Interaction of curcumin with lipid monolayers and liposomal bilayers

The Molecular Basis for the Pharmacokinetics and Pharmacodynamics of Curcumin and Its Metabolites in Relation to Cancer

“…Fluorescence quenching experiments established that liposome-encapsulated curcumin fluorescence is quenched more extensively by membrane-penetrating quenchers Cancer Pharmacology of Curcumin (acrylamide) than by less membrane-permeant quenchers (iodine) (Kunwar et al, 2006). Similar assays with brominated carboxylic acid derivatives (2-or 16-bromohexadecanoic acid or 11-bromoundecanoic acid), which more or less behave as component phospholipids in model membranes, corroborated that curcumin fluorescence is most intensely quenched by the bromine at C Δ11 (Karewicz et al, 2011), i.e., in a very hydrophobic region of the bilayer (Bemporad et al, 2005). Accordingly, the lipophilic methines of curcumin most likely facilitate hydrophobic interactions with the acyl chains of phospholipids in cell and subcellular membranes, as was shown for erythrocytes (Jaruga et al, 1998), whereby the polar flanking regions may undergo Hbonding with water molecules embedded in the more distal portions of the membrane relative to the bilayer center (Bemporad et al, 2005).…”

“…The association of curcumin with model membranes occurs at relatively high partition constants, i.e., in the range of 2.5 Â 10 4 M 21 (Kunwar et al, 2006) to 4.3 Â 10 4 M 21 (Karewicz et al, 2011) for egg yolk phosphatidylcholine liposomes and 2.4 Â 10 4 M 21 for dioleoylphosphatidyl choline liposomes , indicating that curcumin can be taken up by cells by direct intercalation into the cell membrane.…”

“…Second, the relatively high partition coefficient of curcumin is indicative of the molecule's capacity to interact with biomembranes (Jaruga et al, 1998), which is reflected by the intercalation of curcumin into model membranes (liposomes) composed of saturated (dipalmitoylphosphatidyl choline or dimyristoylphosphatidyl choline) (Barry et al, 2009;Perez-Lara et al, 2010), monounsaturated (dioleoylphosphatidyl choline) (Ingolfsson et al, 2007;Hung et al, 2008;Sun et al, 2008), or egg yolk phosphatidyl cholines (Kunwar et al, 2006;Karewicz et al, 2011). The association of curcumin with model membranes occurs at relatively high partition constants, i.e., in the range of 2.5 Â 10 4 M 21 (Kunwar et al, 2006) to 4.3 Â 10 4 M 21 (Karewicz et al, 2011) for egg yolk phosphatidylcholine liposomes and 2.4 Â 10 4 M 21 for dioleoylphosphatidyl choline liposomes , indicating that curcumin can be taken up by cells by direct intercalation into the cell membrane.…”

Influence of Lipid Composition, pH, and Temperature on Physicochemical Properties of Liposomes with Curcumin as Model Drug

“…Incorporation of curcumin into liposomes caused fluorescence enhancement with a significant blue shift in λ em values, indicating its transfer to the less polar region of the liposome 15,24,57,58 . These results suggest that curcumin resides in the palisade layer of liposomes because of its amphiphilic nature.…”

In vitro effects of prolonged exposure to quercetin and epigallocatechin gallate of the peripheral blood mononuclear cell membrane

“…They also reduce the severity and progression of already developed lesions and lead to a reduction in dyslipidemia, endothelial dysfunction and hypertension. These benefits occur through several mechanisms, including: inhibition of LDL peroxidation, increase in the HDL level, reduction of platelet activation and thrombosis, inhibition of inflammatory processes, inhibition of MMP-2 expression and activity in vascular tissues, and anti-angiogenic properties [15][16][17][18]. The ability of polyphenols to enter membrane lipid bilayers is critical in explaining their antioxidant and cardio-protective effects.…”