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Polycaprolactone/α-cyclodextrin polyrotaxanes with cellular uptake enhancing properties.

Gergely Kali1, Alexander H Mayer1, Dennis To1

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Journal of Materials Chemistry. B
|February 14, 2025
PubMed
Summary
This summary is machine-generated.

Biodegradable poly(ε-caprolactone) polyrotaxanes were created using cyclodextrins. These novel materials show enhanced cellular uptake for potential use in treating lysosomal storage dysfunctions.

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Area of Science:

  • Polymer Chemistry
  • Supramolecular Chemistry
  • Biomaterials Science

Background:

  • Biodegradable polymers like poly(ε-caprolactone) (PCL) are crucial for biomedical applications.
  • Cyclodextrins (CDs) are widely explored for drug delivery but often face solubility challenges.

Purpose of the Study:

  • To synthesize and characterize biodegradable polyrotaxanes using PCL and cyclodextrins.
  • To evaluate the impact of cyclodextrin inclusion on polyrotaxane solubility and cellular uptake.
  • To explore the potential of these polyrotaxanes for intracellular delivery and treatment of lysosomal storage dysfunctions.

Main Methods:

  • Rotaxanation of PCL with α-cyclodextrin (α-CD) and a mixture of α-CD/2-hydroxypropyl-α-CD (HP-α-CD).
  • Disulfide end-stoppering using 2-mercaptosuccinic acid (MSA).
  • Structural confirmation via 1H NMR and molar mass determination by gel permeation chromatography.
  • Solubility, dethreading, degradability, and cellular uptake studies (flow cytometry, confocal microscopy).

Main Results:

  • Successfully synthesized polyrotaxanes with 75-80 wt% threaded CD and a molar mass of ~18 kDa.
  • Polyrotaxane solubility increased significantly with HP-α-CD inclusion (20.2 g L-1 to 74.7 g L-1).
  • Dethreading was achieved via glutathione-induced disulfide-exchange reactions.
  • Lipase-mediated degradation of the PCL backbone was confirmed.
  • Polyrotaxanes exhibited up to 50-fold higher cellular uptake compared to free CDs.

Conclusions:

  • Disulfide end-stoppered polyrotaxanes of biodegradable PCL are effectively synthesized.
  • The inclusion of HP-α-CD enhances aqueous solubility and cellular uptake.
  • These polyrotaxanes show promise as intracellular delivery vehicles for CDs.
  • Potential therapeutic applications for lysosomal storage dysfunctions are indicated.