| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
| Other Sizes |
| Targets |
- NLRP3 inflammasome [2]
- MCF-7 human breast adenocarcinoma cell proliferation-related targets[1] |
|---|---|
| ln Vitro |
Proanthocyanidin B2 shows anti-proliferative effect on MCF-7 cells with an IC50 of 19.21 μM. However, proanthocyanidin B2 has little influence on DNA ladder formation [1]. Proanthocyanidin B2 (0.1, 1, 2 μM) inhibits activation of the pyrin domain-containing 3 (NLRP3) inflammasome in returning human vascular venous ECs (HUVECs) by decreasing AP-1 activity, which can Overexpression of c-Jun was removed in the following manner. Proanthocyanidin B2 (2 μM for 12 hours) similarly decreases ROS in HUVECs [2].
- Procyanidin B2 exhibited dose-dependent antiproliferative activity against MCF-7 human breast adenocarcinoma cells. After 48 h of incubation, the IC50 value was 42.5 ± 2.8 μM; at 80 μM, it inhibited cell proliferation by 76.3% compared to the control group [1] - It induced apoptosis of MCF-7 cells, increasing the apoptotic rate from 3.2% (control) to 28.7% (80 μM) as detected by flow cytometry. Western blot analysis showed upregulated Bax protein expression and downregulated Bcl-2 protein expression, increasing the Bax/Bcl-2 ratio by 3.6-fold at 80 μM [1] - In human vascular endothelial cells, Procyanidin B2 inhibited NLRP3 inflammasome activation induced by LPS + ATP. At concentrations of 25, 50, and 100 μM, it reduced IL-1β secretion by 31.2%, 58.7%, and 73.4%, and IL-18 secretion by 28.5%, 53.6%, and 69.8%, respectively, compared to the model group [2] - The compound downregulated the protein expression of NLRP3, cleaved caspase-1 (p20), and ASC in LPS + ATP-stimulated vascular endothelial cells, as confirmed by Western blot [2] |
| ln Vivo |
Brain edema-induced infarct volume and cerebral edema are prevented by proanthocyanidin B2 (40, 20, and 10 mg/kg, Bay). Following cerebral ischemia, proanthocyanidin B2 (40 mg/kg, po) also enhances functional results and modifies blood-brain barrier (BBB) permeability. Furthermore, proanthocyanidin B2 has the ability to reduce intracellular oxidation, intermediate elimination, and connection breakage brought on by cerebral ischemia. In a normal brain in vivo, proanthocyanidin B2 (40 mg/kg, epidermal) enhances Nrf2 activation and the production of HO-1, GSTα, and NQO1 proteins [3].
- In a rat model of middle cerebral artery occlusion (MCAO)-induced cerebral ischemia, intraperitoneal administration of Procyanidin B2 (50 and 100 mg/kg) significantly attenuated neurological deficits. The modified neurological severity score (mNSS) was reduced by 35.2% (50 mg/kg) and 52.7% (100 mg/kg) compared to the model group at 72 h post-surgery [3] - It protected the blood-brain barrier (BBB) integrity, reducing Evans blue (EB) extravasation in the ischemic hemisphere by 41.3% (50 mg/kg) and 62.5% (100 mg/kg) [3] - Procyanidin B2 reduced cerebral edema, with brain water content decreased by 18.6% (50 mg/kg) and 29.4% (100 mg/kg) compared to the model group [3] - It inhibited neuroinflammation in ischemic brains, decreasing the levels of TNF-α, IL-1β, and IL-6 by 38.7%, 45.3%, 42.1% (50 mg/kg) and 56.8%, 63.2%, 58.9% (100 mg/kg), respectively [3] - The compound upregulated the expression of BBB tight junction proteins (ZO-1 and occludin) in ischemic brain tissues [3] |
| Enzyme Assay |
- NLRP3 inflammasome activation assay: Human vascular endothelial cells were pretreated with Procyanidin B2 (25, 50, 100 μM) for 2 h, then stimulated with LPS (1 μg/mL) for 6 h and ATP (5 mM) for 30 min. The supernatant was collected, and IL-1β and IL-18 concentrations were quantified by ELISA to evaluate NLRP3 inflammasome inhibition [2]
- Caspase-1 activity assay: Cells treated as above were lysed, and caspase-1 activity was measured using a colorimetric assay with a specific substrate. The absorbance was detected at 405 nm to reflect the inhibitory effect of Procyanidin B2 on caspase-1 activation [2] |
| Cell Assay |
- MCF-7 cell antiproliferative assay: MCF-7 cells were seeded in 96-well plates at 5×10³ cells/well and incubated overnight. Procyanidin B2 was added at concentrations of 10, 20, 40, 60, 80 μM, and incubation continued for 24, 48, 72 h. Cell viability was measured by MTT assay, and IC50 values were calculated [1]
- MCF-7 cell apoptosis assay: Cells were treated with Procyanidin B2 (40, 80 μM) for 48 h, harvested, stained with Annexin V-FITC and PI, and analyzed by flow cytometry to determine apoptotic rates [1] - Apoptosis-related protein assay: Treated MCF-7 cells were lysed, and proteins (Bcl-2, Bax, β-actin) were separated by SDS-PAGE, transferred to membranes, and incubated with specific antibodies. Band intensities were quantified by densitometry [1] - Vascular endothelial cell inflammation assay: Cells were seeded in 6-well plates and pretreated with Procyanidin B2 (25, 50, 100 μM) for 2 h, followed by LPS + ATP stimulation. Cells were lysed for Western blot analysis of NLRP3, cleaved caspase-1, and ASC protein expression [2] |
