O9381

Okadaic acid

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

• Synonym(s): OA
• 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

Properties

• 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

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 Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331,H315
• Precautionary Statements: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves