Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog
Novel and known ellipticine derivatives exhibit important in vitro inhibition of human malaria parasites. Ellipticine has been shown previously to exhibit excellent in vitro antiplasmodial activity and in vivo antimalarial properties that are comparable to those of the control drug chloroquine in a...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2014-06, Vol.24 (12), p.2631-2634 |
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| creator | Montoia, Andreia Rocha e Silva, Luiz F. Torres, Zelina E. Costa, David S. Henrique, Marycleuma C. Lima, Emerson S. Vasconcellos, Marne C. Souza, Rita C.Z. Costa, Monica R.F. Grafov, Andriy Grafova, Iryna Eberlin, Marcos N. Tadei, Wanderli P. Amorim, Rodrigo C.N. Pohlit, Adrian M. |
| description | Novel and known ellipticine derivatives exhibit important in vitro inhibition of human malaria parasites.
Ellipticine has been shown previously to exhibit excellent in vitro antiplasmodial activity and in vivo antimalarial properties that are comparable to those of the control drug chloroquine in a mouse malaria model. Ellipticine derivatives and analogs exhibit antimalarial potential however only a few have been studied to date. Herein, ellipticine and a structural analog were isolated from Aspidosperma vargasii bark. A-ring brominated and nitrated ellipticine derivatives exhibit good in vitro inhibition of Plasmodium falciparum K1 and 3D7 strains. Several of the compounds were found not to be toxic to human fetal lung fibroblasts. 9-Nitroellipticine (IC50=0.55μM) exhibits greater antiplasmodial activity than ellipticine. These results are further evidence of the antimalarial potential of ellipticine derivatives. |
| doi_str_mv | 10.1016/j.bmcl.2014.04.070 |
| format | Article |
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Ellipticine has been shown previously to exhibit excellent in vitro antiplasmodial activity and in vivo antimalarial properties that are comparable to those of the control drug chloroquine in a mouse malaria model. Ellipticine derivatives and analogs exhibit antimalarial potential however only a few have been studied to date. Herein, ellipticine and a structural analog were isolated from Aspidosperma vargasii bark. A-ring brominated and nitrated ellipticine derivatives exhibit good in vitro inhibition of Plasmodium falciparum K1 and 3D7 strains. Several of the compounds were found not to be toxic to human fetal lung fibroblasts. 9-Nitroellipticine (IC50=0.55μM) exhibits greater antiplasmodial activity than ellipticine. These results are further evidence of the antimalarial potential of ellipticine derivatives.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2014.04.070</identifier><identifier>PMID: 24813729</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>2-Methyl-1,2,3,4-tetrahydroellipticine ; 7,9-Dibromoellipticine ; 7-Nitroellipticine ; 9-Nitroellipticine ; Animals ; Antimalarials - chemical synthesis ; Antimalarials - chemistry ; Antimalarials - pharmacology ; Aspidosperma - chemistry ; Chloroquine - chemistry ; Chloroquine - pharmacology ; Disease Models, Animal ; Ellipticines - chemical synthesis ; Ellipticines - chemistry ; Ellipticines - pharmacology ; Fibroblasts - drug effects ; Humans ; Mice ; Molecular Structure ; Plant Bark - chemistry ; Plasmodium falciparum ; Plasmodium falciparum - drug effects</subject><ispartof>Bioorganic & medicinal chemistry letters, 2014-06, Vol.24 (12), p.2631-2634</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c455t-7ec90692d1bc7ba8920d3a00269a575c2911cfa711640d19017ddedab6ed98013</citedby><cites>FETCH-LOGICAL-c455t-7ec90692d1bc7ba8920d3a00269a575c2911cfa711640d19017ddedab6ed98013</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X14004272$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24813729$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Montoia, Andreia</creatorcontrib><creatorcontrib>Rocha e Silva, Luiz F.</creatorcontrib><creatorcontrib>Torres, Zelina E.</creatorcontrib><creatorcontrib>Costa, David S.</creatorcontrib><creatorcontrib>Henrique, Marycleuma C.</creatorcontrib><creatorcontrib>Lima, Emerson S.</creatorcontrib><creatorcontrib>Vasconcellos, Marne C.</creatorcontrib><creatorcontrib>Souza, Rita C.Z.</creatorcontrib><creatorcontrib>Costa, Monica R.F.</creatorcontrib><creatorcontrib>Grafov, Andriy</creatorcontrib><creatorcontrib>Grafova, Iryna</creatorcontrib><creatorcontrib>Eberlin, Marcos N.</creatorcontrib><creatorcontrib>Tadei, Wanderli P.</creatorcontrib><creatorcontrib>Amorim, Rodrigo C.N.</creatorcontrib><creatorcontrib>Pohlit, Adrian M.</creatorcontrib><title>Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Novel and known ellipticine derivatives exhibit important in vitro inhibition of human malaria parasites.
