A9978
AICAR
≥98% (HPLC), powder, AMPK activator
Synonym(s):
5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside, Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide
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About This Item
Empirical Formula (Hill Notation):
C9H14N4O5
CAS Number:
Molecular Weight:
258.23
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
220-097-5
MDL number:
Product Name
AICAR, ≥98% (HPLC), powder
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
SMILES string
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N
assay
≥98% (HPLC)
form
powder
color
tan
mp
214-215 °C
solubility
H2O: >7 mg/mL
shipped in
dry ice
storage temp.
−20°C
Quality Level
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General description
Adenosine monophosphate protein kinase (AMPK) activator 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) modulates cellular energy. It regulates lipid and glucose metabolism, pro-inflammatory responses, cytokine production, cell proliferation and apoptosis. AICAR improves ischemia or reperfusion injury and kidney fibrosis in rats. It provides protection against acute tubular necrosis.
Application
AICAR has been used to provide protection against cisplatin-induced acute kidney injury through the JAK (tyrosine-protein kinase )/STAT (signal transducer and activator of transcription )/SOCS (suppressor of cytokine signaling) pathway. It also has been used in the assay of FapR (malonyl-CoA responsive bacterial transcriptional factor )-NLuc (nanoLuciferase) biosensor activity.
Biochem/physiol Actions
AICAR is a cell permeable activator of AMP-activated protein kinase (AMPK), a metabolic master regulator that is activated in times of reduced energy availability (high cellular AMP:ATP ratios) and serves to inhibit anabolic processes. In vivo, pharmacologic activation of AMPK with AICAR mimics exercise and triggers insulin-independent glucose uptake by skeletal muscle.
AICAR is a cell permeable activator of AMP-activated protein kinase (AMPK).
Features and Benefits
This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
Storage Class
11 - Combustible Solids
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WGK 3
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Hiroaki Sunaga et al.
Scientific reports, 9(1), 11841-11841 (2019-08-16)
Fibroblast growth factor 21 (FGF21) is a metabolic hormone having anti-oxidative and anti-hypertrophic effects. However, the regulation of FGF21 expression during acute myocardial infarction (AMI) remains unclear. We tested blood samples from 50 patients with AMI and 43 patients with
Ai Ushiyama et al.
Biology of reproduction, 100(6), 1482-1491 (2019-02-06)
Despite knowledge that glucose metabolism is essential for the regulation of signaling cascades in the sperm that are pre-assembled into specific areas and function at multistage for fertilization, the physiological roles of glucose in avian sperm are poorly understood. Accumulated
AICAR, an AMPK activator, protects against cisplatin-induced acute kidney injury through the JAK/STAT/SOCS pathway
Tsogbadrakh B, et al.
Biochemical and Biophysical Research Communications (2019)
Genetically-encoded FapR-NLuc as a biosensor to determine malonyl-CoA in situ at subcellular scales
Du Y, et al.
Bioconjugate Chemistry (2019)
Hongshun Wang et al.
Cell death & disease, 10(9), 627-627 (2019-08-21)
Oxysterol-binding protein like 2 (OSBPL2) was identified as a novel causal gene for autosomal dominant nonsyndromic hearing loss. However, the pathogenesis of OSBPL2 deficits in ADNSHL was still unclear. The function of OSBPL2 as a lipid-sensing regulator in multiple cellular
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