Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives
We report the synthesis and anticancer effects of 3-O-acyl and alkyl-(−)-epicatechin derivatives. By changing the structure or replacing the gallate group of (−)-ECG, 3-O-acyl and alkyl-(−)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro agains...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2004-10, Vol.14 (20), p.5189-5192 |
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| creator | Park, Ki Duk Lee, Sul Gi Kim, Sung Uk Kim, Sung Han Sun, Won Suck Cho, Sung Jin Jeong, Do Hyeon |
| description | We report the synthesis and anticancer effects of 3-O-acyl and alkyl-(−)-epicatechin derivatives.
By changing the structure or replacing the gallate group of (−)-ECG, 3-O-acyl and alkyl-(−)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(−)-epicatechin derivatives (4–25) exhibited better anticancer activity than (−)-ECG and specially, compounds 6–8, 17–19, which were modified aliphatic chains with moderate sizes (C8–C12) showed strong anticancer activity (IC50=6.4–31.2μM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(−)-epicatechin (18) (IC50=8.9, 7.9, 6.4μM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group. |
| doi_str_mv | 10.1016/j.bmcl.2004.07.063 |
| format | Article |
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By changing the structure or replacing the gallate group of (−)-ECG, 3-O-acyl and alkyl-(−)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(−)-epicatechin derivatives (4–25) exhibited better anticancer activity than (−)-ECG and specially, compounds 6–8, 17–19, which were modified aliphatic chains with moderate sizes (C8–C12) showed strong anticancer activity (IC50=6.4–31.2μM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(−)-epicatechin (18) (IC50=8.9, 7.9, 6.4μM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2004.07.063</identifier><identifier>PMID: 15380225</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>3-O-Acyl-(−)-epicatechin ; 3-O-Alkyl-(−)-epicatechin ; Anticancer activity ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Camellia sinensis - chemistry ; Catechin - analogs & derivatives ; Catechin - chemistry ; Catechin - pharmacology ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Drug Stability ; Humans ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2004-10, Vol.14 (20), p.5189-5192</ispartof><rights>2004 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c418t-a3ac37afe846a2289c36dfc09ccdca2db838b616735267f1235966336eeee0703</citedby><cites>FETCH-LOGICAL-c418t-a3ac37afe846a2289c36dfc09ccdca2db838b616735267f1235966336eeee0703</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.2004.07.063$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15380225$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Park, Ki Duk</creatorcontrib><creatorcontrib>Lee, Sul Gi</creatorcontrib><creatorcontrib>Kim, Sung Uk</creatorcontrib><creatorcontrib>Kim, Sung Han</creatorcontrib><creatorcontrib>Sun, Won Suck</creatorcontrib><creatorcontrib>Cho, Sung Jin</creatorcontrib><creatorcontrib>Jeong, Do Hyeon</creatorcontrib><title>Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>We report the synthesis and anticancer effects of 3-O-acyl and alkyl-(−)-epicatechin derivatives.
