Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars
l-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4-guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroa...
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| Veröffentlicht in: | Journal of medicinal chemistry 1997-08, Vol.40 (16), p.2626-2633 |
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| container_title | Journal of medicinal chemistry |
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| creator | Nishimura, Yoshio Satoh, Takahiko Adachi, Hayamitsu Kondo, Shinichi Takeuchi, Tomio Azetaka, Masayuki Fukuyasu, Harumi Iizuka, Yumiko |
| description | l-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4-guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid (9 and 10, respectively), were synthesized from siastatin B (1), isolated from Streptomyces culture, by the intramolecular Michael addition of O-imidate to its α,β-unsaturated ester through cis oxiamination as a key step. Preincubation of B16 BL6 cells with these compounds inhibited invasion of the cells through reconstituted basement membranes. Pulmonary metastasis of B16 BL6 cells in mice was remarkably inhibited by pretreatment of the cells with these compounds in culture. |
| doi_str_mv | 10.1021/jm960627l |
| format | Article |
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Preincubation of B16 BL6 cells with these compounds inhibited invasion of the cells through reconstituted basement membranes. Pulmonary metastasis of B16 BL6 cells in mice was remarkably inhibited by pretreatment of the cells with these compounds in culture.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm960627l</identifier><identifier>PMID: 9258369</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Carcinogenesis, carcinogens and anticarcinogens ; Chemical agents ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; Iduronic Acid - analogs & derivatives ; Iduronic Acid - pharmacology ; Lung Neoplasms - secondary ; Medical sciences ; Mice ; Models, Chemical ; Neoplasm Metastasis - prevention & control ; Piperidines - chemistry ; Piperidines - pharmacology ; Structure-Activity Relationship ; Tumor Cells, Cultured ; Tumors</subject><ispartof>Journal of medicinal chemistry, 1997-08, Vol.40 (16), p.2626-2633</ispartof><rights>Copyright © 1997 American Chemical Society</rights><rights>1997 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a443t-455b612224e72b5abad1f603cd553260e1e4a6fac367f6d9bab60e475ea384cb3</citedby><cites>FETCH-LOGICAL-a443t-455b612224e72b5abad1f603cd553260e1e4a6fac367f6d9bab60e475ea384cb3</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/jm960627l$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm960627l$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2767466$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9258369$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nishimura, Yoshio</creatorcontrib><creatorcontrib>Satoh, Takahiko</creatorcontrib><creatorcontrib>Adachi, Hayamitsu</creatorcontrib><creatorcontrib>Kondo, Shinichi</creatorcontrib><creatorcontrib>Takeuchi, Tomio</creatorcontrib><creatorcontrib>Azetaka, Masayuki</creatorcontrib><creatorcontrib>Fukuyasu, Harumi</creatorcontrib><creatorcontrib>Iizuka, Yumiko</creatorcontrib><title>Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>l-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4-guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid (9 and 10, respectively), were synthesized from siastatin B (1), isolated from Streptomyces culture, by the intramolecular Michael addition of O-imidate to its α,β-unsaturated ester through cis oxiamination as a key step. Preincubation of B16 BL6 cells with these compounds inhibited invasion of the cells through reconstituted basement membranes. Pulmonary metastasis of B16 BL6 cells in mice was remarkably inhibited by pretreatment of the cells with these compounds in culture.