| Identification | Back Directory | [Name]
9-(BETA-D-ARABINOFURANOSYL)GUANINE | [CAS]
38819-10-2 | [Synonyms]
Ara-G
Ara-Gr
9-&beta
Nsc 76352
Araguanosine
ara-Guanosine
Ara-G hydrate
Arabinoguanosine
Arabinosylguanine
Guanine arabinoside
GUANINE-9-ARABINOSIDE
ARABINOFURANOSYL-GUANINE
9-beta-Arabinosylguanine
9-arabinofuranosylguanine
9-β-D-Arabinofuranosylguanine
1-β-D-Arabinofuranosylguanine
-methyl-pregn-4-ene-3,20-dione
-Epoxy-17,21-dihydroxy-16&beta
9-(b-D-Arabinofuranosyl)guanine
-Epoxy-21dehydroxy Betamethasone
Arabinofuranosyl-guanine (ara-G)
9-(beta-d-arabinofuranosyl)-guanin
9-(BETA-D-ARABINOFURANOSYL)GUANINE
9-(β-D-Arabinoribofuranosyl)-guanine
9-(β-D-Arabinofuranosyl)guanine ,97%
Guanine, 9-(beta-D-arabinofuranosyl)-
9-β-D-Arabinofuranosylguanine Hydrate
9-β-D-Arabinofuranosyl guanine hydrate
9-beta-D-Arabinofuranosylguanine Hydrate
ARA-G 9-(BETA-D-ARABINOFURANOSYL)-GUANINE
9-β-D-Arabinofuranosylguanine Hydrate >
9-(BETA-D-ARABINOFURANOSYL)GUANINE USP/EP/BP
9-β-D-Arabinofuranosyl-2-amino-9H-purin-6-ol
)-9,11-Epoxy-pregna-1,4,16-triene-3,20-dione
-D-Arabinofuranosylguanine Hydrate
2-Amino-9-β-D-arabinofuranosyl-9H-purine-6(1H)-one
)-9,11-Epoxy-6-fluoropregna-1,4,16-triene-3,20-dione
2-Amino-9-β-D-arabinofuranosyl-1,9-dihydro-6H-purin-6-one
9-β-D-Arabinofuranosyl-1,6-dihydro-2-amino-6-oxo-9H-purine
6H-Purin-6-one,2-amino-9-b-D-arabinofuranosyl-1,9-dihydro-
)-21-(Acetyloxy)-9,11-epoxypregna-1,4,16-triene-3,20-dione
6H-Purin-6-one, 2-amino-9-β-D-arabinofuranosyl-1,9-dihydro-
2-amino-9-beta-d-arabinofuranosyl-1,9-dihydro-6h-purin-6-on
)-9,11-Epoxy-21-hydroxy-16-methyl-pregna-1,4-diene-3,20-dione
)-10-Bromo-8,9,10,11-tetrahydrobenz[a]anthracene-8,9,11-triol
2-amino-9-(beta-D-arabinofuranosyl)-3,9-dihydro-6H-purin-6-one
6H-Purin-6-one, 2-amino-9-beta-D-arabinofuranosyl-1,9-dihydro-
)-9-Bromo-8,9,10,11-tetrahydrobenz[a]anthracene-8,10,11-triol-d9
)-21-(Acetyloxy)-9,11-epoxy-6-fluoro-pregna-1,4,16-triene-3,20-dione
)-9,11-Epoxy-6-fluoro-21-hydroxy-16-methyl-pregna-1,4-diene-3,20-dione
)-21-(Acetyloxy)-9,11-epoxy-6-fluoro-16-methyl-d3-pregna-1,4-diene-3,20-dione
)-9,11-Epoxy-1,21-dihydroxy-4,16-dimethyl-19-norpregna-1,3,5(10)-trien-20-one
)-21-(Acetyloxy)-9,11-epoxy-6-fluoro-17-hydroxy-16-methylpregna-1,4-diene-3,20-dione
Ara-G hydrate, 98%, inhibitor of DNA synthesis, an antimetabolite and antineoplastic.
2-AMino-9-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one | [Molecular Formula]
C10H13N5O5 | [MDL Number]
MFCD00065486 | [MOL File]
38819-10-2.mol | [Molecular Weight]
283.24 |
| Chemical Properties | Back Directory | [Melting point ]
225°C(lit.) | [density ]
2.25±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >10mg/mL | [form ]
solid | [pka]
9?+-.0.20(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22-36/37/38 | [Safety Statements ]
26 | [WGK Germany ]
3 | [RTECS ]
MF8301000 | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 | [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 |
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