(-)-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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Synonym: EGCG; Teavigo
Ansökan An inhibitor of Bcl-2 and NOS2
Momsregistreringsnummer :: 989-51-5
Purity: ≥98%
Molecular Weight: 458.37
Molecular Formula: C22H18O11
* Refer to Certificate of Analysis for lot specific data (including water content).
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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).


Konferenser

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

Physical State :
Solid
Solubility :
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.
LAGRING :
Store at -20° C
Melting Point :
315.59° C (Predicted)
Boiling Point :
~909.11° C at 760 mmHg (Predicted)
Density :
~1.90 g/cm3 (Predicted)
Refractive Index :
n20D 1.86
Optical Activity :
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
pK Values :
pKa: 7.75
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
RTECS :
KB5200000
PubChem CID :
65064
Merck Index :
14: 3526
MDL Number :
MFCD00075940
EC Number :
479-560-7
Beilstein Registry :
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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Certificate of Analysis

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(-)-Epigallocatechin Gallate  Produkt Citat

See how others have used (-)-Epigallocatechin Gallate. Click on the entry to view the PubMed entry .

Citations 1 to 7 of 7 total

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.

Citations 1 to 7 of 7 total
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