| Size | Price | Stock | Qty |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
| Targets |
Peroxisome proliferator-activated receptor gamma (PPARγ) [1]
Competitive binding to PPARγ-ligand binding domain (LBD) with EC50 = 6115 ± 1140 nM [1] |
|---|---|
| ln Vitro |
Glabridin has an EC50 of 6115 nM for binding to and activating PPARγ [1]. After 24 and 48 hours of treatment, Glabridin (40, 80 μM) suppresses the swelling of SAS and SCC-9 cell lines in a dose- and time-regulated manner [2]. (0 - 80 μM) also causes cellular candles in SCC-9 and SAS cell lines, which results in sub-G1 cell cycle signaling [2]. ERK1/2, JNK1/2, and p in SCC-9 cells -38 MAPK were considerably phosphorylated by glycyrrhizin (0, 20, 40, and 80 μM) dosages, which also enhanced PARP space and mimicked the activation of caspase-3, -8, and -9[2].
Glabridin activated PPARγ in a concentration-dependent manner in a Gal4-PPARγ-LBD luciferase reporter assay using stably transfected CHO-K1 cells[1] Glabridin activated full-length PPARγ in a PPAR response element (4X-PPAR-RE) luciferase reporter assay in transiently transfected HepG2 cells in a concentration-dependent manner [1] The PPARγ activation by Glabridin was blocked by the specific PPARγ antagonist T0070907 in a concentration-dependent manner in the Gal4-PPARγ-LBD luciferase assay[1] In HepG2 cells, Glabridin (20 and 100 μM) up-regulated PCK1 mRNA expression; this up-regulation was inhibited by the PPARγ antagonist T0070907 (10 μM) [1] Glabridin slightly down-regulated FABP1 mRNA expression and completely down-regulated HMGCS2 mRNA expression in HepG2 cells; both were further down-regulated with the addition of T0070907 [1] Glabridin was non-toxic at the doses and cellular conditions tested as determined by WST-1 cell proliferation assay [1] |
| ln Vivo |
Glycyrrhizin (50 mg/kg, once daily) reduces inflammation brought on by changes in sodium sulfate (DSS) caused by glucose and has strong anti-inflammatory properties [3].
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| Enzyme Assay |
The LanthaScreen TR-FRET PPARγ competitive binding assay was performed to evaluate Glabridin binding to PPARγ-LBD. Increasing concentrations of test compounds were added to an assay mixture containing GST-PPARγ-LBD fusion protein (lacking the DNA binding domain of PPARγ), a fluorescent pan-PPARγ ligand (fluoromone), and a terbium-labeled GST antibody. Changes in fluoromone binding to the terbium-labeled LBD complex were measured using a spectrophotometer with excitation at 340 nm and emission at 520 nm (for fluorescein) and 490 nm (for terbium). The TR-FRET ratio was calculated by dividing the emission signal at 520 nm by the emission signal at 490 nm. Competition curves were plotted as TR-FRET ratio against concentration of test compounds. Glabridin displaced fluoromone binding in a concentration-dependent manner with an EC50 of 6115 ± 1140 nM [1]
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| Cell Assay |
For the PPARγ-LBD luciferase reporter assay, stably transfected CHO-K1 cells expressing Gal4-PPARγ-LBD and a luciferase reporter under 9XGAL4 UAS were plated (1.5×10^4 cells/well) in 96-well plates and incubated overnight. Cells were serum-starved for 24 h, then treated with specified concentrations of Glabridin for 18 h. Luciferase activity was quantified using a luciferase assay kit: cells were rinsed with DPBS, lysed with lysis buffer for 20 min at room temperature, D-luciferin was added, and light emission was read immediately. Glabridin showed concentration-dependent activation that was blocked by the PPARγ antagonist T0070907 [1]
For the full-length PPARγ luciferase reporter assay, HepG2 cells were plated (1.2×10^4 cells/well) in 96-well plates and incubated overnight. Cells were transiently transfected with full-length human PPARγ (200 ng) and a 4X-PPAR-RE luciferase reporter construct (10 ng) using Fugene 6. After 24 h serum starvation, cells were treated with increasing concentrations of Glabridin for 18 h, and luciferase activity was measured as above. Glabridin activated full-length PPARγ in a concentration-dependent manner (Fig. 8), and this activation was inhibited by T0070907 [1] For quantitative PCR, HepG2 cells were seeded at 1×10^6 cells/well in 6-well plates and grown for 24 h, then media was replaced with 0.5% BSA-supplemented media for 24 h. Cells were incubated for 18 h with Glabridin (20 and 100 μM) with or without 10 μM T0070907 (added 20 min prior). Total RNA was purified, reverse transcribed, and real-time qPCR was performed using primers for PCK1, FABP1, HMGCS2, and housekeeping gene HPRT1. Glabridin up-regulated PCK1, down-regulated FABP1 and HMGCS2 [1] Cytotoxicity was assessed using WST-1 cell proliferation reagent. Glabridin was found to be non-toxic at the doses and cellular conditions tested [1] |
| References |
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| Additional Infomation |
Glabridin belongs to the hydroxyisoflavone class of compounds, with the structure (R)-isoflavone, substituted with hydroxyl groups at the 2' and 4' positions and substituted with 2,2-dimethyl-2H-pyran groups at the 7 and 8 positions. It is an antimalarial drug. Glabridin is derived from the hydride of (R)-isoflavone. It has been reported to be found in licorice (Glycyrrhiza uralensis), wild pea (Ornithopus sativus), and other organisms with relevant data. See also: Glycyrrhiza glabra (partial).
Glabridin is a prenylated isoflavan identified from Glycyrrhiza glabra L. (licorice) root extract. Its chemical structure (C20H20O4) is presented in Fig. 4. Quantification of glabridin content in licorice extracts was 1.00% in methanol extract and 3.24% in chloroform extract [1] In this study, Glabridin was identified as a PPARγ-activating phytochemical through HPLC fractionation and LC-MS analysis, with the glabridin peak (retention time 24.87 min) coinciding with the greatest PPARγ luciferase activity in collected fractions [1] |
| Molecular Formula |
C20H20O4
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|---|---|
| Molecular Weight |
324.37
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| Exact Mass |
324.136
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| CAS # |
59870-68-7
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| PubChem CID |
124052
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
518.6±50.0 °C at 760 mmHg
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| Melting Point |
154-155ºC
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| Flash Point |
267.4±30.1 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.623
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| LogP |
4.26
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
24
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| Complexity |
488
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC1(C=CC2=C(O1)C=CC3=C2OC[C@H](C3)C4=C(C=C(C=C4)O)O)C
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| InChi Key |
LBQIJVLKGVZRIW-ZDUSSCGKSA-N
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| InChi Code |
InChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
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| Chemical Name |
(R)-4-(8,8-dimethyl-3,4-dihydro-2H,8H-pyrano[2,3-f]chromen-3-yl)benzene-1,3-diol
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| Synonyms |
Glabridin Q-100692 Q 100692Q100692 KB289522 KB 289522KB-289522 LS176045 LS 176045LS-176045
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| 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)
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| Solubility (In Vitro) |
DMSO : ~25 mg/mL (~77.07 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.71 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 (7.71 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 (7.71 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0829 mL | 15.4145 mL | 30.8290 mL | |
| 5 mM | 0.6166 mL | 3.0829 mL | 6.1658 mL | |
| 10 mM | 0.3083 mL | 1.5414 mL | 3.0829 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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