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Eric Uwimana, Anna Maiers, Xueshu Li, Hans-Joachim Lehmler
Polychlorinated biphenyl (PCB) congeners with multiple ortho chlorine substituents and their metabolites exist as stable rotational isomers, or atropisomers, that are nonsuperimposable mirror images of each other. Additionally, the oxidation of certain axially prochiral PCBs, such as 2,2',4,6'-tetrachlorobiphenyl (PCB 51) and 2,2',4,5,6'-pentachlorobiphenyl (PCB 102), in the meta position of the symmetrically substituted phenyl ring is expected to form axially chiral hydroxylated metabolites (OH-PCBs); however, the formation of chiral OH-PCBs from prochiral PCBs has not been demonstrated experimentally...
February 7, 2017: Environmental Science & Technology
Eric Uwimana, Xueshu Li, Hans-Joachim Lehmler
Exposure to neurotoxic, chiral PCBs has been associated with neurodevelopmental disorders, but their metabolism in humans remains unexplored. We investigated the enantioselective metabolism of PCB 95 by human liver microsomes (HLMs) to potentially neurotoxic, hydroxylated metabolites (OH-PCBs). OH-PCB profiles formed in experiments with HLMs differed from metabolite profiles reported for rodent species. The second eluting atropisomer of 2,2',3,5',6-pentachlorobiphenyl-4'-ol, the major metabolite, was preferentially formed by all HLM preparations investigated...
December 19, 2016: Chemical Research in Toxicology
Shalini D Soechitram, Sietske A Berghuis, Theo J Visser, Pieter J J Sauer
BACKGROUND: Several studies have shown effects of polychlorinated biphenyls (PCBs) on serum thyroid hormone levels in pregnant woman and their infants, while other studies did not find such effects. How PCBs might affect thyroid hormone metabolism, is still unclear. Potential mechanisms are direct influence on the thyroid gland, binding to thyroid binding proteins, increased excretion or metabolism of thyroid hormones by deiodinases or sulfatases. It is also not well known whether the effect on thyroid hormone levels is caused by PCBs themselves, or by their hydroxylated metabolites (OH-PCBs)...
October 3, 2016: Science of the Total Environment
Satomi Mizukami-Murata, Futa Sakakibara, Katsuhide Fujita, Makiko Fukuda, Masato Kuramata, Kazuhiro Takagi
To examine the biodegradation of hydroxylated polychlorobiphenyls (OH-PCBs), we isolated Sphingomonas sp. strain N-9 from forest soil using mineral salt medium containing 4-hydroxy-3-chlorobiphenyl (4OH-3CB) at the concentration of 10 mg/L. Following incubation with strain N-9, the concentration of 4OH-3CB decreased in inverse proportion to strain N-9 proliferation, and it was converted to 3-chloro-4-hydroxybenzoic acid (4OH-3CBA) after 1 day. We observed that strain N-9 efficiently degraded lowly chlorinated OH-PCBs (1-4 Cl), while highly chlorinated OH-PCBs (5-6 Cl) were less efficiently transformed...
December 2016: Chemosphere
Natalia Quinete, André Esser, Thomas Kraus, Thomas Schettgen
The present study evaluates for the first time the determination of 20 hydroxylated polychlorinated biphenyl (OH-PCB) congeners and their glucuronide and sulfate conjugates in urine as a biomarker of exposure to PCBs in humans. Thereby, a fast, sensitive and selective online solid phase extraction (SPE) method coupled to LC-MS/MS was validated for the determination of OH-PCBs in human urine, being previously successfully developed and applied for the separation and quantitation of OH-PCBs in human plasma. The lowest limit of quantification (LLOQ) ranged from 0...
December 2016: Environment International
Wen Xin Koh, Keri C Hornbuckle, Kai Wang, Peter S Thorne
Factors contributing to the inter-individual variation in body burden of polychlorinated biphenyls (PCBs) and their hydroxylated metabolites (OH-PCBs) have not been fully elucidated. We examined associations between total serum concentrations of 209 PCBs, 64 OH-PCBs, and frequently detected individual congeners with demographic characteristics (age, gender, ethnicity and community of residence), body mass index (BMI or BMI percentile), and breastfeeding history in children and their mothers from 83 U.S. households...
September 2016: Environment International
Heli Routti, Martin S Andersen, Eva Fuglei, Anuschka Polder, Nigel G Yoccoz
Concentrations and patterns of hydroxylated (OH) polybrominated diphenyl ethers (PBDEs) and polychlorinated biphenyls (PCBs) were investigated in liver from arctic foxes (Vulpes lagopus) sampled from Svalbard 1997-2011 (n = 100). The most important OH-PBDE in the arctic foxes was 6-OH-BDE47 detected in 24% of the samples. Relationships between 6-OH-BDE47, δ(13)C and BDE47 suggest that 6-OH-BDE47 residues in arctic foxes are related to marine dietary input, while the relative importance of the metabolic/natural origin of this compound remains unclear...
