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Keywords:

  • biodegradable;
  • polyesters;
  • functionalization of polymers;
  • polymer–drug conjugate;
  • click chemistry

Abstract

The aim of this study is to develop azido-carrying biodegradable polymers and their postfunctionalization with alkynyl compounds via click chemistry and to investigate their potential use in drug delivery. Azido polymers were prepared by ring-opening polymerization of cyclic carbonate monomer, 2,2-bis(azidomethyl)trimethylene carbonate (ATC) with lactide using stannous octoate as catalyst. Several alkynyl compounds were selected to investigate the feasibility and reaction condition of click chemistry. With microwave-assisting, the reaction time of click chemistry was shortened to 5 min. By using poly(ethylene glycol) (PEG) as macroinitiator, amphiphilic block copolymer mPEG-b-P(LA-co-ATC) was obtained and it could self-assemble into micelles by solvent replacement method. The pendant groups were used for conjugating anticancer drugs gemcitabine and paclitaxel and fluorescent dye Rhodamine B. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide was used to assay the cytotoxicity of the conjugate micelles against SKOV-3 and HeLa cell lines. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013