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3',4'-Dimethoxyflavone

Cat No.:V43316 Purity: ≥98%
3',4'-Dimethoxyflavone, lipophilic flavone
3',4'-Dimethoxyflavone
3',4'-Dimethoxyflavone Chemical Structure CAS No.: 4143-62-8
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
3',4'-Dimethoxyflavone is a natural lipophilic flavonoid tht can be isolated from the leaves of Primula veris, with various biological activities, including antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidaemic, and neuroprotective or neurotrophic effects. It can reduce the synthesis and accumulation of PARP and protect cortical neurones against cell death induced by Parthanatos.
3',4'-Dimethoxyflavone is a flavone compound that acts as an inhibitor of poly (ADP-ribose) polymerase (PARP) enzymes. It has the molecular formula C17H14O4 and a molecular weight of 282.29 g/mol. The compound has various biological activities, including antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidemic, and neuroprotective or neurotrophic effects. 3',4'-Dimethoxyflavone prevents the production and accumulation of poly (ADP-ribose) (PAR) polymer. It appears as a white to light yellow powder to crystal.
Biological Activity I Assay Protocols (From Reference)
Targets
3',4'-Dimethoxyflavone targets poly (ADP-ribose) polymerase (PARP) enzymes. PARP enzymes are involved in DNA repair and cell death pathways. By inhibiting PARP, the compound reduces the synthesis and accumulation of poly (ADP-ribose) (PAR) polymer. This inhibition protects cortical neurons against cell death induced by parthanatos. The compound also has antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidemic, and neuroprotective effects.
ln Vitro
3',4'-Dimethoxyflavone (10 and 20 μM) inhibits methylnitrosoguanidine (MNNG)-induced reduction in SH-SY5Y activity [2]. In HeLa cells, 3',4'-Dimethoxyflavone (6.25–25 μM) lowers MNNG-induced PAR levels [2]. When exposed to NMDA, 3',4'-dimethoxyflavone (12.5, 25, 50, and 100 μM; 15-20 hours) lessens cortical neuronal death [2]. Significant inhibition of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-induced EROD activity was seen with 3',4'-dimethoxyflavone (0.1-10 μM; 24 hours)[3]. In T47D and MCF-7 breast cancer cells, 3',4'-Dimethoxyflavone inhibits AhR-mediated inhibition of estrogen-induced gene expression as well as AhR-dependent CYP1A1 activation [3]. 3',4'-Dimethoxyflavone (2.5 μM; 7 days) stimulates the proliferation of human hematopoietic stem cells [4].
In vitro, 3',4'-Dimethoxyflavone has been shown to inhibit PARP enzymes and protect cortical neurons against cell death induced by parthanatos. The compound reduces the synthesis and accumulation of PAR polymer. It has various biological activities, including antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidemic, and neuroprotective or neurotrophic effects. The compound's neuroprotective effects make it a valuable tool for studying neurodegenerative diseases and parthanatos.
ln Vivo
3',4'-Dimethoxyflavone is not used as a therapeutic agent but as a research tool for studying PARP inhibition and neuroprotection. Its in vivo effects would be mediated through PARP inhibition and its various biological activities. The compound has neuroprotective effects and protects cortical neurons against cell death induced by parthanatos. Further studies in animal models are needed to confirm its in vivo efficacy and safety. The compound is currently in the research phase.
Enzyme Assay
In vitro enzyme assays for 3',4'-Dimethoxyflavone typically involve measuring the inhibition of PARP enzymatic activity. The enzyme is incubated with a substrate (e.g., NAD+) in the presence of varying concentrations of the compound. The incorporation of ADP-ribose into the substrate is measured using a luminescent or radiometric detection system. The IC50 value, representing the concentration required to inhibit 50% of the enzyme activity, is calculated from the dose-response curve. The compound's antioxidant and anti-inflammatory activities can be measured using appropriate in vitro assays.
Cell Assay
Cell Viability Assay[2]
Cell Types: Primary cortical neurons (isolated from fetal CD1 mice, incubated with NMDA)
Tested Concentrations: 12.5, 25, 50 and 100 μM
Incubation Duration: 15-20 hrs (hours)
Experimental Results: Reduction by concentration Neuronal death caused by exposure to NMDA.
Cell proliferation assay [4]
Cell Types: CD34+ cells
Tested Concentrations: 2.5 μM
Incubation Duration: 7 days
Experimental Results: Normoxic conditions induced Dramatically higher expansion of the CD34+ cell population.
In vitro cell-based assays for 3',4'-Dimethoxyflavone are performed to study its neuroprotective and cytoprotective effects. Neuronal cells are treated with the compound and exposed to parthanatos-inducing conditions. Cell viability is assessed using MTT or other cell viability assays. PAR polymer accumulation is measured by immunofluorescence or Western blotting. The compound's protective effects are assessed by measuring cell viability and PAR levels. The compound is typically dissolved in DMSO and diluted in cell culture medium.
Animal Protocol
Specific in vivo animal experiment protocols for 3',4'-Dimethoxyflavone are not detailed in the available literature. However, as a neuroprotective agent, it could be tested in animal models of neurodegenerative diseases. The compound could be administered orally or intraperitoneally. Neuroprotective effects would be assessed by measuring neuronal survival and function. The route of administration and dosing would depend on the specific experimental design.
ADME/Pharmacokinetics
3',4'-Dimethoxyflavone has a molecular weight of 282.29 g/mol and the formula C17H14O4. The compound appears as a white to light yellow powder to crystal with a melting point of 151-155°C. For storage, the compound is kept at room temperature in a cool, dark place. Its purity is typically ≥98%. The compound is a flavone that inhibits PARP enzymes and has neuroprotective effects. It has various biological activities, including antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidemic, and neuroprotective or neurotrophic effects.
Toxicity/Toxicokinetics
Specific toxicological data for 3',4'-Dimethoxyflavone are not provided in the available sources. As a research chemical, it is intended for laboratory use only and is not for human consumption. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves and eye protection. The compound may cause irritation to skin, eyes, and respiratory tract upon contact.
References

