Synthesis and Biological Evaluation of (−)-Laulimalide Analogues
The syntheses of five laulimalide analogues are described, incorporating modifications at the C16−C17-epoxide, the C20-alcohol, as well as the C1−C3-enoate of the parent natural product. The resultant analogues are active in drug-sensitive HeLa and MDA-MB-435 cell lines. Significantly, like laulimal...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2003-09, Vol.5 (19), p.3507-3509 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3509 |
|---|---|
| container_issue | 19 |
| container_start_page | 3507 |
| container_title | Organic letters |
| container_volume | 5 |
| creator | Wender, Paul A Hegde, Sayee G Hubbard, Robert D Zhang, Lei Mooberry, Susan L |
| description | The syntheses of five laulimalide analogues are described, incorporating modifications at the C16−C17-epoxide, the C20-alcohol, as well as the C1−C3-enoate of the parent natural product. The resultant analogues are active in drug-sensitive HeLa and MDA-MB-435 cell lines. Significantly, like laulimalide, these analogues are poor substrates for the drug transport protein P-glycoprotein (Pgp) and are thus effective against Taxol-resistant cell lines. |
| doi_str_mv | 10.1021/ol035339f |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_73643949</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>73643949</sourcerecordid><originalsourceid>FETCH-LOGICAL-a311t-f5dfd60110638600173adeb537517a2e559957f085039c132713831392b678003</originalsourceid><addsrcrecordid>eNptkM1KAzEUhYMoVqsLX0Bmo9jFaJLbJJNlW-oPFFyo65DOJJqSTupkRugbuPYRfRIjLXXj6l4uH-ecexA6I_iaYEpugsfAAKTdQ0eEUcgFZnR_t3PcQ8cxLjAm6SIPUY9QyQUQcoTGT-u6fTPRxUzXVTZ2wYdXV2qfTT-073TrQp0Fm119f34N8pnuvFtq7yqTjWqd0M7EE3RgtY_mdDv76OV2-jy5z2ePdw-T0SzXyanNLatsxVMEzKHgKYsAXZk5A8GI0NQwJiUTFhcMgywJUEGgAAKSzrkoMIY-utzorprwnnxbtXSxNN7r2oQuKgF8CHIoEzjYgGUTYmyMVasmpW7WimD1W5jaFZbY861oN1-a6o_cNpSAiw2gy6gWoWvS2_EfoR8qE29-</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>73643949</pqid></control><display><type>article</type><title>Synthesis and Biological Evaluation of (−)-Laulimalide Analogues</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Wender, Paul A ; Hegde, Sayee G ; Hubbard, Robert D ; Zhang, Lei ; Mooberry, Susan L</creator><creatorcontrib>Wender, Paul A ; Hegde, Sayee G ; Hubbard, Robert D ; Zhang, Lei ; Mooberry, Susan L</creatorcontrib><description>The syntheses of five laulimalide analogues are described, incorporating modifications at the C16−C17-epoxide, the C20-alcohol, as well as the C1−C3-enoate of the parent natural product. The resultant analogues are active in drug-sensitive HeLa and MDA-MB-435 cell lines. Significantly, like laulimalide, these analogues are poor substrates for the drug transport protein P-glycoprotein (Pgp) and are thus effective against Taxol-resistant cell lines.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol035339f</identifier><identifier>PMID: 12967311</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; ATP-Binding Cassette, Sub-Family B, Member 1 - metabolism ; Cell Line, Tumor - drug effects ; Drug Resistance, Neoplasm ; Drug Screening Assays, Antitumor ; Epoxy Compounds - chemistry ; HeLa Cells - drug effects ; Humans ; Macrolides ; Molecular Structure ; Stereoisomerism ; Taxoids - chemical synthesis ; Taxoids - metabolism ; Taxoids - pharmacology</subject><ispartof>Organic letters, 2003-09, Vol.5 (19), p.3507-3509</ispartof><rights>Copyright © 2003 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a311t-f5dfd60110638600173adeb537517a2e559957f085039c132713831392b678003</citedby><cites>FETCH-LOGICAL-a311t-f5dfd60110638600173adeb537517a2e559957f085039c132713831392b678003</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/ol035339f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol035339f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12967311$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wender, Paul A</creatorcontrib><creatorcontrib>Hegde, Sayee G</creatorcontrib><creatorcontrib>Hubbard, Robert D</creatorcontrib><creatorcontrib>Zhang, Lei</creatorcontrib><creatorcontrib>Mooberry, Susan L</creatorcontrib><title>Synthesis and Biological Evaluation of (−)-Laulimalide Analogues</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The syntheses of five laulimalide analogues are described, incorporating modifications at the C16−C17-epoxide, the C20-alcohol, as well as the C1−C3-enoate of the parent natural product. The resultant analogues are active in drug-sensitive HeLa and MDA-MB-435 cell lines. Significantly, like laulimalide, these analogues are poor substrates for the drug transport protein P-glycoprotein (Pgp) and are thus effective against Taxol-resistant cell lines.