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Submit ReviewOkadaic acid
Description: Protein phosphatase 1 and 2A inhibitor
Chemical Name: 9,10-Deepithio-9,10-didehydroacanthifolicin
Purity: ≥90% (HPLC)
Biological Activity for Okadaic acid
Okadaic acid is a 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 for Okadaic acid
| M. Wt | 805.01 |
| Formula | C44H68O13 |
| Storage | Store at -20°C |
| Purity | ≥90% (HPLC) |
| CAS Number | 78111-17-8 |
| PubChem ID | 90479758 |
| InChI Key | QNDVLZJODHBUFM-WFXQOWMNSA-N |
| Smiles | [H][C@]1(CC(C)=C[C@@]2(O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]2O)O1)[C@H](C)\C=C\[C@H]1CC[C@@]2(CC[C@@]3([H])O[C@]([H])([C@@H](O)C[C@H](C)[C@@]4([H])O[C@@]5(CCCCO5)CC[C@H]4C)C(=C)[C@@H](O)[C@]3([H])O2)O1 |
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 for Okadaic acid
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 40 | 50 |
Preparing Stock Solutions for Okadaic acid
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 |
|---|---|---|---|
| 0.5 mM | 2.48 mL | 12.42 mL | 24.84 mL |
| 2.5 mM | 0.5 mL | 2.48 mL | 4.97 mL |
| 5 mM | 0.25 mL | 1.24 mL | 2.48 mL |
| 25 mM | 0.05 mL | 0.25 mL | 0.5 mL |
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Product Datasheets for Okadaic acid
References for Okadaic acid
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
If you know of a relevant reference for Okadaic acid, please let us know.
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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
28 Citations for Okadaic acid
Citations are publications that use Tocris products. Selected citations for Okadaic acid include:
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
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
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
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
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
Chiu et al (2019) NMDAR-Activated PP1 Dephosphorylates GluN2B to Modulate NMDAR Synaptic Content. Cell Rep 28 332 PMID: 31291571
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
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
Coates et al (2019) The insect, Galleria mellonella, is a compatible model for evaluating the toxicology of okadaic acid. Cell Biol Toxicol 35 219 PMID: 30426330
Messal et al (2019) Tissue curvature and apicobasal mechanical tension imbalance instruct cancer morphogenesis. 566 126 PMID: 30700911
Livingstone et al (2019) Secreted Amyloid Precursor Protein-Alpha Promotes Arc Protein Synthesis in Hippocampal Neurons. Front Mol Neurosci 12 198 PMID: 31474829
Goffin et al (2010) DA-dependent tuning of striatal inhibitory synaptogenesis. J Neurosci 30 2935 PMID: 20181591
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
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
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
Jones et al (2018) Inflammatory but not mitogenic contexts prime synovial fibroblasts for compensatory signaling responses to p38 inhibition. Sci Signal 11 PMID: 29511118
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
Do you know of a great paper that uses Okadaic acid from Tocris? Please let us know.
Reviews for Okadaic acid
Average Rating: 5 (Based on 2 Reviews.)
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Works as intended..
By
Anonymous on 04/04/2020
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Sprague-Dawley rats primary neuronal
Okadaic acid for PP2A at 20 nM
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.
