000124809 001__ 124809
000124809 005__ 20180913054620.0
000124809 02470 $$2ISI$$a000262321200006
000124809 037__ $$aARTICLE
000124809 245__ $$aSpongistatins : biological activity and synthetic studies
000124809 269__ $$a2008
000124809 260__ $$c2008
000124809 336__ $$aJournal Articles
000124809 500__ $$areview
000124809 520__ $$aDuring the last two decades, marine organisms such as  sponges, tunicates, softcoral and starfish proved to be  productive sources of structurally complex metabolites  presenting unprecedented architectures.[1] These marine  natural products often display unexpected biological  properties that make them potential candidates for  therapeutic applications. Among these fascinating  molecules, the polyketide macrolides having a macrolactone  as key structural feature represent an important class of  biologically active compounds.[2] Many congeners of this  family are potent cancer cell growth inhibitors and thus  appears to represent promising leads for the development of  new anti-cancer agents. Nevertheless, a limitation to their  implementation in clinical evaluation is related to their  low natural abundance, which is stimulating organic  chemists to invent efficient synthetic routes to address  this supply issue.  In 1993, the research groups of Pettit,  Kitagawa/Kobayashi and Fusetani independently reported the  isolation, from marine sponges, of a family of related  highly oxygenated macrolactones containing highly  substituted 6,6-spiroketals and tetrahydropyran rings.[3]  These molecules were found to be among the most potent  cancer cells growth inhibitors tested to date by the U.S.  National Cancer Institute on a panel of 60 human carcinoma  cell lines, with GI50 values in the nanomolar and picomolar  ranges. Despite these promising properties, further  biological investigations were precluded by the extremely  low quantities that can be obtained by extraction of marine  organisms and the unacceptable ecological impact of larger  scale isolation of the producing sponges. This scarce  abundance, combined with remarkable structural complexity,  prompted many research groups to address the challenge of  the synthesis of these macrolides.  We give here an  overview of the biological properties of spongistatins and  related structures and of the different pathways that have  been developed for their total syntheses and the synthesis  of key-subunits.
000124809 700__ $$0241092$$aGerber-Lemaire, Sandrine$$g148571
000124809 700__ $$0240222$$aVogel, Pierre$$g123681
000124809 773__ $$j11$$q1382-1418$$tComptes Rendus de l'Académie des Sciences
000124809 909C0 $$0252076$$pLGSA$$xU10111
000124809 909CO $$ooai:infoscience.tind.io:124809$$pSB$$particle
000124809 937__ $$aLGSA-ARTICLE-2008-015
000124809 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000124809 980__ $$aARTICLE