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However, whether herbicides affect placental 3\u03b2-hydroxysteroid dehydrogenase\/\u03945-\u03944 isomerase (3\u03b2-HSD) remains unclear. This study investigated the inhibitory effects of 14 herbicides, especially dinitroanilines, on human (h3\u03b2-HSD1) and rat (r3\u03b2-HSD4), key enzymes in progesterone biosynthesis. In vitro assays showed isopropalin and oryzalin potently inhibited h3\u03b2-HSD1 (IC50 39.56 and 52.99 \u03bcM) via mixed-type inhibition. Inplacental JAr cells, oryzalin and profluraline suppressed progesterone synthesis at 100 \u03bcM, while isopropalin had no effect. Species-dependent inhibition was observed; oryzalin was most potent against r3\u03b2-HSD4 (IC50 33.52 \u03bcM), and cyanazine also inhibited the rat isoform. Molecular docking indicated their binding to the NAD+-binding pocket. SAR and pharmacophore modeling identified molecular volume and flexibility as key for h3\u03b2-HSD1 potency. Network toxicology linked herbicide exposure to recurrent pregnancy loss via steroidogenic genes. These findings provide mechanistic evidence that specific herbicides disrupt progesterone production and may contribute to adverse reproductive outcomes.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c06079","type":"journal-article","created":{"date-parts":[[2026,8,8]],"date-time":"2026-08-08T16:02:18Z","timestamp":1786204938000},"page":"25059-25074","source":"Crossref","is-referenced-by-count":0,"title":["Herbicides as Isoform-Selective\nInhibitors of Human\n3\u03b2-HSD1 and Rat 3\u03b2-HSD4: Structure\u2013Activity Relationships\nand Implications for Progesterone Biosynthesis and Recurrent Pregnancy\nLoss"],"prefix":"10.1021","volume":"74","author":[{"given":"Huiyi","family":"Che","sequence":"first","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]},{"name":"Wenzhou Medical University , , ,","place":["Wenzhou, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiya","family":"Ren","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]},{"name":"Wenzhou Medical University , , ,","place":["Wenzhou, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaowei","family":"Wang","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]},{"name":"Wenzhou Medical University , , ,","place":["Wenzhou, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lingfei","family":"Wang","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]},{"name":"Wenzhou Medical University , , ,","place":["Wenzhou, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chaochao","family":"Gong","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]},{"name":"Wenzhou Medical University , , ,","place":["Wenzhou, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yu","family":"Shu","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yunbing","family":"Tang","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pu","family":"Zhang","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ren-Shan","family":"Ge","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]},{"name":"Wenzhou Medical University , , ,","place":["Wenzhou, China, 325027"]},{"name":"Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yingfen","family":"Ying","sequence":"additional","affiliation":[{"name":"The Second Affiliated Hospital and Yuying Children\u2019s Hospital of Wenzhou Medical University , , , ,","place":["Wenzhou, Zhejiang, China, 325027"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,8]]},"reference":[{"key":"2026081910192712400_cit1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ecoenv.2025.119174","article-title":"Inhibition\nof human\nand rat 11\u03b2-hydroxysteroid dehydrogenase 2 by parabens: Mechanistic\ninsights into cortisol metabolism disruption and structure-activity\nrelationship and in silico docking","volume":"305","author":"Chen","year":"2025","journal-title":"Ecotoxicol.\nEnviron. Saf."},{"issue":"46","key":"2026081910192712400_cit2","doi-asserted-by":"publisher","first-page":"8710","DOI":"10.1021\/acs.jafc.6b01437","article-title":"Effect of Soil Fumigation\non Degradation\nof Pendimethalin and Oxyfluorfen in Laboratory and Ginger Field Studies","volume":"64","author":"Huang","year":"2016","journal-title":"J. Agric. Food Chem."},{"issue":"23","key":"2026081910192712400_cit3","doi-asserted-by":"publisher","first-page":"6912","DOI":"10.1021\/jf0488965","article-title":"Simultaneous\nresidue measurement\nof pendimethalin, isopropalin, and butralin in tobacco using high-performance\nliquid chromatography with ultraviolet detection and electrospray\nionization\/mass spectrometric identification","volume":"52","author":"Liu","year":"2004","journal-title":"J. Agric. Food Chem."},{"issue":"7","key":"2026081910192712400_cit4","doi-asserted-by":"publisher","first-page":"2640","DOI":"10.1021\/jf0523317","article-title":"Degradation\nof chloroacetanilide\nherbicides by anodic fenton treatment","volume":"54","author":"Friedman","year":"2006","journal-title":"J. Agric.\nFood Chem."},{"issue":"7","key":"2026081910192712400_cit5","doi-asserted-by":"publisher","first-page":"3445","DOI":"10.1021\/acs.jafc.3c09519","article-title":"Mechanisms\nUnderlying Allelopathic Disturbance of Herbicide Imazethapyr on Wheat\nand Its Neighboring Ryegrass (Lolium perenne)","volume":"72","author":"Zhang","year":"2024","journal-title":"J. Agric. Food Chem."},{"issue":"29","key":"2026081910192712400_cit6","doi-asserted-by":"publisher","first-page":"16368","DOI":"10.1021\/acs.jafc.4c00717","article-title":"Nanobody Mediated\nAtrazine Resistance in Plants","volume":"72","author":"Chen","year":"2024","journal-title":"J. Agric. 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Food Chem."},{"issue":"9","key":"2026081910192712400_cit11","doi-asserted-by":"publisher","first-page":"1065","DOI":"10.1016\/s0090-9556(24)14897-0","article-title":"Sex-dependent differences\nin the disposition of 2,4-dichlorophenoxyacetic acid in Sprague-Dawley\nrats, B6C3F1 mice, and Syrian hamsters","volume":"25","author":"Griffin","year":"1997","journal-title":"Drug\nMetab. Dispos."},{"key":"2026081910192712400_cit12","doi-asserted-by":"publisher","DOI":"10.1016\/j.envpol.2025.126113","article-title":"Dinitroaniline herbicide exposure, mitochondrial DNA copy number,\nand 10-year risk of atherosclerotic cardiovascular disease: A community-based\ncohort study","volume":"373","author":"Zhang","year":"2025","journal-title":"Environ. Pollut."},{"issue":"1","key":"2026081910192712400_cit13","doi-asserted-by":"publisher","first-page":"163","DOI":"10.1080\/1547691X.2020.1804492","article-title":"The impact\nand toxicity of glyphosate and glyphosate-based\nherbicides on health and immunity","volume":"17","author":"Peillex","year":"2020","journal-title":"J. Immunotoxicol."},{"issue":"11","key":"2026081910192712400_cit14","doi-asserted-by":"publisher","DOI":"10.3390\/cells10113079","article-title":"Review: Mechanisms\nof Glyphosate and Glyphosate-Based Herbicides Action in Female and\nMale Fertility in Humans and Animal Models","volume":"10","author":"Serra","year":"2021","journal-title":"Cells"},{"key":"2026081910192712400_cit15","doi-asserted-by":"publisher","DOI":"10.1016\/j.mce.2019.110680","article-title":"Mechanisms\nof action of agrochemicals acting as endocrine disrupting chemicals","volume":"502","author":"Warner","year":"2020","journal-title":"Mol. Cell. Endocrinol."