{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,23]],"date-time":"2026-07-23T17:50:41Z","timestamp":1784829041791,"version":"3.55.0"},"reference-count":28,"publisher":"MDPI AG","issue":"21","license":[{"start":{"date-parts":[[2023,10,31]],"date-time":"2023-10-31T00:00:00Z","timestamp":1698710400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"Program for the Natural Science Foundation of China","doi-asserted-by":"publisher","award":["51909090"],"award-info":[{"award-number":["51909090"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"Program for the Natural Science Foundation of 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Science","award":["20B400"],"award-info":[{"award-number":["20B400"]}]},{"name":"Research Foundation of Hunan university of Arts and Science","award":["KFJJ2205"],"award-info":[{"award-number":["KFJJ2205"]}]},{"name":"Research Foundation of Hunan university of Arts and Science","award":["JGYB2220"],"award-info":[{"award-number":["JGYB2220"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Polybrominated diphenyl ethers (PBDEs) are widely used brominated flame retardants. PBDEs and their derivatives, hydroxylated PBDEs (OH-PBDEs), can bind to hormone receptors and impact hormone secretion, transportation, and metabolism, leading to endocrine disruption and the development of various diseases. They have particularly strong interference effects on thyroid hormones. This study used decabromodiphenyl ether (BDE-209); 2,2\u2032,4,4\u2032-tetrabromodiphenyl ether (BDE-47); and 6-OH-BDE-47 as representative compounds of PBDEs and their derivatives, OH-PBDEs. A fluorescence probe, fluorescein-isothiocyanate-L-thyroxine (FITC-T4, F-T4), specific for binding to transthyretin (TTR), a thyroid transport protein, was prepared. The binding capacity of PBDEs and their derivatives, OH-PBDEs, to TTR was quantitatively measured using fluorescence spectroscopy. The principle of quenching the fluorescence intensity of F-T4 after binding to TTR was used to analyze the competitive interaction between the probe and BDE-209, BDE-47, and 6-OH-BDE-47, thereby evaluating the toxic effects of PBDEs and their derivatives on the thyroid system. Additionally, AutoDock molecular docking software (1.5.6) was used to further analyze the interference mechanism of OH-PBDEs on T4. The results of the study are as follows: (1) Different types of PBDEs and OH-PBDEs exhibit varying degrees of interference with T4. Both the degree of bromination and hydroxylation affect their ability to competitively bind to TTR. Higher bromination and hydroxylation degrees result in stronger competitive substitution. (2) The competitive substitution ability of the same disruptor varies at different concentrations. Higher concentrations lead to stronger substitution ability, but there is a threshold beyond which the substitution ability no longer increases. (3) When OH-PBDEs have four or more bromine atoms and exhibit the most structural similarity to T4, their binding affinity to TTR is stronger than that of T4.<\/jats:p>","DOI":"10.3390\/molecules28217374","type":"journal-article","created":{"date-parts":[[2023,10,31]],"date-time":"2023-10-31T12:53:32Z","timestamp":1698756812000},"page":"7374","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Study on the Biomolecular Competitive Mechanism of Polybrominated Diphenyl Ethers and Their Derivatives on Thyroid Hormones"],"prefix":"10.3390","volume":"28","author":[{"given":"Shaoheng","family":"Liu","sequence":"first","affiliation":[{"name":"Engineering Research Center of Hunan Province for Recycling Technology of Electroplating Wastewater, Hunan Provincial Key Laboratory of Water Treatment Functional Materials, College of Chemistry and Material Engineering, Hunan University of Arts and Science, Changde 415000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rong","family":"Hu","sequence":"additional","affiliation":[{"name":"College of Environment, South China Normal University, Guangzhou 510006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hao","family":"Zhan","sequence":"additional","affiliation":[{"name":"College of Environmental Science and Engineering, Guilin University of Technology, Guilin 541006, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wanli","family":"You","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Hunan Province for Recycling Technology of Electroplating Wastewater, Hunan Provincial Key Laboratory of Water Treatment Functional Materials, College of Chemistry and Material Engineering, Hunan University of Arts and Science, Changde 415000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jianjun","family":"Tao","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Hunan Province for Recycling