Comparison of structure-activity relationship for bisphenol analogs in the inhibition of gonadal 3β-hydroxysteroid dehydrogenases among human, rat, and mouse
Bisphenol A (BPA) is a widely used plastic material and its potential endocrine disrupting effect has restricted its use and increasing use of BPA alternatives has raised health concerns. However, the effect of bisphenol alternatives on steroidogenesis remains unclear. The objective of this study wa...
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| Veröffentlicht in: | The Journal of steroid biochemistry and molecular biology 2024-02, Vol.236, p.106424-106424, Article 106424 |
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| container_title | The Journal of steroid biochemistry and molecular biology |
| container_volume | 236 |
| creator | Chen, Ya Zhang, Huina Yu, Yang Wang, Shaowei Wang, Mengyun Pan, Chengshuang Fei, Qianjin Li, Huitao Wang, Yiyan Lv, Jieqiang Ge, Ren-Shan |
| description | Bisphenol A (BPA) is a widely used plastic material and its potential endocrine disrupting effect has restricted its use and increasing use of BPA alternatives has raised health concerns. However, the effect of bisphenol alternatives on steroidogenesis remains unclear. The objective of this study was to compare inhibitory potencies of 10 BPA alternatives in the inhibition of gonadal 3β-hydroxysteroid dehydrogenase (3β-HSD) in three species (human, rat and mouse). The inhibitory potency for human 3β-HSD2, rat 3β-HSD1, and mouse 3β-HSD6 ranged from bisphenol FL (IC
, 3.32 μM for human, 5.19 μM for rat, and 3.26 μM for mouse) to bisphenol E, F, and thiodiphenol (ineffective at 100 μM). Most BPA alternatives were mixed inhibitors of gonadal 3β-HSD and they dose-dependently inhibited progesterone formation in KGN cells. Molecular docking analysis showed that all BPA analogs bind to steroid and NAD
active sites. Lipophilicity of BPA alternatives was inversely correlated with IC
values. In conclusion, BPA alternatives mostly can inhibit gonadal 3β-HSDs and lipophilicity determines their inhibitory strength. |
| doi_str_mv | 10.1016/j.jsbmb.2023.106424 |
| format | Article |
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, 3.32 μM for human, 5.19 μM for rat, and 3.26 μM for mouse) to bisphenol E, F, and thiodiphenol (ineffective at 100 μM). Most BPA alternatives were mixed inhibitors of gonadal 3β-HSD and they dose-dependently inhibited progesterone formation in KGN cells. Molecular docking analysis showed that all BPA analogs bind to steroid and NAD
active sites. Lipophilicity of BPA alternatives was inversely correlated with IC
values. In conclusion, BPA alternatives mostly can inhibit gonadal 3β-HSDs and lipophilicity determines their inhibitory strength.</description><identifier>ISSN: 0960-0760</identifier><identifier>EISSN: 1879-1220</identifier><identifier>DOI: 10.1016/j.jsbmb.2023.106424</identifier><identifier>PMID: 37939739</identifier><language>eng</language><publisher>England</publisher><subject>17-Hydroxysteroid Dehydrogenases - metabolism ; 3-Hydroxysteroid Dehydrogenases - metabolism ; Animals ; Benzhydryl Compounds ; Humans ; Hydroxysteroid Dehydrogenases - metabolism ; Male ; Mice ; Molecular Docking Simulation ; Phenols ; Rats ; Structure-Activity Relationship ; Testis - metabolism</subject><ispartof>The Journal of steroid biochemistry and molecular biology, 2024-02, Vol.236, p.106424-106424, Article 106424</ispartof><rights>Copyright © 2023. