Impact of Mixed β-Cyclodextrin Ratios on Pluronic Rotaxanation Efficiency and Product Solubility.

Water-soluble polyrotaxanes have been prepared under heterogeneous conditions from mixtures of β-cyclodextrin (β-CD), 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), methyl-β-cyclodextrin, or 6-monoazido-β-cyclodextrin with 4-sulfobutyl ether-β-cyclodextrin (SBE-β-CD) and Pluronic L81 copolymer modified with cholesterol end caps. Threading reactions gave polyrotaxane products in modest chemical yield that were reflective of the β-CD feed ratios in the reaction. Polyrotaxanes containing mixtures of HP-β-CD and SBE-β-CD were screened and found to be biologically active in an in vitro model of Niemann-Pick Type C disease where they mobilize aberrantly stored cholesterol similarly to monomeric cyclodextrin controls.