{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,11]],"date-time":"2026-08-11T16:25:31Z","timestamp":1786465531294,"version":"build-2736575974"},"reference-count":74,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T00:00:00Z","timestamp":1785369600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T00:00:00Z","timestamp":1785369600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T00:00:00Z","timestamp":1785369600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100015397","name":"Department of Science and Technology of Inner Mongolia Autonomous Region","doi-asserted-by":"publisher","award":["2024ZY0007"],"award-info":[{"award-number":["2024ZY0007"]}],"id":[{"id":"10.13039\/501100015397","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100015397","name":"Department of Science and Technology of Inner Mongolia Autonomous Region","doi-asserted-by":"publisher","award":["2025KYPT0121"],"award-info":[{"award-number":["2025KYPT0121"]}],"id":[{"id":"10.13039\/501100015397","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China (NSFC)","doi-asserted-by":"crossref","award":["42167033"],"award-info":[{"award-number":["42167033"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Butylated hydroxytoluene (BHT) is a widely used synthetic phenolic antioxidant, ubiquitously detected in aquatic environments. While traditionally considered safe based on in vitro data, BHT adversely affects aquatic organisms at environmentally relevant concentrations. Here, we demonstrate that BHT-induced cardiotoxicity is primarily mediated by its metabolites through disruption of \u03b22-adrenergic receptor (\u03b22AR) signaling. In zebrafish larvae exposed to 0.01\u20131 \u03bcM BHT for 6 days, metabolites BHT-CHO, BHT-COOH, and BHT-Q accumulated prominently, inducing cardiac morphological and histological alterations. Transcriptomic analysis highlighted pronounced neuro-cardiovascular network disruption, with significant suppression of adrenergic signaling in cardiomyocytes at 1 \u03bcM. Molecular docking and biolayer interferometry identified \u03b22AR as a critical target for BHT metabolites, and functional rescue with a \u03b2-adrenoceptor agonist confirmed pathway dependency. However, paradoxical activation of \u03b22AR-cAMP\/PKA with concomitant suppression of downstream PKA-mediated phosphorylation resulting from competitive BHT-Q binding to the PKA catalytic subunit, indicates a functional uncoupling effect. This disrupts intracellular Ca2+ homeostasis in cardiomyocytes and drives cardiomyocyte dysfunction. Our findings reveal an unconventional toxicological paradigm, wherein environmental pollutants exploit kinase ATP pockets to corrupt signaling fidelity rather than simply inhibit or activate receptors, highlighting the necessity of metabolic activation assessment in environmental risk evaluation.<\/jats:p>","DOI":"10.1021\/acs.est.6c04202","type":"journal-article","created":{"date-parts":[[2026,8,4]],"date-time":"2026-08-04T13:21:26Z","timestamp":1785849686000},"page":"21557-21568","source":"Crossref","is-referenced-by-count":0,"title":["BHT\nand Its Metabolites\nDisrupt \u03b22-Adrenergic Signaling: A Biotransformation-Dependent\nCardiotoxicity\nMechanism in Zebrafish"],"prefix":"10.1021","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1889-3009","authenticated-orcid":true,"given":"Xuefang","family":"Liang","sequence":"first","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huina","family":"Gao","sequence":"additional","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiang","family":"Zhang","sequence":"additional","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiachen","family":"Liu","sequence":"additional","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiaoqiao","family":"Hao","sequence":"additional","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qingjian","family":"Meng","sequence":"additional","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2812-3649","authenticated-orcid":true,"given":"Alideertu","family":"Dong","sequence":"additional","affiliation":[{"name":"Inner