Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents
A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil...
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| Veröffentlicht in: | European journal of medicinal chemistry 2013-11, Vol.69, p.159-166 |
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| container_title | European journal of medicinal chemistry |
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| creator | Dai, Ming Yuan, Xing Kang, Jian Zhu, Zhi-Jun Yue, Rong-Cai Yuan, Hu Chen, Bing-Yang Zhang, Wei-Dong Liu, Run-Hui Sun, Qing-Yan |
| description | A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil (5-Fu) on QGY-7703 and SMMC-7721 cells with IC50 values of 6.27 μM, 7.50 μM and 15.56 μM, 14.55 μM, respectively. Furthermore, compounds 6, 14, 16, and 29 exhibited much better selectivity toward the normal hepatic cell line QSG-7701 than 5-Fu. Additionally, compound 6 significantly induced cell apoptosis in QGY-7703 cells. Our findings suggested that these phenylxanthone derivatives may hold promise as chemotherapeutic agents for the treatment of human HCC.
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•Derivatives of phenyl substituted tetramethoxy xanthone were synthesized.•Compound 6 showed more potent activity against HCC cells than 5-Fu.•Compound 6 presented better cytotoxic selectivity.•The structure–activity relationships of compounds have been discussed. |
| doi_str_mv | 10.1016/j.ejmech.2013.08.020 |
| format | Article |
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•Derivatives of phenyl substituted tetramethoxy xanthone were synthesized.•Compound 6 showed more potent activity against HCC cells than 5-Fu.•Compound 6 presented better cytotoxic selectivity.•The structure–activity relationships of compounds have been discussed.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2013.08.020</identifier><identifier>PMID: 24013415</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>Anti-hepatoma ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Apoptosis - drug effects ; Carcinoma, Hepatocellular - drug therapy ; Carcinoma, Hepatocellular - pathology ; Cell Proliferation - drug effects ; Cytotoxic selectivity ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Hep G2 Cells ; Humans ; Liver Neoplasms - drug therapy ; Liver Neoplasms - pathology ; Molecular Structure ; Structure-Activity Relationship ; Tumor Cells, Cultured ; Xanthone ; Xanthones - chemical synthesis ; Xanthones - chemistry ; Xanthones - pharmacology</subject><ispartof>European journal of medicinal chemistry, 2013-11, Vol.69, p.159-166</ispartof><rights>2013 Elsevier Masson SAS</rights><rights>Copyright © 2013 Elsevier Masson SAS. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-cbf18ba62f23d1457f20d6eb6f723c5394eaa2bd1fe17a231c4d76fc864a623d3</citedby><cites>FETCH-LOGICAL-c362t-cbf18ba62f23d1457f20d6eb6f723c5394eaa2bd1fe17a231c4d76fc864a623d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2013.08.020$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24013415$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dai, Ming</creatorcontrib><creatorcontrib>Yuan, Xing</creatorcontrib><creatorcontrib>Kang, Jian</creatorcontrib><creatorcontrib>Zhu, Zhi-Jun</creatorcontrib><creatorcontrib>Yue, Rong-Cai</creatorcontrib><creatorcontrib>Yuan, Hu</creatorcontrib><creatorcontrib>Chen, Bing-Yang</creatorcontrib><creatorcontrib>Zhang, Wei-Dong</creatorcontrib><creatorcontrib>Liu, Run-Hui</creatorcontrib><creatorcontrib>Sun, Qing-Yan</creatorcontrib><title>Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil (5-Fu) on QGY-7703 and SMMC-7721 cells with IC50 values of 6.27 μM, 7.50 μM and 15.56 μM, 14.55 μM, respectively. Furthermore, compounds 6, 14, 16, and 29 exhibited much better selectivity toward the normal hepatic cell line QSG-7701 than 5-Fu. Additionally, compound 6 significantly induced cell apoptosis in QGY-7703 cells. Our findings suggested that these phenylxanthone derivatives may hold promise as chemotherapeutic agents for the treatment of human HCC.
