(-)-Epigallocatechin Gallate CAS: 989-51-5
MF: C22H18O11
MW: 458.37
An inhibitor of Bcl-2 and NOS2.

(−)-Epigallocatechin Gallate (CAS 989-51-5)

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Sinonimo: EGCG; Teavigo
Applicazione: An inhibitor of Bcl-2 and NOS2
Numero CAS: 989-51-5
Purezza: ≥98%
Peso molecolare: 458.37
Formula molecolare: C22H18O11
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(-)-Epigallocatechin Gallate (EGCG) is a strong polyphenol catechin antioxidant found in green tea, reported to have broad efficacy against many conditions generated from oxidative damage. Extensive oxidation of low density lipoproteins (LDLs) is correlated to cardiovascular diseases, and EGCG is reported to strongly inhibit Cu(2+)-mediated oxidative modification of LDLs. The antiapoptotic proteins Bcl-2 and Bcl-x(L) are observed to suppress apoptosis and convey survival to heavily damaged and mutated cells in vitro, and EGCG (along with the other catechins) is shown to directly inhibit these proteins, reestablishing the normal apoptotic pathway in the cell. EGCG also inhibits NOS2 (iNOS).


Referenze

1. Miura, S., et al., 1995. Effects of various natural antioxidants on the Cu(2+)-mediated oxidative modification of low density lipoprotein. Biological & pharmaceutical bulletin. 18(1): 1-4. PMID: 7735221
2. Cherbonnel-Lasserre, C., et al., 1997. Suppression of apoptosis by overexpression of Bcl-2 or Bcl-xL promotes survival and mutagenesis after oxidative damage. Biochimie. 79(9-10): 613-7. PMID: 9466700
3. Lu, L H., et al., 1998. Epigallocatechin suppression of proliferation of vascular smooth muscle cells: correlation with c-jun and JNK. British journal of pharmacology. 124(6): 1227-37. PMID: 9720795
4. Paschka, A G., et al., 1998. Induction of apoptosis in prostate cancer cell lines by the green tea component, (-)-epigallocatechin-3-gallate. Cancer letters. 130(1-2): 1-7. PMID: 9751250
5. Nakagawa, Hiroshi., et al., 2002. Fenton reaction is primarily involved in a mechanism of (-)-epigallocatechin-3-gallate to induce osteoclastic cell death. Biochemical and biophysical research communications. 292(1): 94-101. PMID: 11890677
6. Nakagawa, Takako., et al., 2002. Protective activity of green tea against free radical- and glucose-mediated protein damage. Journal of agricultural and food chemistry. 50(8): 2418-22. PMID: 11929306
7. Nakagawa, T., et al., 2002. Direct scavenging of nitric oxide and superoxide by green tea. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 40(12): 1745-50. PMID: 12419687
8. Leone, Marilisa., et al., 2003. Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins. Cancer research. 63(23): 8118-21. PMID: 14678963
9. Itabe, Hiroyuki., et al., 2009. Oxidative modification of LDL: its pathological role in atherosclerosis. Clinical reviews in allergy & immunology. 37(1): 4-11. PMID: 18987785

Stato fisico :
Solid
Solubilità :
Soluble in ethanol (~20 mg/ml), dimethyl formamide (~20 mg/ml), DMSO (~20 mg/ml), water (>5 mg/ml), DMF, PBS pH 7.2, and Methanol.
CONSERVAZIONE :
Store at -20° C
Punto di scioglimento :
315.59° C (Predicted)
Punto di ebollizione :
~909.11° C at 760 mmHg (Predicted)
Densità :
~1.90 g/cm3 (Predicted)
Indice di rifrazione :
n20D 1.86
Attività ottica :
α20/D -175.5°, c = 1 in ethanol
IC50 :
6-phosphogluconate dehydrogenase: IC50 = 720 nM (human); Human herpesvirus 1: IC50 = 18300 nM; Fatty acid synthase: IC50 = 0.03 µg/ml (Plasmodium falciparum); 3-oxoacyl-acyl-carrier protein reductase: IC50 = 0.32 µg/ml (Plasmodium falciparum); Human immunodeficiency virus 1: IC50 = 19910 nM
Valori pK :
pKa: 7.75
Solo per uso in Ricerca. Non previsto per Uso Diagnostico o Terapeutico.
WGK Germania :
2
RTECS :
KB5200000
PubChem CID :
65064
Indice Merck :
14: 3526
Numero MDL :
MFCD00075940
Numero EC :
479-560-7
Registro Beilstein :
3658838
SMILES :
C1[[email protected]]([[email protected]](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

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(-)-Epigallocatechin Gallate  Citazioni prodotti

Vedi quanti altri hanno usato (-)-Epigallocatechin Gallate. Clicca sulla voce per laccesso a PubMed .

Ciatazioni 1 a7 di 7 totali

PMID: # 29122665  Ferreira, A. et al. 2017. Food Chem. Toxicol. 111: 84-93.

PMID: # 28115242  Jeong, CH.|Seok, JS.|Petriello, MC.|Han, SG.| et al. 2017. Toxicology. 379: 31-39.

PMID: # 27356022  Wang, T. et al. 2016. Biochemistry. 55: 4036-46.

PMID: # 25534770  Cook, I. et al. 2015. Drug metabolism and disposition: the biological fate of chemicals. 43: 418-23.

PMID: # 23448667  Bruchmann, A. et al. 2013. BMC Cancer. 13: 96.

PMID: # 18687687  Shim, JH. et al. 2008. J. Biol. Chem. 283: 28370-28379.

PMID: # 14559356  Koh, SH. et al. 2003. Brain Res. Mol. Brain Res. 118: 72-81.

Ciatazioni 1 a7 di 7 totali
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