Computational insights into the molecular interactions of environmental xenoestrogens 4-tert-octylphenol, 4-nonylphenol, bisphenol A (BPA), and BPA metabolite, 4-methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene (MBP) with human sex hormone-binding globulin
Environmental contamination has been one of the major drawbacks of the industrial revolution. Several man-made chemicals are constantly released into the environment during the manufacturing process and by leaching from the industrial products. As a result, human and animal populations are exposed t...
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creator | Sheikh, Ishfaq A. Tayubi, Iftikhar A. Ahmad, Ejaz Ganaie, Majid A. Bajouh, Osama S. AlBasri, Samera F. Abdulkarim, Ibtihal M.J. Beg, Mohd A. |
description | Environmental contamination has been one of the major drawbacks of the industrial revolution. Several man-made chemicals are constantly released into the environment during the manufacturing process and by leaching from the industrial products. As a result, human and animal populations are exposed to these synthetic chemicals on a regular basis. Many of these chemicals have adverse effects on the physiological functions, particularly on the hormone systems in human and animals and are called endocrine disrupting chemicals (EDCs). Bisphenol A (BPA), 4-tert-octylphenol (OP), and 4-nonylphenol (NP) are three high volume production EDCs that are widely used for industrial purposes and are present ubiquitously in the environment. Bisphenol A is metabolized in the human body to a more potent compound (MBP: 4-Methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene). Epidemiological and experimental studies have shown the three EDCs to be associated with adverse effects on reproductive system in human and animals. Sex hormone-binding globulin (SHBG) is a circulatory protein that binds sex steroids and is a potential target for endocrine disruptors in the human body. The current study was done in order to understand the binding mechanism of OP, BPA, NP, and MBP with human SHBG using in silico approaches. All four compounds showed high binding affinity with SHBG, however, the binding affinity values were higher (more negative) for MBP and NP than for OP and BPA. The four ligands interacted with 19–23 residues of SHBG and a consistent overlapping of the interacting residues for the four ligands with the residues for the natural ligand, dihydrotestosterone (DHT; 82–91% commonality) was shown. The overlapping SHBG interacting residues among DHT and the four endocrine disruptors suggested that these compounds have potential for interference and disruption in the steroid binding function.
●Xenoestrogens OP, BPA, NP, MBP showed high affinity for SHBG on docking simulation.●High overlap of SHBG residues among dihydrotestosterone and the four xenoestrogens.●Common H-bond with residue Asn-82 for dihydrotestosterone and four xenoestrogens.●NP and MBP were more potent xenoestrogens than OP and BPA.●The four xenoestrogens have potential to disrupt androgen-estrogen homoeostasis. |
doi_str_mv | 10.1016/j.ecoenv.2016.10.005 |
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●Xenoestrogens OP, BPA, NP, MBP showed high affinity for SHBG on docking simulation.●High overlap of SHBG residues among dihydrotestosterone and the four xenoestrogens.●Common H-bond with residue Asn-82 for dihydrotestosterone and four xenoestrogens.●NP and MBP were more potent xenoestrogens than OP and BPA.●The four xenoestrogens have potential to disrupt androgen-estrogen homoeostasis.