Structure–Activity Relationships of C-17 Cyano-Substituted Estratrienes as Anticancer Agents
The synthesis, SAR, and preclinical evaluation of 17-cyanated 2-substituted estra-1,3,5(10)-trienes as anticancer agents are discussed. 2-Methoxy-17β-cyanomethylestra-1,3,5(10)-trien-3-ol (14), but not the related 2-ethyl derivative 7, and the related 3-O-sulfamates 8 and 15 display potent antiproli...
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| Veröffentlicht in: | Journal of medicinal chemistry 2008-03, Vol.51 (5), p.1295-1308 |
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| creator | Leese, Mathew P Jourdan, Fabrice L Gaukroger, Keira Mahon, Mary F Newman, Simon P Foster, Paul A Stengel, Chloe Regis-Lydi, Sandra Ferrandis, Eric Fiore, Anna Di De Simone, Giuseppina Supuran, Claudiu T Purohit, Atul Reed, Michael J Potter, Barry V. L |
| description | The synthesis, SAR, and preclinical evaluation of 17-cyanated 2-substituted estra-1,3,5(10)-trienes as anticancer agents are discussed. 2-Methoxy-17β-cyanomethylestra-1,3,5(10)-trien-3-ol (14), but not the related 2-ethyl derivative 7, and the related 3-O-sulfamates 8 and 15 display potent antiproliferative effects (MCF-7 GI50 300, 60 and 70 nM, respectively) against human cancer cells in vitro. Investigation of the SAR reveals that a sterically unhindered hydrogen bond acceptor attached to C-17 is most likely key to the enhanced activity. Compound 8 displayed significant in vitro antiangiogenic activity, and its ability to act as a microtubule disruptor was confirmed. Inhibitory activity of the sulfamate derivatives against steroid sulfatase and carbonic anhydrase II (hCAII) was also observed, and the interaction between 15 and hCAII was investigated by protein crystallography. The potential of these multimechanism anticancer agents was confirmed in vivo, with promising activity observed for both 14 and 15 in an athymic nude mouse MDA-MB-231 human breast cancer xenograft model. |
| doi_str_mv | 10.1021/jm701319c |
| format | Article |
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L</creator><creatorcontrib>Leese, Mathew P ; Jourdan, Fabrice L ; Gaukroger, Keira ; Mahon, Mary F ; Newman, Simon P ; Foster, Paul A ; Stengel, Chloe ; Regis-Lydi, Sandra ; Ferrandis, Eric ; Fiore, Anna Di ; De Simone, Giuseppina ; Supuran, Claudiu T ; Purohit, Atul ; Reed, Michael J ; Potter, Barry V. L</creatorcontrib><description>The synthesis, SAR, and preclinical evaluation of 17-cyanated 2-substituted estra-1,3,5(10)-trienes as anticancer agents are discussed. 2-Methoxy-17β-cyanomethylestra-1,3,5(10)-trien-3-ol (14), but not the related 2-ethyl derivative 7, and the related 3-O-sulfamates 8 and 15 display potent antiproliferative effects (MCF-7 GI50 300, 60 and 70 nM, respectively) against human cancer cells in vitro. Investigation of the SAR reveals that a sterically unhindered hydrogen bond acceptor attached to C-17 is most likely key to the enhanced activity. Compound 8 displayed significant in vitro antiangiogenic activity, and its ability to act as a microtubule disruptor was confirmed. Inhibitory activity of the sulfamate derivatives against steroid sulfatase and carbonic anhydrase II (hCAII) was also observed, and the interaction between 15 and hCAII was investigated by protein crystallography. The potential of these multimechanism anticancer agents was confirmed in vivo, with promising activity observed for both 14 and 15 in an athymic nude mouse MDA-MB-231 human breast cancer xenograft model.