Abstract
Abstract The interfacial behavior of curcumin, a model anti-inflammatory drug was studied upon interaction with cetyl palmitate and 1,2-dioleoyl-sn-glycero-3-phosphatidylcholine. Cetyl palmitate finds applications for topical delivery in nanostructured lipid carriers, while the phosphatidylcholine was used both as a component of the carrier and as a model membrane lipid. Here, surface pressure, thermodynamics, Brewster angle microscopy, molecular dynamics and polarization modulation infrared reflection-absorption spectroscopy were used to better our understanding of the interaction between the components of the delivery systems and, on the other hand, of their interaction with biological membranes. Moreover, thermodynamics was used to analyze the effect of curcumin on the lipid systems and, in particular, on the model membranes. The results obtained indicate that mixtures of curcumin and cetyl palmitate form Langmuir films, while none of the two pure components does. This effect was interpreted in terms of formation of a complex between curcumin and the hydrophobic, water insoluble cetyl palmitate. The hydrophilic-hydrophobic balance of the complex allows its penetration into the monolayer and mixing with the phospholipid phase. This finding may be of interest for further design of phytolipids for drug delivery applications.
Highlights
Curcumin (CC), a diarylheptanoid of plant origin finds applications in food and cosmetics, and new developments in the medicinal chemistry are described in the literature [1]
Overall, taking into account the results obtained with surface pressure measurements and with Brewster angle microscopy (BAM), we propose that the cetyl palmitate (CP) and CC molecules present in the mixed films containing DOPC interact and undergo a rearrangement at the air-water interface upon compression; CC stabilizes the layer by interacting with CP in the region of the DOPC polar heads
This study showed that the effect of curcumin on model membranes formed at the air-water interface with DOPC is intensified by the presence of cetyl palmitate in the lipid film
Summary
Curcumin (CC), a diarylheptanoid of plant origin finds applications in food and cosmetics, and new developments in the medicinal chemistry are described in the literature [1]. Curcumin has low bioavailability as it is poorly soluble in physiological conditions (b3 mg·L−1) and poorly absorbed. It is rapidly metabolized and eliminated [3,4]. M. Girardon et al / Journal of Molecular Liquids 308 (2020) 113040 the Langmuir technique [16] offers an easy way to prepare model membranes and to study the interaction of lipid monolayers with third molecules [17,18,19,20,21,22,23]. The interaction of the SLN and membrane constitutive molecules was investigated using Langmuir compression isotherms, Brewster angle microscopy (BAM) and polarization modulation infrared reflection-absorption spectroscopy (PM-IRRAS), thermodynamic analysis, and molecular modeling. The compression isotherms allowed determining the compressibility modulus, CS−1, [25] as: CS−1 1⁄4 −Að∂Π=∂AÞT ð1Þ
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