Synthesis of Water-Soluble Imidazolium Polyesters as Potential Nonviral Gene Delivery Vehicles

Ashley M. Nelson, Allison M. Pekkanen, Neil L. Forsythe, John H. Herlihy, Musan Zhang, Timothy Edward Long

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The inherent hydrolytic reactivity of polyesters renders them excellent candidates for a variety of biomedical applications. Incorporating ionic groups further expands their potential impact, encompassing charge-dependent function such as deoxyribonucleic acid (DNA) binding, antibacterial properties, and pH-responsiveness. Catalyst-free and solvent-free polycondensation of a bromomethyl imidazolium-containing (BrMeIm) diol with neopentylglycol (NPG) and adipic acid (AA) afforded novel charged copolyesters with pendant imidazolium sites. Varying ionic content influenced thermal properties and offered a wide-range, −41 to 40 °C, of composition-dependent glass transition temperatures (Tgs). In addition to desirable melt and thermal stability, polyesters with ionic concentrations ≥15 mol % readily dispersed in water, suggesting potential as nonviral gene delivery vectors. An electrophoretic gel shift assay confirmed the novel cationic copolyesters successfully bound DNA at an N/P ratio of 4 for 50 mol % and 75 mol % charged copolyesters (P(NA50-co-ImA50) and P(NA25-co-ImA75)), and an N/P ratio of 5 for 100 mol % Im (PImA). Polyplexes exhibited insignificant cytotoxicity even at high concentrations (200 μg/mL), and a Luciferase transfection assay revealed the ionic (co)polyesters transfected DNA significantly better than the untreated controls. The successful transfection of these novel (co)polyesters inspires future imidazolium-containing polyester design.

Original languageEnglish
Pages (from-to)68-76
Number of pages9
JournalBiomacromolecules
Volume18
Issue number1
DOIs
Publication statusPublished - 2017 Jan 9
Externally publishedYes

ASJC Scopus subject areas

  • Bioengineering
  • Biomaterials
  • Polymers and Plastics
  • Materials Chemistry

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  • Cite this

    Nelson, A. M., Pekkanen, A. M., Forsythe, N. L., Herlihy, J. H., Zhang, M., & Long, T. E. (2017). Synthesis of Water-Soluble Imidazolium Polyesters as Potential Nonviral Gene Delivery Vehicles. Biomacromolecules, 18(1), 68-76. https://doi.org/10.1021/acs.biomac.6b01316