Hydroxylated and methylsulfonyl polychlorinated biphenyl metabolites in albatrosses from Midway Atoll, North Pacific Ocean

Klasson-Wehler, Eva; Bergman, Åke; Athanasiadou, María; Ludwig, James P.; Auman, Heidi J.; Kannan, Kurunthachalam; Berg, Martin van den; Murk, Albertinka J.; Feyk, Lori A.; Giesy, John P.

doi:10.1002/etc.5620170825

Cited by 69 publications

(8 citation statements)

References 48 publications

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“…This compound was also identified as the main metabolite for the southern Quebec pooled sample and in other species including polar bears (33) and albatrosses (32). This metabolite is most likely formed from the metabolism of CB183 and/or CB 187, which represent 2 and 5%, respectively, of the Aroclor 1254 mixture (43).…”

mentioning

confidence: 88%

Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian inuit.

Sandau

Ayotte

Dewailly

et al. 2000

Environ Health Perspect

181

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In this study, we identified the main hydroxylated polychlorinated biphenyls (OH-PCBs) and other chlorinated phenolic compounds and we determined their relative concentrations in whole blood from 13 male and 17 female Inuit from northern Quebec, Canada, and from a pooled whole blood sample from southern Quebec. We also determined concentrations of polychlorinated biphenyls (PCBs). Total OH-PCB concentrations were variable among the Inuit samples, ranging over 2 orders of magnitude (0.117-11.6 ng/g whole blood wet weight). These concentradions were equal to and up to 70 times those found for the southern Quebec pooled whole blood sample. Geometric mean concentrations of tota OH-PCBs were 1.73 and 1.01 nglg whole blood for Inuit men and women, respectively, and 0.161 nglg whole blood for the southern population pool. There are limited data available for comparison, but the levels of OH-PCBs in Imuit are higher thn those previously reported in the literature for other populations. There was a significant correlation (p < 0.005) between OH-PCBs and PCBs (r = 0.84) and both correlated significandy (p < 0.005) with age (r= 0.68 and 0.78, respectively). The ratio of OH-PCBs to PCBs was lower in Inuit (0.11) than in the southern Quebec pool (0.33). There is no apparent explanation for the difference. There was considerable variability in the congener pattem of the identified OH-PCBs. The main metabolite, 4-OH-CB109 (4-0H-2,3,3',4',5-pentachlorobiphenyl), constituted 12-62% of the total OH-PCBs in the samples. Pentachlorophenol (PCP) was the dominant phenolic compound in blood, constituting 46% (geometric mean) of the total quantitated chlorinated phenolic compounds. PCP concentrations in Imuit blood ranged from 0.558 to 7.77 ng/g on a wet weight basis. All but two Inuit samples had lower concentrations than the southern Quebec pool (6.29 ng/g). The possible role of OH-PCBs in mediating PCB-induced adverse effects needs to be investigated fiuther.

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mentioning

confidence: 88%

Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian inuit.

Sandau

Ayotte

Dewailly

et al. 2000

Environ Health Perspect

181

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“…In addition, the epoxide can undergo intramolecular hydrogen migration (NIH shift), resulting in mono hydroxy metabolites (which can also be produced by direct insertion of a hydroxy group). 15,16 Methylsulfonyl metabolites of PCBs and DDE have been detected in fish, 12 birds, 17,18 and mammals, 19,20 including humans. 21,22 Some of these metabolites are selectively and strongly retained in liver and lung tissues.…”

Section: Pcb Metabolitesmentioning

confidence: 99%

Enantioselective semipreparative HPLC separation of PCB metabolites and their absolute structure elucidation using electronic and vibrational circular dichroism

Pham-Tuan¹,

Larsson²,

Hoffmann³

et al. 2005

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Polychlorinated biphenyls (PCBs) remain one of the most important groups of environmental contaminants. The fate (transformation) as well as the toxicological implications of the different metabolism steps are subject to considerable debate. The aim of this study is to start a comprehensive investigation of atropisomeric PCB metabolites, i.e., hydroxy, methoxy, methylthionyl, and methylsulfonyl PCBs in different biota. For this purpose, enantioselective semipreparative liquid chromatography is used to obtain pure enantiomers of PCB metabolites. Electronic circular dichroism (UV-CD) and vibrational circular dichroism (VCD) in combination with computational techniques were applied to determine their absolute structures. Approximately 18-25 mg of each enantiomer of the following metabolites were obtained using semipreparative HPLC on beta-cyclodextrin-based columns: 4-MeO-CB149, 4-MeS-CB149, 4-MeSO2-CB149, 3-MeS-CB149, and 3-MeSO2-CB149. The enantiomeric purity of the separated enantiomers was in the range of 95.0-99.9%. Rotational angles and absolute configurations were also determined. This study establishes a sound method for future preparation and absolute structure determination of compounds belonging to the same class.

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“…The most commonly reported procedure used to separate hydroxylated polychlorinated biphenyls or polybrominated biphenyl ethers from its neutral derivatives depends on the socalled pH partitioning [23,24,25,40]. Alkaline extraction of the compounds from the samples is possible due to the acidic phenolic group present in the molecules [26,41,42].…”

Section: Introductionmentioning

confidence: 99%

Simultaneous separation of chlorinated/brominated dioxins, polychlorinated biphenyls, polybrominated diphenyl ethers and their methoxylated derivatives from hydroxylated analogues on molecularly imprinted polymers prior to gas/liquid chromatography and mass spectrometry

Roszko

Szymczyk

Jędrzejczak

2015

Talanta

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Hydroxylated and methylsulfonyl polychlorinated biphenyl metabolites in albatrosses from Midway Atoll, North Pacific Ocean

Cited by 69 publications

References 48 publications

Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian inuit.

Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian inuit.

Enantioselective semipreparative HPLC separation of PCB metabolites and their absolute structure elucidation using electronic and vibrational circular dichroism

Simultaneous separation of chlorinated/brominated dioxins, polychlorinated biphenyls, polybrominated diphenyl ethers and their methoxylated derivatives from hydroxylated analogues on molecularly imprinted polymers prior to gas/liquid chromatography and mass spectrometry

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