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm701319c</identifier><identifier>PMID: 18260615</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Angiogenesis Inhibitors - chemical synthesis ; Angiogenesis Inhibitors - chemistry ; Angiogenesis Inhibitors - pharmacology ; Animals ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Carbonic Anhydrase II - metabolism ; Carbonic Anhydrase Inhibitors - chemical synthesis ; Carbonic Anhydrase Inhibitors - chemistry ; Carbonic Anhydrase Inhibitors - pharmacology ; Cell Line, Tumor ; Crystallography, X-Ray ; Drug Screening Assays, Antitumor ; Estradiol - analogs & derivatives ; Estradiol - chemical synthesis ; Estradiol - chemistry ; Estradiol - pharmacology ; Estrenes - chemical synthesis ; Estrenes - chemistry ; Estrenes - pharmacology ; Female ; General aspects ; Humans ; Medical sciences ; Mice ; Mice, Nude ; Models, Molecular ; Molecular Conformation ; Neoplasm Transplantation ; Nitriles - chemical synthesis ; Nitriles - chemistry ; Nitriles - pharmacology ; Pharmacology. Drug treatments ; Stereoisomerism ; Steryl-Sulfatase - antagonists & inhibitors ; Structure-Activity Relationship ; Transplantation, Heterologous ; Tubulin Modulators - chemical synthesis ; Tubulin Modulators - chemistry ; Tubulin Modulators - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2008-03, Vol.51 (5), p.1295-1308</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a447t-aeca6f6342f2385a42718311c22972989d24e6677524e5f3509ae92d0d13d6123</citedby><cites>FETCH-LOGICAL-a447t-aeca6f6342f2385a42718311c22972989d24e6677524e5f3509ae92d0d13d6123</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/jm701319c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm701319c$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20174846$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18260615$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Leese, Mathew P</creatorcontrib><creatorcontrib>Jourdan, Fabrice L</creatorcontrib><creatorcontrib>Gaukroger, Keira</creatorcontrib><creatorcontrib>Mahon, Mary F</creatorcontrib><creatorcontrib>Newman, Simon P</creatorcontrib><creatorcontrib>Foster, Paul A</creatorcontrib><creatorcontrib>Stengel, Chloe</creatorcontrib><creatorcontrib>Regis-Lydi, Sandra</creatorcontrib><creatorcontrib>Ferrandis, Eric</creatorcontrib><creatorcontrib>Fiore, Anna Di</creatorcontrib><creatorcontrib>De Simone, Giuseppina</creatorcontrib><creatorcontrib>Supuran, Claudiu T</creatorcontrib><creatorcontrib>Purohit, Atul</creatorcontrib><creatorcontrib>Reed, Michael J</creatorcontrib><creatorcontrib>Potter, Barry V. L</creatorcontrib><title>Structure–Activity Relationships of C-17 Cyano-Substituted Estratrienes as Anticancer Agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The synthesis, SAR, and preclinical evaluation of 17-cyanated 2-substituted estra-1,3,5(10)-trienes as anticancer agents are discussed. 2-Methoxy-17β-cyanomethylestra-1,3,5(10)-trien-3-ol (14), but not the related 2-ethyl derivative 7, and the related 3-O-sulfamates 8 and 15 display potent antiproliferative effects (MCF-7 GI50 300, 60 and 70 nM, respectively) against human cancer cells in vitro. Investigation of the SAR reveals that a sterically unhindered hydrogen bond acceptor attached to C-17 is most likely key to the enhanced activity. Compound 8 displayed significant in vitro antiangiogenic activity, and its ability to act as a microtubule disruptor was confirmed. Inhibitory activity of the sulfamate derivatives against steroid sulfatase and carbonic anhydrase II (hCAII) was also observed, and the interaction between 15 and hCAII was investigated by protein crystallography. The potential of these multimechanism anticancer agents was confirmed in vivo, with promising activity observed for both 14 and 15 in an athymic nude mouse MDA-MB-231 human breast cancer xenograft model.