Chiral Separation of Deprenyl-N-Oxide Isomers by Capillary Electrophoresis Using Various Cyclodextrin Derivatives
Chiral separation of deprenyl-N-oxide isomers is presented using capillary electrophoresis in the presence of various cyclodextrin (CD) derivatives. This recently identified metabolite of R-(−)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substitue...
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| Veröffentlicht in: | Journal of chromatographic science 2004-01, Vol.42 (1), p.21-26 |
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| container_title | Journal of chromatographic science |
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| creator | Tábi, Tamás Halász, Attila Sándor Pálfi, Melinda Magyar, Kálmán Szökő, Éva |
| description | Chiral separation of deprenyl-N-oxide isomers is presented using capillary electrophoresis in the presence of various cyclodextrin (CD) derivatives. This recently identified metabolite of R-(−)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substituents of the CD are examined on the enantiomer resolution of the compound having an asymmetric center on a heteroatom. The importance of hydrophilic or hydrogen bonding interaction, as well as the position of the interacting groups is demonstrated. Outstanding selectivity and resolution values are achieved using the chargeable carboxymethyl-β-CD. 2-Hydroxypropyl-β-CD is also suitable for the enantiomer separation of the analyte. Native β-CD and carboxyethyl-β-CD provide only poor enantioselectivity, whereas heptakis-(2,6-di-O-methyl)-β-CD is capable of separating only the diastereomers. No chiral resolution can be observed in the presence of γ-CD. |
| doi_str_mv | 10.1093/chromsci/42.1.21 |
| format | Article |
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This recently identified metabolite of R-(−)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substituents of the CD are examined on the enantiomer resolution of the compound having an asymmetric center on a heteroatom. The importance of hydrophilic or hydrogen bonding interaction, as well as the position of the interacting groups is demonstrated. Outstanding selectivity and resolution values are achieved using the chargeable carboxymethyl-β-CD. 2-Hydroxypropyl-β-CD is also suitable for the enantiomer separation of the analyte. Native β-CD and carboxyethyl-β-CD provide only poor enantioselectivity, whereas heptakis-(2,6-di-O-methyl)-β-CD is capable of separating only the diastereomers. No chiral resolution can be observed in the presence of γ-CD.</description><identifier>ISSN: 0021-9665</identifier><identifier>EISSN: 1945-239X</identifier><identifier>DOI: 10.1093/chromsci/42.1.21</identifier><identifier>PMID: 14965411</identifier><identifier>CODEN: JCHSBZ</identifier><language>eng</language><publisher>Niles, IL: Oxford University Press</publisher><subject>Analysis ; Biological and medical sciences ; Cyclodextrins - chemistry ; Electrophoresis, Capillary - methods ; General pharmacology ; Isomerism ; Medical sciences ; Monoamine Oxidase Inhibitors - chemistry ; Pharmacology. 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This recently identified metabolite of R-(−)-deprenyl may possess desirable pharmacological activities. The effect of the cavity size and the substituents of the CD are examined on the enantiomer resolution of the compound having an asymmetric center on a heteroatom. The importance of hydrophilic or hydrogen bonding interaction, as well as the position of the interacting groups is demonstrated. Outstanding selectivity and resolution values are achieved using the chargeable carboxymethyl-β-CD. 2-Hydroxypropyl-β-CD is also suitable for the enantiomer separation of the analyte. Native β-CD and carboxyethyl-β-CD provide only poor enantioselectivity, whereas heptakis-(2,6-di-O-methyl)-β-CD is capable of separating only the diastereomers. No chiral resolution can be observed in the presence of γ-CD.