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>ATP-Binding Cassette, Sub-Family B, Member 1 - metabolism</subject><subject>Cell Line, Tumor - drug effects</subject><subject>Drug Resistance, Neoplasm</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Epoxy Compounds - chemistry</subject><subject>HeLa Cells - drug effects</subject><subject>Humans</subject><subject>Macrolides</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><subject>Taxoids - chemical synthesis</subject><subject>Taxoids - metabolism</subject><subject>Taxoids - pharmacology</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1KAzEUhYMoVqsLX0Bmo9jFaJLbJJNlW-oPFFyo65DOJJqSTupkRugbuPYRfRIjLXXj6l4uH-ecexA6I_iaYEpugsfAAKTdQ0eEUcgFZnR_t3PcQ8cxLjAm6SIPUY9QyQUQcoTGT-u6fTPRxUzXVTZ2wYdXV2qfTT-073TrQp0Fm119f34N8pnuvFtq7yqTjWqd0M7EE3RgtY_mdDv76OV2-jy5z2ePdw-T0SzXyanNLatsxVMEzKHgKYsAXZk5A8GI0NQwJiUTFhcMgywJUEGgAAKSzrkoMIY-utzorprwnnxbtXSxNN7r2oQuKgF8CHIoEzjYgGUTYmyMVasmpW7WimD1W5jaFZbY861oN1-a6o_cNpSAiw2gy6gWoWvS2_EfoR8qE29-</recordid><startdate>20030918</startdate><enddate>20030918</enddate><creator>Wender, Paul A</creator><creator>Hegde, Sayee G</creator><creator>Hubbard, Robert D</creator><creator>Zhang, Lei</creator><creator>Mooberry, Susan L</creator><general>American Chemical Society</general><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>20030918</creationdate><title>Synthesis and Biological Evaluation of (−)-Laulimalide Analogues</title><author>Wender, Paul A ; Hegde, Sayee G ; Hubbard, Robert D ; Zhang, Lei ; Mooberry, Susan L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a311t-f5dfd60110638600173adeb537517a2e559957f085039c132713831392b678003</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>ATP-Binding Cassette, Sub-Family B, Member 1 - metabolism</topic><topic>Cell Line, Tumor - drug effects</topic><topic>Drug Resistance, Neoplasm</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Epoxy Compounds - chemistry</topic><topic>HeLa Cells - drug effects</topic><topic>Humans</topic><topic>Macrolides</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><topic>Taxoids - chemical synthesis</topic><topic>Taxoids - metabolism</topic><topic>Taxoids - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wender, Paul A</creatorcontrib><creatorcontrib>Hegde, Sayee G</creatorcontrib><creatorcontrib>Hubbard, Robert D</creatorcontrib><creatorcontrib>Zhang, Lei</creatorcontrib><creatorcontrib>Mooberry, Susan L</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wender, Paul A</au><au>Hegde, Sayee G</au><au>Hubbard, Robert D</au><au>Zhang, Lei</au><au>Mooberry, Susan L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Evaluation of (−)-Laulimalide Analogues</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2003-09-18</date><risdate>2003</risdate><volume>5</volume><issue>19</issue><spage>3507</spage><epage>3509</epage><pages>3507-3509</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The syntheses of five laulimalide analogues are described, incorporating modifications at the C16−C17-epoxide, the C20-alcohol, as well as the C1−C3-enoate of the parent natural product. The resultant analogues are active in drug-sensitive HeLa and MDA-MB-435 cell lines. Significantly, like laulimalide, these analogues are poor substrates for the drug transport protein P-glycoprotein (Pgp) and are thus effective against Taxol-resistant cell lines.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>12967311</pmid><doi>10.1021/ol035339f</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2003-09, Vol.5 (19), p.3507-3509 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_73643949 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology ATP-Binding Cassette, Sub-Family B, Member 1 - metabolism Cell Line, Tumor - drug effects Drug Resistance, Neoplasm Drug Screening Assays, Antitumor Epoxy Compounds - chemistry HeLa Cells - drug effects Humans Macrolides Molecular Structure Stereoisomerism Taxoids - chemical synthesis Taxoids - metabolism Taxoids - pharmacology |
| title | Synthesis and Biological Evaluation of (−)-Laulimalide Analogues |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-01T22%3A21%3A20IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20Biological%20Evaluation%20of%20(%E2%88%92)-Laulimalide%20Analogues&rft.jtitle=Organic%20letters&rft.au=Wender,%20Paul%20A&rft.date=2003-09-18&rft.volume=5&rft.issue=19&rft.spage=3507&rft.epage=3509&rft.pages=3507-3509&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol035339f&rft_dat=%3Cproquest_cross%3E73643949%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=73643949&rft_id=info:pmid/12967311&rfr_iscdi=true |