Mongolia University , , ,","place":["Hohhot, China, 010021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christopher J.","family":"Martyniuk","sequence":"additional","affiliation":[{"name":"University of Florida , , , ,","place":["Gainesville, Florida, United States, 32611"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,7,30]]},"reference":[{"key":"2026081110090925400_cit1","doi-asserted-by":"publisher","first-page":"820","DOI":"10.1016\/j.jff.2015.06.018","article-title":"Phenolics and polyphenolics in foods, beverages and\nspices: Antioxidant activity and health effects \u2013 A review","volume":"18","author":"Shahidi","year":"2015","journal-title":"J. Funct. Foods"},{"key":"2026081110090925400_cit2","doi-asserted-by":"publisher","first-page":"295","DOI":"10.1016\/j.ejmech.2015.06.026","article-title":"Understanding\nthe chemistry\nbehind the antioxidant activities of butylated hydroxytoluene (BHT):\nA review","volume":"101","author":"Yehye","year":"2015","journal-title":"Eur. J. Med. Chem."},{"issue":"5","key":"2026081110090925400_cit3","doi-asserted-by":"publisher","first-page":"311","DOI":"10.1016\/0045-6535(79)90115-2","article-title":"Studies on\ndegradation of 2,6-di-tert-butyl-4-methylphenol\n(BHT) in the environment. Part-II Photodegradation of 14C-BHT in water","volume":"8","author":"Mikami","year":"1979","journal-title":"Chemosphere"},{"issue":"6","key":"2026081110090925400_cit4","doi-asserted-by":"publisher","first-page":"383","DOI":"10.1016\/0045-6535(79)90129-2","article-title":"Studies on biodegradation\nof 2,6-di-tert-butyl-4-methylphenol (BHT) in the environment part-III\nBiodegradability of BHT with activated sludge","volume":"8","author":"Inui","year":"1979","journal-title":"Chemosphere"},{"issue":"17","key":"2026081110090925400_cit5","doi-asserted-by":"publisher","first-page":"10124","DOI":"10.1021\/acs.est.8b03322","article-title":"Synthetic\nphenolic antioxidants and their metabolites\nin mollusks from the Chinese Bohai Sea: Occurrence, temporal trend,\nand human exposure","volume":"52","author":"Wang","year":"2018","journal-title":"Environ. Sci. Technol."},{"issue":"4","key":"2026081110090925400_cit6","doi-asserted-by":"publisher","first-page":"2073","DOI":"10.1021\/es505136k","article-title":"Occurrence of synthetic\nphenolic antioxidants and major metabolites in municipal sewage sludge\nin China","volume":"49","author":"Liu","year":"2015","journal-title":"Environ. Sci. Technol."},{"key":"2026081110090925400_cit7","doi-asserted-by":"publisher","first-page":"413","DOI":"10.1016\/j.watres.2017.11.028","article-title":"Inventory, loading\nand discharge of synthetic phenolic\nantioxidants and their metabolites in wastewater treatment plants","volume":"129","author":"Wang","year":"2018","journal-title":"Water Res."},{"key":"2026081110090925400_cit8","doi-asserted-by":"publisher","first-page":"111531","DOI":"10.1016\/j.envres.2021.111531","article-title":"Analysis,\noccurrence,\ntoxicity and environmental health risks of synthetic phenolic antioxidants:\nA review","volume":"201","author":"Wang","year":"2021","journal-title":"Environ. Res."},{"issue":"1","key":"2026081110090925400_cit9","doi-asserted-by":"publisher","first-page":"428","DOI":"10.1021\/acs.est.5b04826","article-title":"Synthetic phenolic antioxidants\nand their metabolites in indoor dust from homes and microenvironments","volume":"50","author":"Wang","year":"2016","journal-title":"Environ. Sci. Technol."