ArticleProceedings of the National Academy of Sciences of the United States of America2017
Discovery of a widespread metabolic pathway within and among phenolic xenobiotics.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 122 citations in OpenAlex.
- Covalently Active Metabolites of Bisphenol A Analogs by Mass Spectrometry Diagnostic Ions: Possible Mechanisms of Their Toxicity.Chemical research in toxicology · 2026Article
- Endocrine Disrupting Agents: Toxicological Aspects on Male Reproduction.Reproductive sciences (Thousand Oaks, Calif.) · 2025Review
- Effects of carminic acid on gene expressions under epigenetic regulation.Biochemistry and biophysics reports · 2025Article
- Charged polystyrene microplastics inhibit uptake and transformation ofJournal of advanced research · 2025Article
- Theoretical Investigation of Cytochrome P450 Enzyme-Mediated Biotransformation Mechanism of BHPF: Unveiling the Metabolic Safety Aspects of an Alternative to BPA.Environment & health (Washington, D.C.) · 2025Article
- Evolution of pollutant biodegradation.Applied microbiology and biotechnology · 2025Review
- Thallium's Threat to Aquatic Life: Stage-Specific Toxicity in Zebrafish Embryos and Larvae.Environment & health (Washington, D.C.) · 2024Article
- Proteomics analysis of human breast milk by two-dimensional polyacrylamide gel electrophoresis (2D-PAGE) coupled with mass spectrometry to assess breast cancer risk.Electrophoresis · 2023Article
- Adverse effects of triclosan exposure on health and potential molecular mechanisms.The Science of the total environment · 2023Review
- Microbiota-mediated reactivation of triclosan oxidative metabolites in colon tissues.Journal of hazardous materials · 2023Article
- Constitutive Androstane Receptor Agonist, TCPOBOP: Maternal Exposure Impairs the Growth and Development of Female Offspring in Mice.International journal of molecular sciences · 2023Article
- Article
- Detection of Azoxystrobin Fungicide and Metabolite Azoxystrobin-Acid in Pregnant Women and Children, Estimation of Daily Intake, and Evaluation of Placental and Lactational Transfer in Mice.Environmental health perspectives · 2022Article
- Biotransformation of 2,4,6-tris(2,4,6-tribromophenoxy)-1,3,5-triazine (TTBP-TAZ) can contribute to high levels of 2,4,6-tribromophenol (2,4,6-TBP) in humans.Environment international · 2022Article
- Synthesis and Characterization of the Ethylene-Carbonate-Linked L-Valine Derivatives of 4,4-Dimethylcurcumin with Potential Anticancer Activities.Molecules (Basel, Switzerland) · 2021Article
- RNA-Seq analysis of the blue light-emitting Orfelia fultoni (Diptera: Keroplatidae) suggest photoecological adaptations at the molecular level.Comparative biochemistry and physiology. Part D, Genomics & proteomics · 2021Article
- Quercetin and Isorhamnetin Attenuate Benzo[a]pyrene-Induced Toxicity by Modulating Detoxification Enzymes through the AhR and NRF2 Signaling Pathways.Antioxidants (Basel, Switzerland) · 2021Article
- Stable Isotope-Assisted Metabolomics for Deciphering Xenobiotic Metabolism in Mammalian Cell Culture.ACS chemical biology · 2020Article
- Modulatory Effects of Silymarin on Benzo[a]pyrene-Induced Hepatotoxicity.International journal of molecular sciences · 2020Article
- Glycosylation of Tetrabromobisphenol A in Pumpkin.Environmental science & technology · 2019Article
Corrections and comments
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Authors and funding
9 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Metabolism is an organism's primary defense against xenobiotics, yet it also increases the production of toxic metabolites. It is generally recognized that phenolic xenobiotics, a group of ubiquitous endocrine disruptors, undergo rapid phase II metabolism to generate more water-soluble glucuronide and sulfate conjugates as a detoxification pathway. However, the toxicological effects of the compounds invariably point to the phase I metabolic cytochrome P450 enzymes. Here we show that phenolic xenobiotics undergo an unknown metabolic pathway to form more lipophilic and bioactive products. In a nontargeted screening of the metabolites of a widely used antibacterial ingredient: triclosan (TCS), we identified a metabolic pathway via in vitro incubation with weever, quail, and human microsomes and in vivo exposure in mice, which generated a group of products: TCS-O-TCS. The lipophilic metabolite of TCS was frequently detected in urine samples from the general population, and TCS-O-TCS activated the constitutive androstane receptor with the binding activity about 7.2 times higher than that of the parent compound. The metabolic pathway was mediated mainly by phase I enzymes localized on the microsomes and widely observed in chlorinated phenols, phenols, and hydroxylated aromatics. The pathway was also present in different phenolic xenobiotics and formed groups of unknown pollutants in organisms (e.g., TCS-O-bisphenol A and TCS-O-benzo(
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