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Natural and semisynthetic analogues of manadoperoxide b reveal new structural requirements for trypanocidal activity

Chianese, Giuseppina
; 
Scala, Fernando
; 
Calcinai, Barbara
; 
Cerrano, Carlo
; 
Dien, Henny
; 
Kaiser, Marcel
; 
Tasdemir, Deniz
; 
Taglialatela-Scafati, Orazio
Repository DOI
Publication Date
2013-08-28
Keywords
manadoperoxide b, marine antitrypanosomals, structure-activity relationships, sponge plakortis-simplex, drug-resistance, in-vitro, cycloperoxides, metabolites, parasites
Type
Article
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Citation
Chianese, Giuseppina; Scala, Fernando; Calcinai, Barbara; Cerrano, Carlo; Dien, Henny; Kaiser, Marcel; Tasdemir, Deniz; Taglialatela-Scafati, Orazio (2013). Natural and semisynthetic analogues of manadoperoxide b reveal new structural requirements for trypanocidal activity. Marine Drugs 11 (9), 3297-3308
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.
Funder
Publisher
MDPI AG
Publisher DOI
10.3390/md11093297
Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (2)