</description><subject>Angiogenesis Inhibitors - chemical synthesis</subject><subject>Angiogenesis Inhibitors - chemistry</subject><subject>Angiogenesis Inhibitors - pharmacology</subject><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Carbonic Anhydrase II - metabolism</subject><subject>Carbonic Anhydrase Inhibitors - chemical synthesis</subject><subject>Carbonic Anhydrase Inhibitors - chemistry</subject><subject>Carbonic Anhydrase Inhibitors - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Crystallography, X-Ray</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Estradiol - analogs & derivatives</subject><subject>Estradiol - chemical synthesis</subject><subject>Estradiol - chemistry</subject><subject>Estradiol - pharmacology</subject><subject>Estrenes - chemical synthesis</subject><subject>Estrenes - chemistry</subject><subject>Estrenes - pharmacology</subject><subject>Female</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Nude</subject><subject>Models, Molecular</subject><subject>Molecular Conformation</subject><subject>Neoplasm Transplantation</subject><subject>Nitriles - chemical synthesis</subject><subject>Nitriles - chemistry</subject><subject>Nitriles - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Stereoisomerism</subject><subject>Steryl-Sulfatase - antagonists & inhibitors</subject><subject>Structure-Activity Relationship</subject><subject>Transplantation, Heterologous</subject><subject>Tubulin Modulators - chemical synthesis</subject><subject>Tubulin Modulators - chemistry</subject><subject>Tubulin Modulators - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9u00AQBvAVAtFQOPACyBeQOBh2Z__Zx8hqAdGqiJQrq-16DBscO-ysEbn1HfqGPAlGidILpznMT59mPsaeC_5GcBBv1xvLhRR1eMAWQgMvVcXVQ7bgHKAEA_KEPSFac86lAPmYnYgKDDdCL9jXVU5TyFPCP7d3y5Djr5h3xWfsfY7jQN_jloqxK5pS2KLZ-WEsV9MN5ZinjG1xRjn5nCIOSIWnYjnkGPwQMBXLbzhkesoedb4nfHaYp-zL-dl18768uHr3oVlelF4pm0uPwZvOSAUdyEp7BVZUUogAUFuoq7oFhcZYq-epO6l57bGGlrdCtmb-6ZS92udu0_hzQspuEylg3_sBx4mc5dLUWtoZvt7DkEaihJ3bprjxaecEd__KdMcyZ_viEDrdbLC9l4f2ZvDyADwF33dpfj3S0QEXVlXKzK7cu0gZfx_3Pv1wxkqr3fWnlbsE_dGcy8bBfa4P5NbjlIa5u_8c-BdhqJa8</recordid><startdate>20080313</startdate><enddate>20080313</enddate><creator>Leese, Mathew P</creator><creator>Jourdan, Fabrice L</creator><creator>Gaukroger, Keira</creator><creator>Mahon, Mary F</creator><creator>Newman, Simon P</creator><creator>Foster, Paul A</creator><creator>Stengel, Chloe</creator><creator>Regis-Lydi, Sandra</creator><creator>Ferrandis, Eric</creator><creator>Fiore, Anna Di</creator><creator>De Simone, Giuseppina</creator><creator>Supuran, Claudiu T</creator><creator>Purohit, Atul</creator><creator>Reed, Michael J</creator><creator>Potter, Barry V. L</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>20080313</creationdate><title>Structure–Activity Relationships of C-17 Cyano-Substituted Estratrienes as Anticancer Agents</title><author>Leese, Mathew P ; Jourdan, Fabrice L ; Gaukroger, Keira ; Mahon, Mary F ; Newman, Simon P ; Foster, Paul A ; Stengel, Chloe ; Regis-Lydi, Sandra ; Ferrandis, Eric ; Fiore, Anna Di ; De Simone, Giuseppina ; Supuran, Claudiu T ; Purohit, Atul ; Reed, Michael J ; Potter, Barry V. 