Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors
Structures of neoboutomellerones isolated from Neoboutonia melleri. The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2012-01, Vol.20 (2), p.819-831 |
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| creator | Beck, Joséphine Guminski, Yves Long, Christophe Marcourt, Laurence Derguini, Fadila Plisson, Fabien Grondin, Antonio Vandenberghe, Isabelle Vispé, Stéphane Brel, Viviane Aussagues, Yannick Ausseil, Frédéric Arimondo, Paola B. Massiot, Georges Sautel, François Cantagrel, Frédéric |
| description | Structures of neoboutomellerones isolated from Neoboutonia melleri.
The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23–C24a and C1–C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents. |
| doi_str_mv | 10.1016/j.bmc.2011.11.066 |
| format | Article |
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The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23–C24a and C1–C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2011.11.066</identifier><identifier>PMID: 22206869</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Anticancer agent ; antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - toxicity ; Biological Products - chemistry ; Cell Line, Tumor ; Cycloartane ; Euphorbiaceae - chemistry ; Humans ; mechanism of action ; melanoma ; Natural product ; Neoboutonia melleri ; Proteasome ; proteasome endopeptidase complex ; Proteasome Endopeptidase Complex - metabolism ; Proteasome Inhibitors ; Signal Transduction - drug effects ; synthetic products ; Triterpenes - chemical synthesis ; Triterpenes - chemistry ; Triterpenes - toxicity ; Ubiquitin - antagonists & inhibitors ; Ubiquitin - metabolism</subject><ispartof>Bioorganic & medicinal chemistry, 2012-01, Vol.20 (2), p.819-831</ispartof><rights>2011 Elsevier Ltd</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c474t-86e1242d4486d6684246db511293899e16787397497c73c9bcefc36d694434bb3</citedby><cites>FETCH-LOGICAL-c474t-86e1242d4486d6684246db511293899e16787397497c73c9bcefc36d694434bb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2011.11.066$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22206869$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Beck, Joséphine</creatorcontrib><creatorcontrib>Guminski, Yves</creatorcontrib><creatorcontrib>Long, Christophe</creatorcontrib><creatorcontrib>Marcourt, Laurence</creatorcontrib><creatorcontrib>Derguini, Fadila</creatorcontrib><creatorcontrib>Plisson, Fabien</creatorcontrib><creatorcontrib>Grondin, Antonio</creatorcontrib><creatorcontrib>Vandenberghe, Isabelle</creatorcontrib><creatorcontrib>Vispé, Stéphane</creatorcontrib><creatorcontrib>Brel, Viviane</creatorcontrib><creatorcontrib>Aussagues, Yannick</creatorcontrib><creatorcontrib>Ausseil, Frédéric</creatorcontrib><creatorcontrib>Arimondo, Paola B.</creatorcontrib><creatorcontrib>Massiot, Georges</creatorcontrib><creatorcontrib>Sautel, François</creatorcontrib><creatorcontrib>Cantagrel, Frédéric</creatorcontrib><title>Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>Structures of neoboutomellerones isolated from Neoboutonia melleri.
The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23–C24a and C1–C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents.</description><subject>Anticancer agent</subject><subject>antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - toxicity</subject><subject>Biological Products - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Cycloartane</subject><subject>Euphorbiaceae - chemistry</subject><subject>Humans</subject><subject>mechanism of action</subject><subject>melanoma</subject><subject>Natural product</subject><subject>Neoboutonia melleri</subject><subject>Proteasome</subject><subject>proteasome endopeptidase complex</subject><subject>Proteasome Endopeptidase Complex - metabolism</subject><subject>Proteasome Inhibitors</subject><subject>Signal Transduction - drug effects</subject><subject>synthetic products</subject><subject>Triterpenes - chemical synthesis</subject><subject>Triterpenes - chemistry</subject><subject>Triterpenes - toxicity</subject><subject>Ubiquitin - antagonists & inhibitors</subject><subject>Ubiquitin - metabolism</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1rGzEQhkVpSdw0PyCXZG89rasvayVyKiFtCoEe0vQqJO24lvGuHEnr4n_fMU5yTGFgLs-8vPMQcsHonFGmvqznfghzThmb41Cl3pEZk0q2Qhj2nsyoUbql2qhT8rGUNaWUS8NOyCnnnCqtzIz8foAhlv1YV1BjaEZIPk01DbDZQE4jND3kuHM17qA0rjSTj09TrHFstzlVcAXRZuvq6q_bN3FcRR9ryuUT-bB0mwLnz_uMPH67_XVz197__P7j5ut9G2Qna6sVMC55L6VWvVJacql6v2CMG6GNAaY63QnTSdOFTgTjAyyDQNRIKaT34ox8PuZim6cJSrX4TcDyDj-ZijVcMGM6of9PMrXgiC6QZEcy5FRKhqXd5ji4vLeM2oN3u7bo3R68Wxz0jjeXz-mTH6B_vXgRjcDVEVi6ZN2fHIt9fMCEBcUUSuUh4vpIAPraRci2hAhjgD5mCNX2Kb5R4B-7tJzE</recordid><startdate>20120115</startdate><enddate>20120115</enddate><creator>Beck, Joséphine</creator><creator>Guminski, Yves</creator><creator>Long, Christophe</creator><creator>Marcourt, Laurence</creator><creator>Derguini, Fadila</creator><creator>Plisson, Fabien</creator><creator>Grondin, Antonio</creator><creator>Vandenberghe, Isabelle</creator><creator>Vispé, Stéphane</creator><creator>Brel, Viviane</creator><creator>Aussagues, Yannick</creator><creator>Ausseil, Frédéric</creator><creator>Arimondo, Paola B.</creator><creator>Massiot, Georges</creator><creator>Sautel, François</creator><creator>Cantagrel, Frédéric</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>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20120115</creationdate><title>Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors</title><author>Beck, Joséphine ; 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The interesting pharmacological properties of neoboutomellerones 1 and 2 were the basis for the assembly of a small library of analogues consisting of natural products isolated from the plant Neoboutonia melleri and of semisynthetic derivatives. As the two enone systems (C23–C24a and C1–C3) and the two hydroxyls groups (C22 and C26) of neoboutomellerones are required for activity, modifications were focused on these functional groups. Biological evaluation by using a cellular assay for proteasome activity provided clues regarding the mechanism of action of these natural products and synthetic derivatives. Certain neoboutomellerone derivatives inhibited the proliferation of human WM-266-4 melanoma tumor cells at submicromolar concentration and warrant evaluation as anticancer agents.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>22206869</pmid><doi>10.1016/j.bmc.2011.11.066</doi><tpages>13</tpages></addata></record> |
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| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2012-01, Vol.20 (2), p.819-831 |
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| subjects | Anticancer agent antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - toxicity Biological Products - chemistry Cell Line, Tumor Cycloartane Euphorbiaceae - chemistry Humans mechanism of action melanoma Natural product Neoboutonia melleri Proteasome proteasome endopeptidase complex Proteasome Endopeptidase Complex - metabolism Proteasome Inhibitors Signal Transduction - drug effects synthetic products Triterpenes - chemical synthesis Triterpenes - chemistry Triterpenes - toxicity Ubiquitin - antagonists & inhibitors Ubiquitin - metabolism |
| title | Semisynthetic neoboutomellerone derivatives as ubiquitin-proteasome pathway inhibitors |
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