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Biophysical and molecular interactions of enantiomeric piperonal-derived trans β-aryl-δ-iodo-γ-lactones with cancer cell membranes, protein and DNA: Implications for anticancer activity
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SYSNO ASEP 0618286 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Biophysical and molecular interactions of enantiomeric piperonal-derived trans β-aryl-δ-iodo-γ-lactones with cancer cell membranes, protein and DNA: Implications for anticancer activity Author(s) Wloch, A. (PL)
Sengupta, P. (PL)
Szulc, N. (PL)
Kral, T. (PL)
Pawlak, A. (PL)
Henklewska, M. (PL)
Pruchnik, H. (PL)
Sýkora, Jan (UFCH-W) RID
Hof, Martin (UFCH-W) RID, ORCID
Gladkowski, W. (PL)Article number 140476 Source Title International Journal of Biological Macromolecules. - : Elsevier - ISSN 0141-8130
Roč. 303, APR 2025 (2025)Number of pages 11 s. Language eng - English Country NL - Netherlands Keywords human serum-albumin ; styryl-lactones ; establishment ; antitumor ; fluidity ; design ; liposomes ; analogs ; drugs ; Enantiomeric iodolactones ; cancer cell membrane ; hsa ; dna ; Single-molecule fluorescence spectroscopy Subject RIV CF - Physical ; Theoretical Chemistry OECD category Physical chemistry R&D Projects GX19-26854X GA ČR - Czech Science Foundation (CSF) GA22-25953S GA ČR - Czech Science Foundation (CSF) EH22_008/0004558 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support UFCH-W - RVO:61388955 UT WOS 001425132000001 EID SCOPUS 85216851899 DOI https://doi.org/10.1016/j.ijbiomac.2025.140476 Annotation Developing novel anticancer agents requires understanding their interactions with biological systems at both the cellular and molecular levels. Enantiomeric lactones have demonstrated notable cytotoxic activities against various cancer cell lines. Building on this foundation, we investigated enantiomeric piperonal-derived trans beta-aryl-delta-iodo-gamma-lactones ((-)-(4S,5R,6S) and (+)-(4R,5S,6R)), focusing on their impact on cancer cells membrane (Jurkat and GL-1), model membranes, and biomacromolecules such as human serum albumin (HSA) and DNA. Also, the cytotoxicity toward red blood cells and the antitumor activity of the compounds were evaluated against a set of canine lymphoma and/or leukemia cell lines. Membrane interaction studies revealed that both enantiomers interact with the hydrophobic core of lipid bilayers, enhancing lipid acyl chain packing, with the (-)-(4S,5R,6S) isomer showing a stronger impact on membrane fluidity. Comprehensive spectroscopic and theoretical studies revealed distinct stereochemical differences in binding affinities to HSA, where the (-)-(4S,5R,6S) isomer showed higher binding affinity and significant hydrophobic interactions. Detailed biological studies demonstrated that both enantiomers exhibit antiproliferative and proapoptotic activities, with the (-)-(4S,5R,6S) enantiomer showing higher activity. This study underscores the biological activity and interactions of enantiomeric iodolactones derived from piperonal with biomacromolecules, providing comprehensive insights into their biophysical behavior and potential anticancer properties. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2026 Electronic address https://www.sciencedirect.com/science/article/pii/S0141813025010256?via%3Dihub
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