Characterization of the complexation of tauro- and glyco-conjugated bile salts with γ-cyclodextrin and 2-hydroxypropyl-γ-cyclodextrin using affinity capillary electrophoresis

Complexation of tauro‐ and glyco‐conjugated bile salts with α‐cyclodextrin and hydroxypropyl‐α‐cyclodextrin studied by affinity capillary electrophoresis and molecular modelling

“…The stability constants for the complexes formed with 2OHpaCD were generally higher than that obtained for the natural a-CD. The larger stability constant observed for the modified CD as compared with the natural CD was contrary to the studies with bile salts and modified b-and g-CDs [29,30,[71][72][73], which indicates different modes of interactions with bile salts among the different CD classes. The stability constants between the 2OHpaCD and the investigated conjugated bile salts showed the strongest interaction with TDC/GDC, and the weakest with TC/GC.…”

“…1). The interaction between bile salts and b-CDs or g-CDs has been investigated to some extent [21][22][23][24][25][26][27][28][29][30]. However, to our knowledge only a limited number of studies have attempted to investigate the interaction between bile salts and a-CDs [21,28,31].…”

Use of correction factors in mobility shift affinity capillary electrophoresis for weak analyte – ligand interactions

“…www.jss-journal.com previously for the interaction with b-and cCDs [38,39]. The change in electrophoretic mobility of the bile salts was investigated in the concentration range 0 -189 mM with respect to 2OHpaCD (Fig.…”

“…CDs possess a relatively hydrophobic interior cavity, a hydrophilic exterior and the ability to form complexes with a wide variety of compounds. Our labs have a continuing interest in the interaction of tauro-and glyco-conjugated bile salts and CDs due to the potential importance in drug absorption and bioavailability after oral drug administration [38,39]. Initial studies revealed that the interaction of glycocholate (GC) and glycodeoxycholate (GDC) with 2-hydroxypropyla-CD (2OHpaCD) was weak and that suitable correction measures had to be taken before the effective electrophoretic mobilities obtained as a function of the 2OHpaCD concentration could be converted into meaningful stability constants.…”

Thermodynamics of Resulting Complexes Between Cyclodextrins and Bile Salts

“…Among the numerous guests researched, bile salts attracted much more attention because they are one kind of important surfactant-like biological amphipathic compounds possessing a steroid skeleton, which have distinctive detergent properties and play an important role in the metabolism and excretion of cholesterol in mammals [6]. For example: the thermodynamics and structure of inclusion compounds of glyco-and tauro-conjugated bile salts with CDs and their derivatives have been studied by Holm et al during the last years [7][8][9][10][11]; the interactions of different kinds of bile salts with -CD dimers linked through their secondary faces have been investigated by Reinhoudt and Vargas-Berenguel et al [12][13][14]. It has been demonstrated that the formation of inclusion complexes between CDs and guest molecules is cooperatively governed by several weak forces, such as van der Waals interactions, hydrophobic interactions, hydrogen bonding, electrostatic interactions, and every weak force does its contribution to the complexation.…”