Chiral Separation of Uncharged Pomalidomide Enantiomers Using Carboxymethyl-β-Cyclodextrin: A Validated Capillary Electrophoretic Method
The racemic mixture of pomalidomide (POM), a second‐generation immunomodulatory uncharged drug, was separated into enantiomers by capillary zone electrophoresis for the first time. Seven different chargeable cyclodextrin (CD) derivatives were screened as complexing agents and chiral selectors, inves...
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| Veröffentlicht in: | Chirality (New York, N.Y.) N.Y.), 2016-03, Vol.28 (3), p.199-203 |
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| creator | Szabó, Zoltán-István Szőcs, Levente Muntean, Daniela-Lucia NoszáL, Béla Tóth, Gergő |
| description | The racemic mixture of pomalidomide (POM), a second‐generation immunomodulatory uncharged drug, was separated into enantiomers by capillary zone electrophoresis for the first time. Seven different chargeable cyclodextrin (CD) derivatives were screened as complexing agents and chiral selectors, investigating the stability of the POM‐CD inclusion complexes and their enantiodiscriminating capacities. Based on preliminary experiments, carboxymethyl‐β‐CD (CM‐β‐CD) was found to be the most effective chiral selector. Factors influencing enantioseparation were systematically optimized, using an orthogonal experimental design. Optimal parameters (background electrolyte [BGE]: 50 mM Tris‐acetate buffer, pH 6.5, containing 15 mM CM‐β‐CD; capillary temperature: 20°C; voltage applied +15 kV) allowed baseline separation of POM enantiomers with a resolution as high as 4.87. The developed method was validated, in terms of sensitivity (limit of detection and limit of quantification), linearity, accuracy, repeatability, and intermediate precision. Chirality 28:199–203, 2016. © 2015 Wiley Periodicals, Inc.
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| doi_str_mv | 10.1002/chir.22563 |
| format | Article |
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▪▪▪</description><subject>Acetal resins</subject><subject>beta-Cyclodextrins - chemistry</subject><subject>Capillarity</subject><subject>capillary zone electrophoresis</subject><subject>Chirality</subject><subject>Cyclodextrins</subject><subject>Cyclodextrins - chemistry</subject><subject>Electrophoresis, Capillary</subject><subject>Enantiomers</subject><subject>experimental design</subject><subject>Hydrogen-Ion Concentration</subject><subject>Imnovid</subject><subject>Linearity</subject><subject>Pomalyst</subject><subject>Selectors</subject><subject>Separation</subject><subject>Stereoisomerism</subject><subject>Thalidomide - analogs & derivatives</subject><subject>Thalidomide - chemistry</subject><subject>validation</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctu1DAUhi1ERYfChgdAXiKkFF8S22FXRUOn0lAu7QA7y3VOOoYkDnZGTB6B1-FB-kx4Om2XsDqb7_90zvkRekHJMSWEvbFrF44ZKwR_hGa0YCQTXHx7jGZElWVGSM4O0dMYvxNCSsHzJ-iQCUmUZHSGflcpbFp8AYMJZnS-x77Bq96uTbiGGn_0nWld7TtXA573pk9IByHiVXT9Na5MuPLbqYNxPbXZzZ-smmzra9iOwfVv8Qn-skubMZkqM7i2NWHC8xbsGPyw9gFGZ_H7lPb1M3TQmDbC87t5hFbv5pfVIlt-OD2rTpaZ5argmZKFrHMDxKpSsDwdJ4vCElWDsLQRnDSW15RTI0VRkqYseCOZZYrz9CAigB-hV3vvEPzPDcRRdy5aSKv14DdRU5U-JqUQ5P-oFDnlZa526Os9aoOPMUCjh-C6dK2mRO9a0ruW9G1LCX55591cdVA_oPe1JIDugV-uhekfKl0tzj7fS7N9xsURtg8ZE35oIbks9NfzU63Y5QVZVJ_0kv8FL9-tXA</recordid><startdate>201603</startdate><enddate>201603</enddate><creator>Szabó, Zoltán-István</creator><creator>Szőcs, Levente</creator><creator>Muntean, Daniela-Lucia</creator><creator>NoszáL, Béla</creator><creator>Tóth, Gergő</creator><general>Blackwell Publishing Ltd</general><scope>BSCLL</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>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>201603</creationdate><title>Chiral Separation of Uncharged