99% Purity ACADESINE Raw Powder AICAR with Discreet Package CasNO.2627-69-2

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Detailed Product Description

Product Name:AICAR
Other Name:ACADESINE
CAS: 2627-69-2
MF:C9H14N4O5
MW:258.23
EINECS:220-097-5
High Light:pharmaceutical anabolic steroids, pharmaceutical fine chemicals


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Product Tags

AICAR(ACADESINE) Product Description

Product Name: AICAR
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
CAS: 2627-69-2
MF: C9H14N4O5
MW: 258.23
EINECS: 220-097-5
Product Categories: Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;Protein Kinase;ARASINE;Cardiovascular APIs;PI3K/Akt/mTOR;Akt;mTOR;PI3K
Mol File: 2627-69-2.mol
 
AICAR Chemical 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
λmax 265nm(NaOH)(lit.)
Merck 14,16
InChIKey RTRQQBHATOEIAF-UUOKFMHZSA-N
CAS DataBase Reference 2627-69-2(CAS DataBase Reference)
EPA Substance Registry System 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2)
 
Safety Information
Hazard Codes Xi,T
Risk Statements 36/37/38-61
Safety Statements 26-36-45-53
WGK Germany 3
TSCA Yes
 
MSDS Information
Provider Language
SigmaAldrich English
 
AICAR Usage And Synthesis
adenosine regulating agents Acadesine is the prototype of a new class of compounds termed adenosine regulating agents. Acadesine is a purine nucleosid analogue that enters the myocyte and is immediately phosphorylated to ZMP (AICA ribotide), which is further metabolised to Inosine mono-phosphate (an intermediate in the synthesis ofadenosine triphosphate (ATP) and guanosine triphos-phate).
Claims that acadesine may serve as a substrate for ATP synthesis and result in repletion of myocardial ATP were supported by some studies and refuted by others. Because acadesine may be a precursor in the synthesis of myocardial ATP it was proposed as a possible agent of myocardial protection during ischaemia, particularly because myocardial ATP depletion has been linked to cell death.
Chemical Properties Solid
Uses glucose uptake stimulant; AMPK activator
Uses AICAR is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) hav e been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.
Definition ChEBI: A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.
Biological Activity 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.

 

AICAR(ACADESINE) 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.

R-C (9)

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