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Hybridizing Oligonucleotides with Hydrophobic Peptide Nucleic Acids Assists Their Cellular Uptake through Aggregate Formation
Author(s) -
Misu Sotaro,
Kurihara Ryohsuke,
Kainuma Reina,
Sato Ryugai,
Nishihara Tatsuya,
Tanabe Kazuhito
Publication year - 2020
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201900607
Subject(s) - nucleic acid , oligonucleotide , aptamer , chemistry , amphiphile , pyrene , peptide , biochemistry , dna , peptide nucleic acid , transfection , hydrophobic effect , biophysics , combinatorial chemistry , biology , microbiology and biotechnology , gene , organic chemistry , copolymer , polymer
We applied hybridization between hydrophobic peptide nucleic acids (PNAs) and oligodeoxynucleotides (ODNs) to achieve their cellular uptake without any need for transfection reagents. We employed a pyrenyl unit as a hydrophobic functional group and introduced it at the terminus of the PNA strand. The pyrene‐tethered PNA (PyPNA) strongly bound with its complementary ODNs to generate amphiphiles; the resulting hybrids formed aggregates that showed efficient cellular uptake and high biological stability. Aggregates containing a functional DNA aptamer that bound to the PyPNA penetrated the cell membrane smoothly, with the aptamer exerting its original function in living cells. Thus, PyPNA efficiently assisted the additive‐free cellular uptake of ODNs.