},{"key":"2026081110090925400_cit10","doi-asserted-by":"publisher","first-page":"649","DOI":"10.1016\/j.jhazmat.2019.04.014","article-title":"Occurrence\nof plastic additives in\noutdoor air particulate matters from two industrial parks of Tarragona,\nSpain: Human inhalation intake risk assessment","volume":"373","author":"Maceira","year":"2019","journal-title":"J. Hazard. Mater."},{"issue":"8","key":"2026081110090925400_cit11","doi-asserted-by":"publisher","first-page":"443","DOI":"10.1021\/acs.estlett.9b00415","article-title":"Identification of unusual antioxidants\nin the natural and built environments","volume":"6","author":"Wu","year":"2019","journal-title":"Environ.\nSci. Technol. 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Total Environ."},{"issue":"8","key":"2026081110090925400_cit14","doi-asserted-by":"publisher","first-page":"3587","DOI":"10.1021\/acsestwater.4c00537","article-title":"Spatial and seasonal\ndistribution, source apportionment, and risk assessment of dissolved-phase\nultraviolet absorbents and synthetic phenolic and amino antioxidants\nin the Pearl River Delta (PRD), China","volume":"4","author":"Qin","year":"2024","journal-title":"ACS ES\nT Water"},{"key":"2026081110090925400_cit15","doi-asserted-by":"publisher","first-page":"104432","DOI":"10.1016\/j.microc.2019.104432","article-title":"UPLC-MS\/MS analysis\nof Sudan I, butylated-hydroxytoluene\nand its major metabolites from sampling sites along the Nile River-Egypt:\nEnvironmentally evaluated study","volume":"153","author":"Zamzam","year":"2020","journal-title":"Microchem.\nJ."},{"issue":"23","key":"2026081110090925400_cit16","doi-asserted-by":"publisher","first-page":"13690","DOI":"10.1021\/acs.est.8b04448","article-title":"Synthetic phenolic antioxidants and their metabolites\nin sediments from the coastal area of Northern China: Spatial and\nvertical distributions","volume":"52","author":"Wang","year":"2018","journal-title":"Environ. 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Toxicol."},{"issue":"23","key":"2026081110090925400_cit25","doi-asserted-by":"publisher","first-page":"11540","DOI":"10.1021\/jf8025524","article-title":"Hepatic retention and\ntoxicological responses during feeding and depuration periods in Atlantic\nsalmon (Salmo salar) fed graded levels of the synthetic\nantioxidant, butylated hydroxytoluene","volume":"56","author":"Holaas","year":"2008","journal-title":"J. Agric.\nFood Chem."},{"issue":"9","key":"2026081110090925400_cit26","doi-asserted-by":"publisher","first-page":"1027","DOI":"10.1016\/S0278-6915(99)00085-X","article-title":"Safety assessment of butylated hydroxyanisole\nand butylated hydroxytoluene as antioxidant food additives","volume":"37","author":"Williams","year":"1999","journal-title":"Food Chem. Toxicol."},{"key":"2026081110090925400_cit27","doi-asserted-by":"publisher","first-page":"108906","DOI":"10.1016\/j.fsi.2023.108906","article-title":"Synthetic phenolic antioxidants evoked hepatoxicity\nin grass carp (Ctenopharyngodon idella) through modulating\nthe ROS-PI3K\/mTOR\/AKT pathway: Apoptosis-autophagy crosstalk","volume":"139","author":"Li","year":"2023","journal-title":"Fish Shellfish Immunol."},{"key":"2026081110090925400_cit28","doi-asserted-by":"publisher","first-page":"120839","DOI":"10.1016\/j.envres.2025.120839","article-title":"Study on the detoxification and toxic effects\nof clam Ruditapes philippinarum exposed to 2,6-ditert-butyl-4-methylphenol\n(BHT): Oxidative stress, neurotoxicity, respiratory toxicity, and\nimmunotoxicity","volume":"268","author":"Li","year":"2025","journal-title":"Environ. Res."},{"key":"2026081110090925400_cit29","doi-asserted-by":"publisher","first-page":"138289","DOI":"10.1016\/j.jhazmat.2025.138289","article-title":"Ovarian toxicity of 2,6-di-tert-butyl-hydroxytoluene\non female Ruditapes philippinarum: Reproductive endocrine\ndisruption and oxidative stress","volume":"492","author":"Zheng","year":"2025","journal-title":"J. Hazard.\nMater."