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Shell-sheddable, pH-sensitive supramolecular nanoparticles based on ortho ester-modified cyclodextrin and adamantyl
Ran Ji1, Jing Cheng, Ting Yang
1Beijing National Laboratory for Molecular Sciences, Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.
Biomacromolecules
|August 22, 2014
Summary
Researchers developed pH-sensitive supramolecular aggregates using ortho ester-modified cyclodextrins. These aggregates exhibit programmable dePEGylation and degradation, offering a versatile platform for designing advanced nanoparticles.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Nanotechnology
Background:
- Developing pH-sensitive drug delivery systems is crucial for targeted therapies.
- Supramolecular self-assembly offers a versatile approach to creating complex nanostructures.
- Controlling the degradation and deprotection of nanoparticles is key for triggered release.
Purpose of the Study:
- To synthesize novel pH-sensitive supramolecular aggregates with programmable dePEGylation and degradation.
- To explore the use of ortho ester-modified beta-cyclodextrin (β-CD) derivatives as a platform for multifunctional supramolecular nanoparticles.
- To investigate the influence of structural parameters on the self-assembly and properties of these aggregates.
Main Methods:
- Synthesis of 6-OH ortho ester-modified β-CD derivatives.
- Host-guest complexation with adamantane-modified PEG to form amphiphilic supramolecules.
- Self-assembly in water to form supramolecular aggregates.
- Characterization using TEM, light scattering, and zeta potential measurements.
- (1)H NMR and LLS for stability and degradation studies.
Main Results:
- Successfully synthesized asymmetric acid-labile β-CD derivatives.
- Demonstrated self-assembly into pH-sensitive supramolecular aggregates (vesicles and nanoparticles) with tunable size (50-500 nm).
- Observed sequential dePEGylation at pH 7.4 and degradation at pH 6.4 due to ortho ester hydrolysis.
- Confirmed surface-functionalization capability via dynamic host-guest interactions.
- Showed improved stability in neutral buffer by incorporating poly(ε-caprolactone).
Conclusions:
- Ortho ester-modified β-CDs provide a robust platform for designing programmable, pH-sensitive supramolecular nanoparticles.
- The sequential dePEGylation and degradation mechanism allows for controlled release and triggered assembly/disassembly.
- These findings open avenues for developing advanced nanocarriers for drug delivery and other biomedical applications.