Technology of Electroplating Wastewater, Hunan Provincial Key Laboratory of Water Treatment Functional Materials, College of Chemistry and Material Engineering, Hunan University of Arts and Science, Changde 415000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luhua","family":"Jiang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Biometallurgy of Ministry of Education, College of Minerals Processing and Bioengineering, Central South University, Changsha 410083, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,10,31]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"164714","DOI":"10.1016\/j.scitotenv.2023.164714","article-title":"Toxicity and risk priority ranking of polybrominated diphenyl ethers (PBDEs): A relative receptor-bound concentration approach","volume":"892","author":"Liu","year":"2023","journal-title":"Sci. Total Environ."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6330","DOI":"10.1021\/acs.est.8b07032","article-title":"Global historical stocks and emissions of PBDEs","volume":"53","author":"Li","year":"2019","journal-title":"Environ. Sci. Technol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/j.fct.2018.10.025","article-title":"Maternal BDE-209 exposure during lactation perturbs steroidogenesis, germ cell kinetics and THR alpha 1 expression in testes of prepubertal mice offspring","volume":"122","author":"Sarkar","year":"2018","journal-title":"Food Chem. Toxicol."},{"key":"ref_4","first-page":"270","article-title":"Research status of photodegradation of polybromin-ated diphenyl ethers (PBDES)","volume":"34","author":"Liu","year":"2015","journal-title":"Environ. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"123674","DOI":"10.1016\/j.jhazmat.2020.123674","article-title":"Current progress in degradation and removal methods of polybrominated diphenyl ethers from water and soil: A review","volume":"403","author":"Yao","year":"2021","journal-title":"J. Hazard. Mater."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1007\/s00204-015-1457-1","article-title":"Human exposure to PBDE and critical evaluation of health hazards","volume":"89","author":"Linares","year":"2015","journal-title":"Arch. Toxicol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"114287","DOI":"10.1016\/j.ecoenv.2022.114287","article-title":"PBDEs disrupt homeostasis maintenance and regeneration of planarians due to DNA damage, proliferation and apoptosis anomaly","volume":"248","author":"Yang","year":"2022","journal-title":"Ecotoxicol. Environ. Safe"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"950","DOI":"10.1039\/C9EM00095J","article-title":"Binding and activity of polybrominated diphenyl ether sulfates to thyroid hormone transport proteins and nuclear receptors","volume":"21","author":"Qin","year":"2019","journal-title":"Environ. Sci.-Proc. Impacts"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"106311","DOI":"10.1016\/j.aquatox.2022.106311","article-title":"Kinetics and toxicity of an environmentally relevant mixture of halogenated organic compounds in zebrafish embryo","volume":"252","author":"Lindqvist","year":"2022","journal-title":"Aquat. Toxicol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"126554","DOI":"10.1016\/j.chemosphere.2020.126554","article-title":"Theoretical investigation of AhR binding property with relevant structural requirements for AhR-mediated toxicity of polybrominated diphenyl ethers","volume":"249","author":"Gu","year":"2020","journal-title":"Chemosphere"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1016\/j.cbpb.2011.12.005","article-title":"Kinetics and thiol requirements of iodothyronine 5\u2032-deiodination are tissue-specific in common carp (Cyprinus carpi L.)","volume":"161","author":"Klaren","year":"2012","journal-title":"Comp. Biochem. Phys. B"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1079","DOI":"10.1289\/ehp.1408996","article-title":"Maternal polybrominated diphenyl ether (PBDE) exposure and thyroid hormones in maternal and cord sera: The home study, Cincinnati, USA","volume":"123","author":"Vuong","year":"2015","journal-title":"Environ. Health Perspect."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1016\/j.envint.2018.02.044","article-title":"Association between persistent endocrine-disrupting chemicals (PBDEs, OH-PBDEs, PCBs, and PFASs) and biomarkers of inflammation and cellular aging during pregnancy and postpartum","volume":"115","author":"Zota","year":"2018","journal-title":"Environ. Int."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"159269","DOI":"10.1016\/j.scitotenv.2022.159269","article-title":"Metabolite alterations in zebrafish embryos exposed to hydroxylated polybrominated diphenyl ethers","volume":"857","author":"Gustafsson","year":"2023","journal-title":"Sci. Total Environ."