},{"issue":"4","key":"2026081910192712400_cit16","doi-asserted-by":"publisher","first-page":"525","DOI":"10.1210\/er.2002-0050","article-title":"Molecular biology of the 3beta-hydroxysteroid\ndehydrogenase\/delta5-delta4\nisomerase gene family","volume":"26","author":"Simard","year":"2005","journal-title":"Endocrine Rev."},{"key":"2026081910192712400_cit17","doi-asserted-by":"publisher","DOI":"10.1016\/j.tox.2019.152253","article-title":"Human placental 3beta-hydroxysteroid dehydrogenase\/steroid\nDelta5,4-isomerase 1: Identity, regulation and environmental inhibitors","volume":"425","author":"Zhu","year":"2019","journal-title":"Toxicology"},{"key":"2026081910192712400_cit18","doi-asserted-by":"publisher","first-page":"90","DOI":"10.1016\/j.cbi.2019.02.027","article-title":"Endocrine disruptors of inhibiting\ntesticular 3beta-hydroxysteroid\ndehydrogenase","volume":"303","author":"Zhang","year":"2019","journal-title":"Chem.-Biol. Interact."},{"key":"2026081910192712400_cit19","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2024.111203","article-title":"Food additive salicylates\ninhibit human and rat placental 3beta-hydroxysteroid dehydrogenase:\n3D-QSAR and in silico analysis","volume":"402","author":"Yang","year":"2024","journal-title":"Chem.-Biol.\nInteract."},{"issue":"22","key":"2026081910192712400_cit20","doi-asserted-by":"publisher","first-page":"21321","DOI":"10.1074\/jbc.M501269200","article-title":"Identification\nof key amino acids responsible for the substantially higher affinities\nof human type 1 3beta-hydroxysteroid dehydrogenase\/isomerase (3beta-HSD1)\nfor substrates, coenzymes, and inhibitors relative to human 3beta-HSD2","volume":"280","author":"Thomas","year":"2005","journal-title":"J. Biol. Chem."},{"issue":"1","key":"2026081910192712400_cit21","doi-asserted-by":"publisher","first-page":"253","DOI":"10.1677\/jme.0.0330253","article-title":"Serine 124 completes\nthe Tyr, Lys and Ser triad responsible\nfor the catalysis of human type 1 3beta-hydroxysteroid dehydrogenase","volume":"33","author":"Thomas","year":"2004","journal-title":"J. Mol. Endocrinol."},{"issue":"13","key":"2026081910192712400_cit22","doi-asserted-by":"publisher","DOI":"10.3390\/ijerph18136840","article-title":"Effects of Endocrine-Disrupting\nChemicals\non Endometrial Receptivity and Embryo Implantation: A Systematic Review\nof 34 Mouse Model Studies","volume":"18","author":"Caserta","year":"2021","journal-title":"Int. J. Environ.\nRes. 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Ethnopharmacol."},{"key":"2026081910192712400_cit25","doi-asserted-by":"publisher","first-page":"151","DOI":"10.1016\/j.reprotox.2016.04.004","article-title":"Structure-activity\nrelationships of phthalates in inhibition of human placental 3\u03b2-hydroxysteroid\ndehydrogenase 1 and aromatase","volume":"61","author":"Xu","year":"2016","journal-title":"Reprod. Toxicol."},{"key":"2026081910192712400_cit26","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsbmb.2024.106638","article-title":"Effects of\nparabens on human and rat placental 3\u03b2-hydroxysteroid dehydrogenase\nisoforms: Structure activity relationship and docking analysis","volume":"245","author":"Xiang","year":"2025","journal-title":"J. Steroid Biochem. Mol. Biol."},{"issue":"D1","key":"2026081910192712400_cit27","doi-asserted-by":"publisher","first-page":"D439","DOI":"10.1093\/nar\/gkab1061","article-title":"AlphaFold protein structure database:\nmassively expanding the structural coverage of protein-sequence space\nwith high-accuracy models","volume":"50","author":"Varadi","year":"2022","journal-title":"Nucleic Acids Res."