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Halochondrine A; CCRIS 3329; HSDB 7243; 9,10-Deepithio-9,10-didehydroacanthifolicin

Chemical

C44H68O13

805.0

14: 6819

78111-17-8

AA8227800

Isolated from Prorocentrum concavum.

≥98% (HPLC)

White crystalline solid.

Soluble in DMSO, ethanol or methanol.

Use only fresh solutions.

QNDVLZJODHBUFM-OQMIOGKESA-N

AMBIENT

+4°C

-20°C

Keep cool and dry.

Stable for at least 2 years after receipt when stored at -20°C.

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• 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 ofokadaic 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 ofokadaic 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 ofokadaic acidon glucose regulation: M.C. Louzao, et at.; Mini Rev. Med. Chem. 5, 207 (2005)(Review)

Marine toxins and the cytoskeleton:okadaic acidand dinophysistoxins: C. Vale & L.M. Botana; FEBS J. 275, 6060 (2008)(Review)

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