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Psoralidin

Cat No.:V8420 Purity: ≥98%
Psoralidin is a dual (bifunctional) inhibitor of COX-2 and 5-LOX.
Psoralidin
Psoralidin Chemical Structure CAS No.: 18642-23-4
Product category: New12
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Psoralidin is a dual (bifunctional) inhibitor of COX-2 and 5-LOX. Has anti-cancer, antibacterial and anti~inflammatory effects. Psoralidin significantly downregulates NOTCH1 signaling. Psoralidin also strongly induces ROS production.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Psoralen treatment (10, 15, 20, and 25 μM; 24 hours) was sensitive to clear breast cancer cell (BCC) populations (ALDH- cells, ALDH+ cells, and commercial BSCS), with an IC50 ranging from 18 to 21 μM. On the other hand, MCF-12A cells treated with psoralidin (30 μM; 24 hours) were able to significantly induce ALDH- cells, ALDH+ cells, and commercial BCSC[2]. Psoralidin's effects on treating ALDH- and ALDH+ cells in AIDS [2]
ln Vivo
Psoralen (5 mg/kg) reduces inflammation in BALB/c infrared-irradiated lungs by modifying the expression of pro-inflammatory cytokines that are crucial in inflammation [1].
Cell Assay
Cell viability assay [2]
Cell Types: ALDH- cells, ALDH+ cells, commercial breast cancer stem cells (BSCS) and normal mammary epithelial cells (MCF-12A)
Tested Concentrations: 10, 15 , 50 and 25. μM
Incubation Duration: 24 hrs (hours)
Experimental Results: IC50 for ALDH- cells, ALDH+ cells, commercial BCSC was 18 to 21 μM.

Apoptosis analysis [2]
Cell Types: ALDH- cells, ALDH+ cells and commercial BCSC
Tested Concentrations: 20 and 30 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: No obvious apoptosis was observed in all three cell types after 20 μM treatment death induction. However, at 30 μMin, 53.60%, 44.1%, and 45.9% of ALDH- cells, ALDH+ cells, and commercial BCSCs were apoptotic, respectively.
Animal Protocol
Animal/Disease Models: balb/c (Bagg ALBino) mouse[1]
Doses: 5 mg/kg
Route of Administration: intraperitoneal (ip) injection; 30 minutes before and 1 hour after IR irradiation (20 Gy).
Experimental Results: Anti-inflammatory effects on mice irradiated with infrared rays.
References

[1]. Psoralidin, a dual inhibitor of COX-2 and 5-LOX, regulates ionizing radiation (IR)-induced pulmonary inflammation.Biochem Pharmacol. 2011 Sep 1;82(5):524-34.

[2]. Silencing NOTCH signaling causes growth arrest in both breast cancer stem cells and breast cancer cells.Br J Cancer. 2013 Nov 12;109(10):2587-96.

Additional Infomation
Psoralidin is a member of the class of coumestans that is coumestan substituted by hydroxy groups at positions 3 and 9 and a prenyl group at position 2 respectively. It has a role as a plant metabolite and an estrogen receptor agonist. It is a member of coumestans, a polyphenol and a delta-lactone. It is functionally related to a coumestan.
Psoralidin has been reported in Phaseolus lunatus, Dolichos trilobus, and other organisms with data available.
See also: Cullen corylifolium fruit (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H16O5
Molecular Weight
336.34
Exact Mass
336.099
CAS #
18642-23-4
PubChem CID
5281806
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
458.8±34.0 °C at 760 mmHg
Melting Point
290-292°
Flash Point
231.3±25.7 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.689
LogP
5.03
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
2
Heavy Atom Count
25
Complexity
554
Defined Atom Stereocenter Count
0
SMILES
O1C2C([H])=C(C([H])=C([H])C=2C2C(=O)OC3C([H])=C(C(C([H])([H])/C(/[H])=C(\C([H])([H])[H])/C([H])([H])[H])=C([H])C=3C1=2)O[H])O[H]
InChi Key
YABIJLLNNFURIJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H16O5/c1-10(2)3-4-11-7-14-17(9-15(11)22)25-20(23)18-13-6-5-12(21)8-16(13)24-19(14)18/h3,5-9,21-22H,4H2,1-2H3
Chemical Name
3,9-dihydroxy-2-(3-methylbut-2-enyl)-[1]benzofuro[3,2-c]chromen-6-one
HS Tariff Code
2934.99.9001
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 : ~50 mg/mL (~148.66 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.08 mg/mL (6.18 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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: ≥ 2.08 mg/mL (6.18 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 20.8 mg/mL clear DMSO 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 2.9732 mL 14.8659 mL 29.7318 mL
5 mM 0.5946 mL 2.9732 mL 5.9464 mL
10 mM 0.2973 mL 1.4866 mL 2.9732 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?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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.

