Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity
The 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...
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MDPI AG
2020-11-01
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| author | Marcelina Mazur Anna Kudrynska Aleksandra Pawlak Beatriz Hernandez-Suarez Bożena Obmińska-Mrukowicz Witold Gładkowski |
| author_facet | Marcelina Mazur Anna Kudrynska Aleksandra Pawlak Beatriz Hernandez-Suarez Bożena Obmińska-Mrukowicz Witold Gładkowski |
| author_sort | Marcelina Mazur |
| collection | DOAJ |
| description | The 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 <i>cis</i>-5-(1-iodoethyl)-4-phenyldihydrofuran-2-one as well as separate enantiomers were transformed in fungal cultures. Among ten tested biocatalysts, three (<i>Absidia cylindrospora</i> AM336, <i>Absidia glauca</i> AM254, and <i>Fusarium culmorum</i> 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 (+)-(4<i>S</i>,5<i>S</i>,6<i>R</i>)-enantiomer of iodolactone compared to its antipode. |
| first_indexed | 2024-03-10T14:53:10Z |
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| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T14:53:10Z |
| publishDate | 2020-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-c0143baf8dd9424689f14082e38c71342023-11-20T20:48:55ZengMDPI AGCatalysts2073-43442020-11-011011131310.3390/catal10111313Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic ActivityMarcelina Mazur0Anna Kudrynska1Aleksandra Pawlak2Beatriz Hernandez-Suarez3Bożena Obmińska-Mrukowicz4Witold Gładkowski5Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandDepartment of Pharmacology and Toxicology, Wrocław University of Environmental and Life Sciences, Norwida 31, 50-375 Wrocław, PolandDepartment of Pharmacology and Toxicology, Wrocław University of Environmental and Life Sciences, Norwida 31, 50-375 Wrocław, PolandDepartment of Pharmacology and Toxicology, Wrocław University of Environmental and Life Sciences, Norwida 31, 50-375 Wrocław, PolandDepartment of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, PolandThe 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 <i>cis</i>-5-(1-iodoethyl)-4-phenyldihydrofuran-2-one as well as separate enantiomers were transformed in fungal cultures. Among ten tested biocatalysts, three (<i>Absidia cylindrospora</i> AM336, <i>Absidia glauca</i> AM254, and <i>Fusarium culmorum</i> 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 (+)-(4<i>S</i>,5<i>S</i>,6<i>R</i>)-enantiomer of iodolactone compared to its antipode.https://www.mdpi.com/2073-4344/10/11/1313lactonesbiotransformationsdehalogenationantiproliferative activity |
| spellingShingle | Marcelina Mazur Anna Kudrynska Aleksandra Pawlak Beatriz Hernandez-Suarez Bożena Obmińska-Mrukowicz Witold Gładkowski Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity Catalysts lactones biotransformations dehalogenation antiproliferative activity |
| title | Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity |
| title_full | Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity |
| title_fullStr | Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity |
| title_full_unstemmed | Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity |
| title_short | Biotechnological Approach for the Production of Enantiomeric Hydroxylactones Derived from Benzaldehyde and Evaluation of Their Cytotoxic Activity |
| title_sort | biotechnological approach for the production of enantiomeric hydroxylactones derived from benzaldehyde and evaluation of their cytotoxic activity |
| topic | lactones biotransformations dehalogenation antiproliferative activity |
| url | https://www.mdpi.com/2073-4344/10/11/1313 |
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