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Curcumin amorphous solid dispersions: the influence of intra and intermolecular bonding on physical stability.

Pharmaceutical development and technology (2013-11-07)
Lindsay A Wegiel, Yuhong Zhao, Lisa J Mauer, Kevin J Edgar, Lynne S Taylor
ABSTRACT

We have investigated the physical stability of amorphous curcumin dispersions and the role of curcumin-polymer intermolecular interactions in delaying crystallization. Curcumin is an interesting model compound as it forms both intra and intermolecular hydrogen bonds in the crystal. A structurally diverse set of amorphous dispersion polymers was investigated; poly(vinylpyrrolidone), Eudragit E100, carboxymethyl cellulose acetate butyrate, hydroxypropyl methyl cellulose (HPMC) and HPMC-acetate succinate. Mid-infrared spectroscopy was used to determine and quantify the extent of curcumin-polymer interactions. Physical stability under different environmental conditions was monitored by powder X-ray diffraction. Curcumin chemical stability was monitored by UV-Vis spectroscopy. Isolation of stable amorphous curcumin was difficult in the absence of polymers. Polymers proved to be effective curcumin crystallization inhibitors enabling the production of amorphous solid dispersions; however, the polymers showed very different abilities to inhibit crystallization during long-term storage. Curcumin intramolecular hydrogen bonding reduced the extent of its hydrogen bonding with polymers; hence most polymers were not highly effective crystallization inhibitors. Overall, polymers proved to be crystallization inhibitors, but inhibition was limited due to the intramolecular hydrogen bonding in curcumin, which leads to a decrease in the ability of the polymers to interact at a molecular level.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Polyvinylpyrrolidone, K 30
Sigma-Aldrich
Polyvinylpyrrolidone, powder, average Mw ~29,000
Sigma-Aldrich
Polyvinylpyrrolidone, powder, average Mw ~55,000
Sigma-Aldrich
Polyvinylpyrrolidone, average Mw ~1,300,000 by LS
Sigma-Aldrich
Polyvinylpyrrolidone, K 90
Sigma-Aldrich
Methocel® A15 LV, 27.5-31.5% methoxyl basis
Sigma-Aldrich
Polyvinylpyrrolidone solution, K 60, 45% in H2O
Sigma-Aldrich
Polyvinylpyrrolidone, K 25, tested according to Ph. Eur.
Supelco
Curcumin, analytical standard
Curcumin, primary reference standard
Supelco
Curcumin, matrix substance for MALDI-MS, ≥99.5% (HPLC)
USP
Curcumin, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Carboxymethylcellulose sodium salt, Medium viscosity
Sigma-Aldrich
Carboxymethylcellulose sodium salt, High viscosity
Sigma-Aldrich
Curcumin, ≥94% (curcuminoid content), ≥80% (Curcumin)
Sigma-Aldrich
Carboxymethylcellulose sodium salt, low viscosity
Sigma-Aldrich
Polyvinylpyrrolidone, powder, BioXtra, suitable for mouse embryo cell culture
Sigma-Aldrich
Polyvinylpyrrolidone, suitable for plant cell culture, average mol wt 10,000
Sigma-Aldrich
Polyvinylpyrrolidone, for molecular biology, nucleic acid hybridization tested, mol wt 360,000
Sigma-Aldrich
Curcumin, from Curcuma longa (Turmeric), powder
Sigma-Aldrich
Polyvinylpyrrolidone, average mol wt 40,000
Sigma-Aldrich
Polyvinylpyrrolidone, mol wt (number average molecular weight Mn 360)
Sigma-Aldrich
Polyvinylpyrrolidone, average mol wt 10,000
Sigma-Aldrich
Sodium carboxymethyl cellulose, average Mw ~250,000, degree of substitution 0.9
Sigma-Aldrich
Sodium carboxymethyl cellulose, average Mw ~250,000, degree of substitution 1.2
Sigma-Aldrich
(Hydroxypropyl)methyl cellulose, average Mn ~90,000
Sigma-Aldrich
(Hydroxypropyl)methyl cellulose, average Mn ~10,000
Sigma-Aldrich
(Hydroxypropyl)methyl cellulose, average Mn ~86,000
Sigma-Aldrich
(Hydroxypropyl)methyl cellulose, average Mn ~120,000
Sigma-Aldrich
Carboxymethylcellulose sodium, meets USP testing specifications, Medium viscosity