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O9381

Sigma-Aldrich

Okadaic acid

from Prorocentrum concavum, 92-100% (HPLC), powder, protein phosphatase 1 inhibitor

Synonym(s):

OA

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About This Item

Empirical Formula (Hill Notation):
C44H68O13
CAS Number:
78111-17-8
Molecular Weight:
805.00
MDL number:
MFCD00083455
UNSPSC Code:
12352106
PubChem Substance ID:
24898069
NACRES:
NA.77

product name

Okadaic acid from Prorocentrum concavum, 92-100% (HPLC)

Quality Level

200

assay

92-100% (HPLC)

form

powder

solubility

DMSO: ≥1 mg/mL
ethanol: ≥1 mg/mL
methanol: ≥1 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

O[C@@H](C[C@@H]([C@@]1([H])O[C@@]2(CCCCO2)CC[C@H]1C)C)[C@]3([H])C([C@@H](O)[C@]4([H])O[C@]5(CC[C@@](/C=C/[C@@H](C)[C@@]6([H])O[C@]7(O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]7O)C=C(C)C6)([H])O5)CC[C@@]4([H])O3)=C

InChI

1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1

InChI key

QNDVLZJODHBUFM-WFXQOWMNSA-N

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General description

Okadaic acid is a polyether fatty acid. It is a marine toxin produced by the genera of Prorocentrum and Dinophysis.

Application

Okadaic acid from Prorocentrum concavum has been used as a phosphatase inhibitor:
  • to inhibit protein phosphatase 2 in spermatocytes culture
  • to treat SH-SY5Y cells to prevent dephosphorylation to maintain tau
  • to treat human embryonic kidney 293T cells (HEK293T) or H4 cells to analyse its effect on fused in sarcoma (FUS) protein

Biochem/physiol Actions

Dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid. Readily enters cells. Inhibitor of type 1 and type 2A protein phosphatases. Does not inhibit tyrosine phosphatases, alkaline phosphatases or acid phosphatase. Known tumor promotor. Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling.

Features and Benefits

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Isolated from unialgal cultures of dinoflagellates.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Okadaic acid, an inhibitor of protein phosphatase 1 and 2A, induces premature separation of sister chromatids during meiosis I and aneuploidy in mouse oocytes in vitro
Mailhes JB, et al.
Chromosome Research, 11(6), 619-631 (2003)
The prionlike domain of FUS is multiphosphorylated following DNA damage without altering nuclear localization
Rhoads SN, et al.
Molecular Biology of the Cell, 29(15), 1786-1797 (2018)
Pseudo-phosphorylation at AT8 epitopes regulates the tau truncation at aspartate 421
Cao L, et al.
Experimental Cell Research, 370(1), 103-115 (2018)
Cohesin removal along the chromosome arms during the first meiotic division depends on a NEK1-PP1gamma-WAPL axis in the mouse
Brieno-Enriquez MA, et al.
Testing, 17(4), 977-986 (2016)
Identification of okadaic acid production in the marine dinoflagellate Prorocentrum rhathymum from Florida Bay
An T, et al.
Toxicon, 55(2-3), 653-657 (2010)
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