ArticleEnvironmental science & technology2014
Microsomal oxidation of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) results in species-dependent chiral signatures of the hydroxylated metabolites.
Article in Environmental science & technology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
19 citing papers in PubMed, 37 citations in OpenAlex.
- Rebuttal to Correspondence on "Machine Learning-Assisted Identification and Quantification of Hydroxylated Metabolites of Polychlorinated Biphenyls in Animal Samples".Environmental science & technology · 2023Article
- Probing the Role of CYP2 Enzymes in the Atropselective Metabolism of Polychlorinated Biphenyls Using Liver Microsomes from Transgenic Mouse Models.Chemical research in toxicology · 2022Article
- The dichloroacetamide safener benoxacor is enantioselectively metabolized by monkey liver microsomes and cytosol.Environmental toxicology and pharmacology · 2022Article
- 'Cry-for-help' in contaminated soil: a dialogue among plants and soil microbiome to survive in hostile conditions.Environmental microbiology · 2021Review
- 3,3'-Dichlorobiphenyl Is Metabolized to a Complex Mixture of Oxidative Metabolites, Including Novel Methoxylated Metabolites, by HepG2 Cells.Environmental science & technology · 2020Article
- Atropselective Disposition of 2,2',3,4',6-Pentachlorobiphenyl (PCB 91) and Identification of Its Metabolites in Mice with Liver-Specific Deletion of Cytochrome P450 Reductase.Chemical research in toxicology · 2020Article
- Toxicokinetics of Chiral PCB 136 and Its Hydroxylated Metabolites in Mice with a Liver-Specific Deletion of Cytochrome P450 Reductase.Chemical research in toxicology · 2019Article
- Human CYP2A6, CYP2B6, AND CYP2E1 Atropselectively Metabolize Polychlorinated Biphenyls to Hydroxylated Metabolites.Environmental science & technology · 2019Article
- Sources and toxicities of phenolic polychlorinated biphenyls (OH-PCBs).Environmental science and pollution research international · 2018Article
- Human Liver Microsomes Atropselectively Metabolize 2,2',3,4',6-Pentachlorobiphenyl (PCB 91) to a 1,2-Shift Product as the Major Metabolite.Environmental science & technology · 2018Article
- Microsomal Metabolism of Prochiral Polychlorinated Biphenyls Results in the Enantioselective Formation of Chiral Metabolites.Environmental science & technology · 2017Article
- 2,2',3,5',6-Pentachlorobiphenyl (PCB 95) Is Atropselectively Metabolized to para-Hydroxylated Metabolites by Human Liver Microsomes.Chemical research in toxicology · 2016Article
- Toxicokinetics of chiral polychlorinated biphenyls across different species--a review.Environmental science and pollution research international · 2016Review
- Chiral polychlorinated biphenyls: absorption, metabolism and excretion--a review.Environmental science and pollution research international · 2016Review
- Effects of thiol antioxidants on the atropselective oxidation of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) by rat liver microsomes.Environmental science and pollution research international · 2016Article
- Effect of pregnancy on the disposition of 2,2',3,5',6-pentachlorobiphenyl (PCB 95) atropisomers and their hydroxylated metabolites in female mice.Chemical research in toxicology · 2015Article
- Metabolism and metabolites of polychlorinated biphenyls.Critical reviews in toxicology · 2015Review
- Hepatic metabolism affects the atropselective disposition of 2,2',3,3',6,6'-hexachlorobiphenyl (PCB 136) in mice.Environmental science & technology · 2015Article
- Occurrence and distribution of PCB metabolites in blood and their potential health effects in humans: a review.Environmental science and pollution research international · 2014Review
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Chiral polychlorinated biphenyls (PCBs) display variable atropisomeric enrichment in wildlife and animal models, especially at higher trophic levels. These differences in PCBs' chiral signatures are, at least in part, due to species-dependent oxidation of PCBs to hydroxylated PCB metabolites (OH-PCBs). Here, we investigate the hypothesis that the cytochrome P450 (P450) enzyme-mediated oxidation of chiral PCBs results in species-dependent differences in the chiral signatures of OH-PCBs (i.e., the direction and extent of OH-PCBs' atropisomeric enrichment). To investigate this hypothesis, we incubated PCB 136, a representative chiral PCB, with pooled human liver microsomes (HLMs) or liver microsomes from male guinea pig, hamster, monkey, mouse, and rabbit or female dog and determined average profiles and chiral signatures of the OH-PCBs. 2,2',3,3',6,6'-Hexachlorobiphenyl-4-ol (4-136) was the major metabolite in incubations with HLMs and monkey and rabbit microsomes. 2,2',3,3',6,6'-Hexachlorobiphenyl-5-ol (5-136) was the major metabolite formed by microsomes from all other species. Both 4-136 and 5-136 were formed atropselectively in all microsomal incubations; however, the direction and extent of the atropisomeric enrichment of both OH-PCB metabolites showed considerable differences across microsomal preparations obtained from different species. These differences in OH-PCBs' atropisomeric enrichment may not only be toxicologically relevant but may also be useful to study sources and transport of OH-PCBs in the environment.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.