All Photos(1)

O9381

Sigma-Aldrich

Okadaic acid from Prorocentrum concavum

92-100% (HPLC)

Synonym(s):
OA
Empirical Formula (Hill Notation):
C44H68O13
CAS Number:
Molecular Weight:
805.00
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

92-100% (HPLC)

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

Looking for similar products? Visit Product Comparison Guide

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

6.1B - Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

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)
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)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service