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295176 9-(b-D-Arabinofuranosyl)guanine CAS: 38819-10-2

Specifications
References
CAS Number
38819-10-2
Grade
Highly Purified
Molecular Formula
C10H13N5O5
Molecular Weight
283.24
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
2-Amino-9-β-D-arabinofuranosyl-1,9-dihydro-6H-purin-6-one; 2-Amino-6-hydroxy-9-(β-D-arabinofuranosyl)purine; 9-β-D-Arabinofuranosylguanine; Arabinoguanosine; Araguanosine; Guanine arabinoside; NSC 76352; ara-Guanosine

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

Synonyms
2-Amino-9-β-D-arabinofuranosyl-1,9-dihydro-6H-purin-6-one; 2-Amino-6-hydroxy-9-(β-D-arabinofuranosyl)purine; 9-β-D-Arabinofuranosylguanine; Arabinoguanosine; Araguanosine; Guanine arabinoside; NSC 76352; ara-Guanosine
CAS No
38819-10-2
Molecular Formula
C10H13N5O5
Molecular Weight
283.24
Appearance
White to off-white powder
Purity
≥98%
Melting Point
>245°C (dec.)
Solubility
Aqueous Base (Slightly, Sonicated), DMSO (Slightly)
Storage and Stability
Store at -20°C under inert atmosphere. Hygroscopic. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
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).|5. Cheriyan UO, Ogilvie KK, Nucleosides Nucleotides 1982, 1, p233
USBio References
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