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"28263","DOI":"10.1039\/C7CP03471G","article-title":"Quantum chemical and molecular dynamics modelling of hydroxylated polybrominated diphenyl ethers","volume":"19","author":"Ermilova","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1016\/j.ecoenv.2018.03.064","article-title":"Development of chicken and fish muscle protein-Water partition coefficients predictive models for ionogenic and neutral organic chemicals","volume":"157","author":"Ou","year":"2018","journal-title":"Ecotoxicol. Environ. Safe"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"602","DOI":"10.1289\/ehp.0901457","article-title":"Hormone activity of hydroxylated polybrominated diphenyl ethers on human thyroid receptor-beta: In vitro and in silico investigations","volume":"118","author":"Li","year":"2010","journal-title":"Environ. Health Perspect."},{"key":"ref_18","unstructured":"Ren, X.M. (2013). Molecular Toxicology of Hydroxylated Polybrominated Diphenyl Ethers and Perfluoroalkyl Acid on the Thyroid Hormone System, University of Chinese Academy of Sciences."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4633","DOI":"10.1021\/es2046074","article-title":"Assessment of the binding of hydroxylated polybrominated diphenyl ethers to thyroid hormone transport proteins using a site-specific fluorescence probe","volume":"46","author":"Ren","year":"2012","journal-title":"Environ. Sci. Technol."},{"key":"ref_20","unstructured":"He, X. (2015). Study on Interaction Properties of Polybrominated Diphenyl Ethers and Their Derivatives with Biomolecules, Fuzhou University."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4684","DOI":"10.1021\/acsabm.1c00320","article-title":"Surface plasmon-assisted fluorescence enhancing and quenching: From theory to application","volume":"4","author":"Su","year":"2021","journal-title":"ACS Appl. Bio Mater."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1016\/j.envpol.2014.10.029","article-title":"Quantifying the dynamic fluorescence quenching of phenanthrene and ofloxacin by dissolved humic acids","volume":"196","author":"Wang","year":"2015","journal-title":"Environ. Pollut."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"025002","DOI":"10.1088\/2050-6120\/ab71c3","article-title":"Dynamic and static quenching of 2-aminopurine fluorescence by the natural DNA nucleotides in solution","volume":"8","author":"Paterson","year":"2020","journal-title":"Methods Appl. Fluoresc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1002\/bio.3770","article-title":"Interaction of carbon nanotubes with curcumin: Effect of temperature and pH on simultaneous static and dynamic fluorescence quenching of curcumin using carbon nanotubes","volume":"35","author":"Youssef","year":"2020","journal-title":"Luminescence"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"554","DOI":"10.1016\/j.etap.2014.08.008","article-title":"Effects of BDE-209 and its mixtures with BDE-47 and BDE-99 on multiple biomarkers in Carassius auratus","volume":"38","author":"Xie","year":"2014","journal-title":"Environ. Toxicol. Pharmacol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"736","DOI":"10.1039\/C6MB00638H","article-title":"Understanding the microscopic binding mechanism of hydroxylated and sulfated polybrominated diphenyl ethers with transthyretin by molecular docking, molecular dynamics simulations and binding free energy calculations","volume":"13","author":"Cao","year":"2017","journal-title":"Mol. Biosyst."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1723","DOI":"10.1007\/s11356-014-3364-z","article-title":"Structure-dependent activities of polybrominated diphenyl ethers and hydroxylated metabolites on zebrafish retinoic acid receptor","volume":"22","author":"Zhao","year":"2015","journal-title":"Environ. Sci. Pollut. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"8894","DOI":"10.1021\/acs.est.8b02509","article-title":"Structure-dependent activity of polybrominated diphenyl ethers and their hydroxylated metabolites on estrogen related receptor gamma: In vitro and in silico study","volume":"52","author":"Cao","year":"2018","journal-title":"Environ. Sci. Technol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/21\/7374\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:15:12Z","timestamp":1760130912000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/21\/7374"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,10,31]]},"references-count":28,"journal-issue":{"issue":"21","published-online":{"date-parts":[[2023,11]]}},"alternative-id":["molecules28217374"],"URL":"https:\/\/doi.org\/10.3390\/molecules28217374","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,10,31]]}}}