Focus on the Controversial Activation of Human iNKT Cells by 4-Deoxy Analogue of KRN7000
4-Deoxy-α-GalCer analogues are considered weaker agonists than KRN7000 for the stimulation of human iNKT cells, but this remains strongly debated. In this work, we described a strategy toward 4-deoxy-α-GalCers with, as a key step, a metathesis reaction allowing sphingosine modifications from a singl...
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| Veröffentlicht in: | Journal of medicinal chemistry 2009-08, Vol.52 (15), p.4960-4963 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 52 |
| creator | Lacône, Vivien Hunault, Julie Pipelier, Muriel Blot, Virginie Lecourt, Thomas Rocher, Jézabelle Turcot-Dubois, Anne-Laure Marionneau, Séverine Douillard, Jean-Yves Clément, Monique Le Pendu, Jacques Bonneville, Marc Micouin, Laurent Dubreuil, Didier |
| description | 4-Deoxy-α-GalCer analogues are considered weaker agonists than KRN7000 for the stimulation of human iNKT cells, but this remains strongly debated. In this work, we described a strategy toward 4-deoxy-α-GalCers with, as a key step, a metathesis reaction allowing sphingosine modifications from a single ethylenic α-galactoside precursor. The 4-deoxy-KRN7000 derivative 2, described here, induced potent cytokinic responses, comparable to those of KRN7000, both from human iNKT cells in vitro and from their murine counterpart in vivo. |
| doi_str_mv | 10.1021/jm900290r |
| format | Article |
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In this work, we described a strategy toward 4-deoxy-α-GalCers with, as a key step, a metathesis reaction allowing sphingosine modifications from a single ethylenic α-galactoside precursor. The 4-deoxy-KRN7000 derivative 2, described here, induced potent cytokinic responses, comparable to those of KRN7000, both from human iNKT cells in vitro and from their murine counterpart in vivo.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm900290r</identifier><identifier>PMID: 19580320</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Columbus, OH: American Chemical Society</publisher><subject>Adjuvants, Immunologic - chemical synthesis ; Adjuvants, Immunologic - pharmacology ; Animals ; Biological and medical sciences ; Galactosylceramides - chemical synthesis ; Galactosylceramides - pharmacology ; Humans ; Immunomodulators ; Interferon-gamma - biosynthesis ; Interleukin-4 - biosynthesis ; Lymphocyte Activation - drug effects ; Medical sciences ; Mice ; Natural Killer T-Cells - drug effects ; Pharmacology. Drug treatments ; Structure-Activity Relationship ; Tumor Necrosis Factor-alpha - biosynthesis</subject><ispartof>Journal of medicinal chemistry, 2009-08, Vol.52 (15), p.4960-4963</ispartof><rights>Copyright © 2009 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-108d096f7bdab1f7198f584212c892fdd4b0e963283a85f3389b5430ce6dbbba3</citedby><cites>FETCH-LOGICAL-a343t-108d096f7bdab1f7198f584212c892fdd4b0e963283a85f3389b5430ce6dbbba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm900290r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm900290r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22098223$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19580320$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lacône, Vivien</creatorcontrib><creatorcontrib>Hunault, Julie</creatorcontrib><creatorcontrib>Pipelier, Muriel</creatorcontrib><creatorcontrib>Blot, Virginie</creatorcontrib><creatorcontrib>Lecourt, Thomas</creatorcontrib><creatorcontrib>Rocher, Jézabelle</creatorcontrib><creatorcontrib>Turcot-Dubois, Anne-Laure</creatorcontrib><creatorcontrib>Marionneau, Séverine</creatorcontrib><creatorcontrib>Douillard, Jean-Yves</creatorcontrib><creatorcontrib>Clément, Monique</creatorcontrib><creatorcontrib>Le Pendu, Jacques</creatorcontrib><creatorcontrib>Bonneville, Marc</creatorcontrib><creatorcontrib>Micouin, Laurent</creatorcontrib><creatorcontrib>Dubreuil, Didier</creatorcontrib><title>Focus on the Controversial Activation of Human iNKT Cells by 4-Deoxy Analogue of KRN7000</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>4-Deoxy-α-GalCer analogues are considered weaker agonists than KRN7000 for the stimulation of human iNKT cells, but this remains strongly debated. In this work, we described a strategy toward 4-deoxy-α-GalCers with, as a key step, a metathesis reaction allowing sphingosine modifications from a single ethylenic α-galactoside precursor. The 4-deoxy-KRN7000 derivative 2, described here, induced potent cytokinic responses, comparable to those of KRN7000, both from human iNKT cells in vitro and from their murine counterpart in vivo.