Abstract

Hyodeoxycholic acids anion (HD) and it's 3- and 6-epimers (3e-HD and 6e-HD) are suitable for biopharmaceutical application since they possess α equatorial i.e. β axial OH groups so their membranotoxicity is reduced. Self-association of stereoisomers 3e-HD and 6e-HD has not been studied so far. According to the capacity factor (k, RPHPLC), hydrophobicity decreases in the following series: HD>3e-HD>6e-HD. However, critical micelle concentration (CMC) is the lowest for the 6e-HD (10mM, 25°C) and the highest for 3e-HD (38mM, 25°C), which is contrary to expectations according to their hydrophobicity. Aggregation number (n) has the highest value for 6e-HD (8, 25°C) and the lowest value for the stereoisomer 3e-HD (4, 25°C). The change in demicellisation capacity factor (∆Cp) decreases in the following series: 6e-HD (316Jmol−1K−1)>HD (260Jmol−1K−1)>3e-HD (181Jmol−1K−1). In the plane of ln k – ln CMC epimer 6e-HD is outliner related to the hydrophobic congeneric group. This suggests that, in formation of micelles of HD and 3e-HD, besides hydrophobic effect other interactions are neglected. However, in formation of 6e-HD micelle, beside hydrophobic effect significant interaction exists different from hydrophobic interaction (formation of hydrogen bonds between building units of the micelle).

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