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Merck

5.08226

Calyculin A from Discodermia calyx

InSolution, ≥98%, 100 µM in DMSO, Cell-permeable protein phosphatase 2A (PP2A) inhibitor

Synonym(s):

InSolution Calyculin A, Discodermia calyx

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About This Item

Empirical Formula (Hill Notation):
C50H81N4O15P
CAS Number:
101932-71-2
Molecular Weight:
1009.17
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD06795864

Key Documents

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Product Name

Calyculin A, Discodermia calyx, InSolution, ≥98%, 100 µM in DMSO, Cell-permeable protein phosphatase 2A (PP2A) inhibitor

SMILES string

[P](=O)(O[C@H]1[C@H](O[C@]2(O[C@@H]([C@@H]([C@H](C2)O)C)C\C=C\c3nc([o]c3)[C@H](CCNC(=O)[C@@H](O)[C@@H](O)[C@@H](N(C)C)COC)C)C1(C)C)[C@@H](OC)C[C@H](O)[C@H]([C@H](O)[C@H](C)\C=C(/C)\C(=C\C=C\C(=C/C#N)\C)\C)C)(O)O

InChI

1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34+,35+,37-,38-,39-,40+,41-,42+,43-,44-,45+,46-,50-/m0/s1

InChI key

FKAWLXNLHHIHLA-QJLNTFFJSA-N

assay

≥98% (HPLC)

form

liquid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
avoid repeated freeze/thaw cycles
desiccated (hygroscopic)
protect from light

storage temp.

−70°C

Quality Level

100

Biochem/physiol Actions

Cell permeable: yes
Primary Target
protein phosphatase-2A & -1
Reversible: yes
Target IC50: 0.5-1.0 and 2 nM for PP2A and PP1, respectively

Disclaimer

Toxicity: Standard Handling (A)

General description

Cell-permeable protein phosphatase 2A (PP2A) inhibitor (IC50 = 0.5-1.0 nM). Also inhibits protein phosphatase 1 (PP1; IC50 = 2 nM). A non-phorbol ester type tumor promoter that induces oxidative DNA damage. Selectively increases the efficacy of AMPA receptor-mediated synaptic transmission at excitatory synapses. Recently, it has been used to study the regulation of Ca2+-activated K+ channels in smooth muscle and to correlate shape changes in fibroblasts with the degree of protein phosphorylation. Also known to prevent γ-radiation induced apoptosis in Burkitt′s lymphoma cell line BM13674.

Other Notes

Murakami, N., et al. 1994. Neurosci. Lett.176, 181.
Takeuchi, T., et al. 1994. Biochem. Biophys. Res. Commun.205, 1803.
Figurov, A., et al. 1993. Eur. J. Neurosci.5, 1083.
Song, Q., and Lavin, M.F. 1993. Biochem. Biophys. Res. Commun.190, 47.
Gopalakrishna, R., et al. 1992. Biochem. Biophys. Res. Commun.189, 950.
Carl, A., et al. 1991. Am. J. Physiol.261, C387.
Suganuma, M., et al. 1990. Cancer Res.50, 3521.
Cohen, P. 1989. Annu. Rev. Biochem.58, 453.
Cohen, P., et al. 1989. J. Biol. Chem.264, 21435.
Ishihara, H., et al. 1989. Biochem. Biophys. Res. Commun.159, 871.
Kato, Y., et al. 1988. J. Org. Chem.53, 3930.
Kato, Y., et al. 1986. J. Am. Chem. Soc.108, 2780.

Packaging

Packaged under inert gas

Physical form

A 100 µM (5 µg/50 µL) sterile-filtered solution of Calyculin A, Discodermia calyx (Cat. No. 208851) in DMSO.

Preparation Note

Following initial thaw, aliquot and freeze (-20°C). Aliquots are stable for up to 6 months at -20°C. Use only fresh DMSO for further dilutions.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

188.6 °F - (refers to pure substance)

flash_point_c

87 °C - (refers to pure substance)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Global Trade Item Number

SKUGTIN
5.08226.000104055977261776

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