Synthesis of New Amino-β-Cyclodextrin Polymer, Cross-Linked with Pyromellitic Dianhydride and Their Use for the Synthesis of Polymeric Cyclodextrin Based Nanoparticles

Kinga Kozieł; Jakub Łagiewka; Beata Girek; Agnieszka Folentarska; Tomasz Girek; Wojciech Ciesielski

doi:10.3390/polym13081332

Synthesis of New Amino-β-Cyclodextrin Polymer, Cross-Linked with Pyromellitic Dianhydride and Their Use for the Synthesis of Polymeric Cyclodextrin Based Nanoparticles

Polymers (Basel). 2021 Apr 19;13(8):1332. doi: 10.3390/polym13081332.

Authors

Kinga Kozieł¹, Jakub Łagiewka¹, Beata Girek¹, Agnieszka Folentarska¹, Tomasz Girek¹, Wojciech Ciesielski¹

Affiliation

¹ Faculty of Mathematics and Natural Science, Jan Dlugosz University in Czestochowa, Armii Krajowej Avenue, 13/15, 42 201 Czestochowa, Poland.

Abstract

New water soluble amino β-cyclodextrin-based polymer was synthesized by reaction between amino cyclodextrin derivatives and pyromellitic anhydride. This experiment presents amino derivatives, which were synthesized by attaching amino groups to β-cyclodextrins (β-CDs) used mono-6-azido-6-deoxy-β-cyclodextrin (β-CD-N₃) and triphenylphosphine (Ph₃P) in anhydrous N,N-dimethylformamide (DMF). An amino blocking reaction was conducted. The obtained polymer was purified by ultrafiltration. In addition, an attempt was made to create nanospheres by encapsulating the polymer with chitosan (CT) in an acidic condition. For the first time, nanospheres were obtained in the reaction between an amino β-cyclodextrin polymer and chitosan. Scanning electron microscopy (SEM). ¹H NMR and ESI-MS methods for confirmation of reaction product and for structural characterization were employed. The differential scanning calorimetry (DSC) studies of polymers were also carried out.

Keywords: amino-β-cyclodextrin; nanoparticles; polyampholyte; polymerization; pyromellitic dianhydride.