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Merck

123040

AICAR

≥98% (HPLC), AMPK activator, solid

Synonyme(s) :

AICA-Riboside, Acadesine, AICAr, 5-Aminoimidazole-4-carboxamide-1-β-riboside, Z-Riboside, AMPK Signaling Activator II

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A propos de cet article

Formule empirique (notation de Hill) :
C9H14N4O5
Numéro CAS:
2627-69-2
Poids moléculaire :
258.23
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00869751

Principaux documents

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Nom du produit

AICA-Riboside, AICA-Riboside, CAS 2627-69-2, is a cell-permeable nucleoside compound whose phosphorylated metabolite activates AMPK and acts as a regulator of de novo purine synthesis.

form

solid

SMILES string

[n]2(cnc(c2N)C(=O)N)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO

InChI

1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1

InChI key

RTRQQBHATOEIAF-UUOKFMHZSA-N

assay

≥98% (HPLC)

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white to brown

solubility

methanol: 10 mg/mL
water: soluble

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Catégories apparentées

Biochem/physiol Actions

Cell permeable: yes
Primary Target
Adenosine monophosphate-activated protein kinase (AMPK)
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Standard Handling (A)

General description

A cell-permeable nucleoside compound that is processed intracellularly to form a phosphorylated metabolite, which activates adenosine monophosphate-activated protein kinase (AMPK) without disrupting the cellular concentrations of ATP, ADP, or AMP. Also acts as a regulator of de novo purine synthesis. Stimulates glucose uptake in both perfused and isolated muscle. AICAr-stimulated glucose transport is not affected by Wortmannin (Cat. No. 681675), a PI-3K inhibitor. Shown to inhibit the synthesis of triacylglycerol (TAG), diacylglycerol (DAG), and phospholipid, probably as a result of AMPK activation and the subsequent inhibition of sn-glycerol-3-phosphate acyltransferase (GPAT) by AMPK. Also reported to inhibit Hsp90 chaperone function. Imparts protection against cell death induced by glucose deprivation, chemical hypoxia, and exposure to glutamate and amyloid β (Aβ) peptide.
A cell-permeable nucleoside compound whose phosphorylated metabolite activates adenosine monophosphate-activated protein kinase (AMPK) and acts as a regulator of de novo purine synthesis. Stimulates glucose uptake in perfused and isolated muscle. Offers protection against cell death induced by glucose deprivation, chemical hypoxia, and exposure to glutamate and Aβ peptide.

Other Notes

Meli, M., et al. 2006. J. Med. Chem.in press.
Culmsee, C., et al. 2001. J. Mol. Neurosci.17, 45.
Muoio, D.M., et al. 1999. Biochem. J.338, 783.
Hayashi, T., et al. 1998. Diabetes47, 1369.
Corton, J.M., et al. 1995. Eur. J. Biochem.229, 558.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
May require heating to 50°C to achieve complete solubilization in methanol.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

Certificats d'analyse (COA)

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