New "Click Chemistry Reagents": EdU and EdUTP

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   EdU (5-Ethynyl-2'-deoxyuridine)

EdU (5-Ethynyl-2'-deoxyuridine), a nucleoside analog of thymidine, can be used as a replacement for BrdU (5-Bromo-2'-deoxyuridine) to directly measure de novo DNA synthesis or S-phase synthesis of the cell cycle. Proliferating cells incorporate EdU into replicating DNA instead of thymidine. Incubation of the cells with a fluorescent azide, which is rapidly "click"-coupled to the alkyne group of EdU (Figure 1), will make the newly synthesized DNA visible[1],[2],[3].

Chemical structure of EdU (Cat.-No.: CLK-N001-25)

Advantages of EdU compared to traditional BrdU immunostaining:

  • fast and highly specific "click" reaction
  • requires only a minimal number of steps
  • strong fluorescent signals
  • mild non-denaturation reaction conditions, thus facilitating tissue imaging
  • allows visualization of larger sections of tissues with lower magnification
  • small fluorescent azide molecules will enter cells easily in contrast to BrdU antibodies (500x larger)

Figure 1: "Click reaction" between EdU and azide-modified dye

For more information please see: www.jenabioscience.com/cms/en/1/catalog/1567/

Azides of fluorescent dyes are also available at: www.jenabioscience.com/cms/en/1/catalog/1383/

   EdUTP (5-Ethynyl-dUTP)

Functionalization of DNA is efficiently accomplished by PCR amplification involving unnatural nucleoside triphosphates carrying the desired function. EdUTP (5-Ethynyl-dUTP) can be used to generate large and highly modified DNA strands by PCR incorporation, replacing the natural substrate dTTP. The resulting densely alkyne-modified DNA can be subsequently derivatized by "click" reactions (Figure 2), such as Cu(I)-catalyzed azide-alkyne cycloadditions[4],[5],[6].

Chemical structure of EdUTP (Cat.-No.: CLK-T07)

Figure 2: "Click reaction" between alkyne-modified DNA and different azides

EdUTP and more click chemistry reagents can be found at: www.jenabioscience.com/cms/en/1/catalog/1359/

Nucleotide analogs not on stock may be available as custom synthesis, just send us an e-mail at nucleotides@jenabioscience.com with any questions you may have!

Selected references:
[1] Salic et al. (2008) A chemical method for fast and sensitive detection of DNA synthesis in vivo. Proc. Natl. Acad. Sci. USA 105 (7):2415.
[2] Doerr (2008) DNA synthesis lights up. Nature Methods 5 (4):286.
[3] Chehrehasa et al. (2009) EdU, a new thymidine analog for labeling proliferating cells in the nervous system. Journal of Neuroscience Methods 177:122.
[4] Gierlich et al. (2007) Synthesis of highly modified DNA by a combination of PCR with alkyne-bearing triphosphates and click chemistry. Chem. Eur. J. 13:9486.
[5] Fischler et al. (2007) Formation of bimetallic Ag-Au nanowires by metallization of artificial DNA duplexes. Small 3 (6):1049.
[6] Burley et al. (2006) Directed DNA metallization. J. Am. Chem. Soc. 128:1398.


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