324880

(–)-Epigallocatechin Gallate

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

• Synonim(y): EGCG, (2R,3R)-2-(3,4,5-trihydroksyfenylo)-3,4-dihydro-1[2H]-benzopiran-3,5,7-triol-3-(3,4,5-trihydroksybenzoesan), HAT Inhibitor X, Histone Acetyltransferase Inhibitor X, p300/CBP Inhibitor VIII, PCAF Inhibitor V, DNA MTase Inhibitor IV, DNA Methyltransferase Inhibitor IV
• Wzór empiryczny (zapis Hilla): C₂₂H₁₈O₁₁
• Numer CAS: 989-51-5
• Masa cząsteczkowa: 458.37
• Numer MDL: MFCD00075940
• Kod UNSPSC: 12352200
• NACRES: NA.77

Właściwości

• opis: Merck USA index - 14, 3526
• Poziom jakości: 100
• Próba: ≥95% (HPLC)
• Formularz: solid
• producent / nazwa handlowa: Calbiochem^®
• warunki przechowywania: OK to freeze; protect from light
• kolor: faint pink
• rozpuszczalność: water: 5 mg/mL; DMSO: soluble
• Warunki transportu: ambient
• temp. przechowywania: −20°C
• ciąg SMILES: 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
• Klucz InChI: WMBWREPUVVBILR-WIYYLYMNSA-N

Opis

Opis ogólny

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.

Działania biochem./fizjol.

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

Opakowanie

Packaged under inert gas

Ostrzeżenie

Toxicity: Irritant (B)

Rekonstytucja

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

Inne uwagi

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.

Informacje prawne

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

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Informacja o środkach bezpieczeństwa

• Piktogramy: GHS07,GHS09
• Hasło ostrzegawcze: Warning
• Zwroty wskazujące rodzaj zagrożenia: H302,H317,H319,H411
• Zwroty wskazujące środki ostrożności: P261 - P273 - P280 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Klasyfikacja zagrożeń: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Sens. 1
• Kod klasy składowania: 11 - Combustible Solids
• Klasa zagrożenia wodnego (WGK): WGK 2
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable