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

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. T...

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Autores principales: Sortino, Maximiliano, Postigo, Agustina, Zacchino, Susana
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: MDPI Open Access Publishing 2013
Materias:
biotransformation
Aspergillus fumigatus
enantioselective reduction
enhanced antifungal activity
chiral succinimides
methylated succinimides
Acceso en línea:http://hdl.handle.net/2133/2583
http://hdl.handle.net/2133/2583
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-2583
record_format dspace
institution Universidad Nacional de Rosario
institution_str I-15
repository_str R-121
collection Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language Inglés
orig_language_str_mv en
topic biotransformation
Aspergillus fumigatus
enantioselective reduction
enhanced antifungal activity
chiral succinimides
methylated succinimides
spellingShingle biotransformation
Aspergillus fumigatus
enantioselective reduction
enhanced antifungal activity
chiral succinimides
methylated succinimides
Sortino, Maximiliano
Postigo, Agustina
Zacchino, Susana
Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
topic_facet biotransformation
Aspergillus fumigatus
enantioselective reduction
enhanced antifungal activity
chiral succinimides
methylated succinimides
description 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.
format article
artículo
publishedVersion
author Sortino, Maximiliano
Postigo, Agustina
Zacchino, Susana
author_facet Sortino, Maximiliano
Postigo, Agustina
Zacchino, Susana
author_sort Sortino, Maximiliano
title Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
title_short Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
title_full Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
title_fullStr Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
title_full_unstemmed Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones
title_sort effects of chirality on the antifungal potency of methylated succinimides obtained by aspergillus fumigatus biotransformations. comparison with racemic ones
publisher MDPI Open Access Publishing
publishDate 2013
url http://hdl.handle.net/2133/2583
http://hdl.handle.net/2133/2583
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AT zacchinosusana effectsofchiralityontheantifungalpotencyofmethylatedsuccinimidesobtainedbyaspergillusfumigatusbiotransformationscomparisonwithracemicones
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