Hydroxypropyl cyclic β-(1→2)-d-glucans and epichlorohydrin β-cyclodextrin dimers as effective carbohydrate-solubilizers for polycyclic aromatic hydrocarbons

• Published in: Carbohydrate research 2015-01, Vol.401, p.82-88
• Main Authors: Choi, Jae Min, Jeong, Daham, Piao, Jinglan, Kim, Kyoungtea, Nguyen, Andrew Bao Loc, Kwon, Nak-Jung, Lee, Mi-Kyung, Lee, Im Soon, Yu, Jae-Hyuk, Jung, Seunho
• Format: Article
• Language: English
• Subjects: beta-Cyclodextrins - chemistry; beta-Glucans - chemistry; beta-Glucans - isolation & purification; Complexation; Dimerization; Epichlorohydrin - chemistry; Hydroxypropyl cyclic β-(1→2)-d-glucans; Polycyclic aromatic hydrocarbon; Polycyclic Aromatic Hydrocarbons - chemistry; Polycyclic Aromatic Hydrocarbons - isolation & purification; Rhizobiaceae; Solubility; Solubilization; Water - chemistry; β-Cyclodextrin dimer
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2014.10.025

[Display omitted] •Hydroxypropyl cyclosophoraose enhances solubility of Bap up to 38 fold.•βCD dimer increases solubility of Pyr, Phe, Cor, Chr, Per, and Flu up to 359 fold.•By the complex with carbohydrate, physicochemical properties of PAHs are changed. The removal of polycyclic aromatic hydrocarbons by soil washing using water is extremely difficult due to their intrinsic hydrophobic nature. In this study, the effective aqueous solubility enhancements of seven polycyclic aromatic hydrocarbons by chemically modified hydroxypropyl rhizobial cyclic β-(1→2)-d-glucans and epichlorohydrin β-cyclodextrin dimer have been investigated for the first time. In the presence of hydroxypropyl cyclic β-(1→2)-d-glucans, the solubility of benzo[a]pyrene is increased up to 38 fold of its native solubility. The solubility of pyrene and phenanthrene dramatically increased up to 160 and 359. Coronene, chrysene, perylene, and fluoranthene also show an increase of 11, 23, 23, and 97 fold, respectively, of enhanced solubility by complexation with synthetic epichlorohydrin β-cyclodextrin dimer. The physicochemical properties of the complex are characterized by Fourier-transform infrared spectra and differential scanning calorimetry. Utilizing a scanning electron microscopy, the morphological structures of native benzo[a]pyrene, pyrene, phenanthrene, coronene, chrysene, perylene, fluoranthene and their complex with novel carbohydrate-solubilizers are studied. These results elucidate that polycyclic aromatic hydrocarbons are able to form an efficient complex with hydroxypropyl cyclic β-(1→2)-d-glucans and β-cyclodextrin dimer, suggesting the potential usage of chemically modified novel carbohydrate-solubilizers.