123040

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.

• Synonyme(s) : AICA-Riboside, Acadesine, AICAr, 5-Aminoimidazole-4-carboxamide-1-β-riboside, Z-Riboside, AMPK Signaling Activator II
• Formule empirique (notation de Hill): C₉H₁₄N₄O₅
• Numéro CAS: 2627-69-2
• Poids moléculaire : 258.23
• Numéro MDL: MFCD00869751
• Code UNSPSC : 12352200

Propriétés

• Niveau de qualité: 100
• Pureté: ≥98% (HPLC)
• Forme: solid
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze
• Couleur: white to brown
• Solubilité: methanol: 10 mg/mL; water: soluble
• Conditions d'expédition: ambient
• Température de stockage: 2-8°C
• 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
• Clé InChI: RTRQQBHATOEIAF-UUOKFMHZSA-N

Description

Description générale

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.

Actions biochimiques/physiologiques

Cell permeable: yes

Primary Target
Adenosine monophosphate-activated protein kinase (AMPK)

Product does not compete with ATP.

Reversible: no

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Standard Handling (A)

Notes préparatoires

May require heating to 50°C to achieve complete solubilization in methanol.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Autres remarques

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.

Informations légales

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

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3