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Drug treatments</topic><topic>Stereoisomerism</topic><topic>Steryl-Sulfatase - antagonists & inhibitors</topic><topic>Structure-Activity Relationship</topic><topic>Transplantation, Heterologous</topic><topic>Tubulin Modulators - chemical synthesis</topic><topic>Tubulin Modulators - chemistry</topic><topic>Tubulin Modulators - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Leese, Mathew P</creatorcontrib><creatorcontrib>Jourdan, Fabrice L</creatorcontrib><creatorcontrib>Gaukroger, Keira</creatorcontrib><creatorcontrib>Mahon, Mary F</creatorcontrib><creatorcontrib>Newman, Simon P</creatorcontrib><creatorcontrib>Foster, Paul A</creatorcontrib><creatorcontrib>Stengel, Chloe</creatorcontrib><creatorcontrib>Regis-Lydi, Sandra</creatorcontrib><creatorcontrib>Ferrandis, Eric</creatorcontrib><creatorcontrib>Fiore, Anna Di</creatorcontrib><creatorcontrib>De Simone, Giuseppina</creatorcontrib><creatorcontrib>Supuran, Claudiu T</creatorcontrib><creatorcontrib>Purohit, Atul</creatorcontrib><creatorcontrib>Reed, Michael J</creatorcontrib><creatorcontrib>Potter, Barry V. 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L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Structure–Activity Relationships of C-17 Cyano-Substituted Estratrienes as Anticancer Agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2008-03-13</date><risdate>2008</risdate><volume>51</volume><issue>5</issue><spage>1295</spage><epage>1308</epage><pages>1295-1308</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The synthesis, SAR, and preclinical evaluation of 17-cyanated 2-substituted estra-1,3,5(10)-trienes as anticancer agents are discussed. 2-Methoxy-17β-cyanomethylestra-1,3,5(10)-trien-3-ol (14), but not the related 2-ethyl derivative 7, and the related 3-O-sulfamates 8 and 15 display potent antiproliferative effects (MCF-7 GI50 300, 60 and 70 nM, respectively) against human cancer cells in vitro. Investigation of the SAR reveals that a sterically unhindered hydrogen bond acceptor attached to C-17 is most likely key to the enhanced activity. Compound 8 displayed significant in vitro antiangiogenic activity, and its ability to act as a microtubule disruptor was confirmed. Inhibitory activity of the sulfamate derivatives against steroid sulfatase and carbonic anhydrase II (hCAII) was also observed, and the interaction between 15 and hCAII was investigated by protein crystallography. The potential of these multimechanism anticancer agents was confirmed in vivo, with promising activity observed for both 14 and 15 in an athymic nude mouse MDA-MB-231 human breast cancer xenograft model.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18260615</pmid><doi>10.1021/jm701319c</doi><tpages>14</tpages></addata></record> |
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| subjects | Angiogenesis Inhibitors - chemical synthesis Angiogenesis Inhibitors - chemistry Angiogenesis Inhibitors - pharmacology Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Carbonic Anhydrase II - metabolism Carbonic Anhydrase Inhibitors - chemical synthesis Carbonic Anhydrase Inhibitors - chemistry Carbonic Anhydrase Inhibitors - pharmacology Cell Line, Tumor Crystallography, X-Ray Drug Screening Assays, Antitumor Estradiol - analogs & derivatives Estradiol - chemical synthesis Estradiol - chemistry Estradiol - pharmacology Estrenes - chemical synthesis Estrenes - chemistry Estrenes - pharmacology Female General aspects Humans Medical sciences Mice Mice, Nude Models, Molecular Molecular Conformation Neoplasm Transplantation Nitriles - chemical synthesis Nitriles - chemistry Nitriles - pharmacology Pharmacology. Drug treatments Stereoisomerism Steryl-Sulfatase - antagonists & inhibitors Structure-Activity Relationship Transplantation, Heterologous Tubulin Modulators - chemical synthesis Tubulin Modulators - chemistry Tubulin Modulators - pharmacology |
| title | Structure–Activity Relationships of C-17 Cyano-Substituted Estratrienes as Anticancer Agents |
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