Biological Data
  • Psoralidin inhibits cell growth, mammosphere formation and induces apoptosis in BC and BCSCs. (A) ALDH− cells, ALDH+ cells, commercial BCSCs, and normal breast epithelial cells (MCF-12A) were treated with vehicle (DMSO) or the indicated dose of Pso for 24 h. Cell viability was determined using a trypan blue exclusion assay. Data are expressed as mean±s.e.m. of two independent experiments done in triplicates. (B) Anchorage-independent growth of ALDH− and ALDH+ cells was determined by assessing the colony-forming ability of these cells. Approximately, 5 × 103 cells were treated with Pso at the IC50 value specific to the cell type. Cells were monitored for 10 days, and colonies were stained with crystal violet and counted manually. Data are expressed as mean±s.e.m. of three independent experiments. (C) A mammosphere assay was performed using 4 × 103 cells (ALDH− and ALDH+ cells) on ultra-low attachment plates. Cells were treated with IC50 dose of Pso and allowed to grow for 2 weeks followed by counting of mammospheres. Data are expressed as mean±s.e.m. of two independent experiments. (D) To assess apoptosis induced by Pso, ALDH− cells, ALDH+ cells, and commercial BCSCs were treated with Pso for 24 h. Cells were stained with FITC-Annexin-V and propidium iodide and analyzed by flow cytometery. Data are expressed as mean±s.e.m. of three independent experiments. Student's t-test was used to calculate statistical significance. *P<0.05, **P<0.005, and ***P<0.0001. The full colour version of this figure is available at British Journal of Cancer online.[2]. Suman S, et al. Silencing NOTCH signaling causes growth arrest in both breast cancer stem cells and breast cancer cells.Br J Cancer. 2013 Nov 12;109(10):2587-96.
  • Psoralidin inhibits NOTCH1 signaling and EMT in ALDH− and ALDH+ cells. (A) ALDH− and ALDH+ cells were treated with vehicle or the IC50 dose of Pso. Total cell lysates were prepared, and equal amounts of protein were subjected to western blot analysis for NOTCH1, HES1, and actin proteins. (B) Total protein lysates were utilized for western blot analysis to determine the expression of the EMT markers E-cadherin, β-catenin, and vimentin. Actin was used as a loading control. (C) E-cadherin, and (D) β-catenin expression and localization were visualized by confocal microscopy in vehicle- and Pso-treated ALDH− and ALDH+ cells.[2]. Suman S, et al. Silencing NOTCH signaling causes growth arrest in both breast cancer stem cells and breast cancer cells.Br J Cancer. 2013 Nov 12;109(10):2587-96.
  • Psoralidin inhibits migration and invasion in BCCs and BCSCs. (A) ALDH− cells, ALDH+ cells, and commercial BCSCs were plated in six-well plates and grown until confluent. A uniform wound was created in the center of the monolayer. The wound gap was photographed in a Biostation CT programmed to take pictures every 2 h. The distance between the edges of wound was measured in μm using NIS-Element software, and statistical analysis was performed. Data are expressed as mean±s.e.m. of two independent experiments. (B) A transwell invasion assay was performed with ALDH− cells, ALDH+ cells, and commercial BCSCs using Boyden chambers. The cells were treated with vehicle or the IC50 dose of Pso and allowed to migrate towards the lower chamber. The invasive cells were stained with crystal violet and counted. Data are expressed as mean±s.e.m. of three independent experiments. Student's t-test was used to calculate statistical significance. *P<0.05, **P<0.005, and ***P<0.0001.[2]. Suman S, et al. Silencing NOTCH signaling causes growth arrest in both breast cancer stem cells and breast cancer cells.Br J Cancer. 2013 Nov 12;109(10):2587-96.
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