Custom-modified oligolactide-cyclodextrin derivatives for electrospun drug formulations

Abstract

Custom-synthesized cyclodextrin-oligolactide derivatives (CDLA) were used to produce electrospun nanofibers. The modified cyclodextrins were obtained through solution ring-opening oligomerization initiated by α-, β-, or γ-cyclodextrin in the presence of 4-dimethylaminopyridine. Following the NMR spectroscopy and mass spectrometry structural characterization, the CDLA derivatives are described as low molecular weight compounds having the lactate monomer units placed on the smaller rim of cyclodextrins as multiple short chains. The electrospinning (ESP) of the α-, β- and γ-CDLA homologous series was optimized for the use of high-concentration water/ethanol feed solutions. Scanning electron microscopy was employed for the morphology investigation of the nanofibrous webs, while the dynamic vapor sorption revealed the hygroscopicity changes induced through the ESP process. Further, the applicative potential was investigated by preparing α-, β- and γ-CDLA/curcumin nanofibrous webs. FTIR and NMR spectroscopy characterization, and thermogravimetric analysis were used to describe the particularities of curcumin association with CDLA in ESP process. The preservation of the curcumin antioxidative potential upon the ESP processing was tested, showing that β- and γ-CDLA/curcumin nanofibrous webs are better suited for curcumin formulations.