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Synthesis of Folic Acid‐Containing Imidazolium Copolymers for Potential Gene Delivery Applications
Author(s) -
Allen Michael H.,
Day Kelsea N.,
Hemp Sean T.,
Long Timothy E.
Publication year - 2013
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201200613
Subject(s) - copolymer , transfection , hela , chemistry , amine gas treating , folate receptor , gene delivery , dna , folic acid , polymer chemistry , in vitro , cytotoxicity , combinatorial chemistry , organic chemistry , biochemistry , polymer , gene , cancer cell , biology , medicine , cancer , genetics
Folic acid conjugation onto poly(1‐vinylimidazole) generates imidazolium copolymers for potential receptor‐mediated nonviral gene delivery. Homopolymer quaternization with various t Boc‐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.