Supramolecular architectures of beta-cyclodextrin-modified chitosan and pyrene derivatives mediated by carbon nanotubes and their DNA condensation

Abstract

Beta-cyclodextrin-modified chitosan 1 was synthesized via the Schiff base reaction between 6-O-(4-formylphenyl)-beta-cyclodextrin and chitosan (CHIT), and then the supramolecular dyad assemblies 2 and 3 were respectively fabricated from the subunit 1 through the inclusion of adamantane-modified pyrene into the beta-cyclodextrin cavity and the wrapping of a CHIT chain on multiwalled carbon nanotubes (MWCNTs). The water-soluble dyad 3 further interacted with adamantane-modified pyrene, forming a stable triad assembly 4. They were extensively characterized by NMR, thermogravimetric analysis, UV-vis, Raman spectroscopy, X-ray photoelectron spectroscopy, transmission electron microscopy, and atomic force microscopy (AFM). Furthermore, the DNA condensation abilities of 1-4 were validated by AFM and dynamic light scattering, which indicates that the DNA-condensing capability of CHIT can be pronouncedly improved by either the pyrene grafts or the MWCNT medium. The cooperation between cationic and aromatic groups as well as the dispersion of CHIT agglomerates by MWCNTs are the key factors to enhance DNA condensation of cationic polymers.