Abstract
Ionizable cyclodextrins have attracted increasing attention in host–guest chemistry and pharmaceutical industry, mainly due to the introduction of favorable electrostatic interactions. The ionizable cyclodextrins could not only enhance its own solubility but also induce oppositely charged guests to form more stable complex. However, the aggregation induced by charged cyclodextrins has rarely been reported. In this work, guided by the concept of molecular-induced aggregation, a series of carboxyl modified cyclodextrins were synthesized via “click” and hydrolysis reaction. Then, UV-vis spectrum was used to investigate the aggregating behaviors induced by these cyclodextrins towards the cationic guest molecules. The results showed that only the hepta-carboxyl-β-cyclodextrin could induce the guest molecules to self-assemble into supramolecular spherical nanoparticles. Meanwhile, it could form stable inclusion complex with amantadine, a drug for anti-Parkinson and antiviral. The assembly behaviors were investigated by dynamic light scattering, scanning electron microscope, atomic force microscope, transmission electron microscope and NMR spectroscopy. The supramolecular nanoparticles induced by hepta-carboxyl-β-CD and its inclusion with amantadine could be used to encapsulate the model drug and achieve its controlled releasing behaviors.
Highlights
Ionizable cyclodextrins have attracted increasing attention in host–guest chemistry and pharmaceutical industry, mainly due to the introduction of favorable electrostatic interactions
The low stability of the inclusion complexes limits the further application of native CDs
Molecular induced aggregation has become an important tool for water soluble macrocycle host molecules, including cucurbiturils[21,22], sulfonatocalixarenes[23,24], water-soluble pillararene[25,26,27,28], and cyclodextrins[29,30,31,32], to construct functional supramolecular assemblies
Summary
Ionizable cyclodextrins have attracted increasing attention in host–guest chemistry and pharmaceutical industry, mainly due to the introduction of favorable electrostatic interactions. The results showed that only the hepta-carboxyl-β-cyclodextrin could induce the guest molecules to self-assemble into supramolecular spherical nanoparticles It could form stable inclusion complex with amantadine, a drug for anti-Parkinson and antiviral. With the introduction of coulomb interaction, the ionic CDs could improve its own solubility and form highly stable complex with oppositely charged guest molecules[10,11] This property leads to the wide applications of the ionizable CDs, such as gene[12,13,14] and drug delivery[15,16,17], separation technology[18,19], and pharmaceutical[9,20]. The hepta-carboxyl cyclodextrin (H3) can induce the G aggregate into nanoparticle below its critical aggregation concentration (CAC), indicating the multi-charge plays a key role in molecular induced aggregation
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