</description><subject>Analysis</subject><subject>Biological and medical sciences</subject><subject>Cyclodextrins - chemistry</subject><subject>Electrophoresis, Capillary - methods</subject><subject>General pharmacology</subject><subject>Isomerism</subject><subject>Medical sciences</subject><subject>Monoamine Oxidase Inhibitors - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Selegiline - analogs & derivatives</subject><subject>Selegiline - chemistry</subject><subject>Selegiline - isolation & purification</subject><subject>Stereoisomerism</subject><issn>0021-9665</issn><issn>1945-239X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkM1vEzEQxS0Eomnhzgn5Qi9oU48_9uOItqWpFFEhAqp6sbzeWWLYrLf2pkr-e1wl0Cun0Yx-82beI-QdsDmwSlzYdfCbaN2F5HOYc3hBZlBJlXFR3b0kM8Y4ZFWeqxNyGuOvpxZK9ZqcgKxyJQFm5KFeu2B6-g1HE8zk_EB9Ry9xDDjs--xLdrtzLdKb6DcYIm32tDaj63sT9vSqRzsFP659wOgi_R7d8JP-MMH5baT13va-xd0U3JAEg3tM8o8Y35BXnekjvj3WM7L6fLWqF9ny9vqm_rTMrJQwZQaAI2utYUZ1BbKKJWcNRy4KK1uAQrS2FGnIWIO2rYQsZFOgtapqSsnFGTk_yI7BP2wxTnrjosX0-YDpPV0yUGUuVQLZAbTBxxiw02Nwm-RPA9NPKeu_KWvJNWgOaeX9UXvbbLB9XjjGmoAPR8BEa_oumMG6-MwpmfxIkbiPB85vx_85mx1oFyfc_eNN-K3zQhRKL-7u9eJ-xb5esqXm4g_7Nqbh</recordid><startdate>200401</startdate><enddate>200401</enddate><creator>Tábi, Tamás</creator><creator>Halász, Attila Sándor</creator><creator>Pálfi, Melinda</creator><creator>Magyar, Kálmán</creator><creator>Szökő, Éva</creator><general>Oxford University Press</general><general>Preston Publications</general><scope>BSCLL</scope><scope>IQODW</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></search><sort><creationdate>200401</creationdate><title>Chiral Separation of Deprenyl-N-Oxide Isomers by Capillary Electrophoresis Using Various Cyclodextrin Derivatives</title><author>Tábi, Tamás ; Halász, Attila Sándor ; Pálfi, Melinda ; Magyar, Kálmán ; Szökő, Éva</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441t-a112e0dca0a5f7e090194b2e237c4d1173dc8301900becd93474b7ecc59b8423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Analysis</topic><topic>Biological and medical sciences</topic><topic>Cyclodextrins - chemistry</topic><topic>Electrophoresis, Capillary - methods</topic><topic>General pharmacology</topic><topic>Isomerism</topic><topic>Medical sciences</topic><topic>Monoamine Oxidase Inhibitors - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Selegiline - analogs & derivatives</topic><topic>Selegiline - chemistry</topic><topic>Selegiline - isolation & purification</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tábi, Tamás</creatorcontrib><creatorcontrib>Halász, Attila Sándor</creatorcontrib><creatorcontrib>Pálfi, Melinda</creatorcontrib><creatorcontrib>Magyar, Kálmán</creatorcontrib><creatorcontrib>Szökő, Éva</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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><jtitle>Journal of chromatographic science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tábi, Tamás</au><au>Halász, Attila Sándor</au><au>Pálfi, Melinda</au><au>Magyar, Kálmán</au><au>Szökő, Éva</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Separation of Deprenyl-N-Oxide Isomers by Capillary Electrophoresis Using Various Cyclodextrin Derivatives</atitle><jtitle>Journal of chromatographic science</jtitle><stitle>Journal of Chromatographic Science</stitle><addtitle>Journal of Chromatographic Science</addtitle><date>2004-01</date><risdate>2004</risdate><volume>42</volume><issue>1</issue><spage>21</spage><epage>26</epage><pages>21-26</pages><issn>0021-9665</issn><eissn>1945-239X</eissn><coden>JCHSBZ</coden><abstract>Chiral separation of deprenyl-N-oxide isomers is presented using capillary electrophoresis in the presence of various cyclodextrin (CD) derivatives. 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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Oxford University Press Journals All Titles (1996-Current); Free Full-Text Journals in Chemistry |
| subjects | Analysis Biological and medical sciences Cyclodextrins - chemistry Electrophoresis, Capillary - methods General pharmacology Isomerism Medical sciences Monoamine Oxidase Inhibitors - chemistry Pharmacology. Drug treatments Selegiline - analogs & derivatives Selegiline - chemistry Selegiline - isolation & purification Stereoisomerism |
| title | Chiral Separation of Deprenyl-N-Oxide Isomers by Capillary Electrophoresis Using Various Cyclodextrin Derivatives |
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