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O9381 Sigma-Aldrich

Okadaic acid from Prorocentrum concavum

92-100% (HPLC)

Synonym: OA

  • CAS Number 78111-17-8

  • Empirical Formula (Hill Notation) C44H68O13

  • Molecular Weight 805.00

  •  MDL number MFCD00083455

  •  PubChem Substance ID 24898069

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Kinase/Phosphatase Biology,
Quality Level   200
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

Description

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.

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3462 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
AA8227800
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

LC/MS/MS Analysis of Marine Toxins in Shellfish According to EU Regulations on Ascentis® Express C18

From our library of Articles, Sigma-Aldrich presents LC/MS/MS Analysis of Marine Toxins in Shellfish According to EU Regulations on Ascentis® Express C18
Keywords: Chromatography, High performance liquid chromatography, Liquid chromatography mass spectrometry, Mass spectrometry, Separation

Peer-Reviewed Papers
15

References

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