Mar. Drugs 2013, 11(9), 3297-3308; doi:10.3390/md11093297
Article

Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity

1 Department of Pharmacy, University of Naples "Federico II", Via D. Montesano, 49, Naples I-80131, Italy 2 Department of Marine Sciences, Polytechnic University of Marche, Via Brecce Bianche, Ancona 60131, Italy 3 Faculty of Fishery and Marine Science, Sam Ratulangi University, Manado 95115, Indonesia 4 Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Basel CH-4002, Switzerland 5 University of Basel, Petersplatz 1, Basel CH-4003, Switzerland 6 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
(This article belongs to the Special Issue Antiprotozoal Marine Natural Products)
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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 (68) 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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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