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).

• Sinonimo/i: Piceatannol, trans-3,3ʹ,4,5ʹ-Tetrahydroxystilbene
• Formula empirica (notazione di Hill): C₁₄H₁₂O₄
• Numero CAS: 10083-24-6
• Peso molecolare: 244.24
• Numero MDL: MFCD00221715
• Codice UNSPSC: 12352200
• NACRES: NA.77

Proprietà

• Livello qualitativo: 100
• Saggio: ≥95% (HPLC)
• Stato: crystalline solid
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: off-white
• Solubilità: DMSO: 10 mg/mL; ethanol: 10 mg/mL
• Condizioni di spedizione: ambient
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: 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+; CDRPUGZCRXZLFL-OWOJBTEDSA-N

Descrizione

Descrizione generale

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.

Azioni biochim/fisiol

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

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Standard Handling (A)

Ricostituzione

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

Altre note

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.

Note legali

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

Informazioni sulla sicurezza

• Pittogrammi: GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H302 + H312 + H332
• Consigli di prudenza: P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312
• Classi di pericolo: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable