Derivatization of carboxylic acids with 4-APEBA for detection by positive-ion LC-ESI–MS(/MS) applied for the analysis of prostanoids and NSAID in urine
In order to develop a generic positive ionization ESI LC–MS method for a variety of interesting substance classes, a new derivatization strategy for carboxylic acids was developed. The carboxylic acid group is labeled with the bromine containing 4-APEBA reagent based on carbodiimide chemistry. The d...
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| Veröffentlicht in: | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences Analytical technologies in the biomedical and life sciences, 2011-05, Vol.879 (17), p.1393-1401 |
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| container_title | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences |
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| creator | Kretschmer, A. Giera, M. Wijtmans, M. de Vries, L. Lingeman, H. Irth, H. Niessen, W.M.A. |
| description | In order to develop a generic positive ionization ESI LC–MS method for a variety of interesting substance classes, a new derivatization strategy for carboxylic acids was developed. The carboxylic acid group is labeled with the bromine containing 4-APEBA reagent based on carbodiimide chemistry. The derivatization reaction can be carried out under aqueous conditions, thereby greatly simplifying sample preparation. In this paper, the derivatization of carboxylic acids is exemplified for the determination of prostanoids and non-steroidal anti-inflammatory drugs (NSAID). Optimization of the derivatization conditions was studied. In order to prove the applicability of the presented approach, we applied the described protocol to urine samples from complex regional pain syndrome (CRPS) patients and were able to detect several prostanoids not visible in the urine of healthy volunteers. Further, the determination of the non-steroidal anti-inflammatory drug ibuprofen in a urine sample was possible. |
| doi_str_mv | 10.1016/j.jchromb.2010.11.028 |
| format | Article |
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The carboxylic acid group is labeled with the bromine containing 4-APEBA reagent based on carbodiimide chemistry. The derivatization reaction can be carried out under aqueous conditions, thereby greatly simplifying sample preparation. In this paper, the derivatization of carboxylic acids is exemplified for the determination of prostanoids and non-steroidal anti-inflammatory drugs (NSAID). Optimization of the derivatization conditions was studied. In order to prove the applicability of the presented approach, we applied the described protocol to urine samples from complex regional pain syndrome (CRPS) patients and were able to detect several prostanoids not visible in the urine of healthy volunteers. Further, the determination of the non-steroidal anti-inflammatory drug ibuprofen in a urine sample was possible.</description><identifier>ISSN: 1570-0232</identifier><identifier>EISSN: 1873-376X</identifier><identifier>DOI: 10.1016/j.jchromb.2010.11.028</identifier><identifier>PMID: 21176889</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>Aniline Compounds - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - urine ; bromine ; Carboxylic acid ; Carboxylic acids ; Carboxylic Acids - chemistry ; Chromatography ; Chromatography, High Pressure Liquid - methods ; Complex Regional Pain Syndromes - urine ; Derivatization ; Drugs ; electrospray ionization mass spectrometry ; Humans ; Ibuprofen ; Ibuprofen - urine ; Ionization ; Isoprostane ; LC–MS ; liquid chromatography ; NSAID ; Optimization ; pain ; patients ; Prostaglandin ; prostaglandins ; Prostaglandins - urine ; Quaternary Ammonium Compounds - chemistry ; Spectrometry, Mass, Electrospray Ionization - methods ; Strategy ; Tandem Mass Spectrometry - methods ; Urine ; volunteers</subject><ispartof>Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 2011-05, Vol.879 (17), p.1393-1401</ispartof><rights>2010 Elsevier B.V.</rights><rights>Copyright © 2010 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c420t-7fa85147d71b7c723194f69ea6a2516e330b7611c084e5b7fceb92576f93e0e3</citedby><cites>FETCH-LOGICAL-c420t-7fa85147d71b7c723194f69ea6a2516e330b7611c084e5b7fceb92576f93e0e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S1570023210007312$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21176889$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kretschmer, A.</creatorcontrib><creatorcontrib>Giera, M.</creatorcontrib><creatorcontrib>Wijtmans, M.</creatorcontrib><creatorcontrib>de Vries, L.</creatorcontrib><creatorcontrib>Lingeman, H.</creatorcontrib><creatorcontrib>Irth, H.</creatorcontrib><creatorcontrib>Niessen, W.M.A.</creatorcontrib><title>Derivatization of carboxylic acids with 4-APEBA for detection by positive-ion LC-ESI–MS(/MS) applied for the analysis of prostanoids and NSAID in urine</title><title>Journal of chromatography. B, Analytical technologies in the biomedical and life sciences</title><addtitle>J Chromatogr B Analyt Technol Biomed Life Sci</addtitle><description>In order to develop a generic positive ionization ESI LC–MS method for a variety of interesting substance classes, a new derivatization strategy for carboxylic acids was developed. The carboxylic acid group is labeled with the bromine containing 4-APEBA reagent based on carbodiimide chemistry. The derivatization reaction can be carried out under aqueous conditions, thereby greatly simplifying sample preparation. In this paper, the derivatization of carboxylic acids is exemplified for the determination of prostanoids and non-steroidal anti-inflammatory drugs (NSAID). Optimization of the derivatization conditions was studied. In order to prove the applicability of the presented approach, we applied the described protocol to urine samples from complex regional pain syndrome (CRPS) patients and were able to detect several prostanoids not visible in the urine of healthy volunteers. Further, the determination of the non-steroidal anti-inflammatory drug ibuprofen in a urine sample was possible.</description><subject>Aniline Compounds - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - urine</subject><subject>bromine</subject><subject>Carboxylic acid</subject><subject>Carboxylic acids</subject><subject>Carboxylic Acids - chemistry</subject><subject>Chromatography</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Complex Regional Pain Syndromes - urine</subject><subject>Derivatization</subject><subject>Drugs</subject><subject>electrospray ionization mass spectrometry</subject><subject>Humans</subject><subject>Ibuprofen</subject><subject>Ibuprofen - urine</subject><subject>Ionization</subject><subject>Isoprostane</subject><subject>LC–MS</subject><subject>liquid chromatography</subject><subject>NSAID</subject><subject>Optimization</subject><subject>pain</subject><subject>patients</subject><subject>Prostaglandin</subject><subject>prostaglandins</subject><subject>Prostaglandins - urine</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Spectrometry, Mass, Electrospray Ionization - methods</subject><subject>Strategy</subject><subject>Tandem Mass Spectrometry - methods</subject><subject>Urine</subject><subject>volunteers</subject><issn>1570-0232</issn><issn>1873-376X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc2O0zAUhSMEYn7gEQDvgEU6_klsZzUqnQKVOoCUQWJnOc4NdZXGwU47lBXvwIrX40lwpoXtLCz7Wt-959gnSZ4RPCGY8Iv1ZG1W3m2qCcXjHZlgKh8kp0QKljLBvzyM51zgFFNGT5KzENYYE4EFe5ycUEIEl7I4TX5fgbc7PdgfcbkOuQYZ7Sv3fd9ag7SxdUC3dlihLJ1-mr-ZosZ5VMMA5g6v9qh3wQ52B-lYL2fpvFz8-fnrunx1cV2-RrrvWwv1XduwAqQ73e6DDaNQ710YdOdGDd3V6EM5XVwh26Gttx08SR41ug3w9LifJzdv5zez9-ny47vFbLpMTUbxkIpGy5xkohakEkZQRoqs4QVormlOODCGK8EJMVhmkFeiMVAVNBe8KRhgYOfJy8PY6ObbFsKgNjYYaFvdgdsGJSXmOaUiv5_kOS-yopCRzA-kiS8MHhrVe7vRfq8IVmN6aq2O6akxPUWIiunFvudHhW21gfp_17-4IvDiADTaKf3V26A-l3ECxzi6ZFRE4vJAQPyynQWvgrHQGaitj5mp2tl7TPwFAdG3ag</recordid><startdate>20110515</startdate><enddate>20110515</enddate><creator>Kretschmer, A.</creator><creator>Giera, M.</creator><creator>Wijtmans, M.</creator><creator>de Vries, L.</creator><creator>Lingeman, H.</creator><creator>Irth, H.</creator><creator>Niessen, W.M.A.</creator><general>Elsevier B.V</general><scope>FBQ</scope><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>7TB</scope><scope>8FD</scope><scope>FR3</scope></search><sort><creationdate>20110515</creationdate><title>Derivatization of carboxylic acids with 4-APEBA for detection by positive-ion LC-ESI–MS(/MS) applied for the analysis of prostanoids and NSAID in urine</title><author>Kretschmer, A. ; Giera, M. ; Wijtmans, M. ; de Vries, L. ; Lingeman, H. ; Irth, H. ; Niessen, W.M.A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c420t-7fa85147d71b7c723194f69ea6a2516e330b7611c084e5b7fceb92576f93e0e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aniline Compounds - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - urine</topic><topic>bromine</topic><topic>Carboxylic acid</topic><topic>Carboxylic acids</topic><topic>Carboxylic Acids - chemistry</topic><topic>Chromatography</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Complex Regional Pain Syndromes - urine</topic><topic>Derivatization</topic><topic>Drugs</topic><topic>electrospray ionization mass spectrometry</topic><topic>Humans</topic><topic>Ibuprofen</topic><topic>Ibuprofen - urine</topic><topic>Ionization</topic><topic>Isoprostane</topic><topic>LC–MS</topic><topic>liquid chromatography</topic><topic>NSAID</topic><topic>Optimization</topic><topic>pain</topic><topic>patients</topic><topic>Prostaglandin</topic><topic>prostaglandins</topic><topic>Prostaglandins - urine</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Spectrometry, Mass, Electrospray Ionization - methods</topic><topic>Strategy</topic><topic>Tandem Mass Spectrometry - methods</topic><topic>Urine</topic><topic>volunteers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kretschmer, A.</creatorcontrib><creatorcontrib>Giera, M.</creatorcontrib><creatorcontrib>Wijtmans, M.</creatorcontrib><creatorcontrib>de Vries, L.</creatorcontrib><creatorcontrib>Lingeman, H.</creatorcontrib><creatorcontrib>Irth, H.</creatorcontrib><creatorcontrib>Niessen, W.M.A.</creatorcontrib><collection>AGRIS</collection><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>Mechanical & Transportation Engineering Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><jtitle>Journal of chromatography. 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B, Analytical technologies in the biomedical and life sciences</jtitle><addtitle>J Chromatogr B Analyt Technol Biomed Life Sci</addtitle><date>2011-05-15</date><risdate>2011</risdate><volume>879</volume><issue>17</issue><spage>1393</spage><epage>1401</epage><pages>1393-1401</pages><issn>1570-0232</issn><eissn>1873-376X</eissn><abstract>In order to develop a generic positive ionization ESI LC–MS method for a variety of interesting substance classes, a new derivatization strategy for carboxylic acids was developed. The carboxylic acid group is labeled with the bromine containing 4-APEBA reagent based on carbodiimide chemistry. The derivatization reaction can be carried out under aqueous conditions, thereby greatly simplifying sample preparation. In this paper, the derivatization of carboxylic acids is exemplified for the determination of prostanoids and non-steroidal anti-inflammatory drugs (NSAID). Optimization of the derivatization conditions was studied. In order to prove the applicability of the presented approach, we applied the described protocol to urine samples from complex regional pain syndrome (CRPS) patients and were able to detect several prostanoids not visible in the urine of healthy volunteers. Further, the determination of the non-steroidal anti-inflammatory drug ibuprofen in a urine sample was possible.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>21176889</pmid><doi>10.1016/j.jchromb.2010.11.028</doi><tpages>9</tpages></addata></record> |
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| ispartof | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 2011-05, Vol.879 (17), p.1393-1401 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Aniline Compounds - chemistry Anti-Inflammatory Agents, Non-Steroidal - urine bromine Carboxylic acid Carboxylic acids Carboxylic Acids - chemistry Chromatography Chromatography, High Pressure Liquid - methods Complex Regional Pain Syndromes - urine Derivatization Drugs electrospray ionization mass spectrometry Humans Ibuprofen Ibuprofen - urine Ionization Isoprostane LC–MS liquid chromatography NSAID Optimization pain patients Prostaglandin prostaglandins Prostaglandins - urine Quaternary Ammonium Compounds - chemistry Spectrometry, Mass, Electrospray Ionization - methods Strategy Tandem Mass Spectrometry - methods Urine volunteers |
| title | Derivatization of carboxylic acids with 4-APEBA for detection by positive-ion LC-ESI–MS(/MS) applied for the analysis of prostanoids and NSAID in urine |
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