STO-609 acetate

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Cat.No. 1551 - STO-609 acetate | C19H10N2O3.C2H4O2 | CAS No. 1173022-21-3
Description: Selective CaM kinase kinase inhibitor
Chemical Name: 7-Oxo-7H-benzimidazo[2,1-a]benz[de]isoquinoline-3-carboxylic acid acetate
Purity: ≥98% (HPLC)
Datasheet
Citations (29)

Biological Activity

Selective, cell-permeable inhibitor of Ca2+-calmodulin-dependent protein kinase kinase (Ki values are 80 and 15 ng/ml for inhibition of CaM-KKα and CaM-KKβ respectively); competes for the ATP-binding site. Displays > 80-fold selectivity over CaMK1, CaMK2, CaMK4, MLCK, PKC, PKA and p42 MAPK.

Chemicalprobes.org is a portal that offers independent guidance on the selection and/or application of small molecules for research. The use of STO-609 acetate is reviewed on the Chemical Probes website.

Technical Data

M. Wt 374.35
Formula C19H10N2O3.C2H4O2
Storage Desiccate at RT
Purity ≥98% (HPLC)
CAS Number 1173022-21-3
PubChem ID 16760660
InChI Key WNRSTFUVBWNELX-UHFFFAOYSA-N
Smiles CC(O)=O.OC(=O)C1=C2C=CC=C3C(=O)N4C5=CC=CC=C5N=C4C(C=C1)=C23

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
100mM NaOH 16.85 45
DMSO 3.74 10mM with sonication

Preparing Stock Solutions

The following data is based on the product molecular weight 374.35. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.67 mL 13.36 mL 26.71 mL
5 mM 0.53 mL 2.67 mL 5.34 mL
10 mM 0.27 mL 1.34 mL 2.67 mL
50 mM 0.05 mL 0.27 mL 0.53 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Tokumitsu et al (2002) STO-609, a specific inhibitor of the Ca2+/calmodulin-dependent protein kinase kinase. J.Biol.Chem. 277 15813 PMID: 11867640


If you know of a relevant reference for STO-609 acetate, please let us know.

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29 Citations for STO-609 acetate

Citations are publications that use Tocris products. Selected citations for STO-609 acetate include:

Kim et al (2013) Epigallocatechin gallate (EGCG) stimulates autophagy in vascular endothelial cells: a potential role for reducing lipid accumulation. J Biol Chem 288 22693 PMID: 23754277

Parker et al (2013) Rapamycin prevents seizures after depletion of STRADA in a rare neurodevelopmental disorder. Sci Transl Med 5 182ra53 PMID: 23616120

Iseli et al (2013) Activation of AMPK by bitter melon triterpenoids involves CaMKKβ. PLoS One 8 e62309 PMID: 23638033

Hutchins et al (2013) Calcium release-dependent actin flow in the leading process mediates axophilic migration. J Neurosci 33 11361 PMID: 23843509

Fortin et al (2012) Brain-derived neurotrophic factor activation of CaM-kinase kinase via transient receptor potential canonical channels induces the translation and synaptic incorporation of GluA1-containing calcium-permeable AMPA receptors. J Neurosci 32 8127 PMID: 22699894

Gaamouch et al (2012) Interaction between αCaMKII and GluN2B controls ERK-dependent plasticity. J Neurosci 32 10767 PMID: 22855824

Ashpole et al (2012) Calcium/calmodulin-dependent protein kinase II (CaMKII) inhibition induces neurotoxicity via dysregulation of glutamate/calcium signaling and hyperexcitability. J Biol Chem 287 8495 PMID: 22253441

Karacosta et al (2012) A regulatory feedback loop between Ca2+/calmodulin-dependent protein kinase kinase 2 (CaMKK2) and the androgen receptor in prostate cancer progression. J Biol Chem 287 24832 PMID: 22654108

Kawashima et al (2012) Ca2+/calmodulin-dependent protein kinase kinase is not involved in hypothalamic AMP-activated protein kinase activation by neuroglucopenia. J Immunol 7 e36335 PMID: 22590531

