A dehydroxylated derivative of uridine
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3′-Deoxyuridine

Item No. 36547

Technical Information
Formal Name
3′-deoxy-uridine
CAS Number
7057-27-4
Molecular Formula
C9H12N2O5
Formula Weight
Purity
≥98%
A solid
DMF: 10 mg/mlDMSO: 10 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
264 nm
SMILES
[H][C@]1(O[C@H](CO)C[C@H]1O)N2C(NC(C=C2)=O)=O
InChi Code
InChI=1S/C9H12N2O5/c12-4-5-3-6(13)8(16-5)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1
InChi Key
QOXJRLADYHZRGC-SHYZEUOFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    3′-Deoxyuridine is a dehydroxylated derivative of uridine (Item No. 20300).1 It inhibits T. gondii uridine phosphorylase (apparent Ki = 2.459 mM). 3′-Deoxyuridine decreases the proliferation of CCRF CEM and L1210 human leukemia, P388 mouse leukemia, and S180 mouse sarcoma cells (EC50s = 25, 5, 2.5, and 15 µM, respectively).2 It reduces the infection rate and number of T. cruzi amastigotes in HeLa cells when used at a concentration of 1 µM.3 3′-Deoxyuridine (500 µM) is less effective than 2′-deoxyuridine (Item No. 27803) at inducing sodium currents in X. laevis oocytes expressing human concentrative nucleoside transporter 1 (CNT 1) or CNT 3.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. el Kouni, M.H., Naguib, F.N., Panzica, R.P., et alEffects of modifications in the pentose moiety and conformational changes on the binding of nucleoside ligands to uridine phosphorylase from Toxoplasma gondii. Biochem. Pharmacol. 51(12), 1687-1700 (1996).

    2. Lin, T.-S., Yang, Y.-H., Liu, M.-C., et alSynthesis and anticancer activity of various 3'-deoxy pyrimidine nucleoside analogues and crystal structure of 1-(3-deoxy-β-D-threo-pentofuranosyl)cytosine. J. Med. Chem. 34(2), 693-701 (1991).

    3. Nakajima-Shimada, J., Hirota, Y., and Aoki, T. Inhibition of Trypanosoma cruzi growth in mammalian cells by purine and pyrimidine analogs. Antimicrob. Agents Chemother. 40(11), 2455-2458 (1996).

    4. Zhang, J., Smith, K.M., Tackaberry, T., et alUridine binding and transportability determinants of human concentrative nucleoside transporters. Mol. Pharmacol. 68(3), 830-839 (2005).