title: 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.
authors.affiliation: Department of Bioscience and Biotechnology, Bio/Molecular Informatics Center & Institute for Ubiquitous Information Technology and Applications (CBRU), Konkuk University, Seoul 143-701, South Korea.
authors.forename: Jinglan
authors.initials: J
authors.lastname: Piao
authors.forename: Ahri
authors.initials: A
authors.lastname: Jang
authors.forename: Youngjin
authors.initials: Y
authors.lastname: Choi
authors.forename: Muhammad Nazir
authors.initials: MN
authors.lastname: Tahir
authors.forename: Yunjoo
authors.initials: Y
authors.lastname: Kim
authors.forename: Seyeon
authors.initials: S
authors.lastname: Park
authors.forename: Eunae
authors.initials: E
authors.lastname: Cho
authors.forename: Seunho
authors.initials: S
authors.lastname: Jung
mesh_terms: D001571:Benzoflavones / Q000737:chemistry*; D005936:Glucans / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: D001571:Benzoflavones; D005936:Glucans; D014867:Water; C011512:alpha-naphthoflavone
keywords: Complexation; Cyclodextrin; Cyclosophoraoses; Hydroxypropyl cyclosophoraoses; Solubility; α-Naphthoflavone