An anticancer nucleoside analog
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Parent Compound(s)
20248Nelarabine
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Ara-G

Item No. 27984

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-9-β-D-arabinofuranosyl-1,9-dihydro-6H-purin-6-one
CAS Number
38819-10-2
Synonyms
  • ara-Guanosine
  • Guanine Arabinoside
  • NSC 76352
Molecular Formula
C10H13N5O5
Formula Weight
283.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 5 mg/mlEthanol: Partially solublePBS (pH 7.2): 0.3 mg/ml
λmax
253 nm
SMILES
O[C@H]1[C@H](O)[C@H](N2C=NC3=C2NC(N)=NC3=O)O[C@@H]1CO
InChi Code
InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6+,9-/m1/s1
InChi Key
NYHBQMYGNKIUIF-FJFJXFQQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    Product Description

    Ara-G is an analog of the nucleoside guanosine and an active metabolite of nelarabine (Item No. 20248).1,2 Ara-G accumulates in T lymphoblasts and malignant T-lymphoid cells, where it is phosphorylated to produce ara-GTP and incorporated into the DNA.3,1 Ara-G inhibits DNA replication by 92% after 30 minutes when used at a concentration of 50 µM in CEM cells, which are used as a model for human T lymphoblasts.1 It also halts the cell cycle at the sub-G1 phase and induces apoptosis in CEM cells.3 Syngeneic bone marrow containing 6C3HED tumor cells treated with ara-G (100 mM) ex vivo prior to transplantation increases survival of lethally irradiated mice and induces reconstitution of lymphoid, myeloid, and erythroid cell linages.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Leanza, L., Miazzi, C., Ferraro, P., et al. Activation of guanine-β-D-arabinofuranoside and deoxyguanosine to triphosphates by a common pathway blocks T lymphoblasts at different checkpoints. Exp. Cell Res. 316(20), 3443-3453 (2010).

    2. Lambe, C.U., Averett, D.R., Paff, M.T., et al. 2-Amino-6-methoxypurine arabinoside: An agent for T-cell malignancies. Cancer Res. 55(15), 3352-3356 (1995).

    3. Rodriguez, C.O., Jr., Stellrecht, C.M., and Gandhi, V. Mechanisms for T-cell selective cytotoxicity of arabinosylguanine. Blood 102(5), 1842-1848 (2003).

    4. Kurtzberg, J. Guanine arabinoside as a bone marrow-purging agent. Ann. N. Y. Acad. Sci. 685(1), 225-236 (1993).