The interaction with tubulin of a series of stilbenes based on combretastatin A-4
A series of stilbenes, based on combretastatin A-4, were synthesised. A structure-activity study was carried out to characterise the interaction of these agents with tubulin. The substitution of small alkyl substituents for the 4'-methoxy group of combretastatin A-4 and the loss of the 3'-...
Gespeichert in:
| Veröffentlicht in: | British journal of cancer 1995-04, Vol.71 (4), p.705-711 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 711 |
|---|---|
| container_issue | 4 |
| container_start_page | 705 |
| container_title | British journal of cancer |
| container_volume | 71 |
| creator | Woods, JA Hadfield, JA Pettit, GR Fox, BW McGown, AT |
| description | A series of stilbenes, based on combretastatin A-4, were synthesised. A structure-activity study was carried out to characterise the interaction of these agents with tubulin. The substitution of small alkyl substituents for the 4'-methoxy group of combretastatin A-4 and the loss of the 3'-hydroxyl group does not have a major effect on the interaction with tubulin. trans-Stilbenes were shown to bind tubulin, but do not inhibit microtubule assembly. This work, together with previous studies, has been used to propose an idealised structure for a tubulin-binding agent of this type. |
| doi_str_mv | 10.1038/bjc.1995.138 |
| format | Article |
| fullrecord | <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2033763</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>7710932</sourcerecordid><originalsourceid>FETCH-LOGICAL-c471t-44ca8f04e6126233ac7c06204a2b6f6278c886411976b8368dec3542553db0d33</originalsourceid><addsrcrecordid>eNp1kEtLAzEURoMoWh87t8IsXDo1r0kyG6EUX1AQQdchyWRsyjRTkozivzdDS9GFq-TynftdOABcIjhFkIhbvTJTVNfVFBFxACaoIrhEAvNDMIEQ8hLWGJ6A0xhXeayh4MfgmHMEa4In4PVtaQvnkw3KJNf74sulZZEGPXTOF31bqCLa4Gwc_zG5TlufB62ibYqMm36tg00qJpXywqyk5-CoVV20F7v3DLw_3L_Nn8rFy-PzfLYoDeUolZQaJVpILUOYYUKU4QYyDKnCmrUMc2GEYBShmjMtCBONNaSiuKpIo2FDyBm42_ZuBr22jbE-BdXJTXBrFb5lr5z8m3i3lB_9p8SQEM7GgpttgQl9jMG2-10E5WhWZrNyNCuz2Yxf_b63h3cqc369y1U0qmuD8sbFPUYo55SxjJVbLObEf9ggV_0QfDb139liy3uVhmD3fRkamRH5ATGLmto</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>The interaction with tubulin of a series of stilbenes based on combretastatin A-4</title><source>MEDLINE</source><source>Nature</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><creator>Woods, JA ; Hadfield, JA ; Pettit, GR ; Fox, BW ; McGown, AT</creator><creatorcontrib>Woods, JA ; Hadfield, JA ; Pettit, GR ; Fox, BW ; McGown, AT</creatorcontrib><description>A series of stilbenes, based on combretastatin A-4, were synthesised. A structure-activity study was carried out to characterise the interaction of these agents with tubulin. The substitution of small alkyl substituents for the 4'-methoxy group of combretastatin A-4 and the loss of the 3'-hydroxyl group does not have a major effect on the interaction with tubulin. trans-Stilbenes were shown to bind tubulin, but do not inhibit microtubule assembly. This work, together with previous studies, has been used to propose an idealised structure for a tubulin-binding agent of this type.</description><identifier>ISSN: 0007-0920</identifier><identifier>EISSN: 1532-1827</identifier><identifier>DOI: 10.1038/bjc.1995.138</identifier><identifier>PMID: 7710932</identifier><identifier>CODEN: BJCAAI</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents, Phytogenic - chemistry ; Antineoplastic Agents, Phytogenic - toxicity ; Binding, Competitive ; Biological and medical sciences ; Biomedical and Life Sciences ; Biomedicine ; Cancer Research ; Cell Cycle - drug effects ; Drug Resistance ; Epidemiology ; experimental-oncology ; General aspects ; Leukemia P388 ; Medical sciences ; Mice ; Microtubules - drug effects ; Microtubules - ultrastructure ; Mitotic Index - drug effects ; Molecular Medicine ; Molecular Structure ; Oncology ; Pharmacology. Drug treatments ; Stilbenes - chemical synthesis ; Stilbenes - chemistry ; Stilbenes - toxicity ; Structure-Activity Relationship ; Thermodynamics ; Tubulin - chemistry ; Tumor Cells, Cultured</subject><ispartof>British journal of cancer, 1995-04, Vol.71 (4), p.705-711</ispartof><rights>Cancer Research Campaign 1995</rights><rights>1995 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c471t-44ca8f04e6126233ac7c06204a2b6f6278c886411976b8368dec3542553db0d33</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2033763/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC2033763/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,2727,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3477466$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/7710932$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Woods, JA</creatorcontrib><creatorcontrib>Hadfield, JA</creatorcontrib><creatorcontrib>Pettit, GR</creatorcontrib><creatorcontrib>Fox, BW</creatorcontrib><creatorcontrib>McGown, AT</creatorcontrib><title>The interaction with tubulin of a series of stilbenes based on combretastatin A-4</title><title>British journal of cancer</title><addtitle>Br J Cancer</addtitle><addtitle>Br J Cancer</addtitle><description>A series of stilbenes, based on combretastatin A-4, were synthesised. A structure-activity study was carried out to characterise the interaction of these agents with tubulin. The substitution of small alkyl substituents for the 4'-methoxy group of combretastatin A-4 and the loss of the 3'-hydroxyl group does not have a major effect on the interaction with tubulin. trans-Stilbenes were shown to bind tubulin, but do not inhibit microtubule assembly. This work, together with previous studies, has been used to propose an idealised structure for a tubulin-binding agent of this type.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents, Phytogenic - chemistry</subject><subject>Antineoplastic Agents, Phytogenic - toxicity</subject><subject>Binding, Competitive</subject><subject>Biological and medical sciences</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Cancer Research</subject><subject>Cell Cycle - drug effects</subject><subject>Drug Resistance</subject><subject>Epidemiology</subject><subject>experimental-oncology</subject><subject>General aspects</subject><subject>Leukemia P388</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Microtubules - drug effects</subject><subject>Microtubules - ultrastructure</subject><subject>Mitotic Index - drug effects</subject><subject>Molecular Medicine</subject><subject>Molecular Structure</subject><subject>Oncology</subject><subject>Pharmacology. Drug treatments</subject><subject>Stilbenes - chemical synthesis</subject><subject>Stilbenes - chemistry</subject><subject>Stilbenes - toxicity</subject><subject>Structure-Activity Relationship</subject><subject>Thermodynamics</subject><subject>Tubulin - chemistry</subject><subject>Tumor Cells, Cultured</subject><issn>0007-0920</issn><issn>1532-1827</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1995</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kEtLAzEURoMoWh87t8IsXDo1r0kyG6EUX1AQQdchyWRsyjRTkozivzdDS9GFq-TynftdOABcIjhFkIhbvTJTVNfVFBFxACaoIrhEAvNDMIEQ8hLWGJ6A0xhXeayh4MfgmHMEa4In4PVtaQvnkw3KJNf74sulZZEGPXTOF31bqCLa4Gwc_zG5TlufB62ibYqMm36tg00qJpXywqyk5-CoVV20F7v3DLw_3L_Nn8rFy-PzfLYoDeUolZQaJVpILUOYYUKU4QYyDKnCmrUMc2GEYBShmjMtCBONNaSiuKpIo2FDyBm42_ZuBr22jbE-BdXJTXBrFb5lr5z8m3i3lB_9p8SQEM7GgpttgQl9jMG2-10E5WhWZrNyNCuz2Yxf_b63h3cqc369y1U0qmuD8sbFPUYo55SxjJVbLObEf9ggV_0QfDb139liy3uVhmD3fRkamRH5ATGLmto</recordid><startdate>19950401</startdate><enddate>19950401</enddate><creator>Woods, JA</creator><creator>Hadfield, JA</creator><creator>Pettit, GR</creator><creator>Fox, BW</creator><creator>McGown, AT</creator><general>Nature Publishing Group UK</general><general>Nature Publishing Group</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>5PM</scope></search><sort><creationdate>19950401</creationdate><title>The interaction with tubulin of a series of stilbenes based on combretastatin A-4</title><author>Woods, JA ; Hadfield, JA ; Pettit, GR ; Fox, BW ; McGown, AT</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c471t-44ca8f04e6126233ac7c06204a2b6f6278c886411976b8368dec3542553db0d33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1995</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents, Phytogenic - chemistry</topic><topic>Antineoplastic Agents, Phytogenic - toxicity</topic><topic>Binding, Competitive</topic><topic>Biological and medical sciences</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Cancer Research</topic><topic>Cell Cycle - drug effects</topic><topic>Drug Resistance</topic><topic>Epidemiology</topic><topic>experimental-oncology</topic><topic>General aspects</topic><topic>Leukemia P388</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Microtubules - drug effects</topic><topic>Microtubules - ultrastructure</topic><topic>Mitotic Index - drug effects</topic><topic>Molecular Medicine</topic><topic>Molecular Structure</topic><topic>Oncology</topic><topic>Pharmacology. Drug treatments</topic><topic>Stilbenes - chemical synthesis</topic><topic>Stilbenes - chemistry</topic><topic>Stilbenes - toxicity</topic><topic>Structure-Activity Relationship</topic><topic>Thermodynamics</topic><topic>Tubulin - chemistry</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Woods, JA</creatorcontrib><creatorcontrib>Hadfield, JA</creatorcontrib><creatorcontrib>Pettit, GR</creatorcontrib><creatorcontrib>Fox, BW</creatorcontrib><creatorcontrib>McGown, AT</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>PubMed Central (Full Participant titles)</collection><jtitle>British journal of cancer</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Woods, JA</au><au>Hadfield, JA</au><au>Pettit, GR</au><au>Fox, BW</au><au>McGown, AT</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The interaction with tubulin of a series of stilbenes based on combretastatin A-4</atitle><jtitle>British journal of cancer</jtitle><stitle>Br J Cancer</stitle><addtitle>Br J Cancer</addtitle><date>1995-04-01</date><risdate>1995</risdate><volume>71</volume><issue>4</issue><spage>705</spage><epage>711</epage><pages>705-711</pages><issn>0007-0920</issn><eissn>1532-1827</eissn><coden>BJCAAI</coden><abstract>A series of stilbenes, based on combretastatin A-4, were synthesised. A structure-activity study was carried out to characterise the interaction of these agents with tubulin. The substitution of small alkyl substituents for the 4'-methoxy group of combretastatin A-4 and the loss of the 3'-hydroxyl group does not have a major effect on the interaction with tubulin. trans-Stilbenes were shown to bind tubulin, but do not inhibit microtubule assembly. This work, together with previous studies, has been used to propose an idealised structure for a tubulin-binding agent of this type.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>7710932</pmid><doi>10.1038/bjc.1995.138</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0007-0920 |
| ispartof | British journal of cancer, 1995-04, Vol.71 (4), p.705-711 |
| issn | 0007-0920 1532-1827 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_2033763 |
| source | MEDLINE; Nature; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Animals Antineoplastic agents Antineoplastic Agents, Phytogenic - chemistry Antineoplastic Agents, Phytogenic - toxicity Binding, Competitive Biological and medical sciences Biomedical and Life Sciences Biomedicine Cancer Research Cell Cycle - drug effects Drug Resistance Epidemiology experimental-oncology General aspects Leukemia P388 Medical sciences Mice Microtubules - drug effects Microtubules - ultrastructure Mitotic Index - drug effects Molecular Medicine Molecular Structure Oncology Pharmacology. Drug treatments Stilbenes - chemical synthesis Stilbenes - chemistry Stilbenes - toxicity Structure-Activity Relationship Thermodynamics Tubulin - chemistry Tumor Cells, Cultured |
| title | The interaction with tubulin of a series of stilbenes based on combretastatin A-4 |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T15%3A33%3A44IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=The%20interaction%20with%20tubulin%20of%20a%20series%20of%20stilbenes%20based%20on%20combretastatin%20A-4&rft.jtitle=British%20journal%20of%20cancer&rft.au=Woods,%20JA&rft.date=1995-04-01&rft.volume=71&rft.issue=4&rft.spage=705&rft.epage=711&rft.pages=705-711&rft.issn=0007-0920&rft.eissn=1532-1827&rft.coden=BJCAAI&rft_id=info:doi/10.1038/bjc.1995.138&rft_dat=%3Cpubmed_cross%3E7710932%3C/pubmed_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/7710932&rfr_iscdi=true |