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.
Multi-disciplinary Cancer Research Facility, Bindley Bioscience Center, Department of Chemistry, Purdue University , 1203 West State Street, West Lafayette, Indiana 47907, United States.
Yawo A
YA
Mondjinou
Multi-disciplinary Cancer Research Facility, Bindley Bioscience Center, Department of Chemistry, Purdue University , 1203 West State Street, West Lafayette, Indiana 47907, United States.
Seok-Hee
SH
Hyun
Multi-disciplinary Cancer Research Facility, Bindley Bioscience Center, Department of Chemistry, Purdue University , 1203 West State Street, West Lafayette, Indiana 47907, United States.
Manxi
M
Xiong
Multi-disciplinary Cancer Research Facility, Bindley Bioscience Center, Department of Chemistry, Purdue University , 1203 West State Street, West Lafayette, Indiana 47907, United States.
Christopher J
CJ
Collins
Multi-disciplinary Cancer Research Facility, Bindley Bioscience Center, Department of Chemistry, Purdue University , 1203 West State Street, West Lafayette, Indiana 47907, United States.
Pooi Ling
PL
Thong
Multi-disciplinary Cancer Research Facility, Bindley Bioscience Center, Department of Chemistry, Purdue University , 1203 West State Street, West Lafayette, Indiana 47907, United States.
David H
DH
Thompson
D000073738:2-Hydroxypropyl-beta-cyclodextrin; D002784:Cholesterol / Q000737:chemistry; D003505:Cyclodextrins / Q000737:chemistry; D005347:Fibroblasts / Q000378:metabolism; D006801:Humans; D046529:Microscopy, Electron, Transmission; D052556:Niemann-Pick Disease, Type C / Q000235:genetics / Q000378:metabolism; D020442:Poloxamer / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry; D043862:Rotaxanes / Q000737:chemistry*; D012995:Solubility; D014867:Water / Q000737:chemistry; D047392:beta-Cyclodextrins / Q000737:chemistry*
D003505:Cyclodextrins; D011108:Polymers; D043862:Rotaxanes; D047392:beta-Cyclodextrins; C108732:methyl-beta-cyclodextrin; D014867:Water; D020442:Poloxamer; D000073738:2-Hydroxypropyl-beta-cyclodextrin; C093196:SBE4-beta-cyclodextrin; D002784:Cholesterol; C031215:betadex
Niemann-Pick Type C; Pluronic; amorphous solid; cyclodextrin; inclusion efficiency; macrocyclic; mixed rotaxanation; polyrotaxane; supramolecule