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Abstract
Curcumin, a poorly water-soluble bioactive compound, was successfully loaded into three different aromatic contents of hydroxypropylmethacrylamide (HPMA)-based polymeric micelles in order to develop water-soluble curcumin nanoformulations (Cur-Nano). The stability study of Cur-Nano was done by keeping the formulations at 4, 30, and 40 °C for 90 days. The physical appearance, curcumin remaining, and particle size of Cur-Nano were examined by visual inspection, high-performance liquid chromatography, and dynamic light scattering, respectively. After the storage period, the Cur-Nano composed of 100% aromatic-substituted polymer exhibited the highest stability of curcumin (80% of curcumin remaining) with a similar particle size as measured on the first day (50–60 nm) in all storage conditions. Curcumin in Cur-Nano composed of 25% and 0% aromatic-substituted polymer was significantly less stable accordingly. The results suggested that aromatic substitution to HPMA-based polymeric micelles can significantly enhance the stability of the loaded curcumin, considerably due to the π-π stacking interactions between the aromatic groups of curcumin and the polymer. It is concluded that curcumin-loaded polymeric micelles with high substituted aromatic content can be promising candidates with good storage stability for further clinical evaluations.
Highlights
Curcumin ([1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione]) is a natural yellow-colored phenolic antioxidant
Curcumin was successfully loaded into different aromatic content HPMA-based polymers (Figure 2), polyethylene glycol (PEG)-HPMA-DL (0% aromatic substitution), PEG-HPMA-BZ-ML (25% aromatic substitution), and PEG-HPMA-BZ (100% aromatic substitution)
The EE and loading capacity (LC) of Cur-Nano was different in each nanoformulation
Summary
Curcumin ([1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione]) is a natural yellow-colored phenolic antioxidant. Curcumin from different natural sources as well as that available as a commercial product is isolated from the rhizome of Curcuma longa L. in which it presents in relatively high concentrations. It was reported that curcumin solubility in aqueous buffer (pH 5.0) was only 11 ng/mL [7]. Only 0.6 μmol/L of free curcumin and its conjugates were detected in the rat’s serum [8]. Another reason that limits clinical application of curcumin is that curcumin degrades quickly in neutral or alkaline buffer solution [9]
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