Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice
Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2- [N-((R)-2- hydroxytetracosanoyl)-amino]- 1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relati...
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| Veröffentlicht in: | Journal of medicinal chemistry 1995-06, Vol.38 (12), p.2176-2187 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 38 |
| creator | Morita, Masahiro Motoki, Kazuhiro Akimoto, Kohji Natori, Takenori Sakai, Teruyuki Sawa, Eiji Yamaji, Kazuo Koezuka, Yasuhiko Kobayashi, Eiichi Fukushima, Hideaki |
| description | Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2- [N-((R)-2- hydroxytetracosanoyl)-amino]- 1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(alpha-D- galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol , was selected as a candidate for clinical application. |
| doi_str_mv | 10.1021/jm00012a018 |
| format | Article |
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Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(alpha-D- galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol , was selected as a candidate for clinical application.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00012a018</identifier><identifier>PMID: 7783149</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Division - drug effects ; Drug Screening Assays, Antitumor ; Female ; Fetal Blood ; Galactosylceramides - chemistry ; Galactosylceramides - pharmacology ; General aspects ; Humans ; Lymphocytes - cytology ; Lymphocytes - drug effects ; Medical sciences ; Melanoma, Experimental - pathology ; Mice ; Mice, Inbred BALB C ; Mice, Inbred C57BL ; Pharmacology. Drug treatments ; Porifera - chemistry ; Spleen - cytology ; Spleen - drug effects ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1995-06, Vol.38 (12), p.2176-2187</ispartof><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a449t-6ee158521a6d4f704ad5a7af935614a30444dc73a93bdaf2da50c9ca0732ba9d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00012a018$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00012a018$$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=3570866$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7783149$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Morita, Masahiro</creatorcontrib><creatorcontrib>Motoki, Kazuhiro</creatorcontrib><creatorcontrib>Akimoto, Kohji</creatorcontrib><creatorcontrib>Natori, Takenori</creatorcontrib><creatorcontrib>Sakai, Teruyuki</creatorcontrib><creatorcontrib>Sawa, Eiji</creatorcontrib><creatorcontrib>Yamaji, Kazuo</creatorcontrib><creatorcontrib>Koezuka, Yasuhiko</creatorcontrib><creatorcontrib>Kobayashi, Eiichi</creatorcontrib><creatorcontrib>Fukushima, Hideaki</creatorcontrib><title>Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2- [N-((R)-2- hydroxytetracosanoyl)-amino]- 1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(alpha-D- galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol , was selected as a candidate for clinical application.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Female</subject><subject>Fetal Blood</subject><subject>Galactosylceramides - chemistry</subject><subject>Galactosylceramides - pharmacology</subject><subject>General aspects</subject><subject>Humans</subject><subject>Lymphocytes - cytology</subject><subject>Lymphocytes - drug effects</subject><subject>Medical sciences</subject><subject>Melanoma, Experimental - pathology</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Mice, Inbred C57BL</subject><subject>Pharmacology. Drug treatments</subject><subject>Porifera - chemistry</subject><subject>Spleen - cytology</subject><subject>Spleen - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EtvEzEUBWALUZW0sGKNNAsEi8rh-j2zbCtoKgWBSBFL68bjaR3mEWxP1fx7pkoUsWB1F-fT0dUh5C2DOQPOPm06AGAcgZUvyIwpDlSWIF-SGQDnlGsuXpGzlDYTE4yLU3JqTCmYrGbk1yrH0eUxenrpcngMeVf88C3mMPTpIWyLoSnm2G4fcE5vsEWXh7RrnY_YhdqnAu8x9CkXV0zTK48x9PfF1-D8a3LSYJv8m8M9Jz-_fL67XtDlt5vb68slRSmrTLX3TJWKM9S1bAxIrBUabCqhNJMoQEpZOyOwEusaG16jAlc5BCP4GqtanJMP-95tHP6MPmXbheR822LvhzFZY4QwGvgEL_bQxSGl6Bu7jaHDuLMM7POM9p8ZJ_3uUDuuO18f7WG3KX9_yDE5bJuIvQvpyIQyUGo9MbpnIWX_dIwx_rbaCKPs3feVXejVUlWLlX32H_ceXbKbYYz9tN1_H_wLeBeVCA</recordid><startdate>19950601</startdate><enddate>19950601</enddate><creator>Morita, Masahiro</creator><creator>Motoki, Kazuhiro</creator><creator>Akimoto, Kohji</creator><creator>Natori, Takenori</creator><creator>Sakai, Teruyuki</creator><creator>Sawa, Eiji</creator><creator>Yamaji, Kazuo</creator><creator>Koezuka, Yasuhiko</creator><creator>Kobayashi, Eiichi</creator><creator>Fukushima, Hideaki</creator><general>American Chemical Society</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>19950601</creationdate><title>Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice</title><author>Morita, Masahiro ; Motoki, Kazuhiro ; Akimoto, Kohji ; Natori, Takenori ; Sakai, Teruyuki ; Sawa, Eiji ; Yamaji, Kazuo ; Koezuka, Yasuhiko ; Kobayashi, Eiichi ; Fukushima, Hideaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a449t-6ee158521a6d4f704ad5a7af935614a30444dc73a93bdaf2da50c9ca0732ba9d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Female</topic><topic>Fetal Blood</topic><topic>Galactosylceramides - chemistry</topic><topic>Galactosylceramides - pharmacology</topic><topic>General aspects</topic><topic>Humans</topic><topic>Lymphocytes - cytology</topic><topic>Lymphocytes - drug effects</topic><topic>Medical sciences</topic><topic>Melanoma, Experimental - pathology</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Mice, Inbred C57BL</topic><topic>Pharmacology. Drug treatments</topic><topic>Porifera - chemistry</topic><topic>Spleen - cytology</topic><topic>Spleen - drug effects</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Morita, Masahiro</creatorcontrib><creatorcontrib>Motoki, Kazuhiro</creatorcontrib><creatorcontrib>Akimoto, Kohji</creatorcontrib><creatorcontrib>Natori, Takenori</creatorcontrib><creatorcontrib>Sakai, Teruyuki</creatorcontrib><creatorcontrib>Sawa, Eiji</creatorcontrib><creatorcontrib>Yamaji, Kazuo</creatorcontrib><creatorcontrib>Koezuka, Yasuhiko</creatorcontrib><creatorcontrib>Kobayashi, Eiichi</creatorcontrib><creatorcontrib>Fukushima, Hideaki</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 medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Morita, Masahiro</au><au>Motoki, Kazuhiro</au><au>Akimoto, Kohji</au><au>Natori, Takenori</au><au>Sakai, Teruyuki</au><au>Sawa, Eiji</au><au>Yamaji, Kazuo</au><au>Koezuka, Yasuhiko</au><au>Kobayashi, Eiichi</au><au>Fukushima, Hideaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1995-06-01</date><risdate>1995</risdate><volume>38</volume><issue>12</issue><spage>2176</spage><epage>2187</epage><pages>2176-2187</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Agelasphin-9b, (2S,3S,4R)-1-O-(alpha-D-galactopyranosyl)-16-methyl-2- [N-((R)-2- hydroxytetracosanoyl)-amino]- 1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(alpha-D- galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol , was selected as a candidate for clinical application.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>7783149</pmid><doi>10.1021/jm00012a018</doi><tpages>12</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1995-06, Vol.38 (12), p.2176-2187 |
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| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Cell Division - drug effects Drug Screening Assays, Antitumor Female Fetal Blood Galactosylceramides - chemistry Galactosylceramides - pharmacology General aspects Humans Lymphocytes - cytology Lymphocytes - drug effects Medical sciences Melanoma, Experimental - pathology Mice Mice, Inbred BALB C Mice, Inbred C57BL Pharmacology. Drug treatments Porifera - chemistry Spleen - cytology Spleen - drug effects Structure-Activity Relationship |
| title | Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice |
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