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).

• Synonim(y): Piceatannol, trans-3,3ʹ,4,5ʹ-Tetrahydroxystilbene
• Wzór empiryczny (zapis Hilla): C₁₄H₁₂O₄
• Numer CAS: 10083-24-6
• Masa cząsteczkowa: 244.24
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00221715
• Assay: ≥95% (HPLC)
• Form: crystalline solid
• Storage condition: OK to freeze, protect from light

Właściwości

• Quality Segment: 100
• 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

Opis

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 p72^syk (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 p72^syk (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

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

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Informacja o środkach bezpieczeństwa

• pictograms: GHS07
• signalword: Warning
• hcodes: H302 + H312 + H332
• pcodes: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
• Klasa składowania: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable