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  4. Okadaic acid

Okadaic acid, a marine toxin, is an inhibitor of protein phosphatases (PP). Okadaic acid has a significantly higher affinity for PP2A (IC50=0.1-0.3 nM), and inhibits PP1 (IC50=15-50 nM), PP3 (IC50=3.7-4 nM), PP4 (IC50=0.1 nM), PP5 (IC50=3.5 nM), but does not inhibit PP2C. Okadaic acid increases of phosphorylation of a number of proteins by inhibiting PP, and acts a tumor promoter. Okadaic acid induces tau phosphorylation.

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Okadaic acid Chemical Structure

Okadaic acid Chemical Structure

CAS No. : 78111-17-8

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25 μg (124.2 μM * 250 μL in Ethanol) In-stock
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Based on 11 publication(s) in Google Scholar

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Description

Okadaic acid, a marine toxin, is an inhibitor of protein phosphatases (PP). Okadaic acid has a significantly higher affinity for PP2A (IC50=0.1-0.3 nM), and inhibits PP1 (IC50=15-50 nM), PP3 (IC50=3.7-4 nM), PP4 (IC50=0.1 nM), PP5 (IC50=3.5 nM), but does not inhibit PP2C. Okadaic acid increases of phosphorylation of a number of proteins by inhibiting PP, and acts a tumor promoter. Okadaic acid induces tau phosphorylation[1][2].

IC50 & Target[1]

PP1

15-50 nM (IC50)

PP2A

0.1-0.3 nM (IC50)

PP3

3.7-4 nM (IC50)

PP4

0.1 nM (IC50)

PP5

3.5 nM (IC50)

PP2B

~4000 nM (IC50)

PP7

>1000 nM (IC50)

Cellular Effect
Cell Line Type Value Description References
HCT-116 IC50
0.67 μM
Compound: OA
Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay
Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay
[PMID: 28383915]
HepG2 IC50
0.54 μM
Compound: OA
Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay
Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay
[PMID: 28383915]
N2a IC50
0.85 μM
Compound: OA
Cytotoxicity against mouse Neuro2a cells after 24 hrs by MTT assay
Cytotoxicity against mouse Neuro2a cells after 24 hrs by MTT assay
[PMID: 28383915]
P388 EC50
87 nM
Compound: OA
Blockade of okadaic acid-induced cytotoxicity in mouse P388 cells after 2 days by WST-8 assay in presence of Halichondria okadai recombinant OABP 2.3
Blockade of okadaic acid-induced cytotoxicity in mouse P388 cells after 2 days by WST-8 assay in presence of Halichondria okadai recombinant OABP 2.3
[PMID: 20863709]
P388 EC50
92 nM
Compound: OA
Blockade of okadaic acid-induced cytotoxicity in mouse P388 cells after 2 days by WST-8 assay in presence of Halichondria okadai recombinant OABP 2.1
Blockade of okadaic acid-induced cytotoxicity in mouse P388 cells after 2 days by WST-8 assay in presence of Halichondria okadai recombinant OABP 2.1
[PMID: 20863709]
In Vitro

Okadaic acid (0-100 nM; 24 h or 48 h) inhibits the proliferation of AGS, MNK-45, Caco 2 cells[3].
Okadaic acid (10 nM; 8 hours) increases Drp1 phosphorylation and mitochondrial fission in rat cortical neurons[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay[3]

Cell Line: AGS, MNK-45 and Caco 2 cell lines
Concentration: 0-100 nM
Incubation Time: 24 h or 48 h
Result: Inhibited the proliferation of AGS, MNK-45, Caco 2 cells.
In Vivo

Okadaic acid can be used to induce Alzheimer's disease models[6].

Induction of Alzheimer's disease model[6]
Background
Okadaic acid is a Ser/Thr phosphatase enzyme inhibitor that causes Tau hyperphosphorylation and induces the intracellular aggregation of neurofibrillary tangles.
Specific Mmodeling Methods
Mice: Wistar • male •-250–300 g
Administration: 100μg • icv • single dose
Note
Modeling Indicators
Molecular changes: Induced increases in pTauser396 in the hippocampus.
Correlated Product(s): /
Opposite Product(s): /

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

805.00

Formula

C44H68O13

CAS No.
Appearance

Liquid

Color

Colorless to light yellow

SMILES

O[C@H](CC[C@@H](C[C@@](C)(O)C(O)=O)O1)[C@@]1(C=C(C)C2)O[C@]2([H])[C@H](C)/C=C/[C@@H]3O[C@@]4(O[C@]([C@@H]5O)([H])[C@@](O[C@@]([C@@H](O)C[C@@H]([C@@]6([H])O[C@@]7(CCCCO7)CC[C@H]6C)C)([H])C5=C)([H])CC4)CC3

Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Solution, -20°C, 2 years

Purity & Documentation

Purity: 99.19%

References
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    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

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Okadaic acid
Cat. No.:
HY-N6785
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