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A4233

Sigma-Aldrich

Ara-G hydrate

≥98% (HPLC), solid

Synonym(e):

9-β-D-Arabinofuranosyl guanine hydrate

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About This Item

Empirische Formel (Hill-System):
C10H13N5O5 · xH2O
CAS-Nummer:
38819-10-2
Molekulargewicht:
283.24 (anhydrous basis)
MDL-Nummer:
MFCD00065486
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329770852
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

solid

Löslichkeit

DMSO: >10 mg/mL
H2O: insoluble

Lagertemp.

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

InChIKey

NYHBQMYGNKIUIF-FJFJXFQQSA-N

Anwendung

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. Wirkung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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
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
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
Sheryl A Flanagan et al.
Biochemical pharmacology, 66(5), 733-737 (2003-09-02)
We studied acceptance of various deoxyguanosine analogues by the unique guanosine preferring nucleoside transport system exhibited by NB4 cells, csg. Indirect assessment of acceptance using transport inhibition assays revealed that both 1-beta-D-arabinofuranosylguanine (ara-G) and 4'-thio-beta-D-xylofuranosylguanine (thio-xyl-G) compete with guanosine for
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
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