A DNA labeling agent
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(2′S)-2′-Deoxy-2′-fluoro-5-ethynyluridine

Item No. 46464

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynyl-2,4(1H,3H)-pyrimidinedione
CAS Number
95740-26-4
Synonyms
  • F-ara-EdU
Molecular Formula
C11H11FN2O5
Formula Weight
270.2
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O=C(N1)N([C@@H]2O[C@H](CO)[C@H]([C@@H]2F)O)C=C(C#C)C1=O
InChi Code
InChI=1S/C11H11FN2O5/c1-2-5-3-14(11(18)13-9(5)17)10-7(12)8(16)6(4-15)19-10/h1,3,6-8,10,15-16H,4H2,(H,13,17,18)/t6-,7+,8-,10-/m1/s1
InChi Key
YEEGMPUOCRQFRV-IBCQBUCCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $36

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    5 mg

    $171

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    10 mg

    $306

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    25 mg

    $450

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    Product Description

    (2′S)-2′-Deoxy-2′-fluoro-5-ethynyluridine (F-ara-EdU) is a DNA labeling agent.1 It is incorporated into DNA during active DNA synthesis and can be detected using an azide-functionalized fluorophore. F-ara-EdU also has antiviral activity against herpes simplex virus 1 (HSV-1) and HSV-2 in vitro (EC50s = 1.9 and 3 µM, respectively) and inhibits the growth of L1210 and P815 leukemia cells (IC50s = 23.5 and 20.4 µM, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Neef, A.B., and Luedtke, N.W. Dynamic metabolic labeling of DNA in vivo with arabinosyl nucleosides. Proc. Natl. Acad. Sci. U.S.A. 108(51), 20404-20409 (2011).

    2. Perlman, M.E., Watanabe, K.A., Schinazi, R.F., et al. Nucleosides. 133. Synthesis of 5-alkenyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)cytosines and related pyrimidine nucleosides as potential antiviral agents. J. Med. Chem. 28(6), 741-748 (1985).