Analysis of electrochemical and liver microsomal transformation products of lasalocid by LC/HRMS
Rationale Lasalocid (LAS), an ionophore, is used in cattle and poultry farming as feed additive for its antibiotic and growth‐promoting properties. Literature on transformation products (TP) resulting from LAS degradation is limited. So far, only hydroxylation is found to occur as the metabolic reac...
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description | Rationale
Lasalocid (LAS), an ionophore, is used in cattle and poultry farming as feed additive for its antibiotic and growth‐promoting properties. Literature on transformation products (TP) resulting from LAS degradation is limited. So far, only hydroxylation is found to occur as the metabolic reaction during the LAS degradation. To investigate potential TPs of LAS, we used electrochemistry (EC) and liver microsome (LM) assays to synthesize TPs, which were identified using liquid chromatography high‐resolution mass spectrometry (LC/HRMS).
Methods
Electrochemically produced TPs were analyzed online by direct coupling of the electrochemical cell to the electrospray ionization (ESI) source of a Sciex Triple‐TOF high resolution mass spectrometer. Then, EC‐treated LAS solution was collected and analyzed offline using LC/HRMS to confirm stable TPs and improve their annotation with a chemical structure due to informative MS/MS spectra. In a complementary approach, TPs formed by rat and human microsomal incubation were investigated using LC/HRMS. The resulting data were used to investigate LAS modification reactions and elucidate the chemical structure of obtained TPs.
Results
The online measurements identified a broad variety of TPs, resulting from modification reactions like (de‐)hydrogenation, hydration, methylation, oxidation as well as adduct formation with methanol. We consistently observed different ion complexations of LAS and LAS‐TPs (Na+; 2Na+ K+; NaNH4+; KNH4+). Two stable methylated EC‐TPs were found, structurally annotated, and assigned to a likely modification reaction. Using LM incubation, seven TPs were formed, mostly by oxidation/hydroxylation. After the identification of LM‐TPs as Na+‐complexes, we identified LM‐TPs as K+‐complexes.
Conclusion
We identified and characterized TPs of LAS using EC‐ and LM‐based methods. Moreover, we found different ion complexes of LAS‐based TPs. This knowledge, especially the different ion complexes, may help elucidate the metabolic and environmental degradation pathways of LAS. |
doi_str_mv | 10.1002/rcm.9349 |
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Lasalocid (LAS), an ionophore, is used in cattle and poultry farming as feed additive for its antibiotic and growth‐promoting properties. Literature on transformation products (TP) resulting from LAS degradation is limited. So far, only hydroxylation is found to occur as the metabolic reaction during the LAS degradation. To investigate potential TPs of LAS, we used electrochemistry (EC) and liver microsome (LM) assays to synthesize TPs, which were identified using liquid chromatography high‐resolution mass spectrometry (LC/HRMS).
Methods
Electrochemically produced TPs were analyzed online by direct coupling of the electrochemical cell to the electrospray ionization (ESI) source of a Sciex Triple‐TOF high resolution mass spectrometer. Then, EC‐treated LAS solution was collected and analyzed offline using LC/HRMS to confirm stable TPs and improve their annotation with a chemical structure due to informative MS/MS spectra. In a complementary approach, TPs formed by rat and human microsomal incubation were investigated using LC/HRMS. The resulting data were used to investigate LAS modification reactions and elucidate the chemical structure of obtained TPs.
Results
The online measurements identified a broad variety of TPs, resulting from modification reactions like (de‐)hydrogenation, hydration, methylation, oxidation as well as adduct formation with methanol. We consistently observed different ion complexations of LAS and LAS‐TPs (Na+; 2Na+ K+; NaNH4+; KNH4+). Two stable methylated EC‐TPs were found, structurally annotated, and assigned to a likely modification reaction. Using LM incubation, seven TPs were formed, mostly by oxidation/hydroxylation. After the identification of LM‐TPs as Na+‐complexes, we identified LM‐TPs as K+‐complexes.
Conclusion
We identified and characterized TPs of LAS using EC‐ and LM‐based methods. Moreover, we found different ion complexes of LAS‐based TPs. This knowledge, especially the different ion complexes, may help elucidate the metabolic and environmental degradation pathways of LAS.</description><identifier>ISSN: 0951-4198</identifier><identifier>EISSN: 1097-0231</identifier><identifier>DOI: 10.1002/rcm.9349</identifier><language>eng</language><publisher>Bognor Regis: Wiley Subscription Services, Inc</publisher><subject>Annotations ; Antibiotics ; Chemical reactions ; Coupling (molecular) ; Degradation ; Electrochemical cells ; Electrochemistry ; Food additives ; Hydroxylation ; Ions ; Liquid chromatography ; Liver ; Mass spectrometry ; Metabolism ; Oxidation ; Poultry farming</subject><ispartof>Rapid communications in mass spectrometry, 2022-09, Vol.36 (18), p.e9349-n/a</ispartof><rights>2022 The Authors. published by John Wiley & Sons Ltd.</rights><rights>2022. This article is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3609-1dfc1bdd7d87c2d44fe7e193eef00e872d654575c1dc6e46ecd7a0ed1eaceb603</citedby><cites>FETCH-LOGICAL-c3609-1dfc1bdd7d87c2d44fe7e193eef00e872d654575c1dc6e46ecd7a0ed1eaceb603</cites><orcidid>0000-0001-7616-4413 ; 0000-0003-1220-2286 ; 0000-0003-2039-5567</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Frcm.9349$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Frcm.9349$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Knoche, Lisa</creatorcontrib><creatorcontrib>Lisec, Jan</creatorcontrib><creatorcontrib>Koch, Matthias</creatorcontrib><title>Analysis of electrochemical and liver microsomal transformation products of lasalocid by LC/HRMS</title><title>Rapid communications in mass spectrometry</title><description>Rationale
Lasalocid (LAS), an ionophore, is used in cattle and poultry farming as feed additive for its antibiotic and growth‐promoting properties. Literature on transformation products (TP) resulting from LAS degradation is limited. So far, only hydroxylation is found to occur as the metabolic reaction during the LAS degradation. To investigate potential TPs of LAS, we used electrochemistry (EC) and liver microsome (LM) assays to synthesize TPs, which were identified using liquid chromatography high‐resolution mass spectrometry (LC/HRMS).
Methods
Electrochemically produced TPs were analyzed online by direct coupling of the electrochemical cell to the electrospray ionization (ESI) source of a Sciex Triple‐TOF high resolution mass spectrometer. Then, EC‐treated LAS solution was collected and analyzed offline using LC/HRMS to confirm stable TPs and improve their annotation with a chemical structure due to informative MS/MS spectra. In a complementary approach, TPs formed by rat and human microsomal incubation were investigated using LC/HRMS. The resulting data were used to investigate LAS modification reactions and elucidate the chemical structure of obtained TPs.
Results
The online measurements identified a broad variety of TPs, resulting from modification reactions like (de‐)hydrogenation, hydration, methylation, oxidation as well as adduct formation with methanol. We consistently observed different ion complexations of LAS and LAS‐TPs (Na+; 2Na+ K+; NaNH4+; KNH4+). Two stable methylated EC‐TPs were found, structurally annotated, and assigned to a likely modification reaction. Using LM incubation, seven TPs were formed, mostly by oxidation/hydroxylation. After the identification of LM‐TPs as Na+‐complexes, we identified LM‐TPs as K+‐complexes.
Conclusion
We identified and characterized TPs of LAS using EC‐ and LM‐based methods. Moreover, we found different ion complexes of LAS‐based TPs. This knowledge, especially the different ion complexes, may help elucidate the metabolic and environmental degradation pathways of LAS.</description><subject>Annotations</subject><subject>Antibiotics</subject><subject>Chemical reactions</subject><subject>Coupling (molecular)</subject><subject>Degradation</subject><subject>Electrochemical cells</subject><subject>Electrochemistry</subject><subject>Food additives</subject><subject>Hydroxylation</subject><subject>Ions</subject><subject>Liquid chromatography</subject><subject>Liver</subject><subject>Mass spectrometry</subject><subject>Metabolism</subject><subject>Oxidation</subject><subject>Poultry farming</subject><issn>0951-4198</issn><issn>1097-0231</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNp1kFFLwzAQx4MoOKfgRwj44ku3S5s27eMo6oQNYepzzZIrdqTNTFql3952EwTBp-OO3_25-xFyzWDGAMK5U_Usi3h2QiYMMhFAGLFTMoEsZgFnWXpOLrzfATAWhzAhb4tGmt5XntqSokHVOqvesa6UNFQ2mprqEx0deme9rYdh62TjS-tq2Va2oXtndafaw76RXhqrKk23PV3l8-Vm_XxJzkppPF791Cl5vb97yZfB6unhMV-sAhUlkAVMl4pttRY6FSrUnJcokGURYgmAqQh1EvNYxIpplSBPUGkhATVDqXCbQDQlt8fc4aCPDn1b1JVXaIxs0Ha-CJM0higSYkRv_qA727nBw0AJGKAk5fw3cPzcOyyLvatq6fqCQTGqLgbVxah6QIMj-lUZ7P_lik2-PvDf0qSA1A</recordid><startdate>20220930</startdate><enddate>20220930</enddate><creator>Knoche, Lisa</creator><creator>Lisec, Jan</creator><creator>Koch, Matthias</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>JQ2</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7616-4413</orcidid><orcidid>https://orcid.org/0000-0003-1220-2286</orcidid><orcidid>https://orcid.org/0000-0003-2039-5567</orcidid></search><sort><creationdate>20220930</creationdate><title>Analysis of electrochemical and liver microsomal transformation products of lasalocid by LC/HRMS</title><author>Knoche, Lisa ; Lisec, Jan ; Koch, Matthias</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3609-1dfc1bdd7d87c2d44fe7e193eef00e872d654575c1dc6e46ecd7a0ed1eaceb603</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Annotations</topic><topic>Antibiotics</topic><topic>Chemical reactions</topic><topic>Coupling (molecular)</topic><topic>Degradation</topic><topic>Electrochemical cells</topic><topic>Electrochemistry</topic><topic>Food additives</topic><topic>Hydroxylation</topic><topic>Ions</topic><topic>Liquid chromatography</topic><topic>Liver</topic><topic>Mass spectrometry</topic><topic>Metabolism</topic><topic>Oxidation</topic><topic>Poultry farming</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Knoche, Lisa</creatorcontrib><creatorcontrib>Lisec, Jan</creatorcontrib><creatorcontrib>Koch, Matthias</creatorcontrib><collection>Open Access: Wiley-Blackwell Open Access Journals</collection><collection>Wiley Online Library website</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Rapid communications in mass spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Knoche, Lisa</au><au>Lisec, Jan</au><au>Koch, Matthias</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Analysis of electrochemical and liver microsomal transformation products of lasalocid by LC/HRMS</atitle><jtitle>Rapid communications in mass spectrometry</jtitle><date>2022-09-30</date><risdate>2022</risdate><volume>36</volume><issue>18</issue><spage>e9349</spage><epage>n/a</epage><pages>e9349-n/a</pages><issn>0951-4198</issn><eissn>1097-0231</eissn><abstract>Rationale
Lasalocid (LAS), an ionophore, is used in cattle and poultry farming as feed additive for its antibiotic and growth‐promoting properties. Literature on transformation products (TP) resulting from LAS degradation is limited. So far, only hydroxylation is found to occur as the metabolic reaction during the LAS degradation. To investigate potential TPs of LAS, we used electrochemistry (EC) and liver microsome (LM) assays to synthesize TPs, which were identified using liquid chromatography high‐resolution mass spectrometry (LC/HRMS).
Methods
Electrochemically produced TPs were analyzed online by direct coupling of the electrochemical cell to the electrospray ionization (ESI) source of a Sciex Triple‐TOF high resolution mass spectrometer. Then, EC‐treated LAS solution was collected and analyzed offline using LC/HRMS to confirm stable TPs and improve their annotation with a chemical structure due to informative MS/MS spectra. In a complementary approach, TPs formed by rat and human microsomal incubation were investigated using LC/HRMS. The resulting data were used to investigate LAS modification reactions and elucidate the chemical structure of obtained TPs.
Results
The online measurements identified a broad variety of TPs, resulting from modification reactions like (de‐)hydrogenation, hydration, methylation, oxidation as well as adduct formation with methanol. We consistently observed different ion complexations of LAS and LAS‐TPs (Na+; 2Na+ K+; NaNH4+; KNH4+). Two stable methylated EC‐TPs were found, structurally annotated, and assigned to a likely modification reaction. Using LM incubation, seven TPs were formed, mostly by oxidation/hydroxylation. After the identification of LM‐TPs as Na+‐complexes, we identified LM‐TPs as K+‐complexes.
Conclusion
We identified and characterized TPs of LAS using EC‐ and LM‐based methods. Moreover, we found different ion complexes of LAS‐based TPs. This knowledge, especially the different ion complexes, may help elucidate the metabolic and environmental degradation pathways of LAS.</abstract><cop>Bognor Regis</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/rcm.9349</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0001-7616-4413</orcidid><orcidid>https://orcid.org/0000-0003-1220-2286</orcidid><orcidid>https://orcid.org/0000-0003-2039-5567</orcidid><oa>free_for_read</oa></addata></record> |
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subjects | Annotations Antibiotics Chemical reactions Coupling (molecular) Degradation Electrochemical cells Electrochemistry Food additives Hydroxylation Ions Liquid chromatography Liver Mass spectrometry Metabolism Oxidation Poultry farming |
title | Analysis of electrochemical and liver microsomal transformation products of lasalocid by LC/HRMS |
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