In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum
Tris(2-butoxyethyl) phosphate (TBOEP) is a plasticizer present in indoor dust, reaching levels of several micrograms per gram. Such levels could lead to significant daily exposure of adults and children. Currently, no toxicokinetic data are available to estimate TBOEP clearance in humans after uptak...
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| Veröffentlicht in: | Toxicology and applied pharmacology 2015-04, Vol.284 (2), p.246-253 |
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| creator | Van den Eede, Nele Erratico, Claudio Exarchou, Vassiliki Maho, Walid Neels, Hugo Covaci, Adrian |
| description | Tris(2-butoxyethyl) phosphate (TBOEP) is a plasticizer present in indoor dust, reaching levels of several micrograms per gram. Such levels could lead to significant daily exposure of adults and children. Currently, no toxicokinetic data are available to estimate TBOEP clearance in humans after uptake and therefore, one objective of this study was to investigate intrinsic clearance of TBOEP by human liver microsome (HLM) and serum enzymes. Another objective was to generate information to identify and prioritize several metabolites of TBOEP for investigation of human exposure by biomonitoring. 1D and 2D-NMR methodologies were successfully applied on a mixture of the metabolites to confirm the structure of 3-HO-TBOEP (bis(2-butoxyethyl) 3-hydroxyl-2-butoxyethyl phosphate) and to tentatively assign structures to 1-HO-TBOEP and 2-HO-TBOEP. HO-TBOEP isomers and bis(2-butoxyethyl) phosphate (BBOEP), bis(2-butoxyethyl) hydroxyethyl phosphate (BBOEHEP) were further monitored by liquid chromatography–tandem mass spectrometry. Rates of formation of BBOEHEP and HO-TBOEP metabolites by liver enzymes were best described by the Michaelis–Menten model. Apparent Km values for BBOEHEP, 3-HO-TBOEP, and sum of 1- and 2-HO-TBOEP isomer formation were 152, 197 and 148μM, respectively. Apparent Vmax values for the formation of BBOEHEP, 3-HO-TBOEP, and the sum of 1- and 2-HO-TBOEP isomers were 2560, 643, and 254pmol/min/mg protein, respectively. No detectable formation of BBOEP occurred with liver or serum enzymes. Our findings indicate that intrinsic clearance of TBOEP is mainly catalyzed by oxidative enzymes in the liver and that its major in vitro metabolite is BBOEHEP. These findings can be applied in human biomonitoring studies and risk assessment.
•First steps in the elucidation of TBOEP toxicokinetics•Quantification of TBOEP metabolites in human serum and liver microsomes•No detectable formation of BBOEP occurred with liver or serum enzymes.•Oxidative dealkylation to BBOEHEP was likely the major metabolic pathway.•1D-NMR and 2D-NMR were used to tentatively assign structures of HO-TBOEP isomers. |
| doi_str_mv | 10.1016/j.taap.2015.01.021 |
| format | Article |
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•First steps in the elucidation of TBOEP toxicokinetics•Quantification of TBOEP metabolites in human serum and liver microsomes•No detectable formation of BBOEP occurred with liver or serum enzymes.•Oxidative dealkylation to BBOEHEP was likely the major metabolic pathway.•1D-NMR and 2D-NMR were used to tentatively assign structures of HO-TBOEP isomers.</description><identifier>ISSN: 0041-008X</identifier><identifier>EISSN: 1096-0333</identifier><identifier>DOI: 10.1016/j.taap.2015.01.021</identifier><identifier>PMID: 25681655</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>60 APPLIED LIFE SCIENCES ; BIOLOGICAL PATHWAYS ; Biotransformation ; Chromatography, Liquid - methods ; CLEARANCE ; DATA ; Dust - analysis ; DUSTS ; Environmental Monitoring - methods ; ENZYMES ; Female ; Human liver microsomes ; HUMAN POPULATIONS ; Humans ; IN VITRO ; In vitro clearance ; In Vitro Techniques ; ISOMERS ; Kinetics ; LIQUID COLUMN CHROMATOGRAPHY ; LIVER ; Liver - metabolism ; Magnetic Resonance Imaging - methods ; Male ; MASS SPECTROSCOPY ; METABOLISM ; METABOLITES ; MICROSOMES ; Microsomes, Liver - metabolism ; NUCLEAR MAGNETIC RESONANCE ; Organophosphorus Compounds - blood ; Organophosphorus Compounds - pharmacokinetics ; PHOSPHATES ; PLASTICIZERS ; Plasticizers - pharmacokinetics ; RISK ASSESSMENT ; Serum ; Tandem Mass Spectrometry - methods ; TBOEP ; Tris(2-butoxyethyl) phosphate ; UPTAKE</subject><ispartof>Toxicology and applied pharmacology, 2015-04, Vol.284 (2), p.246-253</ispartof><rights>2015 Elsevier Inc.