Talanta

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a b s t r a c tHydroxylated polychlorinated biphenyls (OH-PCBs) can be detected by liquid chromatography-mass spectrometry coupled to solid-phase extraction (SPE) using a dummy molecularly imprinted polymer (DMIP) as a sorbent. The DMIP is prepared by using an analogue of OH-PCBs (i.e., 4, 4-dihydroxybiphenyl) as a dummy template, to avoid the leakage of the target molecules. The DMIP-SPE sorbent shows good recoveries for OH-PCBs at pH 11 due to the charge-assisted hydrogen bondings between OH-PCBs and the DMIP. It has been found that the DMIP is much more effective and selective than the traditional C 18 -SPE method. The sample pH, polymer dosage, elution solvent and volume have been optimized for higher recoveries. Under the optimum experimental conditions, OH-PCBs can be detected in the linear concentration range of 0.05-1.0 pM, with the detection limits ranging from 11 fM to 82 fM for 4′-OH-CB 9, 4′-OH-CB 30, 4′-OH-CB 61, 4′-OH-CB 106 and 4′-OH-CB 112. The proposed system has been successfully applied to the determination of trace OH-PCBs in spiked water samples with recoveries in the range of 89-110%.

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Methyl Sulfone and Hydroxylated Metabolites of Polychlorinated Biphenyls

Cited by 239 publications

References 156 publications

Can polychlorinated biphenyl (PCB) signatures and enantiomer fractions be used for source identification and to age date occupational exposure?

Can polychlorinated biphenyl (PCB) signatures and enantiomer fractions be used for source identification and to age date occupational exposure?

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

Determination of hydroxylated polychlorinated biphenyls by offline solid-phase extraction-liquid chromatography–tandem mass spectrometry using a molecularly imprinted polymer as a sorbent for sample preconcentration

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