},{"issue":"19","key":"2026081910192712400_cit28","doi-asserted-by":"publisher","DOI":"10.3390\/molecules27196338","article-title":"Homology Modeling,\nMolecular Docking, Molecular Dynamic Simulation, and Drug-Likeness\nof the Modified Alpha-Mangostin against the \u03b2-Tubulin Protein\nof Acanthamoeba Keratitis","volume":"27","author":"Ongtanasup","year":"2022","journal-title":"Molecules"},{"issue":"1","key":"2026081910192712400_cit29","doi-asserted-by":"publisher","first-page":"177","DOI":"10.1021\/ci049714+","article-title":"ZINC--a free database of commercially available compounds\nfor virtual screening","volume":"45","author":"Irwin","year":"2005","journal-title":"J. Chem. Inf. Model."},{"issue":"6","key":"2026081910192712400_cit30","doi-asserted-by":"publisher","first-page":"2265","DOI":"10.3390\/ijerph8062265","article-title":"Effect of endocrine\ndisruptor pesticides: a review","volume":"8","author":"Mnif","year":"2011","journal-title":"Int. J. Environ.\nRes. Public Health"},{"key":"2026081910192712400_cit31","doi-asserted-by":"publisher","DOI":"10.1016\/j.tox.2022.153281","article-title":"Comparative\ncytotoxicity of seven per- and polyfluoroalkyl substances (PFAS) in\nsix human cell lines","volume":"477","author":"Solan","year":"2022","journal-title":"Toxicology"},{"issue":"6","key":"2026081910192712400_cit32","doi-asserted-by":"publisher","first-page":"1117","DOI":"10.2174\/157340612804075142","article-title":"3D QSAR pharmacophore modeling for\nc-Met kinase inhibitors","volume":"8","author":"Huang","year":"2012","journal-title":"Med. Chem."},{"issue":"1","key":"2026081910192712400_cit33","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-025-13201-1","article-title":"Mechanism exploration\nof di(2-ethylhexyl) phthalate (DEHP)-induced\nbreast cancer via network toxicology and molecular docking analysis","volume":"15","author":"Wang","year":"2025","journal-title":"Sci. Rep."},{"key":"2026081910192712400_cit34","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2024.111251","article-title":"Inhibition of human\nand rat placental 3beta-hydroxysteroid dehydrogenases by bisphenol\nA analogues depends on their hydrophobicity: In silico docking analysis","volume":"403","author":"Wang","year":"2024","journal-title":"Chem.-Biol. Interact."},{"key":"2026081910192712400_cit35","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2022.110292","article-title":"Inhibition of human and rat placental 3beta-hydroxysteroid dehydrogenase\/Delta(5,4)-isomerase\nactivities by insecticides and fungicides: Mode action by docking\nanalysis","volume":"369","author":"Li","year":"2023","journal-title":"Chem.-Biol. Interact."},{"issue":"6","key":"2026081910192712400_cit36","doi-asserted-by":"publisher","first-page":"947","DOI":"10.1210\/er.2003-0030","article-title":"Overview of steroidogenic\nenzymes in the pathway from\ncholesterol to active steroid hormones","volume":"25","author":"Payne","year":"2004","journal-title":"Endocr.\nRev."},{"key":"2026081910192712400_cit37","doi-asserted-by":"publisher","first-page":"331","DOI":"10.2147\/IJWH.S100817","article-title":"Recurrent pregnancy\nloss: current perspectives","volume":"9","author":"El Hachem","year":"2017","journal-title":"Int. J. Womens Health"},{"issue":"1","key":"2026081910192712400_cit38","doi-asserted-by":"publisher","DOI":"10.1038\/s41572-020-00228-z","article-title":"Recurrent\npregnancy loss","volume":"6","author":"Dimitriadis","year":"2020","journal-title":"Nat. Rev. Dis Prim."