A direct activator of AMPK
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A-769662

Item No. 11900

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
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
Solubility(Learn about Variance in Solubility)
DMF: 0.5 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 0.5 mg/ml
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    25 mg

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    50 mg

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    Cayman Chemical
    Explore Obesity & Metabolic Disease Resources

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    OBESITY RESEARCH SOLUTIONS
    Product Description

    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 Thr172.1,2 A-769662 specifically activates β1 subunit-containing AMPK heterotrimers, and its effects are independent of kinases upstream of AMPK.1,3 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.3,4,5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

    3. 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. Chem. Biol. 15, 1220-1230 (2013).

    4. 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. Biol. Pharm. Bull. 32(6), 993-998 (2009).

    5. 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. J. Pharmacol. Exp. Ther. 337(1), 125-136 (2011).

    6. 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. Am. J. Physiol. Cell Physiol. 297, C1041-C1052 (2009).

    7. 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. Am. J. Physiol. Heart Circ. Physiol. 300, H84-H93 (2011).