Mechanochemical Preparation of Stable Sub‐100 nm γ‐Cyclodextrin:Buckminsterfullerene (C60) Nanoparticles by Electrostatic or Steric Stabilization

• Published in: Chemistry : a European journal Vol. 24; no. 11; pp. 2758 - 2766
• Main Authors: Van Guyse, Joachim F. R., de la Rosa, Victor R., Hoogenboom, Richard
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 21.02.2018
• Subjects: Agglomeration; aggregation; Bioavailability; Buckminsterfullerene; Chemistry; Cyclodextrin; Cyclodextrins; Electrostatic properties; Extreme values; Fullerenes; Inclusion complexes; Intermolecular forces; Nanoparticles; nanostructures; poly(2-oxazoline)s; Polyoxazolines; Solubility; Steric hindrance; aggregation; fullerenes; poly(2-oxazoline)s; cyclodextrins; nanostructures
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201705647

Buckminster fullerene (C60)′s main hurdle to enter the field of biomedicine is its low bioavailability, which results from its extremely low water solubility. A well‐known approach to increase the water solubility of C60 is by complexation with γ‐cyclodextrins. However, the formed complexes are not stable in time as they rapidly aggregate and eventually precipitate due to attractive intermolecular forces, a common problem in inclusion complexes of cyclodextrins. In this study we attempt to overcome the attractive intermolecular forces between the complexes by designing custom γ‐cyclodextrin (γCD)‐based supramolecular hosts for C60 that inhibit the aggregation found in native γCD‐C60 complexes. The approach entails the introduction of either repulsive electrostatic forces or increased steric hindrance to prevent aggregation, thus enhancing the biomedical application potential of C60. These modifications have led to new sub‐100 nm nanostructures that show long‐term stability in solution. Overcoming attraction: A well‐known problem of cyclodextrin inclusion complexes is their aggregation. In this study we attempt to overcome the attractive intermolecular forces between the complexes, by designing custom γ‐cyclodextrin(γCD)‐based supramolecular hosts for C60 to inhibit the aggregation found in native‐γCD:C60 complexes, via Coulombic repulsion or steric hindrance. This led to partial inhibition of the aggregation, yielding stable sub‐100 nm nanostructures.