</rights><rights>Copyright © 2015 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c553t-1f26d66a1f7fcb0adb5f44427f7ca93602139967b4561080a59bfd29642a28ae3</citedby><cites>FETCH-LOGICAL-c553t-1f26d66a1f7fcb0adb5f44427f7ca93602139967b4561080a59bfd29642a28ae3</cites><orcidid>0000-0003-0527-1136</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.taap.2015.01.021$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,780,784,885,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25681655$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/22465741$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Van den Eede, Nele</creatorcontrib><creatorcontrib>Erratico, Claudio</creatorcontrib><creatorcontrib>Exarchou, Vassiliki</creatorcontrib><creatorcontrib>Maho, Walid</creatorcontrib><creatorcontrib>Neels, Hugo</creatorcontrib><creatorcontrib>Covaci, Adrian</creatorcontrib><title>In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum</title><title>Toxicology and applied pharmacology</title><addtitle>Toxicol Appl Pharmacol</addtitle><description>Tris(2-butoxyethyl) phosphate (TBOEP) is a plasticizer present in indoor dust, reaching levels of several micrograms per gram. Such levels could lead to significant daily exposure of adults and children. Currently, no toxicokinetic data are available to estimate TBOEP clearance in humans after uptake and therefore, one objective of this study was to investigate intrinsic clearance of TBOEP by human liver microsome (HLM) and serum enzymes. Another objective was to generate information to identify and prioritize several metabolites of TBOEP for investigation of human exposure by biomonitoring. 1D and 2D-NMR methodologies were successfully applied on a mixture of the metabolites to confirm the structure of 3-HO-TBOEP (bis(2-butoxyethyl) 3-hydroxyl-2-butoxyethyl phosphate) and to tentatively assign structures to 1-HO-TBOEP and 2-HO-TBOEP. HO-TBOEP isomers and bis(2-butoxyethyl) phosphate (BBOEP), bis(2-butoxyethyl) hydroxyethyl phosphate (BBOEHEP) were further monitored by liquid chromatography–tandem mass spectrometry. Rates of formation of BBOEHEP and HO-TBOEP metabolites by liver enzymes were best described by the Michaelis–Menten model. Apparent Km values for BBOEHEP, 3-HO-TBOEP, and sum of 1- and 2-HO-TBOEP isomer formation were 152, 197 and 148μM, respectively. Apparent Vmax values for the formation of BBOEHEP, 3-HO-TBOEP, and the sum of 1- and 2-HO-TBOEP isomers were 2560, 643, and 254pmol/min/mg protein, respectively. No detectable formation of BBOEP occurred with liver or serum enzymes. Our findings indicate that intrinsic clearance of TBOEP is mainly catalyzed by oxidative enzymes in the liver and that its major in vitro metabolite is BBOEHEP. These findings can be applied in human biomonitoring studies and risk assessment.
•First steps in the elucidation of TBOEP toxicokinetics•Quantification of TBOEP metabolites in human serum and liver microsomes•No detectable formation of BBOEP occurred with liver or serum enzymes.•Oxidative dealkylation to BBOEHEP was likely the major metabolic pathway.•1D-NMR and 2D-NMR were used to tentatively assign structures of HO-TBOEP isomers.