Description
Okadaic acid is a potent toxin produced by various species of dinoflagellates that accumulates in marine sponges and shellfish. Chemically, okadaic acid is classified as a polyketide and is a polyether derivative of a C38 fatty acid. It is one of the major contributors to diarrhetic shellfish poisoning. Additionally, okadaic acid serves as a powerful inhibitor of specific protein phosphatases, enzymes that play crucial roles in cell signaling and regulation. The inhibition of these phosphatases can lead to a range of detrimental effects on cellular function, highlighting the importance of monitoring and understanding the presence of this toxin in marine environments.
Specification
| Item | Okadaic Acid |
|---|
| Catalog | MC78111178 |
| CAS | 78111-17-8 |
| Synonym | Halochondrine A |
| Molecular Formula | C44H68O13 |
| Molecular Weight | 805.00 |
| Purity | >98% |
| Solubility | Soluble in DMSO, ethanol, or methanol. |
| Appearance | Clear film |
| Melting Point | 171-175 °C |
| MDL Number | MFCD00083455 |
| SMILES | OC([C@](C)(O)C[C@H]1[C@@H](O)CC[C@@]2(OC([C@H](C)/C=C/[C@@H]3O[C@]4(CCC(O[C@H]([C@@H](O)C[C@H](C)[C@H]5O[C@@]6(CCCCO6)CC[C@H]5C)C([C@H]7O)=C)C7O4)CC3)CC(C)=C2)O1)=O |
| InChi Code | 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 |
| Storage Temperature | -20 °C |
Biochemical Properties
Okadaic acid plays a pivotal role in biochemical processes by inhibiting the activity of serine/threonine protein phosphatases, particularly protein phosphatase 1 (PP1) and protein phosphatase 2A (PP2A). These enzymes are integral to the dephosphorylation of various proteins, a crucial regulatory mechanism in cellular signaling pathways. By obstructing these phosphatases, okadaic acid induces a state of hyperphosphorylation in proteins, including tau protein, which has been linked to neurodegenerative disorders such as Alzheimer's disease. Furthermore, this compound also interacts with other biomolecules, including kinases, thereby further influencing its impact on cellular functions.
Research Fields
Okadaic acid is a compound with significant implications across various scientific research fields, primarily due to its potent inhibition of protein phosphatases. Its diverse fields include:
- Chemistry. In the realm of chemistry, okadaic acid serves as a vital tool for elucidating the role of protein phosphatases in numerous biochemical pathways. Researchers utilize it to dissect intricate cellular processes and better understand molecular interactions.
- Biology. In biological research, okadaic acid is employed to explore the mechanisms underlying crucial cellular events such as growth, apoptosis (programmed cell death), and signal transduction. By manipulating protein phosphorylation states, researchers can gain insights into how these processes are regulated and their implications for overall cellular function.
- Medicine. Okadaic acid holds promise in medical research, particularly in the study of neurodegenerative diseases like Alzheimer's disease. Its capacity to induce hyperphosphorylation of tau proteins facilitates investigations into the pathological mechanisms of tau aggregation, which is a hallmark of Alzheimer's. This avenue of research may lead to potential therapeutic targets for intervention.
- Industry. In the industrial sector, okadaic acid plays a role in developing detection methods for marine biotoxins, particularly in seafood safety analysis. Its significance in this area helps ensure public health by providing reliable testing methods to detect harmful substances in food sources.
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For Research Use Only. Not for use in diagnostic or therapeutic procedures.
