Structure of (-)-Epicatechin gallate
CAS No.: 1257-08-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
(-)-Epicatechin gallate, a polyphenol, is a apoptosis inducer of tumor cells that found in green tea.
Synonyms: ECG; (-)-Epicatechin 3-O-gallate; Epicatechin-3-O-gallate.
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CAS No. : | 1257-08-5 |
Formula : | C22H18O10 |
M.W : | 442.37 |
SMILES Code : | O=C(O[C@H]1[C@@H](C2=CC=C(O)C(O)=C2)OC3=CC(O)=CC(O)=C3C1)C4=CC(O)=C(O)C(O)=C4 |
Synonyms : |
ECG; (-)-Epicatechin 3-O-gallate; Epicatechin-3-O-gallate.
|
MDL No. : | MFCD00075936 |
InChI Key : | LSHVYAFMTMFKBA-TZIWHRDSSA-N |
Pubchem ID : | 107905 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
In Vitro:
Cell Line
|
Concentration | Treated Time | Description | References |
SCC7 cells | 100 μM | 24 hours | ECG suppressed cyclin D1 expression in SCC7 cells in a dose- and time-dependent manner. | PMC2430519 |
SW480 cells | 50 μM | 24 hours | Assessed the effect of ECG on ATF3 expression, results suggested p53 expression may not be involved in catechin-induced ATF3 expression | PMC2174270 |
HCT-116 cells | 50 μM | 24 hours | Induced ATF3 expression, assessed the effect of ECG on ATF3 at the transcriptional level | PMC2174270 |
EMRSA-16 | 12.5 µg/mL | 4 hours | To investigate the impact of ECg on phospholipid distribution in the EMRSA-16 cytoplasmic membrane. Results showed that ECg insertion significantly altered cell phenotype, increased cell size and surface roughness, and affected phospholipid distribution. | PMC4581164 |
HCT-116 human colorectal cancer cells | 100 μM | 48 hours | Evaluate the inhibitory effect of ECG on HCT-116 cell proliferation, results showed 100 μM ECG inhibited cell growth by 20.3% | PMC3509513 |
SCC7 cells | 50 μM | 72 hours | ECG significantly inhibited the growth of SCC7 cells via G1 cell cycle arrest and apoptosis induction. | PMC2430519 |
In Vivo:
Species
|
Animal Model
|
Administration | Dosage | Frequency | Description | References |
Mice | TC-1 cell-implanted mice | Intra-tumor infusion | 64 µM | Every 24 h for 5 days | Injected TriCurin causes a dramatic suppression of tumors in TC-1 cell-implanted mice, accompanied by repolarization of TAM from M2 to M1-type and intra-tumor recruitment of NK cells and CTL. | PMC11028238 |
Caenorhabditis elegans | Wild-type N2 nematodes | Smeared on the surface of agar | 200, 500, 1000 μM | Counted every two days from the first day of adulthood until death | Investigated the effect of ECG on lifespan of nematodes, found that ECG could extend lifespan | PMC8235257 |
Sprague-Dawley rats | Full thickness incisional model of dermal wound healing | Intradermally | 0.8 mg/ml | Once daily for 7 days | ECG significantly improved the quality of scar formation, including the maturity and orientation of collagen fibers. The ECG-treated group showed a significant increase in new blood vessel formation at early time points (days 1 and 3) and upregulation of iNOS and COX-2 activity, while decreasing arginase-I activity and protein levels. These effects may be partly due to an acceleration of the angiogenic response and upregulation of NOS and COX enzymes. | PMC1618547 |
Clinical Trial:
NCT Number | Conditions | Phases | Recruitment | Completion Date | Locations |
NCT00611650 | Lung Cancer P... More >>recancerous Condition Tobacco Use Disorder Less << | Phase 2 | Terminated(Slow recruitment) | - | Canada, British Columbia ... More >> British Columbia Cancer Agency - Vancouver Cancer Centre Vancouver, British Columbia, Canada, V5Z 4E6 Less << |