</description><identifier>ISSN: 0147-6513</identifier><identifier>EISSN: 1090-2414</identifier><identifier>DOI: 10.1016/j.ecoenv.2016.10.005</identifier><identifier>PMID: 27750096</identifier><language>eng</language><publisher>Netherlands: Elsevier Inc</publisher><subject>Benzhydryl Compounds - pharmacology ; Binding Sites - drug effects ; Bisphenol A ; Dihydrotestosterone - metabolism ; Docking ; Endocrine disruption ; Endocrine Disruptors - pharmacology ; Environmental Pollutants - pharmacology ; Estrogens - pharmacology ; Humans ; Ligands ; Molecular Docking Simulation ; Nonylphenol ; Octylphenol ; Phenols - pharmacology ; Sex hormone-binding globulin ; Sex Hormone-Binding Globulin - drug effects ; Sex Hormone-Binding Globulin - metabolism</subject><ispartof>Ecotoxicology and environmental safety, 2017-01, Vol.135, p.284-291</ispartof><rights>2016 Elsevier Inc.</rights><rights>Copyright © 2016 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c432t-55b86bbe73d6c95736849ec8916923dc6df5432ef5488bc62a7a303c33e391313</citedby><cites>FETCH-LOGICAL-c432t-55b86bbe73d6c95736849ec8916923dc6df5432ef5488bc62a7a303c33e391313</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ecoenv.2016.10.005$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27750096$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sheikh, Ishfaq A.</creatorcontrib><creatorcontrib>Tayubi, Iftikhar A.</creatorcontrib><creatorcontrib>Ahmad, Ejaz</creatorcontrib><creatorcontrib>Ganaie, Majid A.</creatorcontrib><creatorcontrib>Bajouh, Osama S.</creatorcontrib><creatorcontrib>AlBasri, Samera F.</creatorcontrib><creatorcontrib>Abdulkarim, Ibtihal M.J.</creatorcontrib><creatorcontrib>Beg, Mohd A.</creatorcontrib><title>Computational insights into the molecular interactions of environmental xenoestrogens 4-tert-octylphenol, 4-nonylphenol, bisphenol A (BPA), and BPA metabolite, 4-methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene (MBP) with human sex hormone-binding globulin</title><title>Ecotoxicology and environmental safety</title><addtitle>Ecotoxicol Environ Saf</addtitle><description>Environmental contamination has been one of the major drawbacks of the industrial revolution. Several man-made chemicals are constantly released into the environment during the manufacturing process and by leaching from the industrial products. As a result, human and animal populations are exposed to these synthetic chemicals on a regular basis. Many of these chemicals have adverse effects on the physiological functions, particularly on the hormone systems in human and animals and are called endocrine disrupting chemicals (EDCs). Bisphenol A (BPA), 4-tert-octylphenol (OP), and 4-nonylphenol (NP) are three high volume production EDCs that are widely used for industrial purposes and are present ubiquitously in the environment. Bisphenol A is metabolized in the human body to a more potent compound (MBP: 4-Methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene). Epidemiological and experimental studies have shown the three EDCs to be associated with adverse effects on reproductive system in human and animals. Sex hormone-binding globulin (SHBG) is a circulatory protein that binds sex steroids and is a potential target for endocrine disruptors in the human body. The current study was done in order to understand the binding mechanism of OP, BPA, NP, and MBP with human SHBG using in silico approaches. All four compounds showed high binding affinity with SHBG, however, the binding affinity values were higher (more negative) for MBP and NP than for OP and BPA. The four ligands interacted with 19–23 residues of SHBG and a consistent overlapping of the interacting residues for the four ligands with the residues for the natural ligand, dihydrotestosterone (DHT; 82–91% commonality) was shown. The overlapping SHBG interacting residues among DHT and the four endocrine disruptors suggested that these compounds have potential for interference and disruption in the steroid binding function.
