TY - JOUR
T1 - Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm
AU - Kitamatsu, Mizuki
AU - Takahashi, Akiko
AU - Ohtsuki, Takashi
AU - Sisido, Masahiko
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan (No. 19750143 ), Okayama Foundation for Science and Technology , and the Kurata Memorial Hitachi Science and Technology Foundation .
PY - 2010/12/18
Y1 - 2010/12/18
N2 - We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate.
AB - We synthesized 16 pyrrolidine-based oxy-peptide nucleic acid (POPNA) monomers carrying four different nucleobases onto four different stereoisomers of pyrrolidine rings. Using these monomers, we prepared POPNA oligomers, which formed sequence-specific hybrids with DNAs. The oligomer configurations influenced the hybrid stability. The oligomers were not taken into CHO cells. However, they could enter the cell cytoplasm when mixed with the influenza virus hemagglutinin peptide-arginine heptamer conjugate.
KW - Cell-penetrating peptide
KW - Confocal laser scanning microscopy
KW - Peptide nucleic acid
KW - Solid-phase peptide synthesis
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U2 - 10.1016/j.tet.2010.10.056
DO - 10.1016/j.tet.2010.10.056
M3 - Article
AN - SCOPUS:78650220468
VL - 66
SP - 9659
EP - 9666
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 51
ER -