Synthesis of folic acid-containing imidazolium copolymers for potential gene delivery applications

Michael H. Allen, Kelsea N. Day, Sean T. Hemp, Timothy E. Long

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Folic acid conjugation onto poly(1-vinylimidazole) generates imidazolium copolymers for potential receptor-mediated nonviral gene delivery. Homopolymer quaternization with various tBoc-protected bromoalkylamines imparts a permanent charge for DNA complexation. Incorporation of primary amine groups provides a site for folic acid conjugation onto imidazolium copolymers. DNA binding, cytotoxicity, and in vitro transfection in HeLa cells reveal structure-property-transfection relationships for the imidazolium copolymers. Luciferase expression assays establish that primary amine conjugation onto imidazolium copolymers up to 30 mol% fails to improve transfection efficiency. In sharp contrast, incorporation of folic acid onto the copolymers improves transfection efficiency 250-fold. Synthesis of amine-containing imidazolium copolymers with folic acid generates macromolecules for nonviral gene delivery. Low incorporation of folic acid onto the copolymers remains ideal for nonviral gene delivery as large concentrations produce water-insoluble copolymers. The incorporation of folic acid offers a safe and effective avenue to tailor imidazolium copolymer gene delivery.

Original languageEnglish (US)
Pages (from-to)797-805
Number of pages9
JournalMacromolecular Chemistry and Physics
Volume214
Issue number7
DOIs
StatePublished - Apr 12 2013
Externally publishedYes

Keywords

  • folic acid
  • functionalization of polymers
  • imidazolium copolymers
  • nonviral gene delivery
  • synthesis

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Materials Chemistry

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