Halogenated bisphenol A derivatives potently inhibit human and rat 11β‐hydroxysteroid dehydrogenase 1: Structure–activity relationship and molecular docking
Chlorinated bisphenol A (BPA) derivatives are formed during chlorination process of drinking water, whereas bisphenol S (BPS) and brominated BPA and BPS (TBBPA and TBBPS) were synthesized for many industrial uses such as fire retardants. However, the effect of halogenated BPA and BPS derivatives on...
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| Veröffentlicht in: | Environmental toxicology 2024-05, Vol.39 (5), p.2560-2571 |
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| creator | Wang, Hong Sang, Jianmin Ji, Zhongyao Yu, Yang Wang, Shaowei Zhu, Yang Li, Huitao Wang, Yiyan Ge, Ren‐shan |
| description | Chlorinated bisphenol A (BPA) derivatives are formed during chlorination process of drinking water, whereas bisphenol S (BPS) and brominated BPA and BPS (TBBPA and TBBPS) were synthesized for many industrial uses such as fire retardants. However, the effect of halogenated BPA and BPS derivatives on glucocorticoid metabolizing enzyme 11β‐hydroxysteroid dehydrogenase 1 (11β‐HSD1) remains unclear. The inhibitory effects of 6 BPA derivatives in the inhibition of human and rat 11β‐HSD1 were investigated. The potencies for inhibition on human 11β‐HSD1 were TBBPA (IC50, 3.87 μM) = monochloro BPA (MCBPA, 4.08 μM) = trichloro BPA (TrCBPA, 4.41 μM) > tetrachloro BPA (TCBPA, 9.75 μM) > TBBPS (>100 μM) = BPS (>100 μM), and those for rat 11β‐HSD1 were TrCBPA (IC50, 2.76 μM) = MCBPA (3.75 μM) > TBBPA (39.58 μM) > TCBPA = TBBPS = BPS. All these BPA derivatives are mixed/competitive inhibitors of both human and rat enzymes. Molecular docking studies predict that MCBPA, TrCBPA, TCBPA, and TBBPA all bind to the active site of human 11β‐HSD1, forming hydrogen bonds with catalytic residue Ser170 except TCBPA. Regression of the lowest binding energy with IC50 values revealed a significant inverse linear regression. In conclusion, halogenated BPA derivatives are mostly potent inhibitors of human and rat 11β‐HSD1, and there is structure‐dependent inhibition. |
| doi_str_mv | 10.1002/tox.24124 |
| format | Article |
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However, the effect of halogenated BPA and BPS derivatives on glucocorticoid metabolizing enzyme 11β‐hydroxysteroid dehydrogenase 1 (11β‐HSD1) remains unclear. The inhibitory effects of 6 BPA derivatives in the inhibition of human and rat 11β‐HSD1 were investigated. The potencies for inhibition on human 11β‐HSD1 were TBBPA (IC50, 3.87 μM) = monochloro BPA (MCBPA, 4.08 μM) = trichloro BPA (TrCBPA, 4.41 μM) > tetrachloro BPA (TCBPA, 9.75 μM) > TBBPS (>100 μM) = BPS (>100 μM), and those for rat 11β‐HSD1 were TrCBPA (IC50, 2.76 μM) = MCBPA (3.75 μM) > TBBPA (39.58 μM) > TCBPA = TBBPS = BPS. All these BPA derivatives are mixed/competitive inhibitors of both human and rat enzymes. Molecular docking studies predict that MCBPA, TrCBPA, TCBPA, and TBBPA all bind to the active site of human 11β‐HSD1, forming hydrogen bonds with catalytic residue Ser170 except TCBPA. Regression of the lowest binding energy with IC50 values revealed a significant inverse linear regression. In conclusion, halogenated BPA derivatives are mostly potent inhibitors of human and rat 11β‐HSD1, and there is structure‐dependent inhibition.</description><identifier>ISSN: 1520-4081</identifier><identifier>EISSN: 1522-7278</identifier><identifier>DOI: 10.1002/tox.24124</identifier><identifier>PMID: 38189224</identifier><language>eng</language><publisher>Hoboken, USA: John Wiley & Sons, Inc</publisher><subject>11β‐hydroxysteroid dehydrogenase 1 ; binding mode analysis ; Bisphenol A ; Bromination ; Chlorination ; cortisol ; Dehydrogenase ; Dehydrogenases ; Drinking water ; Flame retardants ; glucocorticoid ; Glucocorticoids ; halogenated bisphenols ; Hydrogen bonding ; Hydrogen bonds ; Hydroxysteroids ; Industrial applications ; Inhibitors ; Molecular docking ; Molecular structure</subject><ispartof>Environmental toxicology, 2024-05, Vol.39 (5), p.2560-2571</ispartof><rights>2024 Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c3134-9083f4c026299c0f5aa4d348af2634de9b00f40222ca6b22286de0667f0b0ebc3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Ftox.24124$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Ftox.24124$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38189224$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hong</creatorcontrib><creatorcontrib>Sang, Jianmin</creatorcontrib><creatorcontrib>Ji, Zhongyao</creatorcontrib><creatorcontrib>Yu, Yang</creatorcontrib><creatorcontrib>Wang, Shaowei</creatorcontrib><creatorcontrib>Zhu, Yang</creatorcontrib><creatorcontrib>Li, Huitao</creatorcontrib><creatorcontrib>Wang, Yiyan</creatorcontrib><creatorcontrib>Ge, Ren‐shan</creatorcontrib><title>Halogenated bisphenol A derivatives potently inhibit human and rat 11β‐hydroxysteroid dehydrogenase 1: Structure–activity relationship and molecular docking</title><title>Environmental toxicology</title><addtitle>Environ Toxicol</addtitle><description>Chlorinated bisphenol A (BPA) derivatives are formed during chlorination process of drinking water, whereas bisphenol S (BPS) and brominated BPA and BPS (TBBPA and TBBPS) were synthesized for many industrial uses such as fire retardants. However, the effect of halogenated BPA and BPS derivatives on glucocorticoid metabolizing enzyme 11β‐hydroxysteroid dehydrogenase 1 (11β‐HSD1) remains unclear. The inhibitory effects of 6 BPA derivatives in the inhibition of human and rat 11β‐HSD1 were investigated. The potencies for inhibition on human 11β‐HSD1 were TBBPA (IC50, 3.87 μM) = monochloro BPA (MCBPA, 4.08 μM) = trichloro BPA (TrCBPA, 4.41 μM) > tetrachloro BPA (TCBPA, 9.75 μM) > TBBPS (>100 μM) = BPS (>100 μM), and those for rat 11β‐HSD1 were TrCBPA (IC50, 2.76 μM) = MCBPA (3.75 μM) > TBBPA (39.58 μM) > TCBPA = TBBPS = BPS. All these BPA derivatives are mixed/competitive inhibitors of both human and rat enzymes. Molecular docking studies predict that MCBPA, TrCBPA, TCBPA, and TBBPA all bind to the active site of human 11β‐HSD1, forming hydrogen bonds with catalytic residue Ser170 except TCBPA. Regression of the lowest binding energy with IC50 values revealed a significant inverse linear regression. In conclusion, halogenated BPA derivatives are mostly potent inhibitors of human and rat 11β‐HSD1, and there is structure‐dependent inhibition.</description><subject>11β‐hydroxysteroid dehydrogenase 1</subject><subject>binding mode analysis</subject><subject>Bisphenol A</subject><subject>Bromination</subject><subject>Chlorination</subject><subject>cortisol</subject><subject>Dehydrogenase</subject><subject>Dehydrogenases</subject><subject>Drinking water</subject><subject>Flame retardants</subject><subject>glucocorticoid</subject><subject>Glucocorticoids</subject><subject>halogenated bisphenols</subject><subject>Hydrogen bonding</subject><subject>Hydrogen bonds</subject><subject>Hydroxysteroids</subject><subject>Industrial applications</subject><subject>Inhibitors</subject><subject>Molecular docking</subject><subject>Molecular structure</subject><issn>1520-4081</issn><issn>1522-7278</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kUFu1TAQhiMEoqWw4ALIEpuySDt2_PwSdlUFFKlSFxSJXeTYk8bFsYPtlGbXIyBxAq7AQThET4L7XmGBxOofjT59M9JfFM8pHFAAdpj89QHjlPEHxS5dMVau2bp-uJmh5FDTneJJjJcA0IiVeFzsVDWtG8b4bvHjRFp_gU4m1KQzcRrQeUuOiMZgrmQyVxjJ5BO6ZBdi3GA6k8gwj9IR6TQJMhFKf_28vfk2LDr46yUmDN7oLNgs7twRCX1NPqQwqzQHvL35LlU2m7SQgDYf8S4OZtoIR29RzVYGor36bNzF0-JRL23EZ_e5V3x8--b8-KQ8PXv3_vjotFQVrXjZQF31XAETrGkU9Cspua54LXsmKq6x6QB6DowxJUWXoxYaQYh1Dx1gp6q9Yn_rnYL_MmNM7WiiQmulQz_HljWU1pyuhMjoy3_QSz8Hl79rK6gaRkXD15l6taVU8DEG7NspmFGGpaXQ3vXW5t7aTW-ZfXFvnLsR9V_yT1EZONwCX43F5f-m9vzs01b5G26Np8I</recordid><startdate>202405</startdate><enddate>202405</enddate><creator>Wang, Hong</creator><creator>Sang, Jianmin</creator><creator>Ji, Zhongyao</creator><creator>Yu, Yang</creator><creator>Wang, Shaowei</creator><creator>Zhu, Yang</creator><creator>Li, Huitao</creator><creator>Wang, Yiyan</creator><creator>Ge, Ren‐shan</creator><general>John Wiley & Sons, Inc</general><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QH</scope><scope>7ST</scope><scope>7TN</scope><scope>7U7</scope><scope>7UA</scope><scope>C1K</scope><scope>F1W</scope><scope>H97</scope><scope>K9.