},{"issue":"4","key":"2026081910192712400_cit39","doi-asserted-by":"publisher","first-page":"293","DOI":"10.1210\/er.2009-0002","article-title":"Endocrine-disrupting\nchemicals: an Endocrine Society scientific statement","volume":"30","author":"Diamanti-Kandarakis","year":"2009","journal-title":"Endocr. Rev."},{"issue":"6","key":"2026081910192712400_cit40","doi-asserted-by":"publisher","first-page":"E1","DOI":"10.1210\/er.2015-1010","article-title":"EDC-2: The Endocrine\nSociety\u2019s Second Scientific Statement on Endocrine-Disrupting\nChemicals","volume":"36","author":"Gore","year":"2015","journal-title":"Endocr. Rev."},{"issue":"1","key":"2026081910192712400_cit41","doi-asserted-by":"publisher","first-page":"241","DOI":"10.1016\/j.etap.2015.06.009","article-title":"A review on\nendocrine disruptors\nand their possible impacts on human health","volume":"40","author":"Kabir","year":"2015","journal-title":"Environ. Toxicol. Pharmacol."},{"issue":"11","key":"2026081910192712400_cit42","doi-asserted-by":"publisher","first-page":"935","DOI":"10.1038\/nrd1549","article-title":"Docking and scoring\nin virtual screening for drug discovery: methods and applications","volume":"3","author":"Kitchen","year":"2004","journal-title":"Nat. Rev. Drug Discovery"},{"key":"2026081910192712400_cit43","doi-asserted-by":"publisher","DOI":"10.1016\/j.jep.2026.121480","article-title":"Inhibitory effects and molecular\nmechanisms of Aristolochic acids on human and rat placental 3\u03b2-hydroxysteroid\ndehydrogenases","volume":"364","author":"Yang","year":"2026","journal-title":"J. Ethnopharmacol."},{"issue":"3","key":"2026081910192712400_cit44","doi-asserted-by":"publisher","first-page":"378","DOI":"10.1210\/er.2011-1050","article-title":"Hormones\nand endocrine-disrupting chemicals: low-dose effects and nonmonotonic\ndose responses","volume":"33","author":"Vandenberg","year":"2012","journal-title":"Endocr. Rev."},{"key":"2026081910192712400_cit45","doi-asserted-by":"publisher","DOI":"10.1016\/j.yrtph.2020.104736","article-title":"Weight of Evidence\nand Human Relevance Evaluation of the Benfluralin\nMode of Action in Rats (Part II): Thyroid carcinogenesis","volume":"117","author":"Strupp","year":"2020","journal-title":"Regul. Toxicol. Pharmacol."},{"key":"2026081910192712400_cit46","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2022.110243","article-title":"Chemicals\nof environmental concern as inhibitors of human placental\n3beta-hydroxysteroid dehydrogenase 1 and aromatase: Screening and\ndocking analysis","volume":"368","author":"Tang","year":"2022","journal-title":"Chem.-Biol. Interact."},{"key":"2026081910192712400_cit47","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsbmb.2024.106638","article-title":"Effects of\nparabens on human and rat placental 3beta-hydroxysteroid dehydrogenase\nisoforms: Structure activity relationship and docking analysis","volume":"245","author":"Xiang","year":"2025","journal-title":"J. Steroid Biochem. Mol. Biol."},{"key":"2026081910192712400_cit48","doi-asserted-by":"publisher","first-page":"40","DOI":"10.1016\/j.toxlet.2024.03.007","article-title":"The metabolic activation\nof pentachlorophenol to chloranil as a potent\ninhibitor of human and rat placental 3beta-hydroxysteroid dehydrogenases","volume":"395","author":"Zhang","year":"2024","journal-title":"Toxicol. Lett."},{"issue":"2","key":"2026081910192712400_cit49","doi-asserted-by":"publisher","first-page":"115","DOI":"10.1016\/j.marenvres.2006.07.003","article-title":"Surflan\nand oryzalin\nimpair reproduction in the teleost medaka (Oryzias latipes)","volume":"63","author":"Hall","year":"2007","journal-title":"Mar. Environ. 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