[1]. Lipophilic flavones of Primula veris L. from field cultivation and in vitro cultures. Phytochemistry. 2005 May;66(9):1033-9.

[2]. Identification through high-throughput screening of 4'-methoxyflavone and 3',4'-dimethoxyflavone as novel neuroprotective inhibitors of parthanatos. Br J Pharmacol. 2013 Jul;169(6):1263-78.

[3]. 3',4'-dimethoxyflavone as an aryl hydrocarbon receptor antagonist in human breast cancer cells. Toxicol Sci. 2000 Dec;58(2):235-42.

[4]. 3',4'-Dimethoxyflavone and valproic acid promotes the proliferation of human hematopoietic stem cells. Stem Cell Res Ther. 2013 May 24;4(3):60.

Additional Infomation
Primrose and Lawsonia spp. reportedly contain 3',4'-dimethoxyflavonoids, and available data exist.
3',4'-Dimethoxyflavone (CAS 4143-62-8) is a flavone compound that acts as an inhibitor of poly (ADP-ribose) polymerase (PARP) enzymes. It has the molecular formula C17H14O4 and a molecular weight of 282.29 g/mol. The compound prevents the production and accumulation of poly (ADP-ribose) (PAR) polymer. It protects cortical neurons against cell death induced by parthanatos. 3',4'-Dimethoxyflavone has various biological activities, including antioxidant, anti-cancer, anti-inflammatory, anti-atherogenic, hypolipidemic, and neuroprotective or neurotrophic effects. It appears as a white to light yellow powder to crystal. The compound is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H14O4
Molecular Weight
282.2907
Exact Mass
282.089
CAS #
4143-62-8
PubChem CID
688674
Appearance
White to light yellow solid powder
Density
1.242g/cm3
Boiling Point
428.5ºC at 760 mmHg
Melting Point
154-155°C
Flash Point
190.6ºC
Index of Refraction
1.598
LogP
3.477
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
21
Complexity
417
Defined Atom Stereocenter Count
0
InChi Key
ZGHORMOOTZTQFL-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H14O4/c1-19-15-8-7-11(9-17(15)20-2)16-10-13(18)12-5-3-4-6-14(12)21-16/h3-10H,1-2H3
Chemical Name
2-(3,4-dimethoxyphenyl)chromen-4-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 (~177.12 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.86 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 (8.86 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5425 mL 17.7123 mL 35.4246 mL
5 mM 0.7085 mL 3.5425 mL 7.0849 mL
10 mM 0.3542 mL 1.7712 mL 3.5425 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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