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c170t-96b69f15f373fa56acd54519c64c2d750cc7f0ece9c1978549b8eaa5300ee71d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37939739$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Ya</creatorcontrib><creatorcontrib>Zhang, Huina</creatorcontrib><creatorcontrib>Yu, Yang</creatorcontrib><creatorcontrib>Wang, Shaowei</creatorcontrib><creatorcontrib>Wang, Mengyun</creatorcontrib><creatorcontrib>Pan, Chengshuang</creatorcontrib><creatorcontrib>Fei, Qianjin</creatorcontrib><creatorcontrib>Li, Huitao</creatorcontrib><creatorcontrib>Wang, Yiyan</creatorcontrib><creatorcontrib>Lv, Jieqiang</creatorcontrib><creatorcontrib>Ge, Ren-Shan</creatorcontrib><title>Comparison of structure-activity relationship for bisphenol analogs in the inhibition of gonadal 3β-hydroxysteroid dehydrogenases among human, rat, and mouse</title><title>The Journal of steroid biochemistry and molecular biology</title><addtitle>J Steroid Biochem Mol Biol</addtitle><description>Bisphenol A (BPA) is a widely used plastic material and its potential endocrine disrupting effect has restricted its use and increasing use of BPA alternatives has raised health concerns. However, the effect of bisphenol alternatives on steroidogenesis remains unclear. The objective of this study was to compare inhibitory potencies of 10 BPA alternatives in the inhibition of gonadal 3β-hydroxysteroid dehydrogenase (3β-HSD) in three species (human, rat and mouse). The inhibitory potency for human 3β-HSD2, rat 3β-HSD1, and mouse 3β-HSD6 ranged from bisphenol FL (IC
, 3.32 μM for human, 5.19 μM for rat, and 3.26 μM for mouse) to bisphenol E, F, and thiodiphenol (ineffective at 100 μM). Most BPA alternatives were mixed inhibitors of gonadal 3β-HSD and they dose-dependently inhibited progesterone formation in KGN cells. Molecular docking analysis showed that all BPA analogs bind to steroid and NAD
active sites. Lipophilicity of BPA alternatives was inversely correlated with IC
values. In conclusion, BPA alternatives mostly can inhibit gonadal 3β-HSDs and lipophilicity determines their inhibitory strength.</description><subject>17-Hydroxysteroid Dehydrogenases - metabolism</subject><subject>3-Hydroxysteroid Dehydrogenases - metabolism</subject><subject>Animals</subject><subject>Benzhydryl Compounds</subject><subject>Humans</subject><subject>Hydroxysteroid Dehydrogenases - metabolism</subject><subject>Male</subject><subject>Mice</subject><subject>Molecular Docking Simulation</subject><subject>Phenols</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><subject>Testis - metabolism</subject><issn>0960-0760</issn><issn>1879-1220</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kcFu1DAURS0EotPCFyAhL1k00-c4seMlGpW2UiU2sI4c-2XiUWIH20HMz_ARfAjf1EynsLrS1b33PekQ8oHBlgETN4ftIXVTty2h5KsjqrJ6RTaskapgZQmvyQaUgAKkgAtymdIBADhn8i254FJxJbnakN-7MM06uhQ8DT1NOS4mLxELbbL76fKRRhx1dsGnwc20D5F2Ls0D-jBS7fUY9ok6T_OAqwyuc6fsaWofvLZ6pPzvn2I42hh-HVPGGJylFp-NPXqdMFE9Bb-nwzJpf02jztfrsKVTWBK-I296PSZ8_6JX5PuX22-7--Lx693D7vNjYZiEXCjRCdWzuueS97oW2ti6qpkyojKllTUYI3tAg8owJZu6Ul2DWtccAFEyy6_Ip_PuHMOPBVNuJ5cMjqP2uP7Rlk3TAC8bAWuUn6MmhpQi9u0c3aTjsWXQnsC0h_YZTHsC057BrK2PLweWbkL7v_OPBH8C2SSQQQ</recordid><startdate>202402</startdate><enddate>202402</enddate><creator>Chen, Ya</creator><creator>Zhang, Huina</creator><creator>Yu, Yang</creator><creator>Wang, Shaowei</creator><creator>Wang, Mengyun</creator><creator>Pan, Chengshuang</creator><creator>Fei, Qianjin</creator><creator>Li, Huitao</creator><creator>Wang, Yiyan</creator><creator>Lv, Jieqiang</creator><creator>Ge, Ren-Shan</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>202402</creationdate><title>Comparison of structure-activity relationship for bisphenol analogs in the inhibition of gonadal 3β-hydroxysteroid dehydrogenases among human, rat, and mouse</title><author>Chen, Ya ; Zhang, Huina ; Yu, Yang ; Wang, Shaowei ; Wang, Mengyun ; Pan, Chengshuang ; Fei, Qianjin ; Li, Huitao ; Wang, Yiyan ; Lv, Jieqiang ; Ge, Ren-Shan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c170t-96b69f15f373fa56acd54519c64c2d750cc7f0ece9c1978549b8eaa5300ee71d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>17-Hydroxysteroid