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Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids
The HPLC enantiomeric separation of the racemic cularinoid alkaloids N- p-methoxy-1,α-dihydroaristoyagonine ( 1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine ( 2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugativ...
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| Published in: | Journal of Chromatography A 2006-09, Vol.1129 (1), p.140-144 |
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| Main Authors: | , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c390t-741fb3c804bb84d9b9341d5cc130e4e489e1264ac943759fa3667682020103843 |
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| cites | cdi_FETCH-LOGICAL-c390t-741fb3c804bb84d9b9341d5cc130e4e489e1264ac943759fa3667682020103843 |
| container_end_page | 144 |
| container_issue | 1 |
| container_start_page | 140 |
| container_title | Journal of Chromatography A |
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| creator | Caccamese, Salvatore Scivoli, Giovanna Bianca, Salvatore López-Romero, Juan Manuel Ortiz-López, Francisco Javier |
| description | The HPLC enantiomeric separation of the racemic cularinoid alkaloids
N-
p-methoxy-1,α-dihydroaristoyagonine (
1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine (
2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugative effect strongly affect the different enantioselectivity of the compounds
1 and
2 on the various CSPs investigated. Single enantiomers of
1 were isolated by repeated injections on an analytical HPLC column, and their circular dichroism spectra and optical rotations were measured. The cytotoxicity of the isolated enantiomers was measured on a human colon carcinoma cell line and compared with that of the racemic compound. |
| doi_str_mv | 10.1016/j.chroma.2006.07.077 |
| format | article |
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N-
p-methoxy-1,α-dihydroaristoyagonine (
1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine (
2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugative effect strongly affect the different enantioselectivity of the compounds
1 and
2 on the various CSPs investigated. Single enantiomers of
1 were isolated by repeated injections on an analytical HPLC column, and their circular dichroism spectra and optical rotations were measured. The cytotoxicity of the isolated enantiomers was measured on a human colon carcinoma cell line and compared with that of the racemic compound.</description><identifier>ISSN: 0021-9673</identifier><identifier>DOI: 10.1016/j.chroma.2006.07.077</identifier><identifier>PMID: 16919651</identifier><identifier>CODEN: JOCRAM</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Alkaloids - analysis ; Alkaloids - chemistry ; Alkaloids - pharmacology ; Analysis ; Antineoplastic agents ; Biological and medical sciences ; Cell Survival - drug effects ; Chromatography, High Pressure Liquid - methods ; Circular Dichroism - methods ; Circular dichroism spectra ; Cularine alkaloids ; Cytotoxicity of enantiomers ; Enantioselective chromatography ; General aspects ; General pharmacology ; HT29 Cells ; Humans ; Isoquinolines - analysis ; Isoquinolines - chemistry ; Isoquinolines - pharmacology ; Medical sciences ; Pharmacology. Drug treatments ; Polysaccharide and Pirkle-type chiral stationary phases ; Reproducibility of Results ; Stereoisomerism</subject><ispartof>Journal of Chromatography A, 2006-09, Vol.1129 (1), p.140-144</ispartof><rights>2006 Elsevier B.V.</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-741fb3c804bb84d9b9341d5cc130e4e489e1264ac943759fa3667682020103843</citedby><cites>FETCH-LOGICAL-c390t-741fb3c804bb84d9b9341d5cc130e4e489e1264ac943759fa3667682020103843</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18103315$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16919651$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Caccamese, Salvatore</creatorcontrib><creatorcontrib>Scivoli, Giovanna</creatorcontrib><creatorcontrib>Bianca, Salvatore</creatorcontrib><creatorcontrib>López-Romero, Juan Manuel</creatorcontrib><creatorcontrib>Ortiz-López, Francisco Javier</creatorcontrib><title>Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids</title><title>Journal of Chromatography A</title><addtitle>J Chromatogr A</addtitle><description>The HPLC enantiomeric separation of the racemic cularinoid alkaloids
N-
p-methoxy-1,α-dihydroaristoyagonine (
1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine (
2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugative effect strongly affect the different enantioselectivity of the compounds
1 and
2 on the various CSPs investigated. Single enantiomers of
