9-(BETA-D-ARABINOFURANOSYL)GUANINE Chemical Properties

Melting point:

225°C(lit.)

Density 

2.25±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,2-8°C

solubility 

DMSO: >10mg/mL

pka

9?+-.0.20(Predicted)

form 

solid

color 

White to Off-White

λmax

252nm(lit.)

InChI

InChI=1/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-/s3

InChIKey

NYHBQMYGNKIUIF-FJFJXFQQSA-N

SMILES

O=C1NC(N)=NC2N([C@H]3[C@H]([C@H](O)[C@@H](CO)O3)O)C=NC1=2 |&1:8,9,10,12,r|

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

RTECS 

MF8301000

HS Code 

29349990

9-(BETA-D-ARABINOFURANOSYL)GUANINE Usage And Synthesis

Description

Ara-G is an analog of the nucleoside guanosine and an active metabolite of nelarabine . Ara-G accumulates in T lymphoblasts and malignant T-lymphoid cells, where it is phosphorylated to produce ara-GTP and incorporated into the DNA. 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. It also halts the cell cycle at the sub-G₁ phase and induces apoptosis in CEM cells. 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.

Uses

Ara-G is an inducer of apoptosis, inhibitor of DNA synthesis, an antimetabolite, and antineoplastic.

Definition

ChEBI: A purine nucleoside in which guanine is attached to arabinofuranose via a beta-N9-glycosidic bond. It inhibits DNA synthesis and causes cell death.

References

[1] LUIGI LEANZA . Activation of guanine-β-d-arabinofuranoside and deoxyguanosine to triphosphates by a common pathway blocks T lymphoblasts at different checkpoints[J]. Experimental cell research, 2010, 316 20: Pages 3443-3453. DOI: 10.1016/j.yexcr.2010.06.023
[2] C U LAMBE. 2-Amino-6-methoxypurine arabinoside: an agent for T-cell malignancies.[J]. Cancer research, 1995, 55 15: 3352-3356.
[3] CARLOS O RODRIGUEZ  Varsha G  Christine M Stellrecht. Mechanisms for T-cell selective cytotoxicity of arabinosylguanine.[J]. Blood, 2003, 102 5: 1842-1848. DOI: 10.1182/blood-2003-01-0317
[4] KURTZBERG J. Guanine Arabinoside as a Bone Marrow-Purging Agenta[J]. Annals of the New York Academy of Sciences, 1993, 685 1: 225-236. DOI: 10.1111/j.1749-6632.1993.tb35870.x

9-(BETA-D-ARABINOFURANOSYL)GUANINE(38819-10-2)Related Product Information

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