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AICAR
- Acadesine - NSC 105823 - AICA-riboside - Arasine
- Optical Purity: Optically pure
- Soluble in water and DMSO
- MF: C9H14N4O5
- MW: 258.23
Description
Potent AMPK activator. AICAR activates AMPK due to increased phosphorylation, causes phosphorylation and inactivation of HMG-CoA reductase, and almost total cessation of fatty acid and sterol synthesis. AICAR causes ZMP (a cellular mimetic of AMP) to accumulate inside the cell but does not perturb the cellular contents of ATP, ADP or AMP, and induces differentiation of acute myeloid leukemia cells, and astroglial differentiation of neural stem cells via activating the JAK/STAT3 pathway independently of AMP-activated protein kinase. AICAR can also significantly up-regulate pluripotency-associated genes and down-regulate differentiation-associated transcription factors.
Caution: Axon Ligands™ are for research purposes only! Not for human consumption!
More Information
| Parent CAS No. | 2627-69-2 |
|---|---|
| Chemical Name | 5-amino-1-((2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carboxamide |
| SMILES | C1(O)[C@H](O[C@@H](N2C(N)=C(C(N)=O)N=C2)[C@H]1O)CO |&1:2,4,14,r| |
| MFCD | N.A. |
| InChi | 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 |
| InChiKey | RTRQQBHATOEIAF-DTUHVUQASA-N |
| CID | 46780289 |
| Short Description | AMPK activator |
References
- J.M. Corton et al. 5-aminoimidazole-4-carboxamide ribonucleoside. A specific method for activating AMP-activated protein kinase in intact cells? Eur J Biochem. 1995 Apr 15;229(2):558-65.
- G.F. Merrill et al. AICA riboside increases AMP-activated protein kinase, fatty acid oxidation, and glucose uptake in rat muscle. Am J Physiol. 1997 Dec;273(6 Pt 1):E1107-12.
- Y. Zang et al. AICAR induces astroglial differentiation of neural stem cells via activating the JAK/STAT3 pathway independently of AMP-activated protein kinase. J Biol Chem. 2008 Mar 7;283(10):6201-8.
- H. Lalic et al. 5-Aminoimidazole-4-carboxamide ribonucleoside induces differentiation of acute myeloid leukemia cells. Leuk Lymphoma. 2014 Oct;55(10):2375-83.
- X. Shi et al. AICAR sustains J1 mouse embryonic stem cell self-renewal and pluripotency by regulating transcription factor and epigenetic modulator expression. Cell Physiol Biochem. 2013;32(2):459-75. doi: 10.1159/000354451. Epub 2013 Aug 27.
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