Ellipticine has been shown previously to exhibit excellent in vitro antiplasmodial activity and in vivo antimalarial properties that are comparable to those of the control drug chloroquine in a mouse malaria model. Ellipticine derivatives and analogs exhibit antimalarial potential however only a few have been studied to date. Herein, ellipticine and a structural analog were isolated from Aspidosperma vargasii bark. A-ring brominated and nitrated ellipticine derivatives exhibit good in vitro inhibition of Plasmodium falciparum K1 and 3D7 strains. Several of the compounds were found not to be toxic to human fetal lung fibroblasts. 9-Nitroellipticine (IC50=0.55μM) exhibits greater antiplasmodial activity than ellipticine. These results are further evidence of the antimalarial potential of ellipticine derivatives.</description><subject>2-Methyl-1,2,3,4-tetrahydroellipticine</subject><subject>7,9-Dibromoellipticine</subject><subject>7-Nitroellipticine</subject><subject>9-Nitroellipticine</subject><subject>Animals</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Aspidosperma - chemistry</subject><subject>Chloroquine - chemistry</subject><subject>Chloroquine - pharmacology</subject><subject>Disease Models, Animal</subject><subject>Ellipticines - chemical synthesis</subject><subject>Ellipticines - chemistry</subject><subject>Ellipticines - pharmacology</subject><subject>Fibroblasts - drug effects</subject><subject>Humans</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Plant Bark - chemistry</subject><subject>Plasmodium falciparum</subject><subject>Plasmodium falciparum - drug effects</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1LAzEQhoMotlb_gAfZo5ddJ9nsR8BLEb-g4EEFbyGbzGrKfrlJC_33Zmn1KMww7-GZl5mXkEsKCQWa36yTqtVNwoDyBEIVcETmlOc8Tjlkx2QOIoe4FPxjRs6cW0MAgfNTMmO8pGnBxJy8Ljtvh0a5tjdWNZHS3m6t30V9Hbld57_QWx1h09ghCNthZHC0WxUodJHqTOjIur5RHietmv7znJzUqnF4cZgL8v5w_3b3FK9eHp_vlqtY8yzzcYFaQC6YoZUuKlUKBiZVACwXKisyzQSlulYFpTkHQwXQwhg0qsrRiBJouiDXe99h7L836LxsrdPhVtVhv3GSZikvM5aXWUDZHtVj79yItRxG26pxJynIKUy5llOYcgpTQqgCwtLVwX9TtWj-Vn7TC8DtHsDw5dbiKJ222Gk0dkTtpentf_4_bIqGaQ</recordid><startdate>20140615</startdate><enddate>20140615</enddate><creator>Montoia, Andreia</creator><creator>Rocha e Silva, Luiz F.</creator><creator>Torres, Zelina E.</creator><creator>Costa, David S.</creator><creator>Henrique, Marycleuma C.</creator><creator>Lima, Emerson S.</creator><creator>Vasconcellos, Marne C.</creator><creator>Souza, Rita C.Z.</creator><creator>Costa, Monica R.F.</creator><creator>Grafov, Andriy</creator><creator>Grafova, Iryna</creator><creator>Eberlin, Marcos N.</creator><creator>Tadei, Wanderli P.</creator><creator>Amorim, Rodrigo C.N.</creator><creator>Pohlit, Adrian M.</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>7QO</scope><scope>8FD</scope><scope>C1K</scope><scope>F1W</scope><scope>FR3</scope><scope>H95</scope><scope>H97</scope><scope>L.G</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20140615</creationdate><title>Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog</title><author>Montoia, Andreia ; Rocha e Silva, Luiz F. ; Torres, Zelina E. ; Costa, David S. ; Henrique, Marycleuma C. ; Lima, Emerson S. ; Vasconcellos, Marne C. ; Souza, Rita C.Z. ; Costa, Monica R.F. ; Grafov, Andriy ; Grafova, Iryna ; Eberlin, Marcos N. ; Tadei, Wanderli P. ; Amorim, Rodrigo C.N. ; Pohlit, Adrian M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c455t-7ec90692d1bc7ba8920d3a00269a575c2911cfa711640d19017ddedab6ed98013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>2-Methyl-1,2,3,4-tetrahydroellipticine</topic><topic>7,9-Dibromoellipticine</topic><topic>7-Nitroellipticine</topic><topic>9-Nitroellipticine</topic><topic>Animals</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - pharmacology</topic><topic>Aspidosperma - chemistry</topic><topic>Chloroquine - chemistry</topic><topic>Chloroquine - pharmacology</topic><topic>Disease Models, Animal</topic><topic>Ellipticines - chemical synthesis</topic><topic>Ellipticines - chemistry</topic><topic>Ellipticines - pharmacology</topic><topic>Fibroblasts - drug effects</topic><topic>Humans</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Plant Bark - chemistry</topic><topic>Plasmodium falciparum</topic><topic>Plasmodium falciparum - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Montoia, Andreia</creatorcontrib><creatorcontrib>Rocha e Silva, Luiz F.