Synthesis of chiral hydroxylated enones as potential anti-tumor agents
A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2012-12, Vol.22 (24), p.7562-7565 |
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| container_end_page | 7565 |
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| container_issue | 24 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Shing, Tony K.M. Wu, Ho T. Kwok, H.F. Lau, Clara B.S. |
| description | A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines. |
| doi_str_mv | 10.1016/j.bmcl.2012.10.026 |
| format | Article |
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The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.10.026</identifier><identifier>PMID: 23102892</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anti-tumor agents ; anticarcinogenic activity ; antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antitumor agents ; Aromatics ; Biological and medical sciences ; Cancer ; Cell Proliferation - drug effects ; chemistry ; COTC analogues ; Cyclohexanones - chemical synthesis ; Cyclohexanones - chemistry ; Cyclohexanones - pharmacology ; Cytotoxicity ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Ethers ; Hep G2 Cells ; HL-60 Cells ; Humans ; Hydroxylated enones ; Hydroxylation ; Inversion ; Medical sciences ; Molecular Structure ; Pharmacology. 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All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c443t-2954f2ba87ca67497220244033594fa31e005e0c80315b7056acd241c050ac833</citedby><cites>FETCH-LOGICAL-c443t-2954f2ba87ca67497220244033594fa31e005e0c80315b7056acd241c050ac833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2012.10.026$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26727655$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23102892$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shing, Tony K.M.</creatorcontrib><creatorcontrib>Wu, Ho T.</creatorcontrib><creatorcontrib>Kwok, H.F.</creatorcontrib><creatorcontrib>Lau, Clara B.S.</creatorcontrib><title>Synthesis of chiral hydroxylated enones as potential anti-tumor agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.</description><subject>Anti-tumor agents</subject><subject>anticarcinogenic activity</subject><subject>antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antitumor agents</subject><subject>Aromatics</subject><subject>Biological and medical sciences</subject><subject>Cancer</subject><subject>Cell Proliferation - drug effects</subject><subject>chemistry</subject><subject>COTC analogues</subject><subject>Cyclohexanones - chemical synthesis</subject><subject>Cyclohexanones - chemistry</subject><subject>Cyclohexanones - pharmacology</subject><subject>Cytotoxicity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Ethers</subject><subject>Hep G2 Cells</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Hydroxylated enones</subject><subject>Hydroxylation</subject><subject>Inversion</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Selective cytotoxicity</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><subject>Tumor cell lines</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFq3DAQhkVpabZpX6CHxJdAL96ORiPZhl5CSJpCoIc00JvQynJWi21tJG_pvn1ldtvcQk8DP9_8Gj4x9pHDkgNXnzfL1WD7JQLHHCwB1Su24KSoFATyNVtAo6CsG_p5wt6ltAHgBERv2QkKDlg3uGA39_txWrvkUxG6wq59NH2x3rcx_N73ZnJt4cYwulSYVGzD5MbJZ8DkUU67IcTCPOYsvWdvOtMn9-E4T9nDzfWPq9vy7vvXb1eXd6UlElOJjaQOV6aurFEVNRUiIBEIIRvqjOAOQDqwNQguVxVIZWyLxC1IMLYW4pR9OvRuY3jauTTpwSfr-t6MLuyS5lhhJaBp6D9QBKEIVZ1RPKA2hpSi6_Q2-sHEveagZ9V6o2fVelY9Z1l1Xjo79u9Wg2v_rfx1m4GLI2CSNX0XzWh9euZUPlVJmbnzA9eZoM1jzMzDfX5J5v8SnHBu-nIgXFb7y7uok_VutK710dlJt8G_dOkfwzijdA</recordid><startdate>20121215</startdate><enddate>20121215</enddate><creator>Shing, Tony K.M.</creator><creator>Wu, Ho T.</creator><creator>Kwok, H.F.</creator><creator>Lau, Clara B.S.</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20121215</creationdate><title>Synthesis of chiral hydroxylated enones as potential anti-tumor agents</title><author>Shing, Tony K.M. ; Wu, Ho T. ; Kwok, H.F. ; Lau, Clara B.S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c443t-2954f2ba87ca67497220244033594fa31e005e0c80315b7056acd241c050ac833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anti-tumor agents</topic><topic>anticarcinogenic activity</topic><topic>antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antitumor agents</topic><topic>Aromatics</topic><topic>Biological and medical sciences</topic><topic>Cancer</topic><topic>Cell Proliferation - drug effects</topic><topic>chemistry</topic><topic>COTC analogues</topic><topic>Cyclohexanones - chemical synthesis</topic><topic>Cyclohexanones - chemistry</topic><topic>Cyclohexanones - pharmacology</topic><topic>Cytotoxicity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Ethers</topic><topic>Hep G2 Cells</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Hydroxylated enones</topic><topic>Hydroxylation</topic><topic>Inversion</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Selective cytotoxicity</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><topic>Tumor cell lines</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shing, Tony K.M.</creatorcontrib><creatorcontrib>Wu, Ho T.</creatorcontrib><creatorcontrib>Kwok, H.F.</creatorcontrib><creatorcontrib>Lau, Clara B.S.</creatorcontrib><collection>AGRIS</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shing, Tony K.M.</au><au>Wu, Ho T.</au><au>Kwok, H.F.</au><au>Lau, Clara B.S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of chiral hydroxylated enones as potential anti-tumor agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-12-15</date><risdate>2012</risdate><volume>22</volume><issue>24</issue><spage>7562</spage><epage>7565</epage><pages>7562-7565</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>23102892</pmid><doi>10.1016/j.bmcl.2012.10.026</doi><tpages>4</tpages></addata></record> |
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| subjects | Anti-tumor agents anticarcinogenic activity antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antitumor agents Aromatics Biological and medical sciences Cancer Cell Proliferation - drug effects chemistry COTC analogues Cyclohexanones - chemical synthesis Cyclohexanones - chemistry Cyclohexanones - pharmacology Cytotoxicity Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Ethers Hep G2 Cells HL-60 Cells Humans Hydroxylated enones Hydroxylation Inversion Medical sciences Molecular Structure Pharmacology. Drug treatments Selective cytotoxicity Structure-Activity Relationship Synthesis Tumor cell lines |
| title | Synthesis of chiral hydroxylated enones as potential anti-tumor agents |
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