Ternary cyclodextrin polyurethanes containing phosphate groups: Synthesis and complexation of ciprofloxacin

Area of Science:

• Polymer Chemistry
• Materials Science
• Biomaterials

Background:

• Polyurethanes (PUs) are versatile polymers with applications in various fields.
• Cyclodextrins are known for their ability to form inclusion complexes with guest molecules.
• Developing novel drug delivery systems with enhanced drug dispersion and controlled release is crucial.

Purpose of the Study:

• To synthesize and characterize novel ternary polyurethanes (PUs) incorporating β-cyclodextrin and β-glycerophosphate.
• To evaluate the potential of these PUs for the inclusion and controlled release of the antibiotic ciprofloxacin.
• To investigate the influence of synthesis parameters on PU properties and drug encapsulation.

Main Methods:

• Synthesis of ternary PUs using hexamethylenediisocyanate, β-cyclodextrin, and β-glycerophosphate (acid and calcium salt).
• Optimization of synthesis parameters including monomer proportion, heating method (reflux vs. microwave), and catalyst amount.
• Characterization using FTIR spectroscopy, X-ray Diffraction (XRD), and Differential Scanning Calorimetry (DSC).
• Evaluation of ciprofloxacin inclusion and in vitro release studies.

Main Results:

• Microwave irradiation and β-glycerophosphoric acid favored the synthesis of ternary PUs.
• FTIR analysis confirmed the formation of secondary urea linkages.
• Characterization confirmed the integrity of cyclodextrin cavities for guest molecule inclusion.
• Ciprofloxacin was found to be molecularly dispersed within the polymer matrix, likely via inclusion in cyclodextrin cavities.
• In vitro release studies indicated both inclusion and non-inclusion interactions, with dialysis membranes potentially altering the observed release profile.

Conclusions:

• Novel ternary polyurethanes incorporating β-cyclodextrin and β-glycerophosphate were successfully synthesized.
• The developed PUs demonstrate effective molecular dispersion of ciprofloxacin, suggesting potential for drug delivery applications.
• Further investigation is needed to fully understand the release mechanisms and optimize the system for therapeutic use.