A nucleoside analog
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5-(Hydroxymethyl)-2’-deoxyuridine

Item No. 23381

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-hydroxy-thymidine
CAS Number
5116-24-5
Molecular Formula
C10H14N2O6
Formula Weight
258.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 25 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
208, 266 nm
SMILES
O=C(NC(C(CO)=C1)=O)N1[C@H]2C[C@H](O)[C@@H](CO)O2
InChi Code
InChI=1S/C10H14N2O6/c13-3-5-2-12(10(17)11-9(5)16)8-1-6(15)7(4-14)18-8/h2,6-8,13-15H,1,3-4H2,(H,11,16,17)/t6-,7+,8+/m0/s1
InChi Key
IPAVKOYJGUMINP-XLPZGREQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $32

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    25 mg

    $76

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    50 mg

    $136

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    100 mg

    $256

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    Product Description

    5-(Hydroxymethyl)-2’-deoxyuridine is a nucleoside analog with anticancer and antiviral activities.1 It inhibits the replication of murine S180 lung carcinoma cells and Ehrlich ascites mammary carcinoma cells (ED50s = 8.5 and 4 μM, respectively) and multiple human leukemia cell lines (IC50s = 1.7-5.8 μM).1,2 5-(Hydroxymethyl)-2’-deoxyuridine acts synergistically with 5-fluorouracil (5-FU; Item No. 14416) against HT-29, HCT116, PANC-1, and EKVX cancer cells with no effect on WI38 embryonic lung fibroblasts.3 It inhibits herpes simplex virus type 1 (HSV-1) pyrimidine 2’-deoxyribonucleoside kinase (Ki = 3.5 μM) and reduces HSV-1 viral titer to 0.05% of the control at a concentration of 200 μM.1 5-(Hydroxymethyl)-2’-deoxyuridine is also a DNA adduct, formed in response to oxidative stress, that is found in hepatic DNA of rats treated with gamma irradiation, diethylnitrosamine, 2-acetylaminofluorene, and ciprofibrate (Item No. 18515).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shiau, G.T., Schinazi, R.F., Chen, M.S., et al. Synthesis and biological activities of 5-(hydroxymethyl, azidomethyl, or aminomethyl)-2'-deoxyuridine and related 5'-substituted analogues. J. Med. Chem. 23(2), 127-133 (1980).

    2. Kahilainen, L.I., Berstrom, D.E., and Vilpo, J.A. 5-Hydroxymethyl-2'-deoxyuridine. Cytotoxicity and DNA incorporation studied by using a novel [2-14C]-derivative with normal and leukemic human hematopoietic cells. Acta. Chem. Scand. B 39(6), 477-484 (1985).

    3. Matsumoto, Y., Rodriguez, V., Whitford, T.A., et al. Synergistic enhancement of 5-fluorouracil cytotoxicity by deoxyuridine analogs in cancer cells. Oncoscience 2(3), 272-284 (2015).

    4. Srinivasan, S., and Glauert, H.P. Formation of 5-hydroxymethyl-2'-deoxyuridine in hepatic DNA of rats treated with gamma-irradiation, diethylnitrosamine, 2-acetylaminofluorene or the peroxisome proliferator ciprofibrate. Carcinogenesis 11(11), 2021-2024 (1990).