Terry et al (2012) Human kinome profiling identifies a requirement for AMP-activated protein kinase during human cytomegalovirus infection. Biochem Biophys Res Commun 109 3071 PMID: 22315427

Fu et al (2011) Bile acid stimulates hepatocyte polarization through a cAMP-Epac-MEK-LKB1-AMPK pathway. Proc Natl Acad Sci U S A 108 1403 PMID: 21220320

Fogarty et al (2010) Calmodulin-dependent protein kinase kinase-beta activates AMPK without forming a stable complex: synergistic effects of Ca2+ and AMP. Biochem J 426 109 PMID: 19958286

Reece et al (2009) The Bα and Bδ regulatory subunits of PP2A are necessary for assembly of the CaMKIV.PP2A signaling complex. J Biol Chem 386 582 PMID: 19538941

Soltoff and Hedden (2008) Regulation of ERK1/2 by ouabain and Na-K-ATPase-dependent energy utilization and AMPK activation in parotid acinar cells. Am J Physiol Cell Physiol 295 C590 PMID: 18632735

Guire et al (2008) Recruitment of calcium-permeable AMPA receptors during synaptic potentiation is regulated by CaM-kinase I. Mol Cell 28 6000 PMID: 18524905

Wayman et al (2008) An activity-regulated microRNA controls dendritic plasticity by down-regulating p250GAP. PLoS One 105 9093 PMID: 18577589

Göransson et al (2007) Mechanism of action of A-769662, a valuable tool for activation of AMP-activated protein kinase. J Biol Chem 282 32549 PMID: 17855357

Reihill et al (2007) AMP-activated protein kinase mediates VEGF-stimulated endothelial NO production. Proc Natl Acad Sci U S A 354 1084 PMID: 17276402

Sanders et al (2007) Defining the mechanism of activation of AMP-activated protein kinase by the small molecule A-769662, a member of the thienopyridone family. Mucosal Immunol 282 32539 PMID: 17728241

Høyer-Hansen et al (2007) Control of macroautophagy by calcium, calmodulin-dependent kinase kinase-β and Bcl-2. Autophagy 25 193 PMID: 17244528

Tamás et al (2006) Regulation of the energy sensor AMP-activated protein kinase by antigen receptor and Ca2+ in T lymphocytes. Biochem Biophys Res Commun 203 1665 PMID: 16818670

Hawley et al (2005) Calmodulin-dependent protein kinase kinase-beta is an alternative upstream kinase for AMP-activated protein kinase. Cell Metab 2 9 PMID: 16054095

Guest et al Ca2+/calmodulin-dependent kinase kinase alpha is expressed by monocytic cells and regulates the activation profile. PLoS One 3 e1606 PMID: 18270593

Horigane et al (2016) Facilitation of axon outgrowth via a Wnt5a-CaMKK-CaMKIα pathway during neuronal polarization. Proc Natl Acad Sci U S A 9 8 PMID: 26772170

Obba et al (2015) The PRKAA1/AMPKα1 pathway triggers autophagy during CSF1-induced human monocyte differentiation and is a potential target in CMML. Mol Brain 11 1114 PMID: 26029847

Lee et al (2015) N-methyl-D-aspartate receptors mediate activity-dependent down-regulation of potassium channel genes during the expression of homeostatic intrinsic plasticity. Biochem Biophys Res Commun 8 4 PMID: 25599691

Cohen et al (2015) Evolutionary and functional perspectives on signaling from neuronal surface to nucleus. Mol Brain 460 88 PMID: 25998737

Zhu et al (2015) Adenosine 5'-monophosphate-activated protein kinase regulates IL-10-mediated anti-inflammatory signaling pathways in macrophages. J Exp Med 194 584 PMID: 25512602

Li et al (2014) Cell cycle-linked MeCP2 phosphorylation modulates adult neurogenesis involving the Notch signalling pathway. Nat Commun 5 5601 PMID: 25420914


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