Okadaic acid

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Cat.No. 1136 - Okadaic acid | C44H68O13 | CAS No. 78111-17-8
Description: Protein phosphatase 1 and 2A inhibitor
Chemical Name: 9,10-Deepithio-9,10-didehydroacanthifolicin
Datasheet
Citations (24)
Reviews (1)
Literature

Biological Activity

Potent inhibitor of protein phosphatase 1 (IC50 = 3 nM) and protein phosphatase 2A (IC50 = 0.2-1 nM). Displays > 100,000,000-fold selectivity over PP2B and PP2C. Tumor promoter. Shown to activate atypical protein kinase C in adipocytes.

Technical Data

M. Wt 805.01
Formula C44H68O13
Storage Desiccate at -20°C
CAS Number 78111-17-8
PubChem ID 90479758
InChI Key QNDVLZJODHBUFM-QRJUTTKYSA-N
Smiles [H][C@@](CCCO5)([H])[C@](CC[C@H]4C)5O[C@@H]4[C@@H](C)C[C@H](O)C(C([C@H]3O)=C)OC(C3O2)CC[C@]12O[C@@H](/C=C/[C@H]([C@H](O7)CC(C)=C[C@@]67[C@H](O)CCC(C[C@](O)(C)C(O)=O)O6)C)CC1

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

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 80.5 100

Preparing Stock Solutions

The following data is based on the product molecular weight 805.01. Batch specific molecular weights may vary from batch to batch due to the degree 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 1.24 mL 6.21 mL 12.42 mL
5 mM 0.25 mL 1.24 mL 2.48 mL
10 mM 0.12 mL 0.62 mL 1.24 mL
50 mM 0.02 mL 0.12 mL 0.25 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Cohen et al (1990) Okadaic acid: a new probe for the study of cellular regulation. TiBS 15 98 PMID: 2158158

Haystead et al (1989) Effects of the tumour promotor okadaic acid on intracellular protein phosphorylation and metabolism. Nature 337 78 PMID: 2562908

McCluskey et al (2002) Serine-threonine protein phosphatase inhibitors: development of therapeutic strategies. J.Med.Chem. 45 1151 PMID: 11881984

Nuydens et al (1998) Okadaic acid-induced apoptosis in neuronal cells: evidence for an abortive mitotic attempt. J.Neurochem. 70 1124 PMID: 9489733

Standaert et al (1999) Okadaic acid activates atypical protein kinase C (ζ/λ) in rat and 3T3/L1 adipocytes. J.Biol.Chem. 274 14074 PMID: 10318822

Merck Index 12 6958


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Keywords: Okadaic acid, Okadaic acid supplier, Protein, phosphatase, 1, 2A, inhibitors, inhibits, Calcineurin, Ser/Thr, Phosphatases, PP1, PP2A, 1136, Tocris Bioscience

24 Citations for Okadaic acid

Citations are publications that use Tocris products. Selected citations for Okadaic acid include:

Martin et al (2014) IKKα negatively regulates ASC-dependent inflammasome activation. Nat Commun 5 4977 PMID: 25266676

Bernard et al (2013) Phosphorylation of FMRP and alterations of FMRP complex underlie enhanced mLTD in adult rats triggered by early life seizures. PLoS One 59 42736 PMID: 23831253

Seto et al (2013) Acute SimV. inhibits K ATP channels of porcine coronary artery myocytes. J Neurosci 8 e66404 PMID: 23799098

Stipanovich et al (2008) A phosphatase cascade by which rewarding stimuli control nucleosomal response. Nature 453 879 PMID: 18496528

Marsden et al (2007) NMDA receptor activation potentiates inhibitory transmission through GABA receptor-associated protein-dependent exocytosis of GABA(A) receptors. J Neurosci 27 14326 PMID: 18160640

Goffin et al (2010) DA-dependent tuning of striatal inhibitory synaptogenesis. J Neurosci 30 2935 PMID: 20181591

Jones et al (2018) Inflammatory but not mitogenic contexts prime synovial fibroblasts for compensatory signaling responses to p38 inhibition. Sci Signal 11 PMID: 29511118

Bartley et al (2016) Mammalian FMRP S499 Is Phosphorylated by CK2 and Promotes Secondary Phosphorylation of FMRP. Eneuro 3 PMID: 27957526

Kii et al (2016) Selective inhibition of the kinase DYRK1A by targeting its folding process. Nat Commun 7 11391 PMID: 27102360

Polito et al (2015) Selective Effects of PDE10A Inhibitors on Striatopallidal Neurons Require Phosphatase Inhibition by DARPP-32(1,2,3). Biochem Biophys Res Commun 2 PMID: 26465004

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

Chen et al (2014) Prolonged adenosine A1 receptor activation in hypoxia and pial vessel disruption focal cortical ischemia facilitates clathrin-mediated AMPA receptor endocytosis and long-lasting synaptic inhibition in rat hippocampal CA3-CA1 synapses: differential regulat J Neurosci 34 9621 PMID: 25031403

Pradhan and Vijayan (2013) Lipid rafts contribute to agonist-induced serine/threonine phosphatase activation and platelet aggregation. J Neurosci 11 1612 PMID: 23789860

Pribiag and Stellwagen (2013) TNF-α Downregulates Inhibitory Neurotransmission through Protein Phosphatase 1-Dependent Trafficking of GABAA Receptors. Mol Pain 33 15879 PMID: 24089494

Bodhinathan et al (2010) Intracellular redox state alters NMDA receptor response during aging through Ca2+/calmodulin-dependent protein kinase II. J Neurosci 30 1914 PMID: 20130200

Dart and Leyland (2001) Targeting of an A kinase-anchoring protein, AKAP79, to an inwardly rectifying potassium channel, Kir2.1. J Biol Chem 276 20499 PMID: 11287423

Hullinger et al (2015) Environmental enrichment improves learning and memory and long-term potentiation in young adult rats through a mechanism requiring mGluR5 signaling and sustained activation of p70s6k. Neurobiol Learn Mem 125 126 PMID: 26341144

Thayer et al (2013) Increased neuronal activity fragments the Golgi complex. Proc Natl Acad Sci U S A 110 1482 PMID: 23297202

Brito et al (2013) Imbalance of p75(NTR)/TrkB protein expression in Huntington's disease: implication for neuroprotective therapies. Cell Death Dis 4 e595 PMID: 23598407

Li et al (2009) Activation of glycogen synthase kinase-3 β is required for hyperDA and D2 receptor-mediated inhibition of synaptic NMDA receptor function in the rat prefrontal cortex. Eneuro 29 15551 PMID: 20007479

Pose-Utrilla et al (2017) Excitotoxic inactivation of constitutive oxidative stress detoxification pathway in neurons can be rescued by PKD1. Nat Commun 8 2275 PMID: 29273751

Rankovic et al (2011) Modulation of calcium-dependent inactivation of L-type Ca2+ channels via β-adrenergic signaling in thalamocortical relay neurons. PLoS One 6 e27474 PMID: 22164209

Li and Burrell (2011) Associative, bidirectional changes in neural signaling utilizing NMDA receptor- and endocannabinoid-dependent mechanisms. Learn Mem 18 545 PMID: 21844187

Kim et al (2008) Aberrant early-phase ERK inactivation impedes neuronal function in fragile X syndrome. J Thromb Haemost 105 4429 PMID: 18332424


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Okadaic acid increases phosphorylation of CaMKII in HL-1 cells.
By Anonymous on 05/15/2019
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: Cardiomyocytes

HL-1 cardiomyocytes were treated with 100 nM fostriecin, 100 nM Okadaic acid or 50 nM 8-bromo-cAMP for 30 min followed by Western blot analysis for pCaMKII expression. Okadaic acid significantly increased phosphorylation of CaMKII; indicating a major role of PP1 in CaMKII dephosphorylation.

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