●Xenoestrogens OP, BPA, NP, MBP showed high affinity for SHBG on docking simulation.●High overlap of SHBG residues among dihydrotestosterone and the four xenoestrogens.●Common H-bond with residue Asn-82 for dihydrotestosterone and four xenoestrogens.●NP and MBP were more potent xenoestrogens than OP and BPA.●The four xenoestrogens have potential to disrupt androgen-estrogen homoeostasis.</description><subject>Benzhydryl Compounds - pharmacology</subject><subject>Binding Sites - drug effects</subject><subject>Bisphenol A</subject><subject>Dihydrotestosterone - metabolism</subject><subject>Docking</subject><subject>Endocrine disruption</subject><subject>Endocrine Disruptors - pharmacology</subject><subject>Environmental Pollutants - pharmacology</subject><subject>Estrogens - pharmacology</subject><subject>Humans</subject><subject>Ligands</subject><subject>Molecular Docking Simulation</subject><subject>Nonylphenol</subject><subject>Octylphenol</subject><subject>Phenols - pharmacology</subject><subject>Sex hormone-binding globulin</subject><subject>Sex Hormone-Binding Globulin - drug effects</subject><subject>Sex Hormone-Binding Globulin - metabolism</subject><issn>0147-6513</issn><issn>1090-2414</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UU2P0zAUjBCILQv_ACEfW2ld7DifF6RuxZe0iD3AOXKc18aVYxfbWZr_zoEXZYEbF3vevBk_25MkrznbcsaLt6ctKAf2YZtihdSWsfxJsuKsZjTNePY0WTGelbTIubhKXoRwYowJlufPk6u0LHPG6mKV_Nq74TxGGbWz0hBtgz72MSCIjsQeyOAMqNFIP1PgpZqVgbgDwdnaOzuAjei8gHUQondHwHZGURupU3Ey5x5b5gY56-y_stVhgWRH1rf3u80NkbYjiMgAUbbO6AizC6t-MjSdMZrIOqP91Hl3mWb_ZDbkjFegnIIFsv5ye78hP3XsST8O0pIAF9I7PzgL6LadtkdyNK4djbYvk2cHaQK8etyvk-8f3n_bf6J3Xz9-3u_uqMpEGmmet1XRtlCKrlB1XoqiympQVc2LOhWdKrpDjkLAtapaVaSylIIJJQSImgsurpP1cu7Zux8j_lIz6KDAGGnBjaHhVVZkvKryGqXZIlXeheDh0Jy9HqSfGs6aOffm1Cy5N3PuM4u5o-3N44SxHaD7a_oTNAreLQLAdz5o8E1QGqyCTntQsemc_v-E33qLw64</recordid><startdate>201701</startdate><enddate>201701</enddate><creator>Sheikh, Ishfaq A.</creator><creator>Tayubi, Iftikhar A.</creator><creator>Ahmad, Ejaz</creator><creator>Ganaie, Majid A.</creator><creator>Bajouh, Osama S.</creator><creator>AlBasri, Samera F.</creator><creator>Abdulkarim, Ibtihal M.J.</creator><creator>Beg, Mohd A.</creator><general>Elsevier Inc</general><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>7ST</scope><scope>7U7</scope><scope>C1K</scope><scope>SOI</scope></search><sort><creationdate>201701</creationdate><title>Computational insights into the molecular interactions of environmental xenoestrogens 4-tert-octylphenol, 4-nonylphenol, bisphenol A (BPA), and BPA metabolite, 4-methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene (MBP) with human sex hormone-binding globulin</title><author>Sheikh, Ishfaq A. ; Tayubi, Iftikhar A. ; Ahmad, Ejaz ; Ganaie, Majid A. ; Bajouh, Osama S. ; AlBasri, Samera F. ; Abdulkarim, Ibtihal M.J. ; Beg, Mohd A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c432t-55b86bbe73d6c95736849ec8916923dc6df5432ef5488bc62a7a303c33e391313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Benzhydryl Compounds - pharmacology</topic><topic>Binding Sites - drug effects</topic><topic>Bisphenol A</topic><topic>Dihydrotestosterone - metabolism</topic><topic>Docking</topic><topic>Endocrine disruption</topic><topic>Endocrine Disruptors - pharmacology</topic><topic>Environmental Pollutants - pharmacology</topic><topic>Estrogens - pharmacology</topic><topic>Humans</topic><topic>Ligands</topic><topic>Molecular Docking Simulation</topic><topic>Nonylphenol</topic><topic>Octylphenol</topic><topic>Phenols - pharmacology</topic><topic>Sex hormone-binding globulin</topic><topic>Sex Hormone-Binding Globulin - drug effects</topic><topic>Sex Hormone-Binding Globulin - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sheikh, Ishfaq A.</creatorcontrib><creatorcontrib>Tayubi, Iftikhar A.</creatorcontrib><creatorcontrib>Ahmad, Ejaz</creatorcontrib><creatorcontrib>Ganaie, Majid A.</creatorcontrib><creatorcontrib>Bajouh, Osama S.</creatorcontrib><creatorcontrib>AlBasri, Samera F.</creatorcontrib><creatorcontrib>Abdulkarim, Ibtihal M.J.</creatorcontrib><creatorcontrib>Beg, Mohd A.