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Carbon Chain Length Determines Inhibitory Potency of Perfluoroalkyl Sulfonic Acids on Human Placental 3β-hydroxysteroid dehydrogenase 1:Screening,Structure-Activity Relationship,and In Silico Analysis

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Biomedical and Environmental Sciences 2023年第11期36卷 1015-1027页

作者： TANG Lu Ming MAO Bai Ping ZHANG Bing Ru LI Jing Jing TANG Yun Bing LI Hui Tao GE Ren Shan Department of Emergency Medicine The Second Affiliated Hospital and Yuying Children Hospital of Wenzhou Medical UniversityWenzhou 325000ZhejiangChina Department of Anesthesiology The Second Affiliated Hospital and Yuying Children Hospital of Wenzhou Medical UniversityWenzhou 325000ZhejiangChina Department of Obstetrics and Gynecology The Second Affiliated Hospital and Yuying Children Hospital of Wenzhou Medical UniversityWenzhou 325000ZhejiangChina Key Laboratory of Structural Malformations in Children of Zhejiang Province Wenzhou 325000ZhejiangChina

Objective This study aimed to compare 9 perfluoroalkyl sulfonic acids(PFSA)with carbon chain lengths(C4–C12)to inhibit human placental 3β-hydroxysteroid dehydrogenase 1(3β-HSD1),aromatase,and rat 3β-HSD4 *** Human and rat placental 3β-HSDs activities were determined by converting pregnenolone to progesterone and progesterone secretion in JEG-3 cells was determined using HPLC/MS–MS,and human aromatase activity was determined by *** PFSA inhibited human 3β-HSD1 structure-dependently in the order:perfluorooctanesulfonic acid(PFOS,half-maximum inhibitory concentration,IC50:9.03±4.83μmol/L)>perfluorodecanesulfonic acid(PFDS,42.52±8.99μmol/L)>perfluoroheptanesulfonic acid(PFHpS,112.6±29.39μmol/L)>perfluorobutanesulfonic acid(PFBS)=perfluoropentanesulfonic acid(PFPS)=perfluorohexanesulfonic acid(PFHxS)=perfluorododecanesulfonic acid(PFDoS)(ineffective at 100μmol/L).6:2FTS(1H,1H,2H,2H-perfluorooctanesulfonic acid)and 8:2FTS(1H,1H,2H,2H-perfluorodecanesulfonic acid)did not inhibit human 3β-*** and PFHpS are mixed inhibitors,whereas PFDS is a competitive ***,1–10μmol/L PFOS and PFDS significantly reduced progesterone biosynthesis in JEG-3 *** analysis revealed that PFSA binds to the steroid-binding site of human 3β-HSD1 in a carbon chain length-dependent *** 100μmol/L PFSA solutions did not affect rat 3β-HSD4 and human placental aromatase *** Carbon chain length determines inhibitory potency of PFSA on human placental 3β-HSD1 in a V-shaped transition at PFOS(C8),with inhibitory potency of PFOS>PFDS>PFHpS>PFBS=PFPS=PFHxS=PFDoS=6:2FTS=8:2FTS.

关键词： 3β-hydroxysteroid dehydrogenase 1 Docking analysis Perfluorooctanesulfonic acid Progesterone Structure-activityrelationship

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