Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling

Siyoong Seo, Kazumitsu Onizuka, Chieko Nishioka, Eiki Takahashi, Satoshi Tsuneda, Hiroshi Abe, Yoshihiro Ito

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The representative DNA-labeling agent 5-ethynyl-2′-deoxyuridine (EdU) was chemically modified to improve its function. Chemical monophosphorylation was expected to enhance the efficiency of the substrate in DNA polymerization by circumventing the enzymatic monophosphorylation step that consumes energy. In addition, to enhance cell permeability, the phosphates were protected with bis-pivaloyloxymethyl that is stable in buffer and plasma, and degradable inside various cell types. The phosphorylated EdU (PEdU) was less toxic than EdU, and had the same or a slightly higher DNA-labeling ability in vitro. PEdU was also successfully applied to DNA labeling in vivo. In conclusion, PEdU can be used as a less toxic DNA-labeling agent for studies that require long-term cell survival or very sensitive cell lines.

Original languageEnglish
Pages (from-to)4589-4595
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number15
DOIs
Publication statusPublished - 2015 Apr 21
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Seo, S., Onizuka, K., Nishioka, C., Takahashi, E., Tsuneda, S., Abe, H., & Ito, Y. (2015). Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling. Organic and Biomolecular Chemistry, 13(15), 4589-4595. https://doi.org/10.1039/c5ob00199d