Business Type:Lab/Research institutions
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Country: China (Mainland)
Business Type:Lab/Research institutions
CAS NO.2627-69-2
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CAS:2627-69-2
MF:C9H14N4O5
MW:258.23
EINECS:220-097-5
Synonyms:ACADESINE;AICAR;AICA-RIBOSIDE;AMPK;5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-RIBOSIDE;5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-B-D-RIBOFURANOSIDE;5-AMINOIMIDAZOLE-4-CARBOXAMIDE 1-BETA-D-RIBOFURANOSIDE;Z-RIBOSIDE
Properties
Melting point:214-215 °C
storage temp. −20°C
solubility H2O: >10 mg/mL
form powder
color tan
Water Solubility Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
λmax265nm(NaOH)(lit.)
Merck 14,16
InChIKeyRTRQQBHATOEIAF-UUOKFMHZSA-N
Safety Information
Symbol(GHS)
Function
AICAR strongly inhibits the transcription of PPAR&alpha and the coactivation of PPAR&alpha. In adipocyte studies it has been shown to antagonize lipolysis induced by isoprenaline and has been suggested for use in kinase cascade research. Additionally, research indicates that AICAR blocks the differentiation of 3T3-L1 (sc-2243) adipocytes. Studies demonstrate that AICAR can mimic the activity of insulin (sc-211647) by activating AMPK, and affecting the expression of PEPCK-M (PEPCK) and glucose-6-phosphatase (G6Pase). The 5-aminoimidazole-4-carboxamide ribonucleoside (ZMP) is the monophosphorylated derivative of AICA-Riboside, and it can serve as the substrate for the aminoimidazole carboxamide ribonucleotide transformylase/inosine monophosphate cyclohydrolase (ATIC). AICAR is an inhibitor of Hsp90, mTOR and p70 S6 Kinase.
AMP-activated protein kinase (AMPK) functions as a metabolic sensor that regulates lipid and glucose metabolism to maintain cellular energy homeostasis and to protect against metabolic stress.AICAR is a selective activator of AMPK in both hepatocytes and adipocytes. At 0.5 mM it inhibits the synthesis of fatty acids and sterols and inactivates HMG-CoA reductase in rat hepatocytes.AICAR (0.5 mM) inhibits insulin-stimulated glucose uptake to 62% of controls and reduces GLUT4 translocation 2.5-fold in 3T3-L1 adipocytes. It also blocks the expression of pro-inflammatory cytokines (TNF-α/IL-1β and IL-6), iNOS, COX-2, and MnSOD genes in glial cells and macrophages by inhibiting NFκB and C/EBP pathways.
Biological Activity
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.
Cell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes. Promotes osteogenic differentiation of hAMSCs and BM-MSCsin vitro.
AMP-activated Protein Kinase
AICAR's principal mechanism of action is activation of AMPK (AMP-activated protein kinase.) Activating AMPK, therefore, causes the same cellular machinery (so to speak) to be turned on as if the cell were energy deprived, for example from intensive exercise, or from low caloric intake.
AICAR, at sufficient and quite substantial concentration, is effective at activating AMPK and inducing a cellular state as if exercise had been performed, or energy stores were low and fat therefore needed to be burned.
AICAR uses metabolic pathways to block certain enzymes, which allows for AMP-activated protein kinase. This can be explained to the layperson like this: once you take a substantial amount of AICAR, it tricks your body at a cellular level in to thinking that exercise has just been preformed. Since the body thinks it has just done a considerable amount of exercise, the energy cycle at the cellular level starts converting fuel sources, like fatty acids, to output the energy that was thought to have been spent during exercise.
This can have a direct effect on the level of endurance activity and the sustainability of that activity. Insulin sensitivity is also noted to be one action that AICAR produces, as the body will think it just went through a series of exercises. Interestingly, in animal studies with obese mice, AICAR showed all of the peptides benefits for obese diet induced mice, yet the healthy lean mice did not reap any of the benefits of insulin sensitivity or increase in glucose uptake. That being said, the application in bodybuilding does not seem very suitable, as these mechanisms are targeted for the out-of-shape and over-weight.