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A4233

Sigma-Aldrich

Ara-G hydrate

≥98% (HPLC), solid

Synonym(s):

9-β-D-Arabinofuranosyl guanine hydrate

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About This Item

Empirical Formula (Hill Notation):
C10H13N5O5 · xH2O
CAS Number:
38819-10-2
Molecular Weight:
283.24 (anhydrous basis)
MDL number:
MFCD00065486
UNSPSC Code:
12352200
PubChem Substance ID:
329770852
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

solubility

DMSO: >10 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

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

InChI key

NYHBQMYGNKIUIF-FJFJXFQQSA-N

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.

Biochem/physiol Actions

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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