Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones

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dc.contributor.author Sortino, Maximiliano
dc.contributor.author Postigo, Agustina
dc.contributor.author Zacchino, Susana
dc.date.accessioned 2013-05-29T20:20:16Z
dc.date.available 2013-05-29T20:20:16Z
dc.date.issued 2013-05-15
dc.identifier.citation Sortino M, Postigo A, Zacchino S. Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones. Molecules. 2013; 18(5):5669-5683. es
dc.identifier.issn 1420-3049
dc.identifier.uri http://hdl.handle.net/2133/2583
dc.description.abstract Eighteen (3R) and (3R,4R)-N-phenyl-, N-phenylalkyl and N-arylsuccinimides were prepared with high enantioselectivity by biotransformation of maleimides with A. fumigatus. This environmentally friendly, clean and economical procedure was performed by the whole-cell fungal bioconversion methodology. Their corresponding eighteen racemic succinimides were prepared instead by synthetic methods. Both, the racemic and the chiral succinimides were tested simultaneously by the microbroth dilution method of CLSI against a panel of human opportunistic pathogenic fungi of clinical importance. Chiral succinimides showed higher antifungal activity than the corresponding racemic ones and the differences in activity were established by statistical methods. The bottlenecks for developing chiral drugs are how to obtain them through a low-cost procedure and with high enantiomeric excess. Results presented here accomplish both these objectives, opening an avenue for the development of asymmetric succinimides as new antifungal drugs for pharmaceutical use. es
dc.language.iso en es
dc.publisher MDPI Open Access Publishing es
dc.rights openAccess es
dc.rights © 2013 by the authors; licensee MDPI, Basel, Switzerland. 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/).
dc.subject biotransformation es
dc.subject Aspergillus fumigatus es
dc.subject enantioselective reduction es
dc.subject enhanced antifungal activity es
dc.subject chiral succinimides es
dc.subject methylated succinimides es
dc.title Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones es
dc.type article es
dc.type artículo
dc.type publishedVersion
dc.description.peerreviewed Peer reviewed es
dc.relation.publisherversion http://www.mdpi.com/1420-3049/18/5/5669 es
dc.description.affiliation Fil: Sortino, Maximiliano. Universidad Nacional de Rosario, Facultad de Farmacia y Bioquímica; Argentina.
dc.description.affiliation Fil: Postigo, Agustina. Universidad Nacional de Rosario, Facultad de Farmacia y Bioquímica; Argentina.
dc.description.affiliation Fil: Zacchino, Susana. Universidad Nacional de Rosario, Facultad de Farmacia y Bioquímica; Argentina.


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