1 were isolated by repeated injections on an analytical HPLC column, and their circular dichroism spectra and optical rotations were measured. The cytotoxicity of the isolated enantiomers was measured on a human colon carcinoma cell line and compared with that of the racemic compound.</description><subject>Alkaloids - analysis</subject><subject>Alkaloids - chemistry</subject><subject>Alkaloids - pharmacology</subject><subject>Analysis</subject><subject>Antineoplastic agents</subject><subject>Biological and medical sciences</subject><subject>Cell Survival - drug effects</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Circular Dichroism - methods</subject><subject>Circular dichroism spectra</subject><subject>Cularine alkaloids</subject><subject>Cytotoxicity of enantiomers</subject><subject>Enantioselective chromatography</subject><subject>General aspects</subject><subject>General pharmacology</subject><subject>HT29 Cells</subject><subject>Humans</subject><subject>Isoquinolines - analysis</subject><subject>Isoquinolines - chemistry</subject><subject>Isoquinolines - pharmacology</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Polysaccharide and Pirkle-type chiral stationary phases</subject><subject>Reproducibility of Results</subject><subject>Stereoisomerism</subject><issn>0021-9673</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp9kU2L1TAUhrtQnHH0H4hko7tekyY3aTeCXPyCATe6Dqfp6fRc26Zz0orzM_zH5novzE44EEie9-XwpCheKblTUtl3x10YOE6wq6S0O-nyuCfFtZSVKhvr9FXxPKWjlMpJVz0rrpRtVGP36rr4cxiIYRQD3Q3lgtxHnmAOKEa636gT59413jEsAwWRcAGGleIsYM7PxGEbgUVHJ5LSJNKCYWUQsRfrgAJnmDM-IafTVXhY4xp_5yZgSmv8l6YZBYw_YYzUpRfF0x7GhC8v503x49PH74cv5e23z18PH27LoBu5ls6ovtWhlqZta9M1baON6vYhKC3RoKkbVJU1EBqj3b7pQVvrbF3JSiqpa6Nvirfn3oXj_YZp9ROlgOMIM8YteVvXGTNVBs0ZDBxTYuz9wjQBP3gl_Um_P_qzJn_S76XL43Ls9aV_ayfsHkMX9xl4cwEgBRh7zt4pPXJ13lOrfebenznMNn4Rsk-BMP9RR5xV-y7S_zf5C5uYqoQ</recordid><startdate>20060929</startdate><enddate>20060929</enddate><creator>Caccamese, Salvatore</creator><creator>Scivoli, Giovanna</creator><creator>Bianca, Salvatore</creator><creator>López-Romero, Juan Manuel</creator><creator>Ortiz-López, Francisco Javier</creator><general>Elsevier B.V</general><general>Elsevier</general><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>20060929</creationdate><title>Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids</title><author>Caccamese, Salvatore ; Scivoli, Giovanna ; Bianca, Salvatore ; López-Romero, Juan Manuel ; Ortiz-López, Francisco Javier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-741fb3c804bb84d9b9341d5cc130e4e489e1264ac943759fa3667682020103843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Alkaloids - analysis</topic><topic>Alkaloids - chemistry</topic><topic>Alkaloids - pharmacology</topic><topic>Analysis</topic><topic>Antineoplastic agents</topic><topic>Biological and medical sciences</topic><topic>Cell Survival - drug effects</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Circular Dichroism - methods</topic><topic>Circular dichroism spectra</topic><topic>Cularine alkaloids</topic><topic>Cytotoxicity of enantiomers</topic><topic>Enantioselective chromatography</topic><topic>General aspects</topic><topic>General pharmacology</topic><topic>HT29 Cells</topic><topic>Humans</topic><topic>Isoquinolines - analysis</topic><topic>Isoquinolines - chemistry</topic><topic>Isoquinolines - pharmacology</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Polysaccharide and Pirkle-type chiral stationary phases</topic><topic>Reproducibility of Results</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Caccamese, Salvatore</creatorcontrib><creatorcontrib>Scivoli, Giovanna</creatorcontrib><creatorcontrib>Bianca, Salvatore</creatorcontrib><creatorcontrib>López-Romero, Juan Manuel</creatorcontrib><creatorcontrib>Ortiz-López, Francisco Javier</creatorcontrib><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 Chromatography A</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Caccamese, Salvatore</au><au>Scivoli, Giovanna</au><au>Bianca, Salvatore</au><au>López-Romero, Juan Manuel</au><au>Ortiz-López, Francisco Javier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids</atitle><jtitle>Journal of Chromatography A</jtitle><addtitle>J Chromatogr A</addtitle><date>2006-09-29</date><risdate>2006</risdate><volume>1129</volume><issue>1</issue><spage>140</spage><epage>144</epage><pages>140-144</pages><issn>0021-9673</issn><coden>JOCRAM</coden><abstract>The HPLC enantiomeric separation of the racemic cularinoid alkaloids
N-
p-methoxy-1,α-dihydroaristoyagonine (
1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine (
2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugative effect strongly affect the different enantioselectivity of the compounds
1 and
2 on the various CSPs investigated. Single enantiomers of
1 were isolated by repeated injections on an analytical HPLC column, and their circular dichroism spectra and optical rotations were measured. The cytotoxicity of the isolated enantiomers was measured on a human colon carcinoma cell line and compared with that of the racemic compound.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><pmid>16919651</pmid><doi>10.1016/j.chroma.2006.07.077</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| source | ScienceDirect Journals |
| subjects | Alkaloids - analysis Alkaloids - chemistry Alkaloids - pharmacology Analysis Antineoplastic agents Biological and medical sciences Cell Survival - drug effects Chromatography, High Pressure Liquid - methods Circular Dichroism - methods Circular dichroism spectra Cularine alkaloids Cytotoxicity of enantiomers Enantioselective chromatography General aspects General pharmacology HT29 Cells Humans Isoquinolines - analysis Isoquinolines - chemistry Isoquinolines - pharmacology Medical sciences Pharmacology. Drug treatments Polysaccharide and Pirkle-type chiral stationary phases Reproducibility of Results Stereoisomerism |
| title | Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids |
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