Pomalidomide Enantiomers Using Carboxymethyl-β-Cyclodextrin: A Validated Capillary Electrophoretic Method</title><author>Szabó, Zoltán-István ; Szőcs, Levente ; Muntean, Daniela-Lucia ; NoszáL, Béla ; Tóth, Gergő</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3853-8757d4ae0c89624042755c08de6c1f630fc3d131a76590f953f72c283325606e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Acetal resins</topic><topic>beta-Cyclodextrins - chemistry</topic><topic>Capillarity</topic><topic>capillary zone electrophoresis</topic><topic>Chirality</topic><topic>Cyclodextrins</topic><topic>Cyclodextrins - chemistry</topic><topic>Electrophoresis, Capillary</topic><topic>Enantiomers</topic><topic>experimental design</topic><topic>Hydrogen-Ion Concentration</topic><topic>Imnovid</topic><topic>Linearity</topic><topic>Pomalyst</topic><topic>Selectors</topic><topic>Separation</topic><topic>Stereoisomerism</topic><topic>Thalidomide - analogs & derivatives</topic><topic>Thalidomide - chemistry</topic><topic>validation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Szabó, Zoltán-István</creatorcontrib><creatorcontrib>Szőcs, Levente</creatorcontrib><creatorcontrib>Muntean, Daniela-Lucia</creatorcontrib><creatorcontrib>NoszáL, Béla</creatorcontrib><creatorcontrib>Tóth, Gergő</creatorcontrib><collection>Istex</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>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>Advanced Technologies Database with Aerospace</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Szabó, Zoltán-István</au><au>Szőcs, Levente</au><au>Muntean, Daniela-Lucia</au><au>NoszáL, Béla</au><au>Tóth, Gergő</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Separation of Uncharged Pomalidomide Enantiomers Using Carboxymethyl-β-Cyclodextrin: A Validated Capillary Electrophoretic Method</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2016-03</date><risdate>2016</risdate><volume>28</volume><issue>3</issue><spage>199</spage><epage>203</epage><pages>199-203</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>The racemic mixture of pomalidomide (POM), a second‐generation immunomodulatory uncharged drug, was separated into enantiomers by capillary zone electrophoresis for the first time. Seven different chargeable cyclodextrin (CD) derivatives were screened as complexing agents and chiral selectors, investigating the stability of the POM‐CD inclusion complexes and their enantiodiscriminating capacities. Based on preliminary experiments, carboxymethyl‐β‐CD (CM‐β‐CD) was found to be the most effective chiral selector. Factors influencing enantioseparation were systematically optimized, using an orthogonal experimental design. Optimal parameters (background electrolyte [BGE]: 50 mM Tris‐acetate buffer, pH 6.5, containing 15 mM CM‐β‐CD; capillary temperature: 20°C; voltage applied +15 kV) allowed baseline separation of POM enantiomers with a resolution as high as 4.87. The developed method was validated, in terms of sensitivity (limit of detection and limit of quantification), linearity, accuracy, repeatability, and intermediate precision. Chirality 28:199–203, 2016. © 2015 Wiley Periodicals, Inc.
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| subjects | Acetal resins beta-Cyclodextrins - chemistry Capillarity capillary zone electrophoresis Chirality Cyclodextrins Cyclodextrins - chemistry Electrophoresis, Capillary Enantiomers experimental design Hydrogen-Ion Concentration Imnovid Linearity Pomalyst Selectors Separation Stereoisomerism Thalidomide - analogs & derivatives Thalidomide - chemistry validation |
| title | Chiral Separation of Uncharged Pomalidomide Enantiomers Using Carboxymethyl-β-Cyclodextrin: A Validated Capillary Electrophoretic Method |
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