324880

(–)-Epigallocatechin Gallate

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

• Synonyme(s) : (–)-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
• Formule empirique (notation de Hill): C₂₂H₁₈O₁₁
• Numéro CAS: 989-51-5
• Poids moléculaire : 458.37
• Numéro MDL: MFCD00075940
• Code UNSPSC : 12352200
• Nomenclature NACRES : NA.77

Propriétés

• Niveau de qualité: 100
• Pureté: ≥95% (HPLC)
• Forme: solid
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; protect from light
• Couleur: faint pink
• Solubilité: water: 5 mg/mL; DMSO: soluble
• Conditions d'expédition: ambient
• Température de stockage: −20°C
• 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
• Clé InChI: WMBWREPUVVBILR-WIYYLYMNSA-N

Description

Description générale

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.

One of the main polyphenolic constituents of green tea that possesses potent antitumor, anti-inflammatory, and antioxidant properties. EGCG has been shown to inhibit PMA-induced skin thickening, activation of protein kinase C, activation of ornithine decarboxylase, and activation of interleukin-1α mRNA and protein expression. Has also been shown to inhibit inducible nitric oxide synthase (iNOS) gene expression and enzyme activity and to inhibit the peroxynitrite-mediated formation of 8-oxodeoxyguanosine and 3-nitrotyrosine. Also strongly and directly inhibits telomerase. 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.

Actions biochimiques/physiologiques

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

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Irritant (B)

Reconstitution

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

Autres remarques

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.

Informations légales

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

Informations sur la sécurité

• Pictogrammes: GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H302,H317,H319,H411
• Conseils de prudence: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Classification des risques: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1
• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 2
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable