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

Organic & Biomolecular Chemistry
Siyoong SeoYoshihiro Ito

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.

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Citations

Jun 29, 2018·Chembiochem : a European Journal of Chemical Biology·Masayuki TeraNathan W Luedtke
Jan 25, 2019·Chembiochem : a European Journal of Chemical Biology·Amarnath Bollu, Nagendra K Sharma
Jul 18, 2018·Beilstein Journal of Organic Chemistry·Yuichi YoshimuraNoriaki Minakawa
Nov 21, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Anna Ligasová, Karel Koberna
Oct 22, 2020·Chemical Society Reviews·Nils KlöckerAndrea Rentmeister
Sep 4, 2021·Translational Vision Science & Technology·Mette Hedegaard CorrellGilles Thuret

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