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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| Format: | Article |
| Language: | English |
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MDPI AG
2013-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/18/5/5669 |
| _version_ | 1818016558889304064 |
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| author | Susana Zacchino Agustina Postigo Maximiliano Sortino |
| author_facet | Susana Zacchino Agustina Postigo Maximiliano Sortino |
| author_sort | Susana Zacchino |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-04-14T07:14:00Z |
| format | Article |
| id | doaj.art-c6ef077f971b4b5692f6b3d30bcbc92a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-14T07:14:00Z |
| publishDate | 2013-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c6ef077f971b4b5692f6b3d30bcbc92a2022-12-22T02:06:21ZengMDPI AGMolecules1420-30492013-05-011855669568310.3390/molecules18055669Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic OnesSusana ZacchinoAgustina PostigoMaximiliano SortinoEighteen (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.http://www.mdpi.com/1420-3049/18/5/5669biotransformationAspergillus fumigatusenantioselective reductionenhanced antifungal activitychiral succinimidesmethylated succinimides |
| spellingShingle | Susana Zacchino Agustina Postigo Maximiliano Sortino Effects of Chirality on the Antifungal Potency of Methylated Succinimides Obtained by Aspergillus fumigatus Biotransformations. Comparison with Racemic Ones Molecules biotransformation Aspergillus fumigatus enantioselective reduction enhanced antifungal activity chiral succinimides methylated succinimides |
| title | 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_short | 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 |
| topic | biotransformation Aspergillus fumigatus enantioselective reduction enhanced antifungal activity chiral succinimides methylated succinimides |
| url | http://www.mdpi.com/1420-3049/18/5/5669 |
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