Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity
| Autor: | Witold Gładkowski, Marcelina Mazur, Beatriz Hernandez-Suarez, Anna Kudrynska, Bożena Obmińska-Mrukowicz, Aleksandra Pawlak |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
antiproliferative activity
Stereochemistry lcsh:Chemical technology 01 natural sciences Catalysis lactones Benzaldehyde lcsh:Chemistry 03 medical and health sciences Hydrolysis chemistry.chemical_compound Biotransformation Fusarium culmorum lcsh:TP1-1185 Physical and Theoretical Chemistry 030304 developmental biology 0303 health sciences biology 010405 organic chemistry Chemistry Halogenation biology.organism_classification 0104 chemical sciences biotransformations lcsh:QD1-999 Cell culture Stereoselectivity dehalogenation Enantiomer |
| Zdroj: | Catalysts, Vol 10, Iss 1313, p 1313 (2020) Catalysts Volume 10 Issue 11 |
| ISSN: | 2073-4344 |
| Popis: | The &beta aryl-&delta halo-&gamma lactones are known for their antiproliferative activity towards numerous cancer cell lines. The aim of this study was to obtain in the biotransformation process new &beta hydroxy-&gamma lactones and compare their activity with the antiproliferative activity of parent compounds. The racemic cis-5-(1-iodoethyl)-4-phenyldihydrofuran-2-one as well as separate enantiomers were transformed in fungal cultures. Among ten tested biocatalysts, three (Absidia cylindrospora AM336, Absidia glauca AM254, and Fusarium culmorum AM10) were able to catalyze the hydrolytic dehalogenation process. The biotransformations processes were highly stereoselective and enantiomerically pure hydroxylactones were obtained (ee &ge 99%). The iodo- and hydroxylactone enantiomers were subjected to cytotoxic activity evaluation on canine leukemia and lymphoma cell lines. The iodolactones exhibited higher biological potential towards tested cell lines than hydroxylactones. Higher cytotoxic potential was also characteristic for (+)-(4S,5S,6R)-enantiomer of iodolactone compared to its antipode. |
| Databáze: | OpenAIRE |
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