Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity
Marcelina Mazur , Anna Kudrynska , Aleksandra Pawlak , Beatriz Hernandez Suarez , Bożena Obmińska-Mrukowicz , Witold Gładkowski
AbstractThe β-aryl-δ-halo-γ-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 β-aryl-δ-hydroxy-γ-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.
|Journal series||Catalysts, ISSN 2073-4344, (N/A 100 pkt)|
|Publication size in sheets||0.5|
|Keywords in English||lactones, biotransformations, dehalogenation, antiproliferative activity|
|License||Journal (articles only); published final; ; with publication|
|Score||= 100.0, 28-04-2021, ArticleFromJournal|
|Publication indicators||= 1; = 1; : 2018 = 0.912; : 2018 = 3.444 (2) - 2018=3.808 (5)|
|Citation count*||2 (2021-05-09)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.