Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm

Mizuki Kitamatsu; Akiko Takahashi; Takashi Ohtsuki; Masahiko Sisido

doi:10.1016/j.tet.2010.10.056

Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm

Mizuki Kitamatsu, Akiko Takahashi, Takashi Ohtsuki, Masahiko Sisido

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	9659-9666
Number of pages	8
Journal	Tetrahedron
Volume	66
Issue number	51
DOIs	https://doi.org/10.1016/j.tet.2010.10.056
Publication status	Published - Dec 18 2010

Keywords

Cell-penetrating peptide
Confocal laser scanning microscopy
Peptide nucleic acid
Solid-phase peptide synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis of pyrrolidine-based oxy-peptide nucleic acids carrying four types of nucleobases and their transport into cytoplasm",

abstract = "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.",

keywords = "Cell-penetrating peptide, Confocal laser scanning microscopy, Peptide nucleic acid, Solid-phase peptide synthesis",

author = "Mizuki Kitamatsu and Akiko Takahashi and Takashi Ohtsuki and Masahiko Sisido",

note = "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 . ",

year = "2010",

month = dec,

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doi = "10.1016/j.tet.2010.10.056",

language = "English",

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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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