NCT00253643 | Precancerous Condition ... More >> Prostate Cancer Less << | Not Applicable | Completed | - | United States, Oregon ... More >> Kaiser Permanente Center for Health Research Portland, Oregon, United States, 97227 OHSU Knight Cancer Institute Portland, Oregon, United States, 97239-3098 Veterans Affairs Medical Center - Portland Portland, Oregon, United States, 97239 Less << |
NCT00253643 | - | Completed | - | - | |
NCT00596011 | Prostatic Hyperplasia | Phase 2 | Completed | - | United States, Florida ... More >> University of Florida/Shands-Department of Urology Gainesville, Florida, United States, 32610 University of Florida - Jacksonville Jacksonville, Florida, United States, 32209 Watson Clinic Center for Research, Inc. Lakeland, Florida, United States, 33805 H Lee Moffitt Cancer Center Tampa, Florida, United States, 33612 James A Haley VA Tampa, Florida, United States, 33612 United States, Illinois University of Chicago - Department of Surgery Chicago, Illinois, United States, 60637 United States, Louisiana Overton Brooks VA Medical Center Shreveport, Louisiana, United States, 71101-4295 LSU Health Sciences Center, Feist-Weiller Cancer Center Shreveport, Louisiana, United States, 71130 United States, Minnesota Minneapolis VA Medical Center Minneapolis, Minnesota, United States, 55417 United States, Pennsylvania Jefferson Medical College - Department of Urology Philadelphia, Pennsylvania, United States, 19107 Less << |
NCT00942422 | Multiple Myeloma and Plasma Ce... More >>ll Neoplasm Precancerous Condition Less << | Phase 2 | Terminated(Low accrual and ear... More >>ly termination) Less << | - | United States, Michigan ... More >> Barbara Ann Karmanos Cancer Institute Detroit, Michigan, United States, 48201 Less << |
NCT00573885 | Lung Cancer T... More >>obacco Use Disorder Less << | Phase 2 | Completed | - | Canada, British Columbia ... More >> British Columbia Cancer Agency - Vancouver Cancer Centre Vancouver, British Columbia, Canada, V5Z 4E6 Less << |
NCT00596011 | - | Completed | - | - | |
NCT00459407 | Adenocarcinoma of the Prostate... More >> Stage I Prostate Cancer Stage II Prostate Cancer Less << | Phase 1 | Completed | - | United States, Arizona ... More >> Arizona Cancer Center - Tucson Tucson, Arizona, United States, 85724-5024 Less << |
NCT00799890 | Multiple Sclerosis | Phase 2 Phase 3 | Completed | - | Germany ... More >> Charité Universitätsmedizin Berlin (NeuroCure Clinical Research Center) Berlin, Germany, 10117 Less << |
NCT03526406 | Cognitive Function ... More >> Mood Less << | Not Applicable | Active, not recruiting | September 2018 | United Kingdom ... More >> University of Reading Reading, Berkshire, United Kingdom, RG6 6AL Less << |
NCT00942422 | - | Terminated(Low accrual and ear... More >>ly termination) Less << | - | - | |
NCT03194620 | Healthy | Not Applicable | Completed | - | United States, California ... More >> UC Davis Davis, California, United States, 95616 Less << |
Bio Calculators | ||||
Preparing Stock Solutions | ![]() |
1mg | 5mg | 10mg |
1 mM 5 mM 10 mM |
2.26mL 0.45mL 0.23mL |
11.30mL 2.26mL 1.13mL |
22.61mL 4.52mL 2.26mL |
Tags: (-)-Epicatechin gallate | ECG | Plant Standard | Phenols | COX | Organic Building Blocks | Immunology/Inflammation | By Structure | Drug Analysis | Tumor Development and Microenvironment Evolution | 1257-08-5
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