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

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

    研究成果: Article

    6 引用 (Scopus)

    抄録

    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.

    元の言語English
    ページ(範囲)4589-4595
    ページ数7
    ジャーナルOrganic and Biomolecular Chemistry
    13
    発行部数15
    DOI
    出版物ステータスPublished - 2015 4 21

    Fingerprint

    Labeling
    marking
    deoxyribonucleic acid
    DNA
    Poisons
    Cells
    cells
    cultured cells
    Polymerization
    Permeability
    Cell Survival
    phosphates
    permeability
    Buffers
    polymerization
    buffers
    Phosphates
    5-ethynyl-2'-deoxyuridine
    Plasmas
    Cell Line

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Biochemistry

    これを引用

    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

    Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling. / Seo, Siyoong; Onizuka, Kazumitsu; Nishioka, Chieko; Takahashi, Eiki; Tsuneda, Satoshi; Abe, Hiroshi; Ito, Yoshihiro.

    :: Organic and Biomolecular Chemistry, 巻 13, 番号 15, 21.04.2015, p. 4589-4595.

    研究成果: Article

    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, 巻. 13, 番号 15, pp. 4589-4595. https://doi.org/10.1039/c5ob00199d
    Seo, Siyoong ; Onizuka, Kazumitsu ; Nishioka, Chieko ; Takahashi, Eiki ; Tsuneda, Satoshi ; Abe, Hiroshi ; Ito, Yoshihiro. / Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling. :: Organic and Biomolecular Chemistry. 2015 ; 巻 13, 番号 15. pp. 4589-4595.
    @article{2e54ae5b6e584b20bbbbc582374cbc4f,
    title = "Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling",
    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.",
    author = "Siyoong Seo and Kazumitsu Onizuka and Chieko Nishioka and Eiki Takahashi and Satoshi Tsuneda and Hiroshi Abe and Yoshihiro Ito",
    year = "2015",
    month = "4",
    day = "21",
    doi = "10.1039/c5ob00199d",
    language = "English",
    volume = "13",
    pages = "4589--4595",
    journal = "Organic and Biomolecular Chemistry",
    issn = "1477-0520",
    publisher = "Royal Society of Chemistry",
    number = "15",

    }

    TY - JOUR

    T1 - Phosphorylated 5-ethynyl-2′-deoxyuridine for advanced DNA labeling

    AU - Seo, Siyoong

    AU - Onizuka, Kazumitsu

    AU - Nishioka, Chieko

    AU - Takahashi, Eiki

    AU - Tsuneda, Satoshi

    AU - Abe, Hiroshi

    AU - Ito, Yoshihiro

    PY - 2015/4/21

    Y1 - 2015/4/21

    N2 - 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.

    AB - 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.

    UR - http://www.scopus.com/inward/record.url?scp=84926288620&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84926288620&partnerID=8YFLogxK

    U2 - 10.1039/c5ob00199d

    DO - 10.1039/c5ob00199d

    M3 - Article

    VL - 13

    SP - 4589

    EP - 4595

    JO - Organic and Biomolecular Chemistry

    JF - Organic and Biomolecular Chemistry

    SN - 1477-0520

    IS - 15

    ER -