Physicochemical Characterization of Liposomal Bilayer Models Loaded with Trans-4-(4′-hydroxy-3′-methoxyphenyl)-5-(1-iodoethyl)dihydrofuran-2-one
- 1Department of Food Chemistry and Biocatalysis, Faculty of Biotechnology and Food Sciences, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
- 2Department of Physics and Biophysics, Faculty of Biotechnology and Food Sciences, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland
- 3Institute of Environmental Engineering, Faculty of Environmental Engineering and Geodesy, Wrocław University of Environmental and Life Sciences, pl. Grunwaldzki 24, 50-363 Wrocław, Poland
Abstract
Trans-4-(4′-hydroxy-3′-methoxyphenyl)-5-(1-iodoethyl)dihydrofuran-2-one (IL), a vanillin-derived iodolactone with previously demonstrated biological activity, was incorporated into DPPC/cholesterol (DPPC/chol) liposomes to develop and characterize a lipid-based delivery system, with particular emphasis on the relationship between IL incorporation and the biophysical properties of the nanocarrier. The physicochemical stability of formulations containing 2, 5, 10, and 20 mol% IL was assessed using dynamic and electrophoretic light scattering (DLS/ELS), while the loading efficiency (LE%) of the highest IL concentration tested (20 mol%) was determined via ultracentrifugation, liquid–liquid extraction, and subsequent gas chromatography (GC) analysis. The formulation exhibited a high LE% of 87.6 ± 7.8%; however, as potential sedimentation of free IL cannot be ruled out, this value represents an indirect estimate of IL loading and remains a technical limitation of the assay. The effect of IL incorporation on bilayer organization was examined using three fluorescent probes, as well as attenuated total reflectance Fourier-transform infrared spectroscopy. DLS/ELS measurements demonstrated the most favorable colloidal stability for liposomes hydrated with milli-Q water and stored at 4 °C, as reflected by the maintenance of low PDI values, a relatively stable hydrodynamic diameter, and a negative zeta potential throughout the one-month storage period. Fluorescence spectroscopy demonstrated that IL modified the temperature-dependent organization of the DPPC/chol bilayer, with effects particularly evident at the membrane interface and, at elevated temperatures, in the hydrophobic region. Complementary ATR-FTIR analysis indicated that IL interacts with the polar headgroup and glycerol backbone regions without significantly disrupting acyl chain organization. Hemolytic assays further demonstrated the low membrane-damaging activity of IL-loaded liposomes in both crude dispersion fractions and the ultracentrifuged liposomal fraction. These results demonstrate that IL can be efficiently incorporated into DPPC/chol liposomes while maintaining favorable physicochemical stability and low hemolytic potential. The observed effect of the tested compound on bilayer organization without disrupting membrane integrity supports the need for further investigation of lipid formulations containing IL.
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BibTeX
@article{dunal2026physicochemical,
title = {{Physicochemical Characterization of Liposomal Bilayer Models Loaded with Trans-4-(4′-hydroxy-3′-methoxyphenyl)-5-(1-iodoethyl)dihydrofuran-2-one}},
author = {Anna Dunal and Aleksandra Włoch and Witold Gładkowski and Magdalena Domańska and Hanna Pruchnik},
journal = {Molecules},
year = {2026},
month = oct,
doi = {10.3390/molecules31203756},
url = {https://www.mdpi.com/1420-3049/31/20/3756},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Physicochemical Characterization of Liposomal Bilayer Models Loaded with Trans-4-(4′-hydroxy-3′-methoxyphenyl)-5-(1-iodoethyl)dihydrofuran-2-one
AU - Anna Dunal
AU - Aleksandra Włoch
AU - Witold Gładkowski
AU - Magdalena Domańska
AU - Hanna Pruchnik
PY - 2026
DA - 2026/10/01
JO - Molecules
DO - 10.3390/molecules31203756
UR - https://www.mdpi.com/1420-3049/31/20/3756
AB - Trans-4-(4′-hydroxy-3′-methoxyphenyl)-5-(1-iodoethyl)dihydrofuran-2-one (IL), a vanillin-derived iodolactone with previously demonstrated biological activity, was incorporated into DPPC/cholesterol (DPPC/chol) liposomes to develop and characterize a lipid-based delivery system, with particular emphasis on the relationship between IL incorporation and the biophysical properties of the nanocarrier. The physicochemical stability of formulations containing 2, 5, 10, and 20 mol% IL was assessed using dynamic and electrophoretic light scattering (DLS/ELS), while the loading efficiency (LE%) of the highest IL concentration tested (20 mol%) was determined via ultracentrifugation, liquid–liquid extraction, and subsequent gas chromatography (GC) analysis. The formulation exhibited a high LE% of 87.6 ± 7.8%; however, as potential sedimentation of free IL cannot be ruled out, this value represents an indirect estimate of IL loading and remains a technical limitation of the assay. The effect of IL incorporation on bilayer organization was examined using three fluorescent probes, as well as attenuated total reflectance Fourier-transform infrared spectroscopy. DLS/ELS measurements demonstrated the most favorable colloidal stability for liposomes hydrated with milli-Q water and stored at 4 °C, as reflected by the maintenance of low PDI values, a relatively stable hydrodynamic diameter, and a negative zeta potential throughout the one-month storage period. Fluorescence spectroscopy demonstrated that IL modified the temperature-dependent organization of the DPPC/chol bilayer, with effects particularly evident at the membrane interface and, at elevated temperatures, in the hydrophobic region. Complementary ATR-FTIR analysis indicated that IL interacts with the polar headgroup and glycerol backbone regions without significantly disrupting acyl chain organization. Hemolytic assays further demonstrated the low membrane-damaging activity of IL-loaded liposomes in both crude dispersion fractions and the ultracentrifuged liposomal fraction. These results demonstrate that IL can be efficiently incorporated into DPPC/chol liposomes while maintaining favorable physicochemical stability and low hemolytic potential. The observed effect of the tested compound on bilayer organization without disrupting membrane integrity supports the need for further investigation of lipid formulations containing IL.
SN - 1420-3049
ER -