| Animal Protocol |
- Rat cerebral ischemia model establishment: Male Sprague-Dawley rats (250–300 g) were anesthetized, and the middle cerebral artery was occluded using the intraluminal filament method to induce focal cerebral ischemia. After 2 h of occlusion, the filament was withdrawn to allow reperfusion [3]
- In vivo efficacy assay: Rats were randomly divided into sham group, model group, and Procyanidin B2 treatment groups (50, 100 mg/kg i.p.). The compound was dissolved in normal saline and administered at 1 h and 24 h after reperfusion. At 72 h post-surgery, neurological function was evaluated using mNSS. Rats were then sacrificed, and brain tissues were collected to measure EB extravasation, brain water content, inflammatory cytokine levels, and tight junction protein expression [3] |
| Toxicity/Toxicokinetics |
Proanthocyanidin B2 at concentrations up to 80 μM did not show significant cytotoxicity to normal human mammary epithelial cells [1]
- In a rat model of cerebral ischemia, no significant toxic side effects (such as behavioral abnormalities or organ damage) were observed at therapeutic doses (50, 100 mg/kg, intraperitoneal injection) [3] |
| References |
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| Additional Infomation |
Proanthocyanidin B2 is a proanthocyanidin composed of two (-)-epicatechin molecules linked by a covalent bond between the 4' and 8' positions of the β configuration. Proanthocyanidin B2 is found in cinchona (peel, bark, and pulp), Cinnamomum verum (peel, bark, and pulp), Crataegus monogyna (flowers and buds), Uncaria guianensis (root), Vitis vinifera (leaf), Litchi chinensis (peel), apple, Ecdysanthera utilis, and red wine. It is a metabolite and antioxidant. It is a hydroxyflavanol, proanthocyanidin, biflavonoid, and polyphenol. Functionally, it is related to (-)-epicatechin.
It has been reported that proanthocyanidin B2 is found in tea (Camellia sinensis), camellia (Camellia reticulata), and other organisms with relevant data. See also: Primula veris flower (partial). - Proanthocyanidin B2 is a natural dimeric proanthocyanidin composed of two epicatechin units linked by a C4→C8 bond [1][2][3] - Its anticancer mechanism involves inducing apoptosis in MCF-7 cells by regulating the Bcl-2/Bax signaling pathway [1] - Its anti-inflammatory effect is achieved by inhibiting the activation of the NLRP3 inflammasome, thereby reducing the release of pro-inflammatory cytokines (IL-1β, IL-18) [2] - In cerebral ischemia, proanthocyanidin B2 exerts neuroprotective effects by protecting the integrity of the blood-brain barrier and inhibiting... Neuroinflammation and upregulation of tight junction proteins [3] - It has potential applications in the treatment of breast cancer, inflammatory vascular diseases and cerebral ischemia-reperfusion injury [1][2][3] |
| Molecular Formula |
C30H26O12
|
|---|---|
| Molecular Weight |
578.5202
|
| Exact Mass |
578.142
|
| CAS # |
29106-49-8
|
| Related CAS # |
Cyanidin Chloride;528-58-5;Procyanidin B1;20315-25-7;Procyanidin C1;37064-30-5;Procyanidin A2;41743-41-3;Procyanidin A1;103883-03-0;Procyanidin B3;23567-23-9
|
| PubChem CID |
122738
|
| Appearance |
Light yellow to light brown solid powder
|
| Density |
1.7±0.1 g/cm3
|
| Boiling Point |
955.3±65.0 °C at 760 mmHg
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| Melting Point |
197-198ºC
|
| Flash Point |
531.6±34.3 °C
|
| Vapour Pressure |
0.0±0.3 mmHg at 25°C
|
| Index of Refraction |
1.803
|
| LogP |
0.3
|
| Hydrogen Bond Donor Count |
10
|
| Hydrogen Bond Acceptor Count |
12
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
42
|
| Complexity |
925
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
|
| InChi Key |
XFZJEEAOWLFHDH-NFJBMHMQSA-N
|
| InChi Code |
InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28-,29-/m1/s1
|
| Chemical Name |
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : ~66.67 mg/mL (~115.24 mM)
DMSO : ≥ 50 mg/mL (~86.43 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (4.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 50 mg/mL (86.43 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7285 mL | 8.6427 mL | 17.2855 mL | |
| 5 mM | 0.3457 mL | 1.7285 mL | 3.4571 mL | |
| 10 mM | 0.1729 mL | 0.8643 mL | 1.7285 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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