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A-769662

Item № 11900
CAS № 844499-71-4
Purity ≥98%
product image
                (CAS 844499-71-4)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     5 mg $98.00 0.00
     10 mg $157.00 0.00
     50 mg $441.00 0.00

Pricing updated 2019-07-23. Prices are subject to change without notice.

Description

AMP-activated protein kinase (AMPK) is an αβγ heterotrimer that functions as a metabolic sensor, regulating lipid and glucose metabolism to maintain cellular energy homeostasis and to protect against metabolic stress.1 A-769662 is a small molecule thienopyridone that activates AMPK directly in cell-free assays (EC50 = 116 nM) and intact cells by allosterically activating AMPK and inhibiting its dephosphorylation on Thr172.2,3 A-769662 specifically activates β1 subunit-containing AMPK heterotrimers, and its effects are independent of kinases upstream of AMPK.2,4 A-769662 has been used to stimulate CYP450-mediated fatty acid oxidation, inhibit adipocyte differentiation, explore glucose uptake in skeletal muscle, and promote endothelial cell survival during metabolic stress.4,5,6,7,8

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Technical Information
Formal Name
6,7-dihydro-4-hydroxy-3-(2'-hydroxy[1,1'-biphenyl]-4-yl)-6-oxo-thieno[2,3-b]pyridine-5-carbonitrile
CAS Number
844499-71-4
Molecular Formula
C20H12N2O3S
Formula Weight
360.4
Purity
≥98%
Formulation
A crystalline solid
λmax
254, 296 nm
SMILES
OC1=CC=CC=C1C2=CC=C(C3=CSC(N4)=C3C(O)=C(C#N)C4=O)C=C2
InChI Code
InChI=1S/C20H12N2O3S/c21-9-14-18(24)17-15(10-26-20(17)22-19(14)25)12-7-5-11(6-8-12)13-3-1-2-4-16(13)23/h1-8,10,23H,(H2,22,24,25)
InChI Key
CTESJDQKVOEUOY-UHFFFAOYSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Hardie, D.G., and Carling, D. The AMP-activated protein kinase. Fuel gauge of the mammalian cell? European Journal of Biochemistry 246, 259-273 (1997).

2. Göransson, O., McBride, A., Hawley, S.A., et al. Mechanism of action of A-769662, a valuable tool for activation of AMP-activated protein kinase The Journal of Biological Chemisty 282(45), 32549-32560 (2007).

3. Sanders, M.J., Ali, Z.S., Hegarty, B.D., et al. Defining the mechanism of activation of AMP-activated protein kinase by the small molecule A-769662, a member of the thienopyridone family The Journal of Biological Chemisty 282(45), 32540-32548 (2007).

4. Scott, J.W., van Denderen, B.J.W., Jorgensen, S.B., et al. Thienopyridone drugs are selective activators of AMP-activated protein kinase β1-containing complexes Chemistry & Biology 15, 1220-1230 (2013).

5. Zhou, Y., Wang, D., Zhu, Q., et al. Inhibitory effects of A-769662, a novel activator of AMP-activated protein kinase, on 3T3-L1 adipogenesis Biological and Pharmaceutical Bullentin 32(6), 993-998 (2009).

6. Hsu, M.H., Savas, Ü., Lasker, J.M., et al. Genistein, resveratrol, and 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside induce cytochrome P450 4F2 expression through an AMP-activated protein kinase-dependent pathway Journal of Pharmacology and Experimental Therapeutics 337(1), 125-136 (2011).

7. Treebak, J.T., Birk, J.B., Hansen, B.F., et al. A-769662 activates AMPK β1-containing complexes but induces glucose uptake through a PI3-kinase-dependent pathway in mouse skeletal muscle American Journal of Physiology.Cell Physiology 297, C1041-C1052 (2009).

8. Liu, X.m., Peyton, K.J., Shebib, A.R., et al. Activation of AMPK stimulates heme oxygenase-1 gene expression and human endothelial cell survival American Journal of Physiology.Heart and Circulatory Physiology 300, H84-H93 (2011).

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