September 2016: Environmental Pollution
Eric A Rodriguez, Xueshu Li, Hans-Joachim Lehmler, Larry W Robertson, Michael W Duffel
The disposition of toxicants is often affected by their binding to serum proteins, of which the most abundant in humans is serum albumin (HSA). There is increasing interest in the toxicities of environmentally persistent polychlorinated biphenyls (PCBs) with lower numbers of chlorine atoms (LC-PCBs) due to their presence in both indoor and outdoor air. PCB sulfates derived from metabolic hydroxylation and sulfation of LC-PCBs have been implicated in endocrine disruption due to high affinity-binding to the thyroxine-carrying protein, transthyretin...
May 17, 2016: Environmental Science & Technology
Wen Xin Koh, Keri C Hornbuckle, Rachel F Marek, Kai Wang, Peter S Thorne
Hydroxylated polychlorinated biphenyls (OH-PCBs) have been detected in human specimens and some are suspected as being more toxic than their parent compounds. We compared 58 OH-PCB congeners (in 51 chromatographic peaks) in serum samples from participants in the AESOP Study, a longitudinal cohort study of adolescents and their mothers living in urban and rural areas in the United States. We hypothesized that adolescents would have lower levels of OH-PCBs than their mothers and that serum concentration of OH-PCBs would be stable over a 3-year period...
March 2016: Chemosphere
Hazuki Mizukawa, Kei Nomiyama, Susumu Nakatsu, Hisato Iwata, Jean Yoo, Akira Kubota, Miyuki Yamamoto, Mayumi Ishizuka, Yoshinori Ikenaka, Shouta M M Nakayama, Tatsuya Kunisue, Shinsuke Tanabe
There are growing concerns about the increase in hyperthyroidism in pet cats due to exposure to organohalogen contaminants and their hydroxylated metabolites. This study investigated the blood contaminants polychlorinated biphenyls (PCBs) and polybrominated diphenyl ethers (PBDEs) and their hydroxylated and methoxylated derivatives (OH-PCBs, OH-PBDEs, and MeO-PBDEs), in pet dogs and cats. We also measured the residue levels of these compounds in commercially available pet foods. Chemical analyses of PCBs and OH-PCBs showed that the OH-PCB levels were 1 to 2 orders of magnitude lower in cat and dog food products than in their blood, suggesting that the origin of OH-PCBs in pet dogs and cats is PCBs ingested with their food...
January 5, 2016: Environmental Science & Technology
Patricia Ruiz, Kundan Ingale, John S Wheeler, Moiz Mumtaz
Mono-hydroxylated polychlorinated biphenyls (OH-PCBs) are found in human biological samples and lack of data on their potential estrogenic activity has been a source of concern. We have extended our previous in silico 2D QSAR study through the application of advance techniques such as docking and 3D QSAR to gain insights into their estrogen receptor (ERα) binding. The results support our earlier findings that the hydroxyl group is the most important feature on the compounds; its position, orientation and surroundings in the structure are influential for the binding of OH-PCBs to ERα...
February 2016: Chemosphere
Marianna Stamou, Eric Uwimana, Brenna M Flannery, Izabela Kania-Korwel, Hans-Joachim Lehmler, Pamela J Lein
Polychlorinated biphenyls (PCBs) are metabolized by cytochrome P450 2B enzymes (CYP2B) and nicotine is reported to alter CYP2B activity in the brain and liver. To test the hypothesis that nicotine influences PCB disposition, 2,2',3,5',6-pentachlorobiphenyl (PCB 95) and its metabolites were quantified in tissues of adult male Wistar rats exposed to PCB 95 (6mg/kg/d, p.o.) in the absence or presence of nicotine (1.0mg/kg/d of the tartrate salt, s.c.) for 7 consecutive days. PCB 95 was enantioselectively metabolized to hydroxylated (OH-) PCB metabolites, resulting in a pronounced enrichment of E1-PCB 95 in all tissues investigated...
December 2, 2015: Toxicology
Izabela Kania-Korwel, Christopher D Barnhart, Pamela J Lein, Hans-Joachim Lehmler
Chiral PCBs, such as PCB 95, are developmental neurotoxicants that undergo atropisomeric enrichment in nonpregnant adult mice. Because pregnancy is associated with changes in hepatic cytochrome P450 enzyme activity as well as lipid disposition and metabolism, this study investigates the effect of pregnancy on the maternal disposition of chiral PCBs. Female C57BL/6 mice (8 weeks old) were dosed daily beginning 2 weeks prior to conception and continuing throughout gestation and lactation (56 days total) with racemic PCB 95 (0, 0...
September 21, 2015: Chemical Research in Toxicology
E J Ekuase, T J van 't Erve, A Rahaman, L W Robertson, M W Duffel, G Luthe
Determining the relationships between the structures of substrates and inhibitors and their interactions with drug-metabolizing enzymes is of prime importance in predicting the toxic potential of new and legacy xenobiotics. Traditionally, quantitative structure activity relationship (QSAR) studies are performed with many distinct compounds. Based on the chemical properties of the tested compounds, complex relationships can be established so that models can be developed to predict toxicity of novel compounds...
