AICAR

AdipoGen Life Sciences
Product Code: AG-CR1-0061
CodeSizePrice
AG-CR1-0061-M01010 mg£30.00
Quantity:
AG-CR1-0061-M05050 mg£60.00
Quantity:
AG-CR1-0061-M100100 mg£95.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
-20°C
Storage:
-20°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
5-Aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside; Acadesine; AICA-Riboside
Appearance:
Off-white solid.
CAS:
2627-69-2
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Hazards:
H315, H319, H335
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)
InChiKey:
RTRQQBHATOEIAF-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 2627-69-2. Formula: C9H14N4O5. MW: 258.2. Cell permeable AMP-activated protein kinase (AMPK) activator. Insulin mimetic. Adipocyte differentiation inhibitor. Apoptosis inducer. PPARalpha inhibitor. mTOR inhibitor. P70S6K inhibitor. LPS-induced TNF-alpha production inhibitor. TORC2 phosphorylation inducer. Anti-inflammatory. Anti-tumor compound. Autophagy inhibitor. HSP90 inhibitor. Autophagy inducer
MDL:
MFCD00869751
Molecular Formula:
C9H14N4O5
Molecular Weight:
258.2
Package Type:
Vial
Precautions:
P261, P271, P280, P312
Product Description:
Cell permeable AMP-activated protein kinase (AMPK) activator [1]. Insulin mimetic [2, 10]. Adipocyte differentiation inhibitor [3]. Apoptosis inducer [4, 11]. PPARalpha inhibitor [5]. mTOR inhibitor [6]. P70S6K inhibitor [6]. LPS-induced TNF-alpha production inhibitor [7]. TORC2 phosphorylation inducer [8]. Anti-inflammatory [9]. Anti-tumor compound [12]. Autophagy inhibitor [13]. HSP90 inhibitor [14]. Autophagy inducer [15]
Purity:
>98% (HPLC)
Signal word:
Warning
SMILES:
NC(=O)C1=C(N)N(C=N1)C1OC(CO)C(O)C1O
Solubility Chemicals:
Soluble in water (9 mg/ml), DMSO or dimethyl formamide.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

References

5-aminoimidazole-4-carboxamide ribonucleoside. A specific method for activating AMP-activated protein kinase in intact cells?: J. M. Corton et al.; Eur. J. Biochem. 229, 558 (1995) | 5-aminoimidazole-4-carboxamide riboside mimics the effects of insulin on the expression of the 2 key gluconeogenic genes PEPCK and glucose-6-phosphatase: P. A, Lochhead et al.; Diabetes 49, 896 (2000) | The effects of AICAR on adipocyte differentiation of 3T3-L1 cells: S. A. Habinowski et al.; Biochem. Biophys. Res. Commun.286, 852 (2001) | 5-Aminoimidazole-4-carboxamide riboside induces apoptosis in Jurkat cells, but the AMP-activated protein kinase is not involved: J. M. Lopez et al.; Biochem. J. 370, 1027 (2003) | Kinase-independent transcriptional co-activation of peroxisome proliferator-activated receptor alpha by AMP-activated protein kinase: M. Bronner et al.; Biochem. J. 384, 295 (2004) | AMP-activated protein kinase activators can inhibit the growth of prostate cancer cells by multiple mechanisms: X. Xiang et al.; Biochem. Biophys. Res. Commun. 321, 161 (2004) | 5-Aminoimidazole-4-carboxamide riboside suppresses lipopolysaccharide-induced TNF-alpha production through inhibition of phosphatidylinositol 3-kinase/Akt activation in RAW 264.7 murine macrophages: B. S. Jhun et al.; Biochem. Biophys. Res. Commun.318, 372 (2004) | The CREB coactivator TORC2 is a key regulator of fasting glucose metabolism: S. H. Koo et al.; Nature 437, 1109 (2005) | 5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside inhibits proinflammatory response in glial cells: a possible role of AMP-activated protein kinase: S. Giri, et al.; J. Neurosci. 24, 479 (2004) | 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR) inhibits insulin-stimulated glucose transport in 3T3-L1 adipocytes: I.P. Salt, et al.; Diabetes 49, 1649 (2000) | AICAR induces apoptosis independently of AMPK and p53 through up-regulation of the BH3-only proteins BIM and NOXA in chronic lymphocytic leukemia cells: A.F. Santidrian, et al.; Blood 116, 3023 (2010) | AICAR inhibits cancer cell growth and triggers cell-type distinct effects on OXPHOS biogenesis, oxidative stress and Akt activation: C. Jose, et al.; Biochim. Biophys. Acta 1807, 707 (2011) | Role of AMP-activated protein kinase in autophagy and proteasome function: R. Viana, et al.; BBRC 369, 964 (2008) | Small-molecule targeting of heat shock protein 90 chaperone function: rational identification of a new anticancer lead: M. Meli, et al.; J. Med. Chem. 49, 7721 (2006) | AMPK promotes skeletal muscle autophagy through activation of forkhead FoxO3a and interaction with Ulk1: A.M. Sanchez, et al.; J. Cell. Biochem. 113, 695 (2012) | AMPK Activation by Zyflamend: A novel pathway regulating metabolism and growth in prostate cancer: A.F. MacDonald; Master's Thesis, University of Tennessee (2017) | Gene-by-environment interactions that disrupt mitochondrial homeostasis cause neurodegeneration in C. elegans Parkinson?s models: H. Kim, et al.; Cell Death Dis. 9, 555 (2018) | AMPK activity is required for the induction of anhydrobiosis in a tardigrade Hypsibius exemplaris, and its potential up?regulator is PP2A: K. Kondo, et al.; Genes Cells, ahead of print (2019)

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