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

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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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

Fingerprint

folic acid
Folic Acid
genes
delivery
copolymers
Copolymers
Genes
Acids
synthesis
conjugation
Amines
amines
DNA
deoxyribonucleic acid
Cytotoxicity
Homopolymerization
Complexation
Luciferases
Macromolecules
macromolecules

Keywords

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

ASJC Scopus subject areas

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

Cite this

Synthesis of folic acid-containing imidazolium copolymers for potential gene delivery applications. / Allen, Michael H.; Day, Kelsea N.; Hemp, Sean T.; Long, Timothy Edward.

In: Macromolecular Chemistry and Physics, Vol. 214, No. 7, 12.04.2013, p. 797-805.

Research output: Contribution to journalArticle

Allen, Michael H. ; Day, Kelsea N. ; Hemp, Sean T. ; Long, Timothy Edward. / Synthesis of folic acid-containing imidazolium copolymers for potential gene delivery applications. In: Macromolecular Chemistry and Physics. 2013 ; Vol. 214, No. 7. pp. 797-805.
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