title: 6-O-alpha-(4-O-alpha-D-glucuronyl)-D-glucosyl-beta-cyclodextrin: solubilizing ability and some cellular effects.
abstract: Some physicochemical and biopharmaceutical properties of a new branched cyclodextrin, 6-O-alpha-(4-O-alpha-D-glucuronyl)-D-glucosyl-beta-cyclodextrin (GUG-beta-CyD), were investigated. The interaction of GUG-beta-CyD with drugs was studied by spectroscopic and solubility methods, and compared with those of parent beta-CyD and 6-O-alpha-maltosyl-beta-CyD (G(2)-beta-CyD). The hemolytic activity of GUG-beta-CyD on rabbit erythrocytes was lower than those of beta-CyD and G(2)-beta-CyD. GUG-beta-CyD and G(2)-beta-CyD showed negligible cytotoxicity on Caco-2 cells up to at least 0.1 M. The inclusion ability of GUG-beta-CyD to neutral and acidic drugs was comparable to or slightly smaller than those of beta-CyD and G(2)-beta-CyD, probably because of a steric hindrance of the branched sugar. On the other hand, GUG-beta-CyD showed greater affinity for the basic drugs, compared with beta-CyD and G(2)-beta-CyD, owing to an electrostatic interaction of its carboxylate anion with positive charge of basic drugs. Thus, GUG-beta-CyD may be useful as a safe solubilizing agent particularly for basic drugs.
authors.affiliation: Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan.
authors.forename: Sumitra
authors.initials: S
authors.lastname: Tavornvipas
authors.forename: Fumitoshi
authors.initials: F
authors.lastname: Hirayama
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Arima
authors.forename: Kaneto
authors.initials: K
authors.lastname: Uekama
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Ishiguro
authors.forename: Masahide
authors.initials: M
authors.lastname: Oka
authors.forename: Kenichi
authors.initials: K
authors.lastname: Hamayasu
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Hashimoto
mesh_terms: D000818:Animals; D018938:Caco-2 Cells / Q000187:drug effects / Q000502:physiology; D003505:Cyclodextrins / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D009844:Oligosaccharides / Q000737:chemistry* / Q000494:pharmacology*; D011817:Rabbits; D012995:Solubility
chemical_list: D003505:Cyclodextrins; D009844:Oligosaccharides; C438085:cyclomaltoheptaosyl-(6-1)-glucopyranosyl-(4-1)-glucopyranosiduronic acid