February 2016: Environmental Science and Pollution Research International
Hazuki Mizukawa, Kei Nomiyama, Tatsuya Kunisue, Michio X Watanabe, Annamalai Subramanian, Hisato Iwata, Mayumi Ishizuka, Shinsuke Tanabe
The concentrations of polychlorinated biphenyls (PCBs), polybrominated diphenyl ethers (PBDEs), and their hydroxylated metabolites (OH-PCBs and OH-PBDEs) were measured in the blood of Eurasian wild pigs (Sus scrofa) from a municipal waste open dumping site (DS) and a reference site (RS) in South India. We showed that contamination with OH-PCBs was higher in female pigs from the DS than in all other adult pigs. The highest OH-PCB concentrations were found in piglets from the DS. Moreover, the hepatic expression levels of CYP1A and CYP2B were higher in piglets than in their dam, implying metabolism of PCBs by cytochrome P450 (CYP) enzymes...
April 2015: Environmental Research
Akifumi Eguchi, Kei Nomiyama, Nguyen Minh Tue, Pham Thi Kim Trang, Pham Hung Viet, Shin Takahashi, Shinsuke Tanabe
This study demonstrated the contamination levels of polychlorinated biphenyls (PCBs), hydroxylated PCBs (OH-PCBs), polybrominated diphenyl ethers (PBDEs), methoxylated PBDEs (MeO-PBDEs), hydroxylated PBDEs (OH-PBDEs), and bromophenols (BPhs), and their relationships with thyroid hormones (THs), in the serum of human donors from an e-waste recycling site and a rural site in Hung Yen province, Vietnam. Occupationally related exposure was indicated by significantly higher residue levels of PCBs, OH-PCBs, PBDEs, and BPhs in the serum of donors from the e-waste recycling site (median: 420, 160, 290, and 300pgg(-1) wet wt, respectively) than those in the serum of donors from the rural site (median: 290, 82, 230, and 200pgg(-)(1) wet wt, respectively)...
February 2015: Environmental Research
Kei Nomiyama, Shusaku Hirakawa, Akifumi Eguchi, Chika Kanbara, Daisuke Imaeda, Jean Yoo, Tatsuya Kunisue, Eun-Young Kim, Hisato Iwata, Shinsuke Tanabe
We have previously reported that high accumulation of dioxins and related compounds induced cytochrome P450 (CYP 1s) isozymes in the liver of wild Baikal seals, implying the enhanced hydroxylation of polychlorinated biphenyls (PCBs). The present study attempted to elucidate the residue concentrations and patterns of PCBs and hydroxylated PCBs (OH-PCBs) in the livers of Baikal seals. The hepatic residue concentrations were used to assess the potential effects of PCBs and OH-PCBs in combination with the analyses of serum thyroid hormones, hepatic mRNA levels, and biochemical markers...
November 18, 2014: Environmental Science & Technology
Rachel F Marek, Peter S Thorne, Jeanne DeWall, Keri C Hornbuckle
Environmental exposures that affect accumulation of polychlorinated biphenyls (PCBs) in humans are complex and not fully understood. One challenge in linking environmental exposure to accumulation is determining variability of PCB concentrations in samples collected from the same person at different times. We hypothesized that PCBs in human blood serum are consistent from year to year in people who live in the same environment between sampling. We analyzed blood serum from children and their mothers from urban and rural U...
November 18, 2014: Environmental Science & Technology
Sietske A Berghuis, Shalini D Soechitram, Pieter J J Sauer, Arend F Bos
Polychlorinated biphenyls (PCBs) are environmental chemicals which are potentially toxic to the developing brain. Their hydroxylated metabolites (OH-PCBs) are suggested to be even more toxic. Knowledge about the health effects of prenatal OH-PCB exposure is limited. We aimed to determine whether prenatal background exposure to PCBs and OH-PCBs is associated with neurological functioning in 3-month-old boys and girls. In a Dutch observational cohort study, we measured 10 PCBs and 6 OH-PCBs in maternal blood samples of 98 pregnant women...
December 2014: Toxicological Sciences: An Official Journal of the Society of Toxicology
Guangshu Zhai, Sarah M Gutowski, Hans-Joachim Lehmler, Jerald L Schnoor
Hydroxylated metabolites of polychlorinated biphenyls (OH-PCBs) have been found to be ubiquitous in the environment due to the oxidative metabolism of their parent PCBs. With more polarity, OH-PCBs may be more toxic and mobile than their parent compounds. However, the behavior and fate of OH-PCBs have been neglected in the environment because they are not the original contaminants. Some of these hydroxylated metabolites are chiral, and chiral compounds can be used to probe biological metabolic processes. Therefore, chiral OH-PCBs were selected to study their uptake, translocation, transformation, and enantioselectivity in plants in this work...
October 21, 2014: Environmental Science & Technology
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