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Merck

123040

AICAR

≥98% (HPLC), AMPK activator, solid

別名:

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

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この商品について

実験式(ヒル表記法):
C9H14N4O5
CAS番号:
分子量:
258.23
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
solid
Storage condition:
OK to freeze
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製品名

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 Segment

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)
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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)


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保管分類

11 - Combustible Solids

wgk

WGK 3



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