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

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), b...

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Autores principales: Chianese, Giuseppina, Scala, Fernando, Calcinai, Barbara, Cerrano, Carlo, Dien, Henny A., Kaiser, Marcel, Tasdemir, Deniz, Taglialatela-Scafati, Orazio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3806476/
https://www.ncbi.nlm.nih.gov/pubmed/23989650
http://dx.doi.org/10.3390/md11093297
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author Chianese, Giuseppina
Scala, Fernando
Calcinai, Barbara
Cerrano, Carlo
Dien, Henny A.
Kaiser, Marcel
Tasdemir, Deniz
Taglialatela-Scafati, Orazio
author_facet Chianese, Giuseppina
Scala, Fernando
Calcinai, Barbara
Cerrano, Carlo
Dien, Henny A.
Kaiser, Marcel
Tasdemir, Deniz
Taglialatela-Scafati, Orazio
author_sort Chianese, Giuseppina
collection PubMed
description 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.
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spelling pubmed-38064762013-10-23 Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity Chianese, Giuseppina Scala, Fernando Calcinai, Barbara Cerrano, Carlo Dien, Henny A. Kaiser, Marcel Tasdemir, Deniz Taglialatela-Scafati, Orazio Mar Drugs Article 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. MDPI 2013-08-28 /pmc/articles/PMC3806476/ /pubmed/23989650 http://dx.doi.org/10.3390/md11093297 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Chianese, Giuseppina
Scala, Fernando
Calcinai, Barbara
Cerrano, Carlo
Dien, Henny A.
Kaiser, Marcel
Tasdemir, Deniz
Taglialatela-Scafati, Orazio
Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
title Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
title_full Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
title_fullStr Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
title_full_unstemmed Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
title_short Natural and Semisynthetic Analogues of Manadoperoxide B Reveal New Structural Requirements for Trypanocidal Activity
title_sort natural and semisynthetic analogues of manadoperoxide b reveal new structural requirements for trypanocidal activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3806476/
https://www.ncbi.nlm.nih.gov/pubmed/23989650
http://dx.doi.org/10.3390/md11093297
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