A nucleoside analog
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3′-Deoxy-3′-fluorothymidine

Item No. 36519

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3'-deoxy-3'-fluoro-thymidine
CAS Number
25526-93-6
Synonyms
  • Alovudine
  • CL 184,824
  • FLT
  • MIV-310
  • NSC 140025
Molecular Formula
C10H13FN2O4
Formula Weight
244.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 11 mg/mlDMSO: 12 mg/mlEthanol: Slightly solublePBS (pH 7.2): 0.33 mg/ml
λmax
265 nm
SMILES
O=C(C(C)=CN1[C@]2(C[C@@H]([C@H](O2)CO)F)[H])NC1=O
InChi Code
InChI=1S/C10H13FN2O4/c1-5-3-13(10(16)12-9(5)15)8-2-6(11)7(4-14)17-8/h3,6-8,14H,2,4H2,1H3,(H,12,15,16)/t6-,7+,8+/m0/s1
InChi Key
UXCAQJAQSWSNPQ-XLPZGREQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

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    Product Description

    3′-Deoxy-3′-fluorothymidine is a nucleoside analog.1 It is phosphorylated by thymidine kinase 1 (TK1) but not TK2 and also inhibits TK1 and TK2 (Kis = 6 and 10 µM, respectively). 3′-Deoxy-3′-fluorothymidine inhibits HIV-1 reverse transcriptase (EC50 = 5 nM) and the replication of HIV-1 in MT-4 human T cell leukemia cells (EC50 = 5 nM).2 It decreases mitochondrial DNA (mtDNA) levels and the oxygen consumption rate (OCR) and induces upregulation of the cell differentiation marker CD11b in OCI-AML-2 and MV4-11 acute myeloid leukemia (AML) cells in a concentration-dependent manner.3 3′-Deoxy-3′-fluorothymidine (50 mg/kg) reduces tumor growth in an OCI-AML-2 AML mouse xenograft model. A radiolabeled form of 3′-deoxy-3′-fluorothymidine, [18F]FLT, is commonly used as a PET tracer for in vivo imaging of tumors.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Munch-Petersen, B., Cloos, L., Tyrsted, G., et al. Diverging substrate specificity of pure human thymidine kinases 1 and 2 against antiviral dideoxynucleosides. The Journal of Biological Chemisty 266(14), 9032-9038 (1991).

    2. Kong, X.-B., Zhu, Q.-Y., Vidal, P.M., et al. Comparisons of anti-human immunodeficiency virus activities, cellular transport, and plasma and intracellular pharmacokinetics of 3'-fluoro-3'-deoxythymidine and 3'-azido-3'-deoxythymidine. Antimicrob. Agents Chemother. 36(4), 808-818 (1992).

    3. Yehudai, D., Liyanage, S.U., Hurren, R., et al. The thymidine dideoxynucleoside analog, alovudine, inhibits the mitochondrial DNA polymerase γ, impairs oxidative phosphorylation and promotes monocytic differentiation in acute myeloid leukemia. Haematologica 104(5), 963-972 (2019).

    4. Salskov, A., Tammisetti, V.S., Grierson, J., et al. FLT: measuring tumor cell proliferation in vivo with positron emission tomography and 3'-deoxy-3'-[18F]fluorothymidine. Semin. Nucl. Med. 37(6), 429-439 (2007).