Isoliquiritigenin (GU17)

Alias:
Cat No.:V2013 Purity: ≥98%
Isoliquiritigenin (also known as ISL; GU17; Isoliquiritigen) is a naturally occuring chalcone compound and NLRP3 antagonist found in licorice root and several other plants that displays antioxidant, anti-inflammatory, and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress.
Isoliquiritigenin (GU17) Chemical Structure CAS No.: 961-29-5
Product category: Aldose Reductase
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Isoliquiritigenin (also known as ISL; GU17; Isoliquiritigen) is a naturally occuring chalcone compound and NLRP3 antagonist found in licorice root and several other plants that displays antioxidant, anti-inflammatory, and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress. Isoliquiritigenin is a soluble guanylyl cyclase activator with antitumor activity.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
By blocking sorbitol buildup in human erythrocytes (IC50=2.0 μM) and rat lens aldose reductase (IC50=320 nM), isoliquiritigenin can avoid diabetic consequences [1]. In cardiomyocytes, hypoxia-induced TPS and TR90 prolongation is markedly inhibited by isoliquiritigenin (100 μM). In comparison to the vehicle group, isoliquiritigenin dramatically increased AMPK Thr172 phosphorylation. Cardiomyocytes treated with isoliquiritigenin also triggered the extracellular signal-regulated kinase (ERK) signaling pathway. During hypoxia/reoxygenation, isoliquiritigenin administration can dramatically lower intracellular ROS levels in isolated cardiomyocytes [3]. Isoliquiritigenin not only downregulates IL-6 expression, but also drastically lowers the levels of phosphorylated ERK and STAT3, and suppresses the phosphorylation levels of ERK and STAT3 caused by recombinant human IL-6, which are critical signals in the IL-6 signal regulatory network. protein[4].
ln Vivo
When different stimulants such CCh (1 mM), KCl (60 mM), and BaCl2 (0.3 mM) are used to generate tetanic contractions in the mouse jejunum, isoliquiritigenin exhibits concentration-dependent suppression of those contractions. 4.96±1.97 mM, 4.03±1.34 mM, and 3.70±0.58 mM are the respective IC50 values[2]. In MM xenograft models, isoliquiritigenin demonstrates strong anti-tumor activity and synergistically increases doxorubicin's anti-myeloma efficacy [4].
References
[1]. Aida K, et al. Isoliquiritigenin: a new aldose reductase inhibitor from glycyrrhizae radix. Planta Med. 1990 Jun;56(3):254-8.
[2]. Sato Y, et al. Isoliquiritigenin, one of the antispasmodic principles of Glycyrrhiza ularensis roots, acts in the lower part of intestine. Biol Pharm Bull. 2007 Jan;30(1):145-9.
[3]. Zhang X. Natural antioxidant-isoliquiritigenin ameliorates contractile dysfunction of hypoxic cardiomyocytes via AMPK signaling pathway. Mediators Inflamm. 2013;2013:390890.
[4]. Chen X, et al. Isoliquiritigenin inhibits the growth of multiple myeloma via blocking IL-6 signaling. J Mol Med (Berl). 2012 Nov;90(11):1311-9.
[5]. Traboulsi H, et al. The Flavonoid Isoliquiritigenin Reduces Lung Inflammation and Mouse Morbidity during Influenza Virus Infection. Antimicrob Agents Chemother. 2015 Oct;59(10):6317-27.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H12O4
Molecular Weight
256.25
CAS #
961-29-5
Related CAS #
961-29-5
SMILES
O([H])C1C([H])=C(C([H])=C([H])C=1C(/C(/[H])=C(\[H])/C1C([H])=C([H])C(=C([H])C=1[H])O[H])=O)O[H]
InChi Key
DXDRHHKMWQZJHT-FPYGCLRLSA-N
InChi Code
InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
Chemical Name
(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Synonyms

GU17; GU-17; GU 17

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 Data
Solubility (In Vitro)
DMSO:> 10 mM
Water: N/A
Ethanol:N/A
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.76 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 (9.76 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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly.


Solubility in Formulation 4: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% EtOH + 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 EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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 5: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% EtOH + 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 EtOH 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.

Solubility in Formulation 6: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), suspension solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9024 mL 19.5122 mL 39.0244 mL
5 mM 0.7805 mL 3.9024 mL 7.8049 mL
10 mM 0.3902 mL 1.9512 mL 3.9024 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.

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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