Modified oligonucleotides containing lithocholic acid in their backbones: Their enhanced cellular uptake and their mimicking of hairpin structures

Su Jeong Kim, Eun Kyoung Bang, Ho Jeong Kwon, Joong Sup Shim, Byeang Hyean Kim

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

Their enhanced cell permeability and their ability to mimic DNA structures make modified oligodeoxyribonucleotides (ODNs) very important substances for increasing our understanding of cell biology and for therapeutic applications. Lithocholic acid is a hydrophobic secondary bile acid that is a substrate of nuclear Pregnane X receptor (PXR). We designed and synthesized novel lithocholic acid-based ODNs (L-ODNs) by using a new phosphoramidite derived from lithocholic acid. By comparing data obtained from circular-dichroism, melting-point, and theoretical studies, we believe that these L-ODNs adopt DNA hairpin structures. Furthermore, L-ODNs have enhanced cellular uptake properties with respect to regular ODNs. To demonstrate their enhanced cell permeabilities, we carried out cellular uptake experiments of L-ODNs in HeLa cells. By attaching fluorescein as a fluorescence label and using confocal microscopy, we observed that the permeability of L-ODNs is much higher than that of natural ODNs.

Original languageEnglish
Pages (from-to)1517-1522
Number of pages6
JournalChemBioChem
Volume5
Issue number11
DOIs
Publication statusPublished - 2004 Nov 5

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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