6-Triazolyl-6-deoxy-β-cyclodextrin derivatives: synthesis, cellular toxicity, and phase-solubility study

Heptakis{6-(4-hydroxymethyl-1H-[1,2,3] triazol-1-yl)-6-deoxy}-beta-cyclodextrin (HTbCD) and heptakis{6(4-sulfonylmethyl-1H-[1,2,3] triazol-1-yl)-6-deoxy}-beta-cyclodextrin (STbCD) were prepared using copper(I)-catalyzed azide-alkyne cycloaddition between 6-azido-6-deoxy-beta-CD and one of two alkynes, propargyl alcohol, and sodium propargyl sulfonate, respectively. The structures of HTbCD and STbCD were characterized by NMR techniques. NMR interpretations and computer modeling suggested that the limited freedom of rotation of the triazole moieties keeps HTbCD and STbCD rigid and compact. Water solubility tests of HTbCD and STbCD showed that the minimum water solubility of HTbCD and STbCD is at least 20 times higher than that of beta-CD. MTT assay showed that HTbCD and STbCD did not influence the cell viability under 1 mM. A phase-solubility study of prednisolone with the CD derivatives showed increased solubility of prednisolone in the presence of increasing concentrations of HTbCD and STbCD. (C) 2014 Elsevier Ltd. All rights reserved.