6-O-α-(4-O-α-d-glucuronyl)-d-glucosyl-β-cyclodextrin: solubilizing ability and some cellular effects

Autor: Kaneto Uekama, Hidetoshi Arima, Hitoshi Hashimoto, Fumitoshi Hirayama, Toshihiro Ishiguro, Kenichi Hamayasu, Masahide Oka, Sumitra Tavornvipas
Rok vydání: 2002
Předmět:
Zdroj: International Journal of Pharmaceutics. 249:199-209
ISSN: 0378-5173
DOI: 10.1016/s0378-5173(02)00537-9
Popis: 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.
Databáze: OpenAIRE
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