324880

(–)-Epigallocatechin Gallate

One of the main polyphenolic constituents of green tea that exhibits potent antitumor, anti-inflammatory, and antioxidant properties.

• Sinonimo/i: (–)-Epigallocatechin Gallate, EGCG, (2R,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol-3-(3,4,5-trihydroxybenzoate), HAT Inhibitor X, Histone Acetyltransferase Inhibitor X, p300/CBP Inhibitor VIII, PCAF Inhibitor V, DNA MTase Inhibitor IV, DNA Methyltransferase Inhibitor IV
• Formula empirica (notazione di Hill): C₂₂H₁₈O₁₁
• Numero CAS: 989-51-5
• Peso molecolare: 458.37
• Numero MDL: MFCD00075940
• Codice UNSPSC: 12352200
• NACRES: NA.77

Proprietà

• Descrizione: Merck USA index - 14, 3526
• Livello qualitativo: 100
• Saggio: ≥95% (HPLC)
• Stato: solid
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: faint pink
• Solubilità: water: 5 mg/mL; DMSO: soluble
• Condizioni di spedizione: ambient
• Temperatura di conservazione: −20°C
• Stringa SMILE: O1[C@@H]([C@@H](Cc4c1cc(cc4O)O)OC(=O)c3cc(c(c(c3)O)O)O)c2cc(c(c(c2)O)O)O
• InChI: 1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1; WMBWREPUVVBILR-WIYYLYMNSA-N

Descrizione

Descrizione generale

One of the main polyphenolic constituents of green tea that exhibits potent antitumor, anti-inflammatory, and antioxidant properties. Arrests cell cycling at G₀/G₁ phase and induces apoptosis in a dose-dependent manner. Shown to inhibit PMA-induced skin thickening and to activate of protein kinase C. Also activates ornithine decarboxylase and interleukin-1α mRNA and protein expression. Acts as an inhibitor of inducible nitric oxide synthase (iNOS) gene expression and enzyme activity. Also blocks peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Strongly and directly inhibits telomerase in cell-free systems and in cancer cell lines. An inhibitor of Dnmt1 (IC₅₀ = 210-470 nM). Acts as a selective and noncompetitive inhibitor of HAT activities (IC₅₀ = 30, 50, 60 and 70 µM for p300, CBP, PCAF and TIP60) with minimal effects on HDAC, SIRT and HMTase.

Azioni biochim/fisiol

Cell permeable: no

Primary Target
PMA-induced skin thickening

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 210-470 nM against Dnmt1; 30, 50, 60 and 70 µM for p300, CBP, PCAF and TIP60

Confezionamento

Packaged under inert gas

Nota sulla preparazione

Following reconstitution, aliquot and freeze at -20°C. DMSO stock solutions are stable for up to 3 months at -20°C.

Altre note

Choi, K.C., et al. 2009. Cancer Res.69, 583.
Dell′Aicia, I., et al. 2004. EMBO reports 5, 1.
Tachibana, H., et al. 2004. Nat. Struct. Mol. Biol.11, 380.
Naasami, I., et al. 1998. Biochem. Biophys. Res. Commun. 249, 391.
Ahmad, N., et al. 1997. J. Natl. Cancer89, 1881.
Chan, M.M.-Y., et al. 1997. Biochem. Pharmacol. 54, 1281.
Lin, Y.-L., and Lin, J.-K. 1997. Mol. Pharmacol. 52, 465.
Fiala, E.S., et al. 1996. Experientia 52, 922.
Katiyar, S.K., et al. 1995. J. Invest. Dermatol. 105, 394.
Liao, S., et al. 1995. Cancer Lett. 96, 239.
Yamane, T., et al. 1995. Cancer Res. 55, 2081.
Huang, M.T., et al. 1992. Carcinogenesis 13, 947.

Note legali

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

Esclusione di responsabilità

Toxicity: Irritant (B)

Informazioni sulla sicurezza

• Pittogrammi: GHS07,GHS09
• Avvertenze: Warning
• Indicazioni di pericolo: H302,H317,H319,H411
• Consigli di prudenza: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Classi di pericolo: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 2
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable