Improvement of the Solubility and Evaluation of the Physical Properties of an Inclusion Complex Formed by a New Ferulic Acid Derivative and γ-Cyclodextrin

Abstract

Ferulic acid derivative 012 (FAD012) is a ferulic acid (FA) derivative. The current study prepared a solid dispersion of FAD012 and γ-cyclodextrin (γCD) and ground it using a threedimensional ball mill (3DGM) to prepare an inclusion complex. This study also assessed the physicochemical properties such as solubility of that complex. A Job's plot indicated that FAD012 and γCD formed an inclusion complex at a molar ratio of 1:1. Phase solubility diagrams revealed that FAD012 produced a B S diagram. According to PXRD, FAD012 produced a diffraction peak at 2θ = 7.0°and γCD produced a diffraction peak at 2θ = 9.1°. Those two peaks were not produced by the 3DGM, but new peaks (2θ = 7.3 and 16.5°) were evident. DSC patterns revealed an endothermic peak due to the melting of FAD012 at 190 °C, but no endothermic peaks were evident with the 3DGM. NIR spectra of the 3DGM indicated that the methyl group of FAD012 produced a higher peak and that the OH groups of γCD produced a higher peak. 1 H-1 H ROESY NMR spectra (D 2 O) revealed cross peaks for protons of the methyl group of FAD012 and a proton (H-3) in the cavity of γCD, so FAD012 presumably interacts with the wide opening of the γCD torus. A solubility test (25 °C) indicated that solubility improved about 5-fold for the 3DGM in comparison to the solubility of FAD012 alone (about 140 μg/mL). Based on these findings, an FAD012/γCD complex was formed by cogrinding, and its solubility improved. These observations are expected to expand the usefulness of cogrinding of FAD012 with γCD using a 3D ball mill.

α-Mangostin/γ-Cyclodextrin Inclusion Complex: Formation and Thermodynamic Study

“…Surprisingly, Figure 2 b describes that solubility of α-M/γ-CD CX significantly improved 31.74-fold compared with α-M. In previous studies, the solubility in water increased due to molecular interaction which occurred from the inclusion complex by solubilization method [ 29 ].…”

“…Polymers 2021, 13, x FOR PEER REVIEW 5 of 13 in water increased due to molecular interaction which occurred from the inclusion complex by solubilization method [29]. The number of α-M to form the complex results in the improvement of its solubility in water.…”

Nano Modification of Antrodia Cinnamomea Exhibits Anti-Inflammatory Action and Improves the Migratory Potential of Myogenic Progenitors

“…According to the SEM analysis, IC appeared to be porous and amorphous in nature, with spherical beads on the surface ( Figure 1 E–H). A disappearance or shift in the melting point of the drug upon complexation with BCD indicates successful inclusion complex formation [ 36 ]. The compounds with higher melting points exhibited lower solubility profiles.…”

Studies of the Formation of Inclusion Complexes Derivatives of Cinnamon Acid with α-Cyclodextrin in a Wide Range of Temperatures Using Conductometric Methods

“…The process of formation of inclusion complexes is an exothermic reaction and is spontaneous. In the literature, there are papers concerning the determination of inclusion complexes of cyclodextrins [ 27 , 28 , 29 ], but they do not apply to the measurement method proposed in this paper and to selected research objects. This confirms the innovativeness of this work as well as the proposed innovative method of calculating the results.…”