Dehydrogenases - metabolism</topic><topic>3-Hydroxysteroid Dehydrogenases - metabolism</topic><topic>Animals</topic><topic>Benzhydryl Compounds</topic><topic>Humans</topic><topic>Hydroxysteroid Dehydrogenases - metabolism</topic><topic>Male</topic><topic>Mice</topic><topic>Molecular Docking Simulation</topic><topic>Phenols</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><topic>Testis - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Ya</creatorcontrib><creatorcontrib>Zhang, Huina</creatorcontrib><creatorcontrib>Yu, Yang</creatorcontrib><creatorcontrib>Wang, Shaowei</creatorcontrib><creatorcontrib>Wang, Mengyun</creatorcontrib><creatorcontrib>Pan, Chengshuang</creatorcontrib><creatorcontrib>Fei, Qianjin</creatorcontrib><creatorcontrib>Li, Huitao</creatorcontrib><creatorcontrib>Wang, Yiyan</creatorcontrib><creatorcontrib>Lv, Jieqiang</creatorcontrib><creatorcontrib>Ge, Ren-Shan</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>The Journal of steroid biochemistry and molecular biology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Ya</au><au>Zhang, Huina</au><au>Yu, Yang</au><au>Wang, Shaowei</au><au>Wang, Mengyun</au><au>Pan, Chengshuang</au><au>Fei, Qianjin</au><au>Li, Huitao</au><au>Wang, Yiyan</au><au>Lv, Jieqiang</au><au>Ge, Ren-Shan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Comparison of structure-activity relationship for bisphenol analogs in the inhibition of gonadal 3β-hydroxysteroid dehydrogenases among human, rat, and mouse</atitle><jtitle>The Journal of steroid biochemistry and molecular biology</jtitle><addtitle>J Steroid Biochem Mol Biol</addtitle><date>2024-02</date><risdate>2024</risdate><volume>236</volume><spage>106424</spage><epage>106424</epage><pages>106424-106424</pages><artnum>106424</artnum><issn>0960-0760</issn><eissn>1879-1220</eissn><abstract>Bisphenol A (BPA) is a widely used plastic material and its potential endocrine disrupting effect has restricted its use and increasing use of BPA alternatives has raised health concerns. However, the effect of bisphenol alternatives on steroidogenesis remains unclear. The objective of this study was to compare inhibitory potencies of 10 BPA alternatives in the inhibition of gonadal 3β-hydroxysteroid dehydrogenase (3β-HSD) in three species (human, rat and mouse). The inhibitory potency for human 3β-HSD2, rat 3β-HSD1, and mouse 3β-HSD6 ranged from bisphenol FL (IC
, 3.32 μM for human, 5.19 μM for rat, and 3.26 μM for mouse) to bisphenol E, F, and thiodiphenol (ineffective at 100 μM). Most BPA alternatives were mixed inhibitors of gonadal 3β-HSD and they dose-dependently inhibited progesterone formation in KGN cells. Molecular docking analysis showed that all BPA analogs bind to steroid and NAD
active sites. Lipophilicity of BPA alternatives was inversely correlated with IC
values. In conclusion, BPA alternatives mostly can inhibit gonadal 3β-HSDs and lipophilicity determines their inhibitory strength.</abstract><cop>England</cop><pmid>37939739</pmid><doi>10.1016/j.jsbmb.2023.106424</doi><tpages>1</tpages></addata></record> |
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| source | MEDLINE; ScienceDirect Journals (5 years ago - present) |
| subjects | 17-Hydroxysteroid Dehydrogenases - metabolism 3-Hydroxysteroid Dehydrogenases - metabolism Animals Benzhydryl Compounds Humans Hydroxysteroid Dehydrogenases - metabolism Male Mice Molecular Docking Simulation Phenols Rats Structure-Activity Relationship Testis - metabolism |
| title | Comparison of structure-activity relationship for bisphenol analogs in the inhibition of gonadal 3β-hydroxysteroid dehydrogenases among human, rat, and mouse |
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