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:
Poids moléculaire :
258.23
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
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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.
Quality Level
assay
≥98% (HPLC)
form
solid
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
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
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.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
Adenosine monophosphate-activated protein kinase (AMPK)
Adenosine monophosphate-activated protein kinase (AMPK)
Product does not compete with ATP.
Reversible: no
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.
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.
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.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
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