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Molecules 2013, 18(5), 5669-5683; doi:10.3390/molecules18055669
Article

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

,
 and
*
Pharmacognosy Area, Faculty of Biochemical and Pharmaceutical Sciences, National University of Rosario, Suipacha 531, 2000-Rosario, Argentina
* Author to whom correspondence should be addressed.
Received: 24 April 2013 / Revised: 13 May 2013 / Accepted: 13 May 2013 / Published: 15 May 2013
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: biotransformation; Aspergillus fumigatus; enantioselective reduction; enhanced antifungal activity; chiral succinimides; methylated succinimides biotransformation; Aspergillus fumigatus; enantioselective reduction; enhanced antifungal activity; chiral succinimides; methylated succinimides
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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, 5669-5683.

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