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A4233

Sigma-Aldrich

Ara-G hydrate

≥98% (HPLC), solid

Sinônimo(s):

9-β-D-Arabinofuranosyl guanine hydrate

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About This Item

Fórmula empírica (Notação de Hill):
C10H13N5O5 · xH2O
Número CAS:
38819-10-2
Peso molecular:
283.24 (anhydrous basis)
Número MDL:
MFCD00065486
Código UNSPSC:
12352200
ID de substância PubChem:
329770852
NACRES:
NA.77

Ensaio

≥98% (HPLC)

forma

solid

solubilidade

DMSO: >10 mg/mL
H2O: insoluble

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

NC1=Nc2c(ncn2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O)C(=O)N1

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

chave InChI

NYHBQMYGNKIUIF-FJFJXFQQSA-N

Aplicação

Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. This active form of Ara-G induces apoptosis and inhibits DNA synthesis. Ara-G is also an antineoplastic and antimetabolite.

Ações bioquímicas/fisiológicas

Ara-G is an inducer of apoptosis; inhibitor of DNA synthesis; antineoplastic; and antimetabolite. Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. Incorporation of Ara-GTP into DNA leads to inhibition of DNA synthesis and apoptosis.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302,H315,H319,H335

Classificações de perigo

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Sophie Curbo et al.
Reviews on recent clinical trials, 1(3), 185-192 (2008-05-14)
GW506U78 or nelarabine (Glaxo-SmithKline) is a nucleoside analog that is rapidly converted by cells of lymphoid lineage to its corresponding arabinosylguanine nucleotide triphosphate (araGTP). The triphosphate form of araG acts as a substrate for DNA polymerases and araG gets incorporated
Stacey L Berg et al.
Cancer chemotherapy and pharmacology, 59(6), 743-747 (2006-09-06)
Nelarabine is a water-soluble prodrug of the cytotoxic deoxyguanosine analog ara-G, to which it is rapidly converted in vivo by adenosine deaminase. Nelarabine has shown activity in the treatment of T-cell malignancies, especially T-cell acute lymphoblastic leukemia. Preliminary data suggested
C Zhu et al.
FEBS letters, 474(2-3), 129-132 (2000-06-06)
The anti-leukemic nucleoside analogs 1-beta-D-arabinofuranosylcytosine (araC) and 9-beta-D-arabinofuranosylguanine (araG) are dependent on intracellular phosphorylation for pharmacological activity. AraC is efficiently phosphorylated by deoxycytidine kinase (dCK). Although araG is phosphorylated by dCK in vitro, it is a preferred substrate of mitochondrial
Takahiro Yamauchi et al.
Oncology reports, 23(2), 499-504 (2010-01-01)
The 9-beta-D-arabinofuranosylguanine (ara-G), an active compound of nelarabine, demonstrates potent cytotoxicity specifically on T-cell malignancies. In cells, ara-G is phosphorylated to ara-G triphosphate (ara-GTP), which is subsequently incorporated into DNA, thereby inhibiting DNA synthesis. Because ara-GTP is crucial to ara-G's
M Bjerke et al.
Nucleosides, nucleotides & nucleic acids, 27(6), 746-749 (2008-07-05)
Incubation of cells with thymidine (dThd) is known to cause dNTP pool imbalance as well as deletions and depletion of the mtDNA. In order to gain further understanding in the events involved in dThd toxicity over time, H9 cells were
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