4.6 Article

Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity

期刊

CATALYSTS
卷 10, 期 11, 页码 -

出版社

MDPI
DOI: 10.3390/catal10111313

关键词

lactones; biotransformations; dehalogenation; antiproliferative activity

资金

  1. statutory activities of the Department of Chemistry, Wroclaw University of Environmental and Life Sciences
  2. Leading Research Groups support project from the subsidy increased for the period 2020-2025

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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-aryl-delta-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 >= 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.

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