</description><subject>Adjuvants, Immunologic - chemical synthesis</subject><subject>Adjuvants, Immunologic - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Galactosylceramides - chemical synthesis</subject><subject>Galactosylceramides - pharmacology</subject><subject>Humans</subject><subject>Immunomodulators</subject><subject>Interferon-gamma - biosynthesis</subject><subject>Interleukin-4 - biosynthesis</subject><subject>Lymphocyte Activation - drug effects</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Natural Killer T-Cells - drug effects</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Necrosis Factor-alpha - biosynthesis</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9LwzAUB_Agis4fB_8ByUXBQ_UlabvkOKpzokyQCd5Kkiba0TaatMP992Y49OLpQd4n7z2-CJ0SuCJAyfWyFQBUgN9BI5JRSFIO6S4axUea0JyyA3QYwhIAGKFsHx0QkXFgFEboder0ELDrcP9ucOG63ruV8aGWDZ7ovl7Jvo5NZ_FsaGWH6_nDAhemaQJWa5wmN8Z9rfGkk417G8zGPTzPx3HTMdqzsgnmZFuP0Mv0dlHMksenu_ti8phIlrI-IcArELkdq0oqYsdEcJvxlBKquaC2qlIFRuSMciZ5ZhnjQmUpA23ySikl2RG6-Jn74d3nYEJftnXQ8UDZGTeEMh_n8W_KIrz8gdq7ELyx5YevW-nXJYFyE2P5G2O0Z9uhg2pN9Se3uUVwvgUyaNlYLztdh19HKQhOKftzUody6QYfgwr_LPwGAEiDjQ</recordid><startdate>20090813</startdate><enddate>20090813</enddate><creator>Lacône, Vivien</creator><creator>Hunault, Julie</creator><creator>Pipelier, Muriel</creator><creator>Blot, Virginie</creator><creator>Lecourt, Thomas</creator><creator>Rocher, Jézabelle</creator><creator>Turcot-Dubois, Anne-Laure</creator><creator>Marionneau, Séverine</creator><creator>Douillard, Jean-Yves</creator><creator>Clément, Monique</creator><creator>Le Pendu, Jacques</creator><creator>Bonneville, Marc</creator><creator>Micouin, Laurent</creator><creator>Dubreuil, Didier</creator><general>American Chemical Society</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>20090813</creationdate><title>Focus on the Controversial Activation of Human iNKT Cells by 4-Deoxy Analogue of KRN7000</title><author>Lacône, Vivien ; Hunault, Julie ; Pipelier, Muriel ; Blot, Virginie ; Lecourt, Thomas ; Rocher, Jézabelle ; Turcot-Dubois, Anne-Laure ; Marionneau, Séverine ; Douillard, Jean-Yves ; Clément, Monique ; Le Pendu, Jacques ; Bonneville, Marc ; Micouin, Laurent ; Dubreuil, Didier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-108d096f7bdab1f7198f584212c892fdd4b0e963283a85f3389b5430ce6dbbba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Adjuvants, Immunologic - chemical synthesis</topic><topic>Adjuvants, Immunologic - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Galactosylceramides - chemical synthesis</topic><topic>Galactosylceramides - pharmacology</topic><topic>Humans</topic><topic>Immunomodulators</topic><topic>Interferon-gamma - biosynthesis</topic><topic>Interleukin-4 - biosynthesis</topic><topic>Lymphocyte Activation - drug effects</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Natural Killer T-Cells - drug effects</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Necrosis Factor-alpha - biosynthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lacône, Vivien</creatorcontrib><creatorcontrib>Hunault, Julie</creatorcontrib><creatorcontrib>Pipelier, Muriel</creatorcontrib><creatorcontrib>Blot, Virginie</creatorcontrib><creatorcontrib>Lecourt, Thomas</creatorcontrib><creatorcontrib>Rocher, Jézabelle</creatorcontrib><creatorcontrib>Turcot-Dubois, Anne-Laure</creatorcontrib><creatorcontrib>Marionneau, Séverine</creatorcontrib><creatorcontrib>Douillard, Jean-Yves</creatorcontrib><creatorcontrib>Clément, Monique</creatorcontrib><creatorcontrib>Le Pendu, Jacques</creatorcontrib><creatorcontrib>Bonneville, Marc</creatorcontrib><creatorcontrib>Micouin, Laurent</creatorcontrib><creatorcontrib>Dubreuil, Didier</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 medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lacône, Vivien</au><au>Hunault, Julie</au><au>Pipelier, Muriel</au><au>Blot, Virginie</au><au>Lecourt, Thomas</au><au>Rocher, Jézabelle</au><au>Turcot-Dubois, Anne-Laure</au><au>Marionneau, Séverine</au><au>Douillard, Jean-Yves</au><au>Clément, Monique</au><au>Le Pendu, Jacques</au><au>Bonneville, Marc</au><au>Micouin, Laurent</au><au>Dubreuil, Didier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Focus on the Controversial Activation of Human iNKT Cells by 4-Deoxy Analogue of KRN7000</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. 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| subjects | Adjuvants, Immunologic - chemical synthesis Adjuvants, Immunologic - pharmacology Animals Biological and medical sciences Galactosylceramides - chemical synthesis Galactosylceramides - pharmacology Humans Immunomodulators Interferon-gamma - biosynthesis Interleukin-4 - biosynthesis Lymphocyte Activation - drug effects Medical sciences Mice Natural Killer T-Cells - drug effects Pharmacology. Drug treatments Structure-Activity Relationship Tumor Necrosis Factor-alpha - biosynthesis |
| title | Focus on the Controversial Activation of Human iNKT Cells by 4-Deoxy Analogue of KRN7000 |
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