Enhanced solubility of guanosine by inclusion complexes with cyclodextrin derivatives: Preparation, characterization, and evaluation.

This study improves the water solubility and cellular uptake of guanosine (GuN) through an inclusion complexation with cyclodextrin derivatives (CDs), namely β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD), and sulfobutyl ether-β-cyclodextrin (SBE-β-CD). Inclusion complexes of GuN and CDs are synthesized in a 1:1 stoichiometric ratio with binding constants calculated using the Benesi-Hildebrand method. Characterizations of the prepared solid complexes using FTIR, XRD, TGA-DSC, and SEM indicate that GuN is found inside the cavity of the CDs. Moreover, in silico molecular modeling analysis identifies the most favorable binding interactions of GuN deeply encapsulated in the hydrophobic cavities of the CDs, as validated by PatchDock and FireDock servers. In addition, human breast cancer MCF-7 cell activity indicates that the SBE-β-CD:GuN complex displays better cell viability and cellular uptake than GuN or other inclusion complexes of β-CD:GuN and HP-β-CD:GuN.