By changing the structure or replacing the gallate group of (−)-ECG, 3-O-acyl and alkyl-(−)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(−)-epicatechin derivatives (4–25) exhibited better anticancer activity than (−)-ECG and specially, compounds 6–8, 17–19, which were modified aliphatic chains with moderate sizes (C8–C12) showed strong anticancer activity (IC50=6.4–31.2μM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(−)-epicatechin (18) (IC50=8.9, 7.9, 6.4μM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group.</description><subject>3-O-Acyl-(−)-epicatechin</subject><subject>3-O-Alkyl-(−)-epicatechin</subject><subject>Anticancer activity</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Camellia sinensis - chemistry</subject><subject>Catechin - analogs & derivatives</subject><subject>Catechin - chemistry</subject><subject>Catechin - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Drug Stability</subject><subject>Humans</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kM1K5EAUhQtx0PbnBVxIVqKLytz6SSUBN43MOILgZgR3RfXNDVabTtqqdEO_get5RJ_Earphdt7N2XznwP0YuxCQCxDm5zyfLbDLJYDOoczBqAM2EdporjQUh2wCtQFe1frlmJ3EOAcQGrQ-YseiUBVIWUzY_bQfPboeKWQOR7_24yYb2kzxJ-5w02WubzLXvW06fv358e-G0zLhI-Gr77OGgl-7VKJ4xn60rot0vs9T9vz719-7P_zx6f7hbvrIUYtq5E45VKVrqdLGSVnVqEzTItSIDTrZzCpVzYwwpSqkKVshVVEbo5ShdFCCOmVXu91lGN5XFEe78BGp61xPwypaY6q6lCATKHcghiHGQK1dBr9wYWMF2K0-O7dbfXarz0Jpk75Uutyvr2YLav5X9r4ScLsDKP249hRsRE_JXuMD4WibwX-3_wVGo4Dc</recordid><startdate>20041018</startdate><enddate>20041018</enddate><creator>Park, Ki Duk</creator><creator>Lee, Sul Gi</creator><creator>Kim, Sung Uk</creator><creator>Kim, Sung Han</creator><creator>Sun, Won Suck</creator><creator>Cho, Sung Jin</creator><creator>Jeong, Do Hyeon</creator><general>Elsevier Ltd</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>20041018</creationdate><title>Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives</title><author>Park, Ki Duk ; Lee, Sul Gi ; Kim, Sung Uk ; Kim, Sung Han ; Sun, Won Suck ; Cho, Sung Jin ; Jeong, Do Hyeon</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c418t-a3ac37afe846a2289c36dfc09ccdca2db838b616735267f1235966336eeee0703</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>3-O-Acyl-(−)-epicatechin</topic><topic>3-O-Alkyl-(−)-epicatechin</topic><topic>Anticancer activity</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Camellia sinensis - chemistry</topic><topic>Catechin - analogs & derivatives</topic><topic>Catechin - chemistry</topic><topic>Catechin - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Drug Stability</topic><topic>Humans</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Park, Ki Duk</creatorcontrib><creatorcontrib>Lee, Sul Gi</creatorcontrib><creatorcontrib>Kim, Sung Uk</creatorcontrib><creatorcontrib>Kim, Sung Han</creatorcontrib><creatorcontrib>Sun, Won Suck</creatorcontrib><creatorcontrib>Cho, Sung Jin</creatorcontrib><creatorcontrib>Jeong, Do Hyeon</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Park, Ki Duk</au><au>Lee, Sul Gi</au><au>Kim, Sung Uk</au><au>Kim, Sung Han</au><au>Sun, Won Suck</au><au>Cho, Sung Jin</au><au>Jeong, Do Hyeon</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2004-10-18</date><risdate>2004</risdate><volume>14</volume><issue>20</issue><spage>5189</spage><epage>5192</epage><pages>5189-5192</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>We report the synthesis and anticancer effects of 3-O-acyl and alkyl-(−)-epicatechin derivatives.
By changing the structure or replacing the gallate group of (−)-ECG, 3-O-acyl and alkyl-(−)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(−)-epicatechin derivatives (4–25) exhibited better anticancer activity than (−)-ECG and specially, compounds 6–8, 17–19, which were modified aliphatic chains with moderate sizes (C8–C12) showed strong anticancer activity (IC50=6.4–31.2μM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(−)-epicatechin (18) (IC50=8.9, 7.9, 6.4μM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>15380225</pmid><doi>10.1016/j.bmcl.2004.07.063</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2004-10, Vol.14 (20), p.5189-5192 |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | 3-O-Acyl-(−)-epicatechin 3-O-Alkyl-(−)-epicatechin Anticancer activity Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Camellia sinensis - chemistry Catechin - analogs & derivatives Catechin - chemistry Catechin - pharmacology Cell Line, Tumor Drug Screening Assays, Antitumor Drug Stability Humans Structure-Activity Relationship |
| title | Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives |
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