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A4233

Ara-G hydrate

Name: Ara-G hydrate
Brand: SIGMA

≥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)

NACRES:

NA.77

PubChem Substance ID:

329770852

UNSPSC Code:

12352200

MDL number:

MFCD00065486

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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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

Related Categories

Bioactive Small Molecule Inhibitors

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 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

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

pcodes

P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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A new high-performance liquid chromatography method determines low production of 9-beta-D-arabinofuranosylguanine triphosphate, an active metabolite of nelarabine, in adult T-cell leukemia cells.

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

A potential role of fetal hemoglobin in the development of multidrug resistance.

A Fyrberg et al.

Biochemical and biophysical research communications, 427(3), 456-460 (2012-08-23)

Our previous data from a human leukemic cell line made resistant to the nucleoside analog (NA) 9-β-D-arabinofuranosylguanine (AraG) revealed a massive upregulation of fetal hemoglobin (HbF) genes and the ABCB1 gene coding for the multidrug resistance P-glycoprotein (P-gp). The expression

Reduced levels of mitochondrial DNA increases the toxicity of 9-beta-D-arabinofuranosylguanine (araG).

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

Synthesis of 2'-deoxy-2'-[18F]fluoro-9-β-D-arabinofuranosylguanine: a novel agent for imaging T-cell activation with PET.

Mohammad Namavari et al.

Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging, 13(5), 812-818 (2010-09-15)

9-(β-D-Arabinofuranosyl)guanine (AraG) is a guanosine analog that has a proven efficacy in the treatment of T-cell lymphoblastic disease. To test the possibility of using a radiofluorinated AraG as an imaging agent, we have synthesized 2'-deoxy-2'-[(18)F]fluoro-9-β-D-arabinofuranosylguanine ([(18)F]F-AraG) and investigated its uptake

In vitro efficacy of forodesine and nelarabine (ara-G) in pediatric leukemia.

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

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Global Trade Item Number

SKU	GTIN
A4233-25MG	04061833217375
A4233-5MG	04061833368619

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