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| | 9-(beta-D-Arabinofuranosyl)guanine Basic information |
| Product Name: | 9-(beta-D-Arabinofuranosyl)guanine | | Synonyms: | 9-beta-D-Arabinofuranosylguanine Hydrate;2-AMino-9-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one;Arabinoguanosine;Araguanosine;ara-Guanosine;Guanine arabinoside;9-β-D-Arabinofuranosyl guanine hydrate;9-beta-Arabinosylguanine | | CAS: | 38819-10-2 | | MF: | C10H13N5O5 | | MW: | 283.24 | | EINECS: | | | Product Categories: | Nucleosides-Arabinonuleosides | | Mol File: | 38819-10-2.mol |  |
| | 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 | | 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| |
| 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 |
| | 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 Preparation Products And Raw materials |
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