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Protonatable Ionenes for Nucleic Acid Complexation
Author(s) -
Ramirez Sean M.,
Layman John M.,
Long Timothy E.
Publication year - 2009
Publication title -
macromolecular bioscience
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.924
H-Index - 105
eISSN - 1616-5195
pISSN - 1616-5187
DOI - 10.1002/mabi.200900137
Subject(s) - chemistry , protonation , amine gas treating , conjugate , cytotoxicity , dna , nucleic acid , polymerization , cationic polymerization , transfection , polymer , stereochemistry , polymer chemistry , biophysics , biochemistry , organic chemistry , in vitro , ion , mathematical analysis , mathematics , biology , gene
Novel tboc‐protected ionenes with $\overline M _{\rm w}$ exceeding 30 kDa were prepared from the step‐growth polymerization of tert‐ butyl bis[3‐(dimethylamino)propyl]carbamate and 1,12‐dibromododecane. The protected ionenes yielded pH‐sensitive, protonatable ionenes with p K a ≈ 6.6 for the conjugate acid of the protonated secondary amine. Polyplexes of the protected and deprotected ionenes, whose cytotoxicity for endothelial cells was analyzed using the MTT assay, efficiently complex plasmid DNA. Polyplexes destabilized cellular membranes as revealed using the lactate dehydrogenase assay at high concentrations. The polyplexes were successfully transfected into HBMECs at mass ratios 2, 4, 8, 12, and 16 (polymer/DNA) at polyplex concentrations less than 10 µg · mL −1 .