Synthesis of artemisinin dimers using the Ugi reaction and their in vitro efficacy on breast cancer cells
The Ugi four-component reaction was used to prepare a series of artemisinin monomers and dimers. We found that the endoperoxide group in artemisinin remains intact during the reaction. The new artemisinin dimers showed potent anti-cancer activity against two human breast cancer cell lines, MDA-MB-23...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-08, Vol.23 (15), p.4424-4427 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Wang, Shusheng Sasaki, Tomikazu |
| description | The Ugi four-component reaction was used to prepare a series of artemisinin monomers and dimers. We found that the endoperoxide group in artemisinin remains intact during the reaction. The new artemisinin dimers showed potent anti-cancer activity against two human breast cancer cell lines, MDA-MB-231 and BT-474. One of the Ugi artemisinin dimers showed an IC50 value of 12nM when tested on BT474 cells, more than 600 times more potent than artesunate. Furthermore, the same Ugi artemisinin dimer showed a low toxicity when tested on MCF10A, a nontumorigenic cell line, resulting in a selectivity index of more than 8000. |
| doi_str_mv | 10.1016/j.bmcl.2013.05.057 |
| format | Article |
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We found that the endoperoxide group in artemisinin remains intact during the reaction. The new artemisinin dimers showed potent anti-cancer activity against two human breast cancer cell lines, MDA-MB-231 and BT-474. One of the Ugi artemisinin dimers showed an IC50 value of 12nM when tested on BT474 cells, more than 600 times more potent than artesunate. Furthermore, the same Ugi artemisinin dimer showed a low toxicity when tested on MCF10A, a nontumorigenic cell line, resulting in a selectivity index of more than 8000.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2013.05.057</identifier><identifier>PMID: 23790541</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>anticarcinogenic activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; Artemisinin ; Artemisinins - chemical synthesis ; Artemisinins - chemistry ; Artemisinins - toxicity ; Breast cancer ; breast neoplasms ; Breast Neoplasms - pathology ; Cell Line, Tumor ; Cell Proliferation - drug effects ; chemistry ; Condensation ; Cytotoxicity ; Dimerization ; Female ; Humans ; inhibitory concentration 50 ; toxicity ; Ugi reaction</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-08, Vol.23 (15), p.4424-4427</ispartof><rights>2013 Elsevier Ltd</rights><rights>Copyright © 2013 Elsevier Ltd. 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We found that the endoperoxide group in artemisinin remains intact during the reaction. The new artemisinin dimers showed potent anti-cancer activity against two human breast cancer cell lines, MDA-MB-231 and BT-474. One of the Ugi artemisinin dimers showed an IC50 value of 12nM when tested on BT474 cells, more than 600 times more potent than artesunate. Furthermore, the same Ugi artemisinin dimer showed a low toxicity when tested on MCF10A, a nontumorigenic cell line, resulting in a selectivity index of more than 8000.</description><subject>anticarcinogenic activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Artemisinin</subject><subject>Artemisinins - chemical synthesis</subject><subject>Artemisinins - chemistry</subject><subject>Artemisinins - toxicity</subject><subject>Breast cancer</subject><subject>breast neoplasms</subject><subject>Breast Neoplasms - pathology</subject><subject>Cell Line, Tumor</subject><subject>Cell Proliferation - drug effects</subject><subject>chemistry</subject><subject>Condensation</subject><subject>Cytotoxicity</subject><subject>Dimerization</subject><subject>Female</subject><subject>Humans</subject><subject>inhibitory concentration 50</subject><subject>toxicity</subject><subject>Ugi reaction</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE2LFDEQhoMo7rj6Bzxojl56rHz0R8CLLH7Bgod1wFtIV1fGGqa716RnYf69aWb1KBSEJE-9qTxCvFawVaCa94dtP-Jxq0GZLdSl2idio2xjK2Ohfio24BqoOmd_XokXOR8AlAVrn4srbVoHtVUbwXfnaflFmbOcowxpoZEzTzzJgUdKWZ7Kbi8LInd7lokCLjxPMkzDeshJFvSBlzRLipEx4FmW676AeZEYJqQkkY7H_FI8i-GY6dXjei12nz_9uPla3X7_8u3m422FVpmlah3q3gwRgusGDY21zqENHQQyFhH6zlDjTBvIYajjgG2rqWvqXtsuNr0y1-LdJfc-zb9PlBdffrROECaaT9mrGqCtO9PpguoLimnOOVH094nHkM5egV8V-4NfFftVsYe6VFua3jzmn_qRhn8tf50W4O0FiGH2YZ84-91dSSjvKqO1g0J8uBBUPDwwJZ-RqagaOBEufpj5fxP8AWzVlyA</recordid><startdate>20130801</startdate><enddate>20130801</enddate><creator>Wang, Shusheng</creator><creator>Sasaki, Tomikazu</creator><general>Elsevier Ltd</general><scope>FBQ</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20130801</creationdate><title>Synthesis of artemisinin dimers using the Ugi reaction and their in vitro efficacy on breast cancer cells</title><author>Wang, Shusheng ; Sasaki, Tomikazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c413t-79c2b3df0a98d2064499c4a80ae34cc0b83e6937ae9ca5fdc772e865b248f6b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>anticarcinogenic activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - toxicity</topic><topic>Artemisinin</topic><topic>Artemisinins - chemical synthesis</topic><topic>Artemisinins - chemistry</topic><topic>Artemisinins - toxicity</topic><topic>Breast cancer</topic><topic>breast neoplasms</topic><topic>Breast Neoplasms - pathology</topic><topic>Cell Line, Tumor</topic><topic>Cell Proliferation - drug effects</topic><topic>chemistry</topic><topic>Condensation</topic><topic>Cytotoxicity</topic><topic>Dimerization</topic><topic>Female</topic><topic>Humans</topic><topic>inhibitory concentration 50</topic><topic>toxicity</topic><topic>Ugi reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Shusheng</creatorcontrib><creatorcontrib>Sasaki, Tomikazu</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</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>Wang, Shusheng</au><au>Sasaki, Tomikazu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of artemisinin dimers using the Ugi reaction and their in vitro efficacy on breast cancer cells</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-08-01</date><risdate>2013</risdate><volume>23</volume><issue>15</issue><spage>4424</spage><epage>4427</epage><pages>4424-4427</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The Ugi four-component reaction was used to prepare a series of artemisinin monomers and dimers. We found that the endoperoxide group in artemisinin remains intact during the reaction. The new artemisinin dimers showed potent anti-cancer activity against two human breast cancer cell lines, MDA-MB-231 and BT-474. One of the Ugi artemisinin dimers showed an IC50 value of 12nM when tested on BT474 cells, more than 600 times more potent than artesunate. Furthermore, the same Ugi artemisinin dimer showed a low toxicity when tested on MCF10A, a nontumorigenic cell line, resulting in a selectivity index of more than 8000.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>23790541</pmid><doi>10.1016/j.bmcl.2013.05.057</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2013-08, Vol.23 (15), p.4424-4427 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | anticarcinogenic activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity Artemisinin Artemisinins - chemical synthesis Artemisinins - chemistry Artemisinins - toxicity Breast cancer breast neoplasms Breast Neoplasms - pathology Cell Line, Tumor Cell Proliferation - drug effects chemistry Condensation Cytotoxicity Dimerization Female Humans inhibitory concentration 50 toxicity Ugi reaction |
| title | Synthesis of artemisinin dimers using the Ugi reaction and their in vitro efficacy on breast cancer cells |
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