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).
Synonyme(s) :
Piceatannol, trans-3,3ʹ,4,5ʹ-Tetrahydroxystilbene
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A propos de cet article
Formule empirique (notation de Hill) :
C14H12O4
Numéro CAS:
Poids moléculaire :
244.24
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥95% (HPLC)
Form:
crystalline solid
Storage condition:
OK to freeze, protect from light
Service technique
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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
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
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.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
Activity of rat liver protein kinase A catalytic subunit
Activity of rat liver protein kinase A catalytic subunit
Product competes with ATP.
Reversible: yes
Target IC50: 3 µM, 8 µM, and 12 µM against the activity of rat liver protein kinase A catalytic subunit, PKC, and MLCK, respectively
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.
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.
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.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
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signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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