Zidovudine insertion in tailor-made propylene and ethylene oxide copolymers

Abstract

A synthetic strategy has been developed to create tailor-made poly(ethylene glycol) and poly(propylene glycol) copolymers functionalized with alkynyl groups that are introduced into the co-polymer chains by the addition of glycidyl propargyl ether (GPE) as co-monomer. The alkynyl-decorated copolymer obtained is used as a starter material to synthesize a drug–copolymer conjugate by copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction (click reaction). This way, hydrophobic drugs can be transformed into water-soluble compounds by improving its absorbability and bioavailability by joining them to tailor-made PEG–PPG–GPE copolymers with low polydispersity and precise molecular weight. In this work, zidovudine (AZT) drug with an azide group was chosen to be attached to the polyether chain. The chemical structure of the copolymer was characterized using infrared spectroscopy, nuclear magnetic resonance, matrix-assisted laser desorption/ionization time of flight mass spectrometry and gel permeation chromatography. Finally, 1H NMR spectrum confirms the successful addition of the zidovudine drug to the synthesized copolymer by the click reaction.