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OKADAIC ACID AMMONIUM SALT, 98

Product Name
OKADAIC ACID AMMONIUM SALT, 98
CAS No.
175522-42-6
Chemical Name
OKADAIC ACID AMMONIUM SALT, 98
Synonyms
OKADAIC ACID AMMONIUM SALT, 98;(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
CBNumber
CB3502101
Molecular Formula
C44H71NO13
Formula Weight
822.05
MOL File
175522-42-6.mol
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OKADAIC ACID AMMONIUM SALT, 98 Property

storage temp. 
Freezer (-20°C)
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Safety

HS Code 
29189990
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Adipogen Life Sciences
Product number
AG-CN2-0058-C100
Product name
Okadaicacid.ammoniumsalt(highpurity)
Purity
≥98%(HPLC)
Packaging
100μg
Price
$200
Updated
2021/12/16
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OKADAIC ACID AMMONIUM SALT, 98 Chemical Properties,Usage,Production

Chemical Properties

white to off-white solid

Uses

Okadaic acid ammonium salt, a marine toxin, is an inhibitor of protein phosphatases (PP). Okadaic acid ammonium salt has a significantly higher affinity for PP2A (IC50=0.1-0.3 nM), and inhibits PP1 (IC50=15-50 nM), PP3 (IC50=3.7-4 nM), PP4 (IC50=0.1 nM), PP5 (IC50=3.5 nM), but does not inhibit PP2C. Okadaic acid ammonium salt increases of phosphorylation of a number of proteins by inhibiting PP, and acts as a tumor promoter. Okadaic acid ammonium salt induces tau phosphorylation[1][2].

in vivo

Okadaic acid ammonium salt can be used in animal modeling to create Alzheimer's disease and skin tumor models[6][7][8].

1. Induction of neurotoxicity[6][7]
Background
Tau protein hyperphosphorylation is a major pathological hallmark of Alzheimer’s disease (AD). Okadaic acid can induce a decrease in protein phosphatase (PP-2A) activity, leading to tau protein hyperphosphorylation[6].
Specific Modeling Methods
Rat: Wistar ? male ? 2-month-old
Administration: 200 ng ? icv ? single dose
Note
(1) Dissolve 200 ng of Okadaic acid in artificial cerebrospinal fluid (aCSF), which contains: 147 mmol/L NaCl, 2.9 mmol/L KCl, 1.6 mmol/L MgCl2, 1.7 mmol/L CaCl2, and 2.2 mmol/L glucose. The injection volume of aCSF is 10 μL per rat.
(2) After intracerebroventricular injection of Okadaic acid, administer intraperitoneal gentamicin (5 mg/kg) to prevent sepsis.
(3) Combined treatment with hypoxia can enhance the neurotoxic effects induced by Okadaic acid. Hypoxia treatment method: After intracerebroventricular injection of Okadaic acid, place the rats in a hypoxic chamber with 10% oxygen for 22 hours/day for 3 consecutive days.
Modeling Indicators
Molecular changes: Reduced levels of procaspase 3, decreased AChE activity and expression, increased levels of caspase 3, β-amyloid protein (Aβ42), and phosphorylated tau protein, and accumulation of ROS and malondialdehyde (MDA).
Phenotypic observations: Neuronal damage and death in the rat brain, with cell swelling and nuclear chromatin condensation.
Correlated Product(s): /
Opposite Product(s): /

