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A Facile and Efficient Approach for the Production of Reversible Disulfide Cross-linked Micelles

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Oligo(ethylene glycol)-modified β-cyclodextrin-based polyrotaxanes for simultaneously modulating solubility and

Atsushi Tamura¹, Moe Ohashi¹, Nobuhiko Yui¹

¹a Department of Organic Biomaterials, Institute of Biomaterials and Bioengineering , Tokyo Medical and Dental University , Tokyo , Japan.

Journal of Biomaterials Science. Polymer Edition

|March 17, 2017

Summary

Stimuli-labile polyrotaxanes (PRXs) show therapeutic potential for Niemann-Pick type C disease by releasing beta-cyclodextrins (β-CDs) to reduce cholesterol. Optimizing oligo(ethylene glycol) (OEG) modifications enhances PRX solubility, reduces toxicity, and improves cellular uptake for better drug delivery.

Keywords:

Polyrotaxane cyclodextrin endocytosis macrophage oligo(ethylene glycol)

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Published on: August 28, 2015

Area of Science:

Biomaterials Science
Drug Delivery Systems
Nanomedicine

Background:

Niemann-Pick type C disease is a rare genetic disorder characterized by cholesterol accumulation.
Stimuli-labile polyrotaxanes (PRXs) show promise for treating Niemann-Pick type C disease by facilitating intracellular cholesterol reduction.
The aqueous solubility and biological efficacy of PRXs are often limited by their inherent hydrophobicity.

Purpose of the Study:

To investigate the impact of oligo(ethylene glycol) (OEG) modification on the physicochemical and biological properties of polyrotaxanes (PRXs).
To optimize OEG structure for enhanced aqueous solubility, reduced toxicity, and improved cellular internalization of PRXs.
To identify the most effective OEG modification for PRX-based therapeutics.

Main Methods:

Synthesis of four series of OEG-modified PRXs with varying ethylene glycol repeating units (2 or 3) and terminal groups (hydroxy or methoxy).
Evaluation of aqueous solubility, cytotoxicity, and cellular uptake efficiency of the modified PRXs in RAW264.7 cells.
Structure-activity relationship analysis to determine the optimal OEG modification.

Main Results:

Hydroxy-terminated OEG-PRXs exhibited excellent aqueous solubility and no toxicity, irrespective of OEG length.
Methoxy-terminated OEG-PRXs with three ethylene glycol units showed sufficient solubility and negligible toxicity.
Methoxy-terminated OEG-PRXs demonstrated higher cellular uptake compared to hydroxy-terminated counterparts.

Conclusions:

The chemical structure of OEG significantly influences the solubility, toxicity, and cellular internalization of PRXs.
Methoxy-terminated OEG with three ethylene glycol units represents the optimal modification for PRXs.
This optimized PRX formulation offers improved aqueous solubility, biocompatibility, and cellular delivery for potential Niemann-Pick type C disease therapeutics.