Inclusion complexes of poorly water-soluble drugs with glucosyl-cyclodextrins.

Abstract

The inclusion complex-forming ability of three glucosyl-cyclodextrins (CDs), 6-O-ƒ¿-Dglucosyl-ƒ¿-CD (G-ƒ¿-CD), 6-O-ƒ¿-D-glucosyl-ƒÀ-CD (G-ƒÀ-CD), and 6A,6D-di-O-ƒ¿-D-glucosyl-ƒÀ-CD (2G-ƒÀ-CD) with slightly soluble or insoluble drugs in aqueous solution and in the solid state was studied by the solubility method, ultraviolet spectroscopy, and differential scanning calorimetry. These glucosyl-CDs were capable of forming inclusion complexes with compounds which can form complexes with the parent CDs. The enhancement of solubility of poorly water-soluble drugs by glucosyl-ƒÀ-CDs was much more marked than that by fl-CD. The hemolytic activity of glucosyl-CD was lower than that of each parent CD. The estriol-glucosyl-ƒÀ-CD complex may be practically applicable to injectable preparations because of its high water-solubility and low hemolytic activity.

A Moderate Interaction of Maltosyl-α-cyclodextrin with Caco-2 Cells in Comparison with the Parent Cyclodextrin

“…7, a noteworthy difference in the effects of CyDs on the surface tension was observed: a-CyD increased the value in a concentration-dependent manner, but not G 2 -a-CyD. It is evident that a-CyD greatly interacted with DPPC monolayers in comparison to G 2 -a-CyD, differing from other lipophilic drugs reported by Koizumi et al and Okada et al 23,24) However, Okada et al 25) also reported that the enhancement in solubility of lipids such as fatty acids, monoacylglycerols and triacylglycerols by G-a-CyD having less steric hindrance than G 2 -a-CyD, was much more marked than that by a-CyD. In addition, a-CyD is reported to interact with phosphatidylinositol strongly, but not phosphatidylcholine.…”

“…Surface Tension Considering the results described above, the inclusion complexation ability of G 2 -a-CyD seems to be poorer than a-CyD. Koizumi et al and Okada et al 23,24) reported, however, that the complexation ability of G 2 -a-CyD and G 2 -b-CyD and their parent CyDs appeared to be almost comparable. Therefore, this finding suggests the possibility of a peculiar interaction between G 2 -a-CyD and a-CyD and phospholipids.…”

“…Branched CyDs have some superior characteristics to the parent CyDs and the amorphous CyDs such as HP-b-CyD and SBE-b-CyD: high purity, excellent solubility in water and organic solvents, and lower surface activity. [4][5][6] Another advantage of branched CyDs is a relatively low local irritancy: the hemolytic activity of branched CyDs is lower than those of the parent CyDs, and the leakage of intestinal constituents induced by gluco-…”

Physicochemical and biological properties of 2-O-α-d-galactosyl-cyclomaltohexaose (α-cyclodexterin) and -cyclomaltoheptaose (β-cyclodextrin)

“…In our continuous efforts to investigate the physicochemical and biological properties of a great variety of branched CDs, we reported that branched CDs have many advantages over non-branched CDs in terms of higher solubility in water and less hemolytic activity. [6][7][8][9][10][11][12] Until now, information about the profile of branched CDs had been restricted to 6-O-glycosyl-CDs, in which saccharide chains are introduced on the primary hydroxyl group of the CD ring through the a-(1?6)-glycosidic linkage. [13][14][15][16][17][18][19][20] On the other hand, there is little data on 2-O-glycosyl-CDs of which the saccharide chain a-(1?2)-linked on the secondary hydroxyl group at the 2-position of glucose of the CD ring.…”

Synthesis of 6-Branched Cyclo-(1→3)-glucohexaose and Glucooctaose

“…In recent years, branched cyclodextrins have attracted much interest in connection with their enhanced solubility in water, their ability to increase the solubility of included hydrophobic compounds in hydroxylic solvent. [3][4][5][6] Besides, there is some evidence that side chain can be involved in host-guest interactions. 7 Our previous work revealed that a synthetic glucohexaose, b-D-Glcp- 8 has good immunoregulating activity.…”