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Synthesis of 2-Hydroxypropyl-β-cyclodextrin/Pluronic-Based Polyrotaxanes via Heterogeneous Reaction as Potential Niemann-Pick Type C Therapeutics
- Source :
- Biomacromolecules. 14:4189-4197
- Publication Year :
- 2013
- Publisher :
- American Chemical Society (ACS), 2013.
-
Abstract
- Five polyrotaxanes were synthesized by threading 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) onto a variety of α,ω-ditriethylenediamino-N-carbamoyl-poly-(ethylene oxide)-block-poly(propylene oxide)-block-poly(ethylene oxide) (Pluronic) triblock copolymers using a two-pot strategy under heterogeneous, nonaqueous conditions. The threaded HP-β-CD units were retained on the pseudopolyrotaxane precursors by end-capping the branched diamine termini with sodium 2,4,6-trinitrobenzene sulfonate. Inclusion of the Pluronic copolymers within the HP-β-CD cavities was more favorable in nonpolar solvents, such as diethyl ether and n-hexane, both of which gave better coverage ratios than polar solvents. (1)H NMR and MALDI-TOF were used to estimate the average molecular weights of the purified polyrotaxane products. A globular morphology of aggregated polyrotaxanes was observed by tapping-mode AFM imaging of dried samples. Treatment of Niemann-Pick C (NPC) type 2-deficient fibroblasts with the polyrotaxane derivatives produced substantial reductions in sterol accumulation, as seen by diminished filipin staining in these cells, suggesting that Pluronic-based polyrotaxanes may be promising vehicles for delivery of HP-β-CD to cells with abnormal cholesterol accumulation.
- Subjects :
- Rotaxanes
Polymers and Plastics
Bioengineering
Beta-Cyclodextrins
Poloxamer
Article
Biomaterials
chemistry.chemical_compound
Diamine
Polymer chemistry
Materials Chemistry
Copolymer
Humans
Organic chemistry
Filipin
Propylene oxide
Cells, Cultured
Cyclodextrins
Drug Carriers
Ethylene oxide
beta-Cyclodextrins
Niemann-Pick Disease, Type C
Fibroblasts
Endocytosis
2-Hydroxypropyl-beta-cyclodextrin
Molecular Weight
Cholesterol
Sulfonate
chemistry
Diethyl ether
Subjects
Details
- ISSN :
- 15264602 and 15257797
- Volume :
- 14
- Database :
- OpenAIRE
- Journal :
- Biomacromolecules
- Accession number :
- edsair.doi.dedup.....63652aa9b2c9a66b1734c535877bf335