</scope><scope>L.G</scope><scope>M7N</scope><scope>SOI</scope><scope>7X8</scope></search><sort><creationdate>202405</creationdate><title>Halogenated bisphenol A derivatives potently inhibit human and rat 11β‐hydroxysteroid dehydrogenase 1: Structure–activity relationship and molecular docking</title><author>Wang, Hong ; Sang, Jianmin ; Ji, Zhongyao ; Yu, Yang ; Wang, Shaowei ; Zhu, Yang ; Li, Huitao ; Wang, Yiyan ; Ge, Ren‐shan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3134-9083f4c026299c0f5aa4d348af2634de9b00f40222ca6b22286de0667f0b0ebc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>11β‐hydroxysteroid dehydrogenase 1</topic><topic>binding mode analysis</topic><topic>Bisphenol A</topic><topic>Bromination</topic><topic>Chlorination</topic><topic>cortisol</topic><topic>Dehydrogenase</topic><topic>Dehydrogenases</topic><topic>Drinking water</topic><topic>Flame retardants</topic><topic>glucocorticoid</topic><topic>Glucocorticoids</topic><topic>halogenated bisphenols</topic><topic>Hydrogen bonding</topic><topic>Hydrogen bonds</topic><topic>Hydroxysteroids</topic><topic>Industrial applications</topic><topic>Inhibitors</topic><topic>Molecular docking</topic><topic>Molecular structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hong</creatorcontrib><creatorcontrib>Sang, Jianmin</creatorcontrib><creatorcontrib>Ji, Zhongyao</creatorcontrib><creatorcontrib>Yu, Yang</creatorcontrib><creatorcontrib>Wang, Shaowei</creatorcontrib><creatorcontrib>Zhu, Yang</creatorcontrib><creatorcontrib>Li, Huitao</creatorcontrib><creatorcontrib>Wang, Yiyan</creatorcontrib><creatorcontrib>Ge, Ren‐shan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Aqualine</collection><collection>Environment Abstracts</collection><collection>Oceanic Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Water Resources Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Environmental toxicology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hong</au><au>Sang, Jianmin</au><au>Ji, Zhongyao</au><au>Yu, Yang</au><au>Wang, Shaowei</au><au>Zhu, Yang</au><au>Li, Huitao</au><au>Wang, Yiyan</au><au>Ge, Ren‐shan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Halogenated bisphenol A derivatives potently inhibit human and rat 11β‐hydroxysteroid dehydrogenase 1: Structure–activity relationship and molecular docking</atitle><jtitle>Environmental toxicology</jtitle><addtitle>Environ Toxicol</addtitle><date>2024-05</date><risdate>2024</risdate><volume>39</volume><issue>5</issue><spage>2560</spage><epage>2571</epage><pages>2560-2571</pages><issn>1520-4081</issn><eissn>1522-7278</eissn><abstract>Chlorinated bisphenol A (BPA) derivatives are formed during chlorination process of drinking water, whereas bisphenol S (BPS) and brominated BPA and BPS (TBBPA and TBBPS) were synthesized for many industrial uses such as fire retardants. However, the effect of halogenated BPA and BPS derivatives on glucocorticoid metabolizing enzyme 11β‐hydroxysteroid dehydrogenase 1 (11β‐HSD1) remains unclear. The inhibitory effects of 6 BPA derivatives in the inhibition of human and rat 11β‐HSD1 were investigated. The potencies for inhibition on human 11β‐HSD1 were TBBPA (IC50, 3.87 μM) = monochloro BPA (MCBPA, 4.08 μM) = trichloro BPA (TrCBPA, 4.41 μM) > tetrachloro BPA (TCBPA, 9.75 μM) > TBBPS (>100 μM) = BPS (>100 μM), and those for rat 11β‐HSD1 were TrCBPA (IC50, 2.76 μM) = MCBPA (3.75 μM) > TBBPA (39.58 μM) > TCBPA = TBBPS = BPS. All these BPA derivatives are mixed/competitive inhibitors of both human and rat enzymes. Molecular docking studies predict that MCBPA, TrCBPA, TCBPA, and TBBPA all bind to the active site of human 11β‐HSD1, forming hydrogen bonds with catalytic residue Ser170 except TCBPA. Regression of the lowest binding energy with IC50 values revealed a significant inverse linear regression. In conclusion, halogenated BPA derivatives are mostly potent inhibitors of human and rat 11β‐HSD1, and there is structure‐dependent inhibition.</abstract><cop>Hoboken, USA</cop><pub>John Wiley & Sons, Inc</pub><pmid>38189224</pmid><doi>10.1002/tox.24124</doi><tpages>12</tpages></addata></record> |
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| subjects | 11β‐hydroxysteroid dehydrogenase 1 binding mode analysis Bisphenol A Bromination Chlorination cortisol Dehydrogenase Dehydrogenases Drinking water Flame retardants glucocorticoid Glucocorticoids halogenated bisphenols Hydrogen bonding Hydrogen bonds Hydroxysteroids Industrial applications Inhibitors Molecular docking Molecular structure |
| title | Halogenated bisphenol A derivatives potently inhibit human and rat 11β‐hydroxysteroid dehydrogenase 1: Structure–activity relationship and molecular docking |
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