Theaflavin-3'-gallate
Based on 2 publication(s) in Google Scholar
Theaflavin-3'-gallate is a monomer of theaflavins found in black tea, which has anti-UVB damage activity and inhibits cell apoptosis and necroptosis. Theaflavin-3'-gallate acts as a pro-oxidant and induces oxidative stress in cancer cells, inhibiting xanthine oxidase (OX), with an IC50 of 7.6 μM.
For research use only. We do not sell to patients.
- Purity : 98.79%
- CAS No.: 28543-07-9
- Formula: C36H28O16
- Molecular Weight:716.60
-
Storage:
-20°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
-
Biological Activity
-
Chemical Information
-
Solvent & Solubility
- Protocols
- Purity & Documentation
- References
-
Help & FAQs
Publications Citing Use of MedChemExpress (MCE) Theaflavin-3'-gallate
More
Biological Activity
Description
IC50 & Target
|
OX 7.6 μM (IC50) |
Cellular Effect
|
Cell Line
|
Type | Value | Description | References |
|---|---|---|---|---|
| H9 | IC50 |
48 μg/mL
Compound: 37
|
Inhibition of uninfected H9 lymphocytic cell growth
Inhibition of uninfected H9 lymphocytic cell growth
|
10.1016/0960-894X(96)00095-9 |
In Vitro
Theaflavin-3'-gallate (0-500 μM, 24 h) has a toxic effect on HF-1, HSC-2, and CAL27 cells[1].
Theaflavin-3'-gallate (0-250 μM, 3 h) generates a high amount of peroxide at pH 7.4, and reduces the GSH levels in HF-1 and CAL27 cells[1].
Theaflavin-3'-gallate is the most effective exogenous H2O2 scavenger, showing superoxide scavenging activity in HL-60 cells with an IC50 of 15.6 μM[2].
Theaflavin-3'-gallate (0.1-40 μM, 6 h) has a protective effect against UV-induced damage in HaCaT cells, with an EC50 of 0.483 μM[3].
Theaflavin-3'-gallate (5-40 μM, 6 h) protects against apoptosis and necrosis induced by UVB in HaCaT cells, inhibiting oxidative stress and preserving mitochondrial membrane potential[3].
Theaflavin-3'-gallate (5-40 μM, 6 h) downregulates the NF-κB inflammatory pathway in UV-irradiated HaCaT cells, inhibits the formation of cytotoxic aggregates, and protects the structure of biomacromolecules[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
-
Cell Line:GN46, HF-1, HSC-2, CAL27
-
Concentration:0, 100, 200, 300, 400, 500 μM
-
Incubation Time:24 h
-
Result:Showed initial toxicity to CAL27, HSC-2, and HF-1 cells at concentrations of 250 μM, 350 μM, and 400 μM respectively, but the initial toxicity to GN46 cells is uncertain.
-
Cell Line:HaCaT
-
Concentration:0.1, 0.25, 0.5, 1, 5, 10, 20, 40 μM
-
Incubation Time:6 h
-
Result:Enhanced cell vitality, showing dose-dependence.
-
Cell Line:HaCaT
-
Concentration:5,10,20,40μM
-
Incubation Time:6 h
-
Result:Reduced the formation of cytotoxic proteins and inhibited their pathways. Lowered the phosphorylation levels of IKKβ and IκBα, reducing the nuclear translocation of NF-κB and the expression of IL-6.
Chemical Information
-
CAS No. 28543-07-9
-
Appearance Solid
-
Molecular Weight 716.60
-
Formula C36H28O16
-
Color Brown to reddish brown
-
SMILES
O=C(O[C@H]1[C@@H](C2=C(C=C([C@@H]3[C@H](O)CC4=C(O)C=C(O)C=C4O3)C=C(O)C5=O)C5=C(O)C(O)=C2)OC6=CC(O)=CC(O)=C6C1)C7=CC(O)=C(O)C(O)=C7
-
Structure Classification
-
Initial Source
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
-20°C, protect from light
* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
Publications (2)
-
Journal Impact Factor
-
Most Recent
-
ACS Omega
Systematic Studies on the Anti-SARS-CoV-2 Mechanisms of Tea Polyphenol-Related Natural Products. [Abstract]2024 May 17;9(22):23984-23997. PMID: 38854515 -
Solvent & Solubility
In Vitro:
DMSO : 50 mg/mL (69.77 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (3.49 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
-
-
-
-
Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
-
%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
-
%+
-
+%Tween-80 + +
-
%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL. * In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Protocols
-
Apoptosis
Apoptosis, also called programmed cell death, is generally characterized by distinct morphological characteristics.
-
TUNEL staining for apoptotic DNA fragmentation
TUNEL staining detects DNA strand breaks by using terminal deoxynucleotidyl transferase to add labeled nucleotides to exposed 3′-OH DNA termini, generating either microscopic staining in fixed cells or tissue sections, or fluorescence/cytometric signal in cell suspensions. TUNEL positivity reflects DNA fragmentation but should not be interpreted alone as definitive apoptosis, because TUNEL can also label necrotic, autolytic, mechanically damaged, or DNA-repair-associated DNA breaks.
-
Cell Cytotoxicity Assay
Cytotoxicity assays are usually based on the assessment of cell membrane damage, which can also be indirectly detected by measuring cell viability. Detection methods include MTT assay, CKK-8 assay, LDH assay and ATP assay, etc.
-
Annexin V plus membrane-impermeant dye apoptosis staining
Annexin V-based apoptosis assays rely on the detection of phosphatidylserine (PS) externalization from the inner leaflet of the plasma membrane to the outer leaflet, an early biochemical hallmark of apoptosis. Fluorescently labeled Annexin V binds PS in a calcium-dependent manner, enabling identification of early apoptotic cells by flow cytometry or fluorescence microscopy. When combined with a membrane-impermeant DNA-binding dye (e. g. , propidium iodide), this approach allows discrimination between viable (Annexin V−/dye−), early apoptotic (Annexin V+/dye−), and late apoptotic or necrotic (Annexin V+/dye+) cell populations by assessing membrane integrity and PS exposure.
-
ROS/oxidative-stress fluorescent staining
ROS/oxidative-stress fluorescent staining uses cell-permeant fluorogenic probes that become fluorescent after oxidation inside cells or tissues; commonly used examples include DCFH-DA/DCFDA for broad cellular oxidant detection, DHE for superoxide-related signal detection, MitoSOX for mitochondrial superoxide-related signal detection, and CellROX probes for oxidative-stress-associated fluorescence readouts. The assay detects probe oxidation rather than a single ROS species unless the probe and analysis method have been chemically validated for that species. DCFH-DA enters cells, is deacetylated by intracellular esterases to DCFH, and produces fluorescent DCF after oxidation, so the readout is used as an operational measure of total cellular oxidative stress rather than a species-specific ROS measurement. DHE and MitoSOX can report superoxide-related oxidation, but red fluorescence alone can include non-specific ethidium-like oxidation products; HPLC or optimized spectral approaches are
-
Apoptosis Solutions
Apoptosis is a regulated, generally non-lytic cell-death pathway that removes unwanted, damaged, infected, or abnormal cells through coordinated morphological changes, caspase activation, DNA fragmentation, and membrane remodeling. The intrinsic apoptosis pathway is controlled mainly by mitochondrial outer membrane permeabilization, BCL-2 family proteins, cytochrome c release, apoptosome formation, caspase-9 activation, and downstream executioner caspase-3/7 activation. The extrinsic apoptosis pathway is initiated by death receptors such as Fas, TNFR, and TRAIL receptors, which recruit adaptor proteins and activate caspase-8 before engaging executioner caspases or mitochondrial amplification through BID cleavage. Apoptosis is linked to many phenotypes, including cancer cell killing, tissue homeostasis, immune regulation, neurodegeneration, infection response, and treatment-induced cytotoxicity; unresolved questions include how apoptosis interacts with necroptosis, pyroptosis, ferroptos
Purity & Documentation
-
Data Sheet (284 KB)
-
SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
-
Handling Instructions (2659 KB)
References
[1]. Babich H, et al. Theaflavin-3-gallate and theaflavin-3'-gallate, polyphenols in black tea with prooxidant properties. Basic Clin Pharmacol Toxicol. 2008 Jul;103(1):66-74. [Content Brief]
[2]. J K Lin, et al.Inhibition of xanthine oxidase and suppression of intracellular reactive oxygen species in HL-60 cells by theaflavin-3,3'-digallate, (-)-epigallocatechin-3-gallate, and propyl gallate. J Agric Food Chem. 2000 Jul;48(7):2736-43. [Content Brief]
[3]. Xin Zheng, et al. Anti-damage effect of theaflavin-3'-gallate from black tea on UVB-irradiated HaCaT cells by photoprotection and maintaining cell homeostasis. J Photochem Photobiol B. 2021 Nov:224:112304. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (protect from light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 1.3955 mL | 6.9774 mL | 13.9548 mL | 34.8870 mL |
| 5 mM | 0.2791 mL | 1.3955 mL | 2.7910 mL | 6.9774 mL | |
| 10 mM | 0.1395 mL | 0.6977 mL | 1.3955 mL | 3.4887 mL | |
| 15 mM | 0.0930 mL | 0.4652 mL | 0.9303 mL | 2.3258 mL | |
| 20 mM | 0.0698 mL | 0.3489 mL | 0.6977 mL | 1.7443 mL | |
| 25 mM | 0.0558 mL | 0.2791 mL | 0.5582 mL | 1.3955 mL | |
| 30 mM | 0.0465 mL | 0.2326 mL | 0.4652 mL | 1.1629 mL | |
| 40 mM | 0.0349 mL | 0.1744 mL | 0.3489 mL | 0.8722 mL | |
| 50 mM | 0.0279 mL | 0.1395 mL | 0.2791 mL | 0.6977 mL | |
| 60 mM | 0.0233 mL | 0.1163 mL | 0.2326 mL | 0.5814 mL |
Theaflavin-3'-gallate Related Classifications
HY-N0244 Related Classifications
Powered by Bioz