curcumin and 1-2-dielaidoylphosphatidylethanolamine

The aim of this study was to develop a green method to fabricate a novel CS modified N-(4-hydroxyphenyl)- methacrylamide conjugate (CSNHMA) and to evaluate its biomedical potential. CSNHMA has been prepared by a simple method via aza Michael addition reaction between CS and N- (4-hydroxyphenyl)-methacrylamide (NHMA) in ethanol. Its structural and morphological properties were characterized by various analysis techniques. The obtained results confirmed that a highly porous network structure of CSNHMA was successfully synthesized via aza Michael addition reaction. Consequently, it was analyzed as a drug and gene carrier. CSNHMA/pGL3 showed an enhanced buffering capacity due to the presence of NHMA moiety leading to higher transfection efficiency in all cancer cells (A549, HeLa and HepG2) as compared to native CS and Lipofectamine®. Therefore, these findings clearly support the possibility of using CSNHMA as a good transfection agent. For in vitro drug release study, we prepared CSNHMA nanoparticles (NPs) and curcumin loaded CSNHMA NPs of size <230 nm respectively via the non-toxic ionic gelation route and the encapsulation efficiency of drug was found to be 77.03%. In vitro drug release studies demonstrated a faster and sustained release of curcumin loaded CSNHMA NPs at pH 5.0 compared to physiological pH.

Topics: A549 Cells; Acrylamides; Carbohydrate Sequence; Cell Line, Tumor; Cell Proliferation; Cell Survival; Chitosan; Curcumin; Delayed-Action Preparations; Drug Carriers; Green Chemistry Technology; HeLa Cells; Hep G2 Cells; Humans; Luciferases; Particle Size; Phosphatidylethanolamines; Porosity; Transfection

Curcumin is a polyphenol present in turmeric, a spice widely used in Asian traditional medicine and cooking. It has many and diverse biological effects and is incorporated in cell membranes. This paper describes the mode in which curcumin modulates the physical properties of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dielaidyl-sn-glycero-3-phosphoetnanolamine (DEPE) multilamellar membranes. Curcumin disordered DPPC membranes at temperatures below T(c) as seen by DSC, FT-IR, (2)H NMR, WAXD, and SAXD. The decrease induced by curcumin in T(c) suggested that it is oriented in the bilayer with its main axis parallel to the acyl chains. Above T(c), too, curcumin introduced disorder as seen by infrared spectroscopy which showed that curcumin also alters the conformation of the polar group of DPPC, increasing the percentage of unhydrated C=O groups, but does not form hydrogen bonds with either the C=O group or the phosphate group of DPPC. Small angle X-ray diffraction showed a notable increase in the repeating spacings as a result of the presence of curcumin, suggesting the formation of a rippled phase. Increasing concentrations of curcumin progressively modified the onset and completion of the phase transition and also DeltaH up to a 6:1 DPPC/curcumin molar ratio. A further increase of curcumin concentration did not produce effects on the transition parameters, suggesting that there is a limit for the solubility of curcumin in DPPC. Additionally, when DEPE was used to test the effect of curcumin on the phospholipid polymorphism, it was found that the temperature at which the H(II) phase is formed decreased, indicating that curcumin favors negative curvature of the membrane, which may be important for explaining its effect on membrane dynamics and on membrane proteins or on proteins which may be activated through membrane insertion.

Topics: 1,2-Dipalmitoylphosphatidylcholine; Calorimetry, Differential Scanning; Curcumin; Lipid Bilayers; Magnetic Resonance Spectroscopy; Phosphatidylethanolamines; Spectrophotometry, Ultraviolet; X-Ray Diffraction