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123040 Sigma-Aldrich

AICA-Riboside - CAS 2627-69-2 - Calbiochem

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.

Synonym: AICA-Riboside - CAS 2627-69-2 - Calbiochem, Acadesine, AICAr, 5-Aminoimidazole-4-carboxamide-1-β-riboside, Z-Riboside, AMPK Signaling Activator II

  • CAS Number 2627-69-2

  • Empirical Formula (Hill Notation) C9H14N4O5

  • Molecular Weight 258.23

  •  MDL number MFCD00869751

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Properties

Related Categories AMP-Activated Protein Kinase (AMPK), Cell Biology, Cell Signaling and Neuroscience, Kinase/Phosphatase Biology, Serine/Threonine Kinase Activators,
Quality Level   100
assay   ≥98% (HPLC)
form   solid
mfr. no.   Calbiochem®
storage condition   OK to freeze
storage conditions   +2C to +8C
color   tan
solubility   methanol: 10 mg/mL
  water: soluble
shipped in   ambient
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

Description

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.

Packaging

50 mg in Plastic ampoule

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Adenosine monophosphate-activated protein kinase (AMPK)

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Preparation Note

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.

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.

Safety & Documentation

Safety Information

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