PMID- 12433448 OWN - NLM STAT- MEDLINE DCOM- 20030520 LR - 20190910 IS - 0378-5173 (Print) IS - 0378-5173 (Linking) VI - 249 IP - 1-2 DP - 2002 Dec 5 TI - 6-O-alpha-(4-O-alpha-D-glucuronyl)-D-glucosyl-beta-cyclodextrin: solubilizing ability and some cellular effects. PG - 199-209 AB - 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. FAU - Tavornvipas, Sumitra AU - Tavornvipas S AD - Faculty of Pharmaceutical Sciences, Kumamoto University, 5-1 Oe-honmachi, Kumamoto 862-0973, Japan. FAU - Hirayama, Fumitoshi AU - Hirayama F FAU - Arima, Hidetoshi AU - Arima H FAU - Uekama, Kaneto AU - Uekama K FAU - Ishiguro, Toshihiro AU - Ishiguro T FAU - Oka, Masahide AU - Oka M FAU - Hamayasu, Kenichi AU - Hamayasu K FAU - Hashimoto, Hitoshi AU - Hashimoto H LA - eng PT - Comparative Study PT - Journal Article PL - Netherlands TA - Int J Pharm JT - International journal of pharmaceutics JID - 7804127 RN - 0 (Cyclodextrins) RN - 0 (Oligosaccharides) RN - 0 (cyclomaltoheptaosyl-(6-1)-glucopyranosyl-(4-1)-glucopyranosiduronic acid) SB - IM MH - Animals MH - Caco-2 Cells/drug effects/physiology MH - Cyclodextrins/*chemistry/*pharmacology MH - Humans MH - Oligosaccharides/*chemistry/*pharmacology MH - Rabbits MH - Solubility EDAT- 2002/11/16 04:00 MHDA- 2003/05/21 05:00 CRDT- 2002/11/16 04:00 PHST- 2002/11/16 04:00 [pubmed] PHST- 2003/05/21 05:00 [medline] PHST- 2002/11/16 04:00 [entrez] AID - S0378517302005379 [pii] AID - 10.1016/s0378-5173(02)00537-9 [doi] PST - ppublish SO - Int J Pharm. 2002 Dec 5;249(1-2):199-209. doi: 10.1016/s0378-5173(02)00537-9.