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Polycationic Pillar[5]arene Derivatives: Interaction with DNA and Biological Applications
Author(s) -
Nierengarten Iwona,
Nothisen Marc,
Sigwalt David,
Biellmann Thomas,
Holler Michel,
Remy JeanSerge,
Nierengarten JeanFrançois
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303029
Subject(s) - pillar , dynamic light scattering , hela , transfection , chemistry , amine gas treating , cleavage (geology) , dendrimer , grafting , dna , nanoparticle , transmission electron microscopy , in vitro , combinatorial chemistry , materials science , biophysics , polymer chemistry , nanotechnology , organic chemistry , biochemistry , polymer , biology , structural engineering , fracture (geology) , engineering , composite material , gene
Dendritic pillar[5]arene derivatives have been efficiently prepared by grafting dendrons with peripheral Boc‐protected amine subunits onto a preconstructed pillar[5]arene scaffold. Upon cleavage of the Boc‐protected groups, water‐soluble pillar[5]arene derivatives with 20 ( 13 ) and 40 ( 14 ) peripheral ammonium groups have been obtained. The capability of these compounds to form stable nanoparticles with plasmid DNA has been demonstrated by gel electrophoresis, transmission electron microscopy (TEM), and dynamic light scattering (DLS) investigations. Transfection efficiencies of the self‐assembled 13 /pCMV‐Luc and 14 /pCMV‐Luc polyplexes have been evaluated in vitro with HeLa cells. The transfection efficiencies found for both compounds are good, and pillar[5]arenes 13 and 14 show very low toxicity if any.