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Issue 35, 2012
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Manadoperoxides, a new class of potent antitrypanosomal agents of marine origin

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Abstract

Chemical investigation of the marine sponge Plakortis cfr. lita afforded a library of endoperoxyketal polyketides, manadoperoxides B–K (3–5 and 7–13) and peroxyplakoric esters B3 (6) and C (14). Eight of these metabolites are new compounds and some contain an unprecedented chlorine-bearing THF-type ring in the side chain. The library of endoperoxide derivatives was evaluated for in vitro activity against Trypanosoma brucei rhodesiense and Leishmania donovani. Some compounds, such as manadoperoxide B, exhibited ultrapotent trypanocidal activity (IC50 = 3 ng mL−1) without cytotoxicity. Detailed examination of the antitrypanosomal activity data and comparison with those available in the literature for related dioxane derivatives enabled us to draw a series of structure–activity relationships. Interestingly, it appears that minor structural changes, such as a shift of the methyl group around the dioxane ring, can dramatically affect the antitrypanosomal activity. This information can be valuable to guide the design of optimized antitrypanosomal agents based on the dioxane scaffold.

Graphical abstract: Manadoperoxides, a new class of potent antitrypanosomal agents of marine origin

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Publication details

The article was received on 12 Jun 2012, accepted on 06 Jul 2012 and first published on 12 Jul 2012


Article type: Paper
DOI: 10.1039/C2OB26124C
Org. Biomol. Chem., 2012,10, 7197-7207

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    Manadoperoxides, a new class of potent antitrypanosomal agents of marine origin

    G. Chianese, E. Fattorusso, F. Scala, R. Teta, B. Calcinai, G. Bavestrello, H. A. Dien, M. Kaiser, D. Tasdemir and O. Taglialatela-Scafati, Org. Biomol. Chem., 2012, 10, 7197
    DOI: 10.1039/C2OB26124C

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