</description><subject>Animals</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Carcinogenesis, carcinogens and anticarcinogens</subject><subject>Chemical agents</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Iduronic Acid - analogs & derivatives</subject><subject>Iduronic Acid - pharmacology</subject><subject>Lung Neoplasms - secondary</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Models, Chemical</subject><subject>Neoplasm Metastasis - prevention & control</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured</subject><subject>Tumors</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1vEzEQBmALgUpaeuAHIO0BKvVgsMdf2WMUaIlUWqSmXK1Zrxcc9iPYXtT8e7ZNlBOnkeZ9NBq9hLzl7CNnwD9tulIzDaZ9QWZcAaNyzuRLMmMMgIIG8ZqcprRhjAkO4oSclKDmQpcz8u1-1-dfPoVUYF8Xiz6HzmdMGXNwxcLl8DfkXTE0RUtX9RiH_nkdarrebX3B6S1ddaEf0vgTY3pDXjXYJn9-mGfk4erLevmV3txdr5aLG4pSikylUpXmACC9gUphhTVvNBOuVkqAZp57ibpBJ7RpdF1WWE1LaZRHMZeuEmfkYn93G4c_o0_ZdiE537bY-2FM1pTApAQxwcs9dHFIKfrGbmPoMO4sZ_apOnusbrLvDkfHqvP1UR66mvL3hxyTw7aJ2LuQjgyMNlLridE9Cyn7x2OM8bfVRhhl19_vrb76MV9_hqV98h_2Hl2ym2GM_dTcf977B7QWkEQ</recordid><startdate>19970801</startdate><enddate>19970801</enddate><creator>Nishimura, Yoshio</creator><creator>Satoh, Takahiko</creator><creator>Adachi, Hayamitsu</creator><creator>Kondo, Shinichi</creator><creator>Takeuchi, Tomio</creator><creator>Azetaka, Masayuki</creator><creator>Fukuyasu, Harumi</creator><creator>Iizuka, Yumiko</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>19970801</creationdate><title>Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars</title><author>Nishimura, Yoshio ; Satoh, Takahiko ; Adachi, Hayamitsu ; Kondo, Shinichi ; Takeuchi, Tomio ; Azetaka, Masayuki ; Fukuyasu, Harumi ; Iizuka, Yumiko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a443t-455b612224e72b5abad1f603cd553260e1e4a6fac367f6d9bab60e475ea384cb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Animals</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Carcinogenesis, carcinogens and anticarcinogens</topic><topic>Chemical agents</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Iduronic Acid - analogs & derivatives</topic><topic>Iduronic Acid - pharmacology</topic><topic>Lung Neoplasms - secondary</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Models, Chemical</topic><topic>Neoplasm Metastasis - prevention & control</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><topic>Tumors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nishimura, Yoshio</creatorcontrib><creatorcontrib>Satoh, Takahiko</creatorcontrib><creatorcontrib>Adachi, Hayamitsu</creatorcontrib><creatorcontrib>Kondo, Shinichi</creatorcontrib><creatorcontrib>Takeuchi, Tomio</creatorcontrib><creatorcontrib>Azetaka, Masayuki</creatorcontrib><creatorcontrib>Fukuyasu, Harumi</creatorcontrib><creatorcontrib>Iizuka, Yumiko</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>Nishimura, Yoshio</au><au>Satoh, Takahiko</au><au>Adachi, Hayamitsu</au><au>Kondo, Shinichi</au><au>Takeuchi, Tomio</au><au>Azetaka, Masayuki</au><au>Fukuyasu, Harumi</au><au>Iizuka, Yumiko</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1997-08-01</date><risdate>1997</risdate><volume>40</volume><issue>16</issue><spage>2626</spage><epage>2633</epage><pages>2626-2633</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>l-Iduronic acid-type 1-N-iminosugars, (3R,4S,5R,6R)- and (3R,4S,5S,6R)-6-acetamido-4-amino-5-hydroxypiperidine-3-carboxylic acid (6 and 7, respectively), (3R,4S,5R,6R)-6-acetamido-4-guanidino-5-hydroxypiperidine-3-carboxylic acid (8), and (3R,4S,5R,6R)-4-amino- and -guanidino-5-hydroxy-6-(trifluoroacetamido)piperidine-3-carboxylic acid (9 and 10, respectively), were synthesized from siastatin B (1), isolated from Streptomyces culture, by the intramolecular Michael addition of O-imidate to its α,β-unsaturated ester through cis oxiamination as a key step. Preincubation of B16 BL6 cells with these compounds inhibited invasion of the cells through reconstituted basement membranes. Pulmonary metastasis of B16 BL6 cells in mice was remarkably inhibited by pretreatment of the cells with these compounds in culture.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>9258369</pmid><doi>10.1021/jm960627l</doi><tpages>8</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1997-08, Vol.40 (16), p.2626-2633 |
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| subjects | Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Biological and medical sciences Carcinogenesis, carcinogens and anticarcinogens Chemical agents Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Iduronic Acid - analogs & derivatives Iduronic Acid - pharmacology Lung Neoplasms - secondary Medical sciences Mice Models, Chemical Neoplasm Metastasis - prevention & control Piperidines - chemistry Piperidines - pharmacology Structure-Activity Relationship Tumor Cells, Cultured Tumors |
| title | Synthesis and Antimetastatic Activity of l-Iduronic Acid-Type 1-N-Iminosugars |
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