</creatorcontrib><creatorcontrib>Torres, Zelina E.</creatorcontrib><creatorcontrib>Costa, David S.</creatorcontrib><creatorcontrib>Henrique, Marycleuma C.</creatorcontrib><creatorcontrib>Lima, Emerson S.</creatorcontrib><creatorcontrib>Vasconcellos, Marne C.</creatorcontrib><creatorcontrib>Souza, Rita C.Z.</creatorcontrib><creatorcontrib>Costa, Monica R.F.</creatorcontrib><creatorcontrib>Grafov, Andriy</creatorcontrib><creatorcontrib>Grafova, Iryna</creatorcontrib><creatorcontrib>Eberlin, Marcos N.</creatorcontrib><creatorcontrib>Tadei, Wanderli P.</creatorcontrib><creatorcontrib>Amorim, Rodrigo C.N.</creatorcontrib><creatorcontrib>Pohlit, Adrian M.</creatorcontrib><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>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Engineering Research Database</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 3: Aquatic Pollution & Environmental Quality</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</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>Montoia, Andreia</au><au>Rocha e Silva, Luiz F.</au><au>Torres, Zelina E.</au><au>Costa, David S.</au><au>Henrique, Marycleuma C.</au><au>Lima, Emerson S.</au><au>Vasconcellos, Marne C.</au><au>Souza, Rita C.Z.</au><au>Costa, Monica R.F.</au><au>Grafov, Andriy</au><au>Grafova, Iryna</au><au>Eberlin, Marcos N.</au><au>Tadei, Wanderli P.</au><au>Amorim, Rodrigo C.N.</au><au>Pohlit, Adrian M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2014-06-15</date><risdate>2014</risdate><volume>24</volume><issue>12</issue><spage>2631</spage><epage>2634</epage><pages>2631-2634</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Novel and known ellipticine derivatives exhibit important in vitro inhibition of human malaria parasites.
Ellipticine has been shown previously to exhibit excellent in vitro antiplasmodial activity and in vivo antimalarial properties that are comparable to those of the control drug chloroquine in a mouse malaria model. Ellipticine derivatives and analogs exhibit antimalarial potential however only a few have been studied to date. Herein, ellipticine and a structural analog were isolated from Aspidosperma vargasii bark. A-ring brominated and nitrated ellipticine derivatives exhibit good in vitro inhibition of Plasmodium falciparum K1 and 3D7 strains. Several of the compounds were found not to be toxic to human fetal lung fibroblasts. 9-Nitroellipticine (IC50=0.55μM) exhibits greater antiplasmodial activity than ellipticine. These results are further evidence of the antimalarial potential of ellipticine derivatives.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>24813729</pmid><doi>10.1016/j.bmcl.2014.04.070</doi><tpages>4</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry letters, 2014-06, Vol.24 (12), p.2631-2634 |
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| subjects | 2-Methyl-1,2,3,4-tetrahydroellipticine 7,9-Dibromoellipticine 7-Nitroellipticine 9-Nitroellipticine Animals Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Aspidosperma - chemistry Chloroquine - chemistry Chloroquine - pharmacology Disease Models, Animal Ellipticines - chemical synthesis Ellipticines - chemistry Ellipticines - pharmacology Fibroblasts - drug effects Humans Mice Molecular Structure Plant Bark - chemistry Plasmodium falciparum Plasmodium falciparum - drug effects |
| title | Antiplasmodial activity of synthetic ellipticine derivatives and an isolated analog |
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