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Preparation and characterization of curcumin solid dispersions

NGUYEN NGOC SAO MAI 東京理科大学 DOI:info:doi/10.20604/00003615

2021.06.09

概要

Solubility is one of the most important physicochemical properties affecting drug bioavailability. One of the approaches to improve drug solubility is the preparation of solid dispersions (SDs) where the active pharmaceutical ingredients (APIs) are dispersed within (a) hydrophilic carrier(s) such as cyclodextrins, celluloses and their derivatives.

Curcumin (CUR), a diarylheptanoid consisting of two aromatic rings joined by a seven-carbon chain, exhibits numerous pharmacological properties such as anticancer, antioxidant, anti-inflammation, anti-tumor, anti-invasion, and wound healing. The efficient first-pass and intestinal metabolism of CUR might explain its poor systematic availability, and a daily oral dose of 3.6 g of CUR might be sufficient to exert pharmacological activity.

It is suggested that there are three majors approaches to overcome the bioavailability problems of CUR: (1) pharmacokinetics approach done by synthesizing its derivatives;(2) pharmaceutical approach realized by modifying formulation, manufacturing processes or physicochemical properties (e.g. complexation, and nano-formulation); and (3) biological approach by altering route of administration (e.g. intravenous, inhalation, and dermal delivery).

Particularly, converting crystalline drug to amorphous drug is a remarkable technique to achieve faster dissolution rate and higher apparent solubility due to changing physicochemical characteristic of API. There are two types of amorphous solids: pure amorphous drug and amorphous solid dispersion (ASD). Amorphous forms show a tendency towards crystallization to reduce the total energy content and pure amorphous forms convert to crystalline forms more rapidly than ASD’s. Therefore, dispersing APIs within polymers to form an ASD might improve drug dissolution rate and solubility while assuring the thermodynamic stability of drugs.

Enhancing the solubility of curcumin using a solid dispersion system with hydroxypropyl-β-cyclodextrin prepared by grinding, freeze-drying and common solvent evaporation methods Cyclodextrins are cyclic oligosaccharides consisting of six, seven, or eight α-(1,4) linked glucopyranoside units, corresponding to α-, β-, and γ-CD, respectively. The CDs can increase the solubility of drugs that are entrapped within their hydrophobic cavity because of their superior hydrophilic exterior when exposed to water. Moreover, modified CDs using hydrophilic functional groups express a superior possibility of improving drug solubility than conventional CDs.In this study, SDs of CUR and modified β-CD (hydroxypropyl-β-CD, HPβCD) were prepared using the grinding, freeze drying (FD), and common solvent evaporation (CSE) methods, and their physicochemical properties were evaluated with solubility, PXRD, FTIR, DSC, and dissolution studies. The second or higher order complex of CUR-HPβCD indicated the co-existence of inclusion complexes (ICs) and/or non-ICs, known as the SD system. When comparing the soluble drug amount with CUR crystals, the solubility of SDs were increased by up to 299-, 180-, and 489-fold, corresponding to the ground mixtures (GMs), FDs, and CSEs, respectively. The total transformation into the amorphous phase of CUR were observed in GMs and several ratios of CSEs. The drug was well dispersed within HPβCD in GMs and CSEs. The melting temperature of CUR in SDs increased in order of CUR in 1:2 ICs (CUR: HPβCD = 1:2), CUR in 1:1 ICs (CUR: HPβCD = 1:1), and CUR crystals. The dissolution rate of CUR increased with increase in the amount of HPβCD in SDs. The SD system consisting of CUR and HPβCD significantly increased the drug solubility compared to ICs.Preparation and characterization of solid dispersions composed of curcumin, hydroxypropyl cellulose and/or sodium dodecyl sulfate by grinding with vibrational ball milling Hydroxypropyl cellulose (HPC) has been used in SD formation to improve drug solubility. In this study, vibrational ball milling, a dry milling method was used to develop ground and co-ground CUR. It is applicable not only in laboratory research but also in pilot and industrial scale studies. During the grinding process, various parameters can influence the efficiency of grinding, such as the frequency of the vibration, type of grinding jar (volume, material), type of grinding media (quantity, material, and diameter), amount of powder filling, percentage of components, and grinding time.

Here, amorphization of CUR and CUR SDs consisting of CUR, HPC and/or SDS were developed by the vibrational ball milling. The resulting ground samples were characterized using PXRD, FTIR, DSC, and a dissolution study. The 60-min GM containing 90% HPC significantly increased the CUR solubility. Presence of SDS in GMs containing 90% HPC reduced grinding time from 60 min to 30 min in forming a ground SD which significantly increased the drug dissolution rate. This amorphous state was stable for 30 days when stored at 40 °C/ relative humidity 75%.

Effects of polymer molecular weight on curcumin amorphous solid dispersion: at- line monitoring system based on attenuated total reflectance mid-infrared and near- infrared spectroscopy An at-line process analysis is defined as a method characterized by manual sampling followed by discontinuous sample preparation, measurement, and evaluation. Analytical instruments (e.g. near-infrared, mid-infrared, and ultra-violet spectroscopy) and chemometric techniques (e.g. multivariate analysis, principal components analysis (PCA),and partial least-squares) are applied in pharmaceutical science for at-line monitoring process. Chemometrics is used in learning the relationships and structure of the system by analyzing very huge and highly complex datasets.

In this study, a ternary SD system containing CUR, HPC (HPC-SSL, HPC-L, or HPC-M), and SDS were prepared with grinding method, and the physicochemical and mechanochemical properties of this system were characterized. The grinding process, such as the grinding time and HPC Mw could be monitored by analyzing data obtained from MIR and NIR spectra. There were two steps in SD formation: (1) simple dispersion with grinding time under 30 min and (2) random dispersion of mixtures with grinding time from 30 to 120 min. The critical Mw of HPC (700,000 Da) could help select HPC(s) for more effectively forming SD systems.

[Conclusion]
CUR SDs were developed using grinding, FD, and CSE method and physicochemically characterized using PXRD, FTIR, DSC, dissolution study as well as scanning electron spectroscopy, particle size measurement, near- infrared. The carrier(s) where the drug was dispersed could influence the SD forming process due to its (their) chemical structure, molecular weight, proportion, and interactions with other components. The CUR-HPβCD SD consists of ICs and non-ICs and significantly increased the dissolution rate of CUR. Particularly, the grinding method with vibrational ball milling performed a total transformation from crystalline to the amorphous phase. The HPC in ground SDs could significantly increase CUR solubility at 90%. Also, the small amount of SDS might reduce the grinding time up to 30 min to manifest a significant enhancement in drug solubility. The forming of SDs can be at-line monitored using simple techniques such as MIR, NIR associated with chemometric.

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