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A4233

Sigma-Aldrich

Ara-G hydrate

≥98% (HPLC), solid

Synonyme(s) :

9-β-D-Arabinofuranosyl guanine hydrate

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About This Item

Formule empirique (notation de Hill) :
C10H13N5O5 · xH2O
Numéro CAS:
38819-10-2
Poids moléculaire :
283.24 (anhydrous basis)
Numéro MDL:
MFCD00065486
Code UNSPSC :
12352200
ID de substance PubChem :
329770852
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

solid

Solubilité

DMSO: >10 mg/mL
H2O: insoluble

Température de stockage

2-8°C

Chaîne 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

Clé InChI

NYHBQMYGNKIUIF-FJFJXFQQSA-N

Catégories apparentées

Application

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.

Actions biochimiques/physiologiques

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

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
123M4706V
118K47001
118K4700

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Consulter la Bibliothèque de documents

Irene Homminga et al.
Blood, 118(8), 2184-2190 (2011-07-07)
Forodesine and nelarabine (the pro-drug of ara-G) are 2 nucleoside analogues with promising anti-leukemic activity. To better understand which pediatric patients might benefit from forodesine or nelarabine (ara-G) therapy, we investigated the in vitro sensitivity to these drugs in 96
D F Kisor et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 18(5), 995-1003 (2000-03-01)
To characterize the pharmacokinetics of nelarabine (506U78), the water-soluble prodrug of 9-beta-D-arabinofuranosyl guanine (ara-G), and ara-G in pediatric and adult patients with refractory hematologic malignancies. Ara-G is phosphorylated within leukemic cells to form ara-G triphosphate (ara-GTP), which acts to terminate
Carlos O Rodriguez et al.
Blood, 102(5), 1842-1848 (2003-05-17)
Nelarabine, prodrug of arabinosylguanine (ara-G), has demonstrated T-lymphoblastic antileukemic activity in cell lines and in the clinic. To investigate the mechanism for lineage-specific toxicity, the effects of ara-G were compared in CEM (T-lymphoblast), Raji (B-lymphoblast), and ML-1 (myeloid) cell lines.
Anna Fyrberg et al.
Cancer chemotherapy and pharmacology, 68(3), 583-591 (2010-11-27)
To characterize resistance mechanisms to the nucleoside analog 9-β-D-arabinofuranosylguanine (AraG) in the T-cell acute lymphoblastic leukemia cell line MOLT-4 and its AraG-resistant variant. A gene expression microarray analysis was performed, as well as gene expression and enzyme activity measurements of
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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