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Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
Department of Pharmacy, University of Naples "Federico II", Via D. Montesano, 49, Naples I-80131, Italy
Department of Marine Sciences, Polytechnic University of Marche, Via Brecce Bianche, Ancona 60131, Italy
Faculty of Fishery and Marine Science, Sam Ratulangi University, Manado 95115, Indonesia
Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Basel CH-4002, Switzerland
University of Basel, Petersplatz 1, Basel CH-4003, Switzerland
School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland
* Author to whom correspondence should be addressed.
Received: 31 July 2013; in revised form: 16 August 2013 / Accepted: 19 August 2013 / Published: 28 August 2013
Abstract: Chemical analysis of the Indonesian sponge Plakortis cfr. lita afforded two new analogues of the potent trypanocidal agent manadoperoxide B (1), namely 12-isomanadoperoxide B (2) and manadoperoxidic acid B (3). These compounds were isolated along with a new short chain dicarboxylate monoester (4), bearing some interesting relationships with the polyketide endoperoxides found in this sponge. Some semi-synthetic analogues of manadoperoxide B (6–8) were prepared and evaluated for antitrypanosomal activity and cytotoxicity. These studies revealed crucial structure–activity relationships that should be taken into account in the design of optimized and simplified endoperoxyketal trypanocidal agents.
Keywords: manadoperoxide B; marine antitrypanosomals; structure–activity relationships
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Chianese, G.; Scala, F.; Calcinai, B.; Cerrano, C.; Dien, H.A.; Kaiser, M.; Tasdemir, D.; Taglialatela-Scafati, O. Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity. Mar. Drugs 2013, 11, 3297-3308.
Chianese G, Scala F, Calcinai B, Cerrano C, Dien HA, Kaiser M, Tasdemir D, Taglialatela-Scafati O. Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity. Marine Drugs. 2013; 11(9):3297-3308.
Chianese, Giuseppina; Scala, Fernando; Calcinai, Barbara; Cerrano, Carlo; Dien, Henny A.; Kaiser, Marcel; Tasdemir, Deniz; Taglialatela-Scafati, Orazio. 2013. "Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity." Mar. Drugs 11, no. 9: 3297-3308.