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Environment Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Environment Abstracts</collection><jtitle>Ecotoxicology and environmental safety</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sheikh, Ishfaq A.</au><au>Tayubi, Iftikhar A.</au><au>Ahmad, Ejaz</au><au>Ganaie, Majid A.</au><au>Bajouh, Osama S.</au><au>AlBasri, Samera F.</au><au>Abdulkarim, Ibtihal M.J.</au><au>Beg, Mohd A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Computational insights into the molecular interactions of environmental xenoestrogens 4-tert-octylphenol, 4-nonylphenol, bisphenol A (BPA), and BPA metabolite, 4-methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene (MBP) with human sex hormone-binding globulin</atitle><jtitle>Ecotoxicology and environmental safety</jtitle><addtitle>Ecotoxicol Environ Saf</addtitle><date>2017-01</date><risdate>2017</risdate><volume>135</volume><spage>284</spage><epage>291</epage><pages>284-291</pages><issn>0147-6513</issn><eissn>1090-2414</eissn><abstract>Environmental contamination has been one of the major drawbacks of the industrial revolution. Several man-made chemicals are constantly released into the environment during the manufacturing process and by leaching from the industrial products. As a result, human and animal populations are exposed to these synthetic chemicals on a regular basis. Many of these chemicals have adverse effects on the physiological functions, particularly on the hormone systems in human and animals and are called endocrine disrupting chemicals (EDCs). Bisphenol A (BPA), 4-tert-octylphenol (OP), and 4-nonylphenol (NP) are three high volume production EDCs that are widely used for industrial purposes and are present ubiquitously in the environment. Bisphenol A is metabolized in the human body to a more potent compound (MBP: 4-Methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene). Epidemiological and experimental studies have shown the three EDCs to be associated with adverse effects on reproductive system in human and animals. Sex hormone-binding globulin (SHBG) is a circulatory protein that binds sex steroids and is a potential target for endocrine disruptors in the human body. The current study was done in order to understand the binding mechanism of OP, BPA, NP, and MBP with human SHBG using in silico approaches. All four compounds showed high binding affinity with SHBG, however, the binding affinity values were higher (more negative) for MBP and NP than for OP and BPA. The four ligands interacted with 19–23 residues of SHBG and a consistent overlapping of the interacting residues for the four ligands with the residues for the natural ligand, dihydrotestosterone (DHT; 82–91% commonality) was shown. The overlapping SHBG interacting residues among DHT and the four endocrine disruptors suggested that these compounds have potential for interference and disruption in the steroid binding function.
●Xenoestrogens OP, BPA, NP, MBP showed high affinity for SHBG on docking simulation.●High overlap of SHBG residues among dihydrotestosterone and the four xenoestrogens.●Common H-bond with residue Asn-82 for dihydrotestosterone and four xenoestrogens.●NP and MBP were more potent xenoestrogens than OP and BPA.●The four xenoestrogens have potential to disrupt androgen-estrogen homoeostasis.</abstract><cop>Netherlands</cop><pub>Elsevier Inc</pub><pmid>27750096</pmid><doi>10.1016/j.ecoenv.2016.10.005</doi><tpages>8</tpages></addata></record> |
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subjects | Benzhydryl Compounds - pharmacology Binding Sites - drug effects Bisphenol A Dihydrotestosterone - metabolism Docking Endocrine disruption Endocrine Disruptors - pharmacology Environmental Pollutants - pharmacology Estrogens - pharmacology Humans Ligands Molecular Docking Simulation Nonylphenol Octylphenol Phenols - pharmacology Sex hormone-binding globulin Sex Hormone-Binding Globulin - drug effects Sex Hormone-Binding Globulin - metabolism |
title | Computational insights into the molecular interactions of environmental xenoestrogens 4-tert-octylphenol, 4-nonylphenol, bisphenol A (BPA), and BPA metabolite, 4-methyl-2, 4-bis (4-hydroxyphenyl) pent-1-ene (MBP) with human sex hormone-binding globulin |
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