</description><subject>60 APPLIED LIFE SCIENCES</subject><subject>BIOLOGICAL PATHWAYS</subject><subject>Biotransformation</subject><subject>Chromatography, Liquid - methods</subject><subject>CLEARANCE</subject><subject>DATA</subject><subject>Dust - analysis</subject><subject>DUSTS</subject><subject>Environmental Monitoring - methods</subject><subject>ENZYMES</subject><subject>Female</subject><subject>Human liver microsomes</subject><subject>HUMAN POPULATIONS</subject><subject>Humans</subject><subject>IN VITRO</subject><subject>In vitro clearance</subject><subject>In Vitro Techniques</subject><subject>ISOMERS</subject><subject>Kinetics</subject><subject>LIQUID COLUMN CHROMATOGRAPHY</subject><subject>LIVER</subject><subject>Liver - metabolism</subject><subject>Magnetic Resonance Imaging - methods</subject><subject>Male</subject><subject>MASS SPECTROSCOPY</subject><subject>METABOLISM</subject><subject>METABOLITES</subject><subject>MICROSOMES</subject><subject>Microsomes, Liver - metabolism</subject><subject>NUCLEAR MAGNETIC RESONANCE</subject><subject>Organophosphorus Compounds - blood</subject><subject>Organophosphorus Compounds - pharmacokinetics</subject><subject>PHOSPHATES</subject><subject>PLASTICIZERS</subject><subject>Plasticizers - pharmacokinetics</subject><subject>RISK ASSESSMENT</subject><subject>Serum</subject><subject>Tandem Mass Spectrometry - methods</subject><subject>TBOEP</subject><subject>Tris(2-butoxyethyl) phosphate</subject><subject>UPTAKE</subject><issn>0041-008X</issn><issn>1096-0333</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU-L1DAYh4Mo7uzoF_AgAS-zh9a8af604EWXXV1YWA8reBBCmqY0Q5vUJB2cb--UWT3qKZcnDzzvD6E3QEogIN7vy6z1XFICvCRQEgrP0AZIIwpSVdVztCGEQUFI_f0CXaa0J4Q0jMFLdEG5qEFwvkE_7jw-uBwDbl3IUfvUhzjp7ILHocc5urSjRbvk8Oto83Acr_A8hDQPOlu8e_z0cPP1CjuPh2XSHo_uYCPWvsPJxmV6hV70ekz29dO7Rd9ubx6vvxT3D5_vrj_eF4bzKhfQU9EJoaGXvWmJ7lreM8ao7KXRTSVOYVXTCNkyLoDURPOm7TvaCEY1rbWttujd2RtSdioZl60ZTPDemqwoZYJLBidqd6bmGH4uNmU1uWTsOGpvw5IUyIrWlIOQ_0eF5LWUElYrPaMmhpSi7dUc3aTjUQFR60xqr9aZ1DqTIqDWmi16--Rf2sl2f7_82eUEfDgD9nS2g7NxrbLe2M7FNaoL7l_-3_ptoZU</recordid><startdate>20150415</startdate><enddate>20150415</enddate><creator>Van den Eede, Nele</creator><creator>Erratico, Claudio</creator><creator>Exarchou, Vassiliki</creator><creator>Maho, Walid</creator><creator>Neels, Hugo</creator><creator>Covaci, Adrian</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>7X8</scope><scope>7ST</scope><scope>7U1</scope><scope>7U2</scope><scope>7U7</scope><scope>C1K</scope><scope>SOI</scope><scope>OTOTI</scope><orcidid>https://orcid.org/0000-0003-0527-1136</orcidid></search><sort><creationdate>20150415</creationdate><title>In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum</title><author>Van den Eede, Nele ; Erratico, Claudio ; Exarchou, Vassiliki ; Maho, Walid ; Neels, Hugo ; Covaci, Adrian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c553t-1f26d66a1f7fcb0adb5f44427f7ca93602139967b4561080a59bfd29642a28ae3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>60 APPLIED LIFE SCIENCES</topic><topic>BIOLOGICAL PATHWAYS</topic><topic>Biotransformation</topic><topic>Chromatography, Liquid - methods</topic><topic>CLEARANCE</topic><topic>DATA</topic><topic>Dust - analysis</topic><topic>DUSTS</topic><topic>Environmental Monitoring - methods</topic><topic>ENZYMES</topic><topic>Female</topic><topic>Human liver microsomes</topic><topic>HUMAN POPULATIONS</topic><topic>Humans</topic><topic>IN VITRO</topic><topic>In vitro clearance</topic><topic>In Vitro Techniques</topic><topic>ISOMERS</topic><topic>Kinetics</topic><topic>LIQUID COLUMN CHROMATOGRAPHY</topic><topic>LIVER</topic><topic>Liver - metabolism</topic><topic>Magnetic Resonance Imaging - methods</topic><topic>Male</topic><topic>MASS SPECTROSCOPY</topic><topic>METABOLISM</topic><topic>METABOLITES</topic><topic>MICROSOMES</topic><topic>Microsomes, Liver - metabolism</topic><topic>NUCLEAR MAGNETIC RESONANCE</topic><topic>Organophosphorus Compounds - blood</topic><topic>Organophosphorus Compounds - pharmacokinetics</topic><topic>PHOSPHATES</topic><topic>PLASTICIZERS</topic><topic>Plasticizers - pharmacokinetics</topic><topic>RISK ASSESSMENT</topic><topic>Serum</topic><topic>Tandem Mass Spectrometry - methods</topic><topic>TBOEP</topic><topic>Tris(2-butoxyethyl) phosphate</topic><topic>UPTAKE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Van den Eede, Nele</creatorcontrib><creatorcontrib>Erratico, Claudio</creatorcontrib><creatorcontrib>Exarchou, Vassiliki</creatorcontrib><creatorcontrib>Maho, Walid</creatorcontrib><creatorcontrib>Neels, Hugo</creatorcontrib><creatorcontrib>Covaci, Adrian</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><collection>Environment