2. Induction of skin tumors[8]
Background
Okadaic acid is a skin irritant and toxic polyether compound that acts as a non-TPA-type tumor promoter. Okadaic acid stimulates ornithine decarboxylase in mouse ears and mouse skin, but does not induce adhesion of human promyelocytic leukemia cells (HL-60 cells), does not inhibit the specific binding of [3H]TPA to mouse particle components, and does not activate protein kinase C[8].
Specific Modeling Methods
Mice: CD-1 ? female ? 8-week-old
Administration: 10 μg ? topical application ? twice a week for 30 weeks
Note
(1) Dissolve 10 μg of Okadaic acid in acetone and apply a volume of 0.1 mL per rat.
(2) The induction of skin tumors can be divided into two stages, with local application of Okadaic acid being the second stage. The first stage involves local application of DMBA dissolved in acetone (100 μg DMBA in 0.1 mL acetone), followed by the second stage one week later. Both Okadaic acid alone and the combination of Okadaic acid and DMBA induce skin tumors, with the combined treatment showing enhanced induction effects.
Modeling Indicators
Phenotypic observations: Increased incidence of papillomas and sarcomas on the skin surface.
Correlated Product(s): DMBA (HY-W011845); Teleocidin
Opposite Product(s): /

Animal Model:Female wild-type C57BL/6 mice (6 to 8 months)[5]
Dosage:100 μM
Administration:Injected unilaterally to the lateral amygdala
Result:Induced Tau phosphorylation and protein aggregation in anatomically distinct brain regions 24 h post-injection.

IC 50

PP1: 15-50 nM (IC50); PP2A: 0.1-0.3 nM (IC50); PP3: 3.7-4 nM (IC50); PP4: 0.1 nM (IC50); PP5: 3.5 nM (IC50); PP2B: ~4000 nM (IC50); PP7: ＞1000 nM (IC50)

References

[1] Kleppe R, et al. Cell Death Inducing Microbial Protein Phosphatase Inhibitors--Mechanisms of Action. Mar Drugs. 2015 Oct 22;13(10):6505-20. DOI:10.3390/md13106505
[2] Valdiglesias V, et al. Okadaic acid: more than a diarrheic toxin. Mar Drugs. 2013 Oct 31;11(11):4328-49. DOI:10.3390/md11114328
[3] del Campo M, et al. Okadaic acid toxin at sublethal dose produced cell proliferation in gastric and colon epithelial cell lines. Mar Drugs. 2013;11(12):4751-4760. DOI:10.3390/md11124751
[4] Cho MH, et al. Increased phosphorylation of dynamin-related protein 1 and mitochondrial fission in okadaic acid-treated neurons. Brain Res. 2012 May 15;1454:100-10. DOI:10.1016/j.brainres.2012.03.010
[5] Baker S, et al. A local insult of okadaic acid in wild-type mice induces tau phosphorylation and protein aggregation in anatomically distinct brain regions. Acta Neuropathol Commun. 2016;4:32. DOI:10.1186/s40478-016-0300-0
[6] Kamat P K, et al. Okadaic acid induced neurotoxicity: an emerging tool to study Alzheimer's disease pathology[J]. Neurotoxicology, 2013, 37: 163-172. DOI:10.1016/j.neuro.2013.05.002
[7] Kaushal A, et al. Okadaic Acid and Hypoxia Induced Dementia Model of Alzheimer's Type in Rats. Neurotox Res. 2019 Apr;35(3):621-634. DOI:10.1007/s12640-019-0005-9
[8] Suganuma M, et al. Okadaic acid: an additional non-phorbol-12-tetradecanoate-13-acetate-type tumor promoter. Proc Natl Acad Sci U S A. 1988 Mar;85(6):1768-71. DOI:10.1073/pnas.85.6.1768
[9] Fujiki H, et al. Cancer progression by the okadaic acid class of tumor promoters and endogenous protein inhibitors of PP2A, SET and CIP2A. J Cancer Res Clin Oncol. 2023 Sep;149(11):9425-9433. DOI:10.1007/s00432-023-04800-4

OKADAIC ACID AMMONIUM SALT, 98 Preparation Products And Raw materials

Raw materials

Preparation Products

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OKADAIC ACID AMMONIUM SALT, 98 Suppliers

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175522-42-6, OKADAIC ACID AMMONIUM SALT, 98Related Search:

OKADAIC ACID OKADAIC ACID AMMONIUM SALT

  • (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
  • OKADAIC ACID AMMONIUM SALT, 98
  • 175522-42-6
  • C44H71NO13