Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives
1,3-Dihydroxy-9,10-anthraquinone ( 4) was reacted with epichlorohydrin or 1,ω-dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9,10-anthraquinone ( 5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy)-9,10-anthraquinone ( 6) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epox...
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| Veröffentlicht in: | European journal of medicinal chemistry 2000-12, Vol.35 (12), p.1089-1098 |
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| creator | Wei, Bai-Luh Wu, Szu-Huei Chung, Mei-Ing Won, Shen-Jeu Lin, Chun-Nan |
| description | 1,3-Dihydroxy-9,10-anthraquinone (
4) was reacted with epichlorohydrin or 1,ω-dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9,10-anthraquinone (
5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy)-9,10-anthraquinone (
6) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (
5) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure–activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound
19. The results show that
19 cause cell death by apoptosis. |
| doi_str_mv | 10.1016/S0223-5234(00)01190-9 |
| format | Article |
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4) was reacted with epichlorohydrin or 1,ω-dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9,10-anthraquinone (
5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy)-9,10-anthraquinone (
6) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (
5) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure–activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound
19. The results show that
19 cause cell death by apoptosis.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/S0223-5234(00)01190-9</identifier><identifier>PMID: 11248407</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>anthraquinone ; Anthraquinones - chemical synthesis ; Anthraquinones - chemistry ; Anthraquinones - pharmacology ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; antitumour ; apoptosis ; Apoptosis - drug effects ; Biological and medical sciences ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; Spectrum Analysis ; Tumor Cells, Cultured</subject><ispartof>European journal of medicinal chemistry, 2000-12, Vol.35 (12), p.1089-1098</ispartof><rights>2000 Éditions scientifiques et médicales Elsevier SAS</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c455t-9ade7ddca6672f805daf34b92d9badde735f65c8e509ade6be2b69855bcef8c93</citedby><cites>FETCH-LOGICAL-c455t-9ade7ddca6672f805daf34b92d9badde735f65c8e509ade6be2b69855bcef8c93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523400011909$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=847948$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11248407$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wei, Bai-Luh</creatorcontrib><creatorcontrib>Wu, Szu-Huei</creatorcontrib><creatorcontrib>Chung, Mei-Ing</creatorcontrib><creatorcontrib>Won, Shen-Jeu</creatorcontrib><creatorcontrib>Lin, Chun-Nan</creatorcontrib><title>Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>1,3-Dihydroxy-9,10-anthraquinone (
4) was reacted with epichlorohydrin or 1,ω-dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9,10-anthraquinone (
5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy)-9,10-anthraquinone (
6) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (
5) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure–activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound
19. The results show that
19 cause cell death by apoptosis.</description><subject>anthraquinone</subject><subject>Anthraquinones - chemical synthesis</subject><subject>Anthraquinones - chemistry</subject><subject>Anthraquinones - pharmacology</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>antitumour</subject><subject>apoptosis</subject><subject>Apoptosis - drug effects</subject><subject>Biological and medical sciences</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Spectrum Analysis</subject><subject>Tumor Cells, Cultured</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0M9r2zAUwHFRVto03Z-wYRiMFqruSbZs6TRK6C8o7aHbWcjSE9VIrERyQv3f12lCd-xJB32envgS8o3BJQNW_3oGzksqeFmdAZwDYwqoOiAT1tSSllxUX8jkgxyTk5z_AYCoAY7IMWO8khU0E_L4PHT9C-aQC9O5wg597ONrsAV6j7Yvoi_YRUldeBlciq8DVRcMqBlnklmtQxc7LBymsDF92GA-JYfezDN-3Z9T8vfm-s_sjj483d7Prh6orYToqTIOG-esqeuGewnCGV9WreJOtcaNd6XwtbASBWxp3SJvayWFaC16aVU5JT937y5TXK0x93oRssX53HQY11k3XDSNLPkIxQ7aFHNO6PUyhYVJg2agtyH1e0i9raQB9HtIvV3wfb9g3S7Q_Z_alxvBjz0w2Zq5T6azIX84WTWqkqP6vVM4xtgETDrbgJ1FF9KYV7sYPvnIG5q3j-Y</recordid><startdate>20001201</startdate><enddate>20001201</enddate><creator>Wei, Bai-Luh</creator><creator>Wu, Szu-Huei</creator><creator>Chung, Mei-Ing</creator><creator>Won, Shen-Jeu</creator><creator>Lin, Chun-Nan</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20001201</creationdate><title>Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives</title><author>Wei, Bai-Luh ; Wu, Szu-Huei ; Chung, Mei-Ing ; Won, Shen-Jeu ; Lin, Chun-Nan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c455t-9ade7ddca6672f805daf34b92d9badde735f65c8e509ade6be2b69855bcef8c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>anthraquinone</topic><topic>Anthraquinones - chemical synthesis</topic><topic>Anthraquinones - chemistry</topic><topic>Anthraquinones - pharmacology</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>antitumour</topic><topic>apoptosis</topic><topic>Apoptosis - drug effects</topic><topic>Biological and medical sciences</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Spectrum Analysis</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wei, Bai-Luh</creatorcontrib><creatorcontrib>Wu, Szu-Huei</creatorcontrib><creatorcontrib>Chung, Mei-Ing</creatorcontrib><creatorcontrib>Won, Shen-Jeu</creatorcontrib><creatorcontrib>Lin, Chun-Nan</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wei, Bai-Luh</au><au>Wu, Szu-Huei</au><au>Chung, Mei-Ing</au><au>Won, Shen-Jeu</au><au>Lin, Chun-Nan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2000-12-01</date><risdate>2000</risdate><volume>35</volume><issue>12</issue><spage>1089</spage><epage>1098</epage><pages>1089-1098</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>1,3-Dihydroxy-9,10-anthraquinone (
4) was reacted with epichlorohydrin or 1,ω-dibromo-alkane to yield 1-hydroxy-3-(2,3-epoxypropoxy)-9,10-anthraquinone (
5) and 1-hydroxy-3-(3-chloro-2-hydroxypropoxy)-9,10-anthraquinone (
6) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinone. Ring-opening of the epoxide (
5) or 1-hydroxy-3-(ω-bromoalkoxy)-9,10-anthraquinones with appropriate amines, afforded various 1-hydroxy-3-(3-alkylamino-2-hydroxypropoxy)-9,10-anthraquinones. The synthetic compounds were tested in vitro inhibition of human T-24, Hep 3B, Hep G2, SiHa, HT-3, PLC/PRF/5 and 212 cells. Almost all compounds showed significant inhibitory activity against several different cancer cell lines. Structure–activity analysis indicated epoxidation of the hydroxyanthraquinone increased cytotoxicity against tumour cells, but ring-opening of the epoxide group with amine did not enhance the cytotoxic activity. The phosphatidylserine (PS) externalization and DNA fragmentation in SiHa cells were significantly observed after 48 h incubation with selected compound
19. The results show that
19 cause cell death by apoptosis.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>11248407</pmid><doi>10.1016/S0223-5234(00)01190-9</doi><tpages>10</tpages></addata></record> |
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| subjects | anthraquinone Anthraquinones - chemical synthesis Anthraquinones - chemistry Anthraquinones - pharmacology Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology antitumour apoptosis Apoptosis - drug effects Biological and medical sciences Drug Screening Assays, Antitumor General aspects Humans Medical sciences Molecular Structure Pharmacology. Drug treatments Spectrum Analysis Tumor Cells, Cultured |
| title | Synthesis and cytotoxic effect of 1,3-dihydroxy-9,10-anthraquinone derivatives |
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