Okadaic Acid
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Category | Enzyme inhibitors |
Catalog number | BBF-04094 |
CAS | 78111-17-8 |
Molecular Weight | 805.00 |
Molecular Formula | C44H68O13 |
Purity | 95% by HPLC |
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Description
Okadaic acid is a marine sponge toxin which potently inhibits certain serine/threonine protein phosphatases. This cell permeable inhibitor targets the multiple isoforms of PP1, both isoforms of PP2A and PP3. It is a very weak inhibitor of PP2B and does not inhibit PP2C or other phosphatases.
Specification
Synonyms | AA8227800; 9,10-Deepithio-9,10-didehydroacanthifolicin |
Shelf Life | Stable under recommended storage conditions |
Storage | Store at -20°C (dark) |
IUPAC Name | (2R)-3-[(2S,6R,8S,11R)-2-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid |
Canonical SMILES | CC1CCC2(CCCCO2)OC1C(C)CC(C3C(=C)C(C4C(O3)CCC5(O4)CCC(O5)C=CC(C)C6CC(=CC7(O6)C(CCC(O7)CC(C)(C(=O)O)O)O)C)O)O |
InChI | 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 |
Source | Okadaic acid is found in the marine sponges Halichondria okadai and Halichondria melanodocia and shellfish. |
Properties
Appearance | White Solid |
Boiling Point | 921.6°C at 760 mmHg |
Melting Point | 164-166°C |
Density | 1.28 g/cm3 |
Solubility | Soluble in chloroform, ethanol, methanol, acetone, ethyl acetate, DMSO |
Toxicity
Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
Mechanism Of Toxicity | Okadaic acid (OA) dramatically increases both nerve growth factor (NGF) mRNA content (50-fold) and NGF secretion (100-fold) in astrocytes. Okadaic acid also activated NGF gene transcription, which was preceded by an induction of c-fos and c-jun gene transcription. The induction of NGF expression by okadaic acid appeared independent from protein kinase C activity because down-regulating protein kinase C activity failed to decrease the okadaic acid stimulation. Results indicate that okadaic acid profoundly stimulates NGF expression in astrocytes mainly by enhancing NGF mRNA stability and suggest important roles for phosphoprotein phosphatases in regulating NGF production. Instead of activating protein kinase C like the phorbol ester tumor promoters, OA specifically inhibits phosphoprotein phosphatases 1 and 2A leading to an increase in the phosphorylation state of many cellular proteins. Interestingly, OA treatment of fibroblasts mimicked the effects of IL-1 on protein phosphorylation, suggesting that one cellular action of IL-1 might be to inhibit phosphoprotein phosphatase activity. OA has also been found to increase NGF mRNA content in mixed glial-neuronal hippocampal cell cultures similar to IL-1. The toxic potency of this phycotoxin is highly associated with the presence of the free carboxylic acid. Therefore, the toxin forms where the carboxylic acid is acylated are less toxic. |
Reference Reading
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2