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Merck

527948

Piceatannol

A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC50 = 3 µM), PKC (IC50 = 8 µM), MLCK (IC50 = 12 µM).

Synonym(s):

Piceatannol, trans-3,3ʹ,4,5ʹ-Tetrahydroxystilbene

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About This Item

Empirical Formula (Hill Notation):
C14H12O4
CAS Number:
10083-24-6
Molecular Weight:
244.24
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00221715

Product Name

Piceatannol, A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC50 = 3 µM), PKC (IC50 = 8 µM), MLCK (IC50 = 12 µM).

SMILES string

Oc1c(ccc(c1)\C=C\c2cc(cc(c2)O)O)O

InChI

1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+

InChI key

CDRPUGZCRXZLFL-OWOJBTEDSA-N

assay

≥95% (HPLC)

form

crystalline solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white

solubility

DMSO: 10 mg/mL
ethanol: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Target IC50: 3 µM, 8 µM, and 12 µM against the activity of rat liver protein kinase A catalytic subunit, PKC, and MLCK, respectively
Cell permeable: yes
Primary Target
Activity of rat liver protein kinase A catalytic subunit
Product competes with ATP.
Reversible: yes

Disclaimer

Toxicity: Standard Handling (A)

General description

A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC50 = 3 µM), PKC (IC50 = 8 µM), MLCK (IC50 = 12 µM). In RBL-2H3 cells, the selective inhibition of Syk by piceatannol results in inhibition of FceR1-mediated signaling. Also inhibits wheat embryo Ca2+-dependent protein kinase (CDPK) (IC50 = 19 µM), and p72syk (IC50 = 10 µM), a non-receptor tyrosine kinase, relative to Lyn in isolated enzyme preparations. Also possesses anti-leukemic properties. Reported to activate sirtuins and promote the survival of eukaryotic cells.
A cell-permeable, substrate competitive, and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC50 = 3 µM), PKC (IC50 = 8 µM), MLCK (IC50 = 12 µM). In RBL-2H3 cells, the selective inhibition of Syk by piceatannol results in inhibition of FceR1-mediated signaling. Also inhibits wheat embryo Ca2+-dependent protein kinase (CDPK) (IC50 = 19 µM), and p72syk (IC50 = 10 µM), a non-receptor tyrosine kinase, relative to Lyn in isolated enzyme preparations. Also possesses anti-leukemic properties. Reported to activate sirtuins and promote the survival of eukaryotic cells.

Other Notes

Howitz, K.T., et al. 2003. Nature425, 191.
Wang, B.H., et al. 1998. Planta Med. 64, 195.
Keely, P.J., and Parise, L.V. 1996. J. Biol. Chem. 271, 26668.
Oliver, J.M., et al. 1994. J. Biol. Chem. 269, 29697.
Thakkar, K., et al. 1993. J. Med. Chem. 36, 2950.
Geahlen, R.L., et al. 1989. Biochem. Biophys. Res. Commun. 165, 241.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot, flush with an inert gas, and freeze (-20°C). Stock solutions are stable for up to 2 weeks at -20°C.

Legal Information

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Sonia Nasi et al.
Annals of the rheumatic diseases, 75(7), 1372-1379 (2015-08-09)
Basic calcium phosphate (BCP) crystal and interleukin 6 (IL-6) have been implicated in osteoarthritis (OA). We hypothesise that these two factors may be linked in a reciprocal amplification loop which leads to OA. Primary murine chondrocytes and human cartilage explants

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