Okadaic acid (free acid) (high purity)

Specifications / Handling

More Information
Product Details
Synonyms	Halochondrine A; CCRIS 3329; HSDB 7243; 9,10-Deepithio-9,10-didehydroacanthifolicin
Product Type	Chemical
Properties
Formula	C₄₄H₆₈O₁₃
MW	805.0
Merck Index	14: 6819
CAS	78111-17-8
RTECS	AA8227800
Source/Host Chemicals	Isolated from Prorocentrum concavum.
Purity Chemicals	≥98% (HPLC)
Appearance	White crystalline solid.
Solubility	Soluble in DMSO, ethanol or methanol.
Other Product Data	Use only fresh solutions.
InChi Key	QNDVLZJODHBUFM-OQMIOGKESA-N
Smiles	[H][C@@]1(CC[C@@]2(CC[C@H]3O[C@@]([H])([C@@H](O)C[C@H](C)[C@H]4O[C@@]5(CCCCO5)CC[C@H]4C)C(=C)[C@@H](O)[C@]3([H])O2)O1)\C=C\[C@@H](C)[C@@]1([H])CC(C)=C[C@@]2(O[C@]([H])(C[C@@](C)(O)C(O)=O)CCC2O)O1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Non-phorbol type tumor promoter [1].
Reversible, potent and selective serine threonine protein phosphatase inhibitor. PP2A (IC₅₀=0.2-1nM), PP1 (IC₅₀=3-15nM), PP2B (IC₅₀=>1µM). Does not inhibit PP2C [2, 6, 7, 18].
Stimulates intracellular protein phosphorylation [3].
Useful tool for studying cellular processes that are regulated by phosphorylation. Does not affect activity of acid phosphatase, alkaline phosphatase and tyrosine phosphatase [4, 5].
Mimics the effects of insulin [7]. Activates atypical protein kinase C (ζ/λ) in 3T3/L1 adipocytes [14, 19].
Enhances transmitter release at neuromuscular junctions [8].
Apoptosis inhibitor [9, 11, 12].
Induces apoptosis in human breast carcinoma cells (MB-231 and MCF-7) and in myeloid cells [10].
Neurotoxic [12, 16].
Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling [13, 15, 17, 18].
Stimulates cell motility, loss of stabilization of focal adhesions and a consequent loss of cytoskeletal organization [20].

Product References

Okadaic acid: an additional non-phorbol-12-tetradecanoate-13-acetate- type tumor promoter: M. Suganuma, et al.; PNAS 85, 1768 (1988)
Inhibitory effect of a marine-sponge toxin, okadaic acid, on protein phosphatases. Specificity and kinetics: C. Bialojan & A. Takai; Biochem. J. 256, 283 (1988)
Effects of the tumour promoter okadaic acid on intracellular protein phosphorylation and metabolism: T.A. Haystead, et al.; Nature 337, 78 (1989)
An improved procedure for identifying and quantitating protein phosphatases in mammalian tissues: P. Cohen, et al.; FEBS Lett. 250, 596 (1989)
Okadaic acid: a new probe for the study of cellular regulation: P. Cohen, et al.; TIPS 15, 98 (1990) (Review)
Use of okadaic acid to inhibit protein phosphatases in intact cells: D.G. Hardie, et al.; Methods Enzymol. 201, 469 (1991)
Effects of okadaic acid, an inhibitor of protein phosphatases-1 and -2A, on glucose transport and metabolism in skeletal muscle: J.F. Tanti, et al.; J. Biol. Chem. 266, 2099 (1991)
Protein phosphatase inhibitor okadaic acid enhances transmitter release at neuromuscular junctions: M. Abdul-Ghani, et al.; PNAS 88, 1803 (1991)
Inhibition of apoptosis in human tumour cells by okadaic acid: Q. Song, et al.; J. Cell Physiol. 153, 550 (1992)
Differential induction of apoptosis in human breast tumor cells by okadaic acid and related inhibitors of protein phosphatases 1 and 2A: K. Kiguchi, et al.; Cell Growth Differentiation 5, 995 (1994)
Differential inhibition and posttranslational modification of protein phosphatase 1 and 2A in MCF7 cells treated with calyculin-A, okadaic acid, and tautomycin: B. Favre, et al.; J. Biol. Chem. 272, 13856 (1997)
Okadaic acid-induced apoptosis in neuronal cells: evidence for an abortive mitotic attempt: R. Nuydens, et al.; J. Neurochem. 70, 1124 (1998)
Inhibitors of protein phosphatase 1 and 2A differentially regulate the expression of inducible nitric-oxide synthase in rat astrocytes and macrophages: K. Pahan, et al.; J. Biol. Chem. 273, 12219 (1998)
Okadaic acid activates atypical protein kinase C (zeta/lambda) in rat and 3T3/L1 adipocytes. An apparent requirement for activation of Glut4 translocation and glucose transport: M.L. Standaert, et al.; J. Biol. Chem. 274, 14074 (1999)
Unique features of the okadaic acid activity class of tumor promoters: H. Fujiki & M. Suganuma; J. Cancer Res. Clin. Oncol. 125, 150 (1999) (Review)
Neurotoxic and synaptic effects of okadaic acid, an inhibitor of protein phosphatases: R. Tapia, et al.; Neurochem. Res. 24, 1423 (1999) (Review)
Okadaic acid, useful tool for studying cellular processes: J.J. Fernández, et at.; Curr. Med. Chem. 9, 229 (2002) (Review)
Okadaic acid: the archetypal serine/threonine protein phosphatase inhibitor: A.B. Dounay & C.J. Forsyth; Curr. Med. Chem. 9, 1939 (2002) (Review)
Effect of okadaic acid on glucose regulation: M.C. Louzao, et at.; Mini Rev. Med. Chem. 5, 207 (2005) (Review)
Marine toxins and the cytoskeleton: okadaic acid and dinophysistoxins: C. Vale & L.M. Botana; FEBS J. 275, 6060 (2008) (Review)

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