Preparation of well-defined ibuprofen prodrug micelles by RAFT polymerization

Urara Hasegawa, André J. Van Der Vlies, Christine Wandrey, Jeffrey A. Hubbell

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

Nonsteroidal anti-inflammatory drugs (NSAIDs) are widely used to treat acute pain, fever, and inflammation and are being explored in a new indication in cancer. Side effects associated with long-term use of NSAIDs such as gastrointestinal damage and elevated risk of stroke, however, can limit their use and exploration in new indications. Here we report a facile method to prepare well-defined amphiphilic diblock copolymer NSAID prodrugs by direct reversible addition-fragmentation transfer (RAFT) polymerization of the acrylamide derivative of ibuprofen (IBU), a widely used NSAID. The synthesis and self-assembling behavior of amphiphilic diblock copolymers (PEG-PIBU) having a hydrophilic poly(ethylene glycol) block and a hydrophobic IBU-bearing prodrug block were investigated. Release profiles of IBU from the micelles by hydrolysis were evaluated. Furthermore, the antiproliferative action of the IBU-containing micelles in human cervical carcinoma (HeLa) and murine melanoma (B16-F10) cells was assessed.

Original languageEnglish (US)
Pages (from-to)3314-3320
Number of pages7
JournalBiomacromolecules
Volume14
Issue number9
DOIs
StatePublished - Sep 9 2013

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ASJC Scopus subject areas

  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

Cite this

Hasegawa, U., Van Der Vlies, A. J., Wandrey, C., & Hubbell, J. A. (2013). Preparation of well-defined ibuprofen prodrug micelles by RAFT polymerization. Biomacromolecules, 14(9), 3314-3320. https://doi.org/10.1021/bm4009149