Solubility enhancement of α-naphthoflavone by synthesized hydroxypropyl cyclic-(1→2)-β-D-glucans (cyclosophoroases)

Abstract

Rhizobium leguminosarum produces unbranched cyclic β-1,2-glucans, cyclosophoraoses (Cys). In the present study, Cys were modified with hydroxypropyl groups via a one step chemical derivatization and the complexation ability and solubility enhancement of hydroxypropyl cyclosophoraoses (HP Cys) with α-naphthoflavone (α-NF) were investigated. In the presence of HP Cys, the aqueous solubility of α-NF greatly increased up to 257-fold. Complex formation of HP Cys and α-NF was confirmed by nuclear magnetic resonance (NMR), Fourier-transform infrared (FT-IR) spectroscopy, and differential scanning calorimetry (DSC). Furthermore, the morphological structure of α-NF with HP Cys was examined using scanning electron microscopy (SEM). A hypothetical model was proposed based on molecular dynamics (MD) simulations and a docking study of α-NF with HP Cys. Our results suggest that HP Cys form complexes with α-NF and can be utilized as a promising solubilizer. This is the first study to identify carbohydrates that can enhance the solubility of α-NF.

Keywords: Complexation; Cyclodextrin; Cyclosophoraoses; Hydroxypropyl cyclosophoraoses; Solubility; α-Naphthoflavone.