Abstracts</collection><collection>Risk Abstracts</collection><collection>Safety Science and Risk</collection><collection>Toxicology Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Environment Abstracts</collection><collection>OSTI.GOV</collection><jtitle>Toxicology and applied pharmacology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Van den Eede, Nele</au><au>Erratico, Claudio</au><au>Exarchou, Vassiliki</au><au>Maho, Walid</au><au>Neels, Hugo</au><au>Covaci, Adrian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum</atitle><jtitle>Toxicology and applied pharmacology</jtitle><addtitle>Toxicol Appl Pharmacol</addtitle><date>2015-04-15</date><risdate>2015</risdate><volume>284</volume><issue>2</issue><spage>246</spage><epage>253</epage><pages>246-253</pages><issn>0041-008X</issn><eissn>1096-0333</eissn><abstract>Tris(2-butoxyethyl) phosphate (TBOEP) is a plasticizer present in indoor dust, reaching levels of several micrograms per gram. Such levels could lead to significant daily exposure of adults and children. Currently, no toxicokinetic data are available to estimate TBOEP clearance in humans after uptake and therefore, one objective of this study was to investigate intrinsic clearance of TBOEP by human liver microsome (HLM) and serum enzymes. Another objective was to generate information to identify and prioritize several metabolites of TBOEP for investigation of human exposure by biomonitoring. 1D and 2D-NMR methodologies were successfully applied on a mixture of the metabolites to confirm the structure of 3-HO-TBOEP (bis(2-butoxyethyl) 3-hydroxyl-2-butoxyethyl phosphate) and to tentatively assign structures to 1-HO-TBOEP and 2-HO-TBOEP. HO-TBOEP isomers and bis(2-butoxyethyl) phosphate (BBOEP), bis(2-butoxyethyl) hydroxyethyl phosphate (BBOEHEP) were further monitored by liquid chromatography–tandem mass spectrometry. Rates of formation of BBOEHEP and HO-TBOEP metabolites by liver enzymes were best described by the Michaelis–Menten model. Apparent Km values for BBOEHEP, 3-HO-TBOEP, and sum of 1- and 2-HO-TBOEP isomer formation were 152, 197 and 148μM, respectively. Apparent Vmax values for the formation of BBOEHEP, 3-HO-TBOEP, and the sum of 1- and 2-HO-TBOEP isomers were 2560, 643, and 254pmol/min/mg protein, respectively. No detectable formation of BBOEP occurred with liver or serum enzymes. Our findings indicate that intrinsic clearance of TBOEP is mainly catalyzed by oxidative enzymes in the liver and that its major in vitro metabolite is BBOEHEP. These findings can be applied in human biomonitoring studies and risk assessment.
•First steps in the elucidation of TBOEP toxicokinetics•Quantification of TBOEP metabolites in human serum and liver microsomes•No detectable formation of BBOEP occurred with liver or serum enzymes.•Oxidative dealkylation to BBOEHEP was likely the major metabolic pathway.•1D-NMR and 2D-NMR were used to tentatively assign structures of HO-TBOEP isomers.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>25681655</pmid><doi>10.1016/j.taap.2015.01.021</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-0527-1136</orcidid></addata></record> |
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| subjects | 60 APPLIED LIFE SCIENCES BIOLOGICAL PATHWAYS Biotransformation Chromatography, Liquid - methods CLEARANCE DATA Dust - analysis DUSTS Environmental Monitoring - methods ENZYMES Female Human liver microsomes HUMAN POPULATIONS Humans IN VITRO In vitro clearance In Vitro Techniques ISOMERS Kinetics LIQUID COLUMN CHROMATOGRAPHY LIVER Liver - metabolism Magnetic Resonance Imaging - methods Male MASS SPECTROSCOPY METABOLISM METABOLITES MICROSOMES Microsomes, Liver - metabolism NUCLEAR MAGNETIC RESONANCE Organophosphorus Compounds - blood Organophosphorus Compounds - pharmacokinetics PHOSPHATES PLASTICIZERS Plasticizers - pharmacokinetics RISK ASSESSMENT Serum Tandem Mass Spectrometry - methods TBOEP Tris(2-butoxyethyl) phosphate UPTAKE |
| title | In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum |
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