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 journalArticle

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 languageEnglish
Pages (from-to)9659-9666
Number of pages8
JournalTetrahedron
Volume66
Issue number51
DOIs
Publication statusPublished - 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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