},{"key":"2026081110090925400_cit30","doi-asserted-by":"publisher","first-page":"154688","DOI":"10.1016\/j.scitotenv.2022.154688","article-title":"Neurotoxic effects of\nsynthetic phenolic antioxidants on dopaminergic, serotoninergic, and\nGABAergic signaling in larval zebrafish (Danio rerio)","volume":"830","author":"Shi","year":"2022","journal-title":"Sci. Total Environ."},{"key":"2026081110090925400_cit31","doi-asserted-by":"publisher","first-page":"113624","DOI":"10.1016\/j.envpol.2019.113624","article-title":"Butylated hydroxytoluene\ninduces hyperactivity and alters dopamine-related gene expression\nin larval zebrafish (Danio rerio)","volume":"257","author":"Liang","year":"2020","journal-title":"Environ. Pollut."},{"issue":"3","key":"2026081110090925400_cit32","doi-asserted-by":"publisher","first-page":"173","DOI":"10.1016\/0378-4274(80)90187-3","article-title":"The acute toxicity of butylated hydroxytoluene\nand its metabolites in mice","volume":"6","author":"Yamamoto","year":"1980","journal-title":"Toxicol. Lett."},{"issue":"1","key":"2026081110090925400_cit33","doi-asserted-by":"publisher","first-page":"7911","DOI":"10.1038\/s41598-025-91409-x","article-title":"Developmental\nand toxicological effects\nof butylated hydroxytoluene metabolites on zebrafish larvae","volume":"15","author":"Noh","year":"2025","journal-title":"Sci. Rep."},{"key":"2026081110090925400_cit34","doi-asserted-by":"publisher","first-page":"177518","DOI":"10.1016\/j.scitotenv.2024.177518","article-title":"Assessment of the relative cardiotoxicity and\nbehavioral effects of butylated hydroxytoluene and its metabolites\nin developing zebrafish (Danio rerio)","volume":"957","author":"Hao","year":"2024","journal-title":"Sci. Total Environ."},{"issue":"8","key":"2026081110090925400_cit35","doi-asserted-by":"publisher","first-page":"552","DOI":"10.1007\/BF01969268","article-title":"DNA cleavage by metabolites of butylated\nhydroxytoluene","volume":"67","author":"Nagai","year":"1993","journal-title":"Arch. Toxicol."},{"issue":"3","key":"2026081110090925400_cit36","doi-asserted-by":"publisher","first-page":"361","DOI":"10.1016\/S0006-2952(98)00037-9","article-title":"Oxidative DNA damage\nand apoptosis induced by metabolites of butylated hydroxytoluene","volume":"56","author":"Oikawa","year":"1998","journal-title":"Biochem. 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Technol."},{"key":"2026081110090925400_cit39","doi-asserted-by":"publisher","first-page":"559","DOI":"10.1016\/j.scitotenv.2018.06.213","article-title":"Developmental toxicity of synthetic phenolic\nantioxidants to the early life stage of zebrafish","volume":"643","author":"Yang","year":"2018","journal-title":"Sci. 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Pharmacol."},{"key":"2026081110090925400_cit44","doi-asserted-by":"publisher","first-page":"122199","DOI":"10.1016\/j.envpol.2023.122199","article-title":"MiR-133b as a crucial\nregulator of TCS-induced cardiotoxicity via activating \u03b2-adrenergic\nreceptor signaling pathway in zebrafish embryos","volume":"334","author":"Wan","year":"2023","journal-title":"Environ. Pollut."},{"issue":"1","key":"2026081110090925400_cit45","doi-asserted-by":"publisher","first-page":"57","DOI":"10.3390\/biom14010057","article-title":"Disruption of atrial\nrhythmicity by the air pollutant 1,2-Naphthoquinone: Role of beta-adrenergic\nand sensory receptors","volume":"14","author":"Soares","year":"2024","journal-title":"Biomolecules"},{"issue":"2","key":"2026081110090925400_cit46","doi-asserted-by":"publisher","first-page":"850","DOI":"10.1021\/acs.est.7b05057","article-title":"Synthetic phenolic antioxidants\ncause perturbation in steroidogenesis in vitro and in vivo","volume":"52","author":"Yang","year":"2018","journal-title":"Environ. Sci. 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