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•Derivatives of phenyl substituted tetramethoxy xanthone were synthesized.•Compound 6 showed more potent activity against HCC cells than 5-Fu.•Compound 6 presented better cytotoxic selectivity.•The structure–activity relationships of compounds have been discussed.</description><subject>Anti-hepatoma</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis - drug effects</subject><subject>Carcinoma, Hepatocellular - drug therapy</subject><subject>Carcinoma, Hepatocellular - pathology</subject><subject>Cell Proliferation - drug effects</subject><subject>Cytotoxic selectivity</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Hep G2 Cells</subject><subject>Humans</subject><subject>Liver Neoplasms - drug therapy</subject><subject>Liver Neoplasms - pathology</subject><subject>Molecular Structure</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured</subject><subject>Xanthone</subject><subject>Xanthones - chemical synthesis</subject><subject>Xanthones - chemistry</subject><subject>Xanthones - pharmacology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1r3DAQhkVpaLZJ_0EpOvZiVxrJsnMplJB-QKCHJmchS6OsFttyLXmJ_321bNpjT8PA-7zDPIS856zmjKtPhxoPI9p9DYyLmnU1A_aK7HirukpAI1-THQMQVQNCXpK3KR0YY41i7A25BFkYyZsdWX9tU95jComaydE-xCE-BWsGikczrCaHONHo6bzHaRtoWvuUQ14zOjrHYYvP2xNO5rQ-m1IUJ6QOl3As4BFL56k2h2qPs8lxNNSUeE7X5MKbIeG7l3lFHr_ePdx-r-5_fvtx--W-skJBrmzvedcbBR6E47JpPTCnsFe-BWEbcSPRGOgd98hbA4Jb6VrlbadkgYQTV-TjuXde4u8VU9ZjSBaHwUwY16S5lDfQAoOuROU5apeY0oJez0sYzbJpzvRJuD7os3B9Eq5Zp4vwgn14ubD2I7p_0F_DJfD5HMDy5zHgopMNOFl0YUGbtYvh_xf-AKVCluA</recordid><startdate>20131101</startdate><enddate>20131101</enddate><creator>Dai, Ming</creator><creator>Yuan, Xing</creator><creator>Kang, Jian</creator><creator>Zhu, Zhi-Jun</creator><creator>Yue, Rong-Cai</creator><creator>Yuan, Hu</creator><creator>Chen, Bing-Yang</creator><creator>Zhang, Wei-Dong</creator><creator>Liu, Run-Hui</creator><creator>Sun, Qing-Yan</creator><general>Elsevier Masson SAS</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>20131101</creationdate><title>Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents</title><author>Dai, Ming ; Yuan, Xing ; Kang, Jian ; Zhu, Zhi-Jun ; Yue, Rong-Cai ; Yuan, Hu ; Chen, Bing-Yang ; Zhang, Wei-Dong ; Liu, Run-Hui ; Sun, Qing-Yan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-cbf18ba62f23d1457f20d6eb6f723c5394eaa2bd1fe17a231c4d76fc864a623d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Anti-hepatoma</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis - drug effects</topic><topic>Carcinoma, Hepatocellular - drug therapy</topic><topic>Carcinoma, Hepatocellular - pathology</topic><topic>Cell Proliferation - drug effects</topic><topic>Cytotoxic selectivity</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Hep G2 Cells</topic><topic>Humans</topic><topic>Liver Neoplasms - drug therapy</topic><topic>Liver Neoplasms - pathology</topic><topic>Molecular Structure</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><topic>Xanthone</topic><topic>Xanthones - chemical synthesis</topic><topic>Xanthones - chemistry</topic><topic>Xanthones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dai, Ming</creatorcontrib><creatorcontrib>Yuan, Xing</creatorcontrib><creatorcontrib>Kang, Jian</creatorcontrib><creatorcontrib>Zhu, Zhi-Jun</creatorcontrib><creatorcontrib>Yue, Rong-Cai</creatorcontrib><creatorcontrib>Yuan, Hu</creatorcontrib><creatorcontrib>Chen, Bing-Yang</creatorcontrib><creatorcontrib>Zhang, Wei-Dong</creatorcontrib><creatorcontrib>Liu, Run-Hui</creatorcontrib><creatorcontrib>Sun, Qing-Yan</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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dai, Ming</au><au>Yuan, Xing</au><au>Kang, Jian</au><au>Zhu, Zhi-Jun</au><au>Yue, Rong-Cai</au><au>Yuan, Hu</au><au>Chen, Bing-Yang</au><au>Zhang, Wei-Dong</au><au>Liu, Run-Hui</au><au>Sun, Qing-Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2013-11-01</date><risdate>2013</risdate><volume>69</volume><spage>159</spage><epage>166</epage><pages>159-166</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>A series of novel derivatives of phenyl substituted tetramethoxy xanthone were synthesized and evaluated for their in vitro cytotoxicity against human hepatocellular carcinoma (HCC) and non-tumor hepatic cells. Among these derivatives, compound 6 was more potent than positive control 5-fluorouracil (5-Fu) on QGY-7703 and SMMC-7721 cells with IC50 values of 6.27 μM, 7.50 μM and 15.56 μM, 14.55 μM, respectively. Furthermore, compounds 6, 14, 16, and 29 exhibited much better selectivity toward the normal hepatic cell line QSG-7701 than 5-Fu. Additionally, compound 6 significantly induced cell apoptosis in QGY-7703 cells. Our findings suggested that these phenylxanthone derivatives may hold promise as chemotherapeutic agents for the treatment of human HCC.
[Display omitted]
•Derivatives of phenyl substituted tetramethoxy xanthone were synthesized.•Compound 6 showed more potent activity against HCC cells than 5-Fu.•Compound 6 presented better cytotoxic selectivity.•The structure–activity relationships of compounds have been discussed.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>24013415</pmid><doi>10.1016/j.ejmech.2013.08.020</doi><tpages>8</tpages></addata></record> |
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| subjects | Anti-hepatoma Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Apoptosis - drug effects Carcinoma, Hepatocellular - drug therapy Carcinoma, Hepatocellular - pathology Cell Proliferation - drug effects Cytotoxic selectivity Dose-Response Relationship, Drug Drug Screening Assays, Antitumor Hep G2 Cells Humans Liver Neoplasms - drug therapy Liver Neoplasms - pathology Molecular Structure Structure-Activity Relationship Tumor Cells, Cultured Xanthone Xanthones - chemical synthesis Xanthones - chemistry Xanthones - pharmacology |
| title | Synthesis and biological evaluation of phenyl substituted polyoxygenated xanthone derivatives as anti-hepatoma agents |
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