| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Natural flavone; anti-inflammatory, anti-tumor, anti-oxidant, neuroprotective, anti-fungal activities
7-Hydroxyflavone targets the enzyme cytochrome P450 1A1 (CYP1A1), acting as a potent inhibitor. It also targets the ERK/Nrf2/HO-1 signaling pathway, which is involved in cellular protection against oxidative stress. Its anti-inflammatory activity is attributed to its ability to modulate inflammatory signaling pathways. |
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| ln Vitro |
Hence, through in silico studies, it may be concluded that querciten, myricetin and 7-hydroxyflavonol can be used as novel drugs (radioprotectors) for protecting normal cells from radiation.[1]
Plant flavonoids are well known as antioxidants against oxidative stress induced by exposure to external pollutants. Nicotine (NIC) is one of those agents which increases renal oxidative stress, an important factor in the pathogenesis of renal epithelial injury in smokers. Although several studies had been conducted on flavonoids and oxidative stress, the mechanism of the protective pathways are not fully understood. Here, we present studies on antioxidant properties of two mono-hydroxyflavone isomers, 3-hydroxyflanove (3HF)- and 7-hydroxyflavone (7HF), against nicotine-associated oxidative stress and injury in cultured renal proximal tubule cells and correlate their antioxidant properties with their chemical structure. Our data clearly demonstrates, for the first time, that while both 3HF and 7HF protect renal cells from NIC-associated cytotoxicity, the mechanism of their action is different: 3HF elicits protective activity via the PKA/CREB/MnSOD pathway while 7HF does so via the ERK/Nrf2/HO-1 pathway. Molecular docking and dynamics simulations with two major signaling pathway proteins showed significant differences in the binding energies of 3HF (-5.67 and -7.39 kcal.mol-1) compared to 7HF (-5.41 and -8.55 kcal.mol-1) in the matrices of CREB and Keap1-Nrf2 proteins respectively, which corroborate with the observed differences in their protective properties in the renal cells. The implications of this novel explorative study is likely to promote the understanding of the mechanisms of the antioxidative functions of different flavones[2]. In vitro, 7-Hydroxyflavone is a potent inhibitor of CYP1A1 with a Ki of 0.015 μM. It protects renal cells from nicotine-induced cytotoxicity through the activation of the ERK/Nrf2/HO-1 pathway. It also exhibits excellent antioxidant properties and has been studied for its potential to enhance cognitive function and protect neurons. |
| ln Vivo |
In vivo, 7-Hydroxyflavone's anti-inflammatory and neuroprotective effects suggest potential therapeutic applications. It has been studied for its ability to reduce oxidative stress and protect against cellular damage. However, specific in vivo data are limited.
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| Enzyme Assay |
In vitro non-cell enzyme assays for 7-Hydroxyflavone typically involve measuring the inhibition of CYP1A1 and CYP1A2 activity using microsomal preparations or purified enzymes and fluorogenic substrates. The compound is incubated with the enzyme and substrate, and the rate of metabolite formation is measured. Ki values are determined from kinetic analysis.
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| Cell Assay |
Measurement of intracellular ROS production[2]
Microplate assay using oxidant-sensitive 2′,7′-dichlorofluorescein-diacetate measured the intracellular generation of ROS. Cells grown in T25 flasks were pretreated with either 20 μM 3HF or 20 μM 7HF for overnight as required and isolated with trypsinization. After washing and counting, cells were loaded with 100 μM DCFDA in HBSS for 30 min at 37°C. After incubation, the excess dye was removed by washing with fresh HBSS and placed in wells of a 96-well plate (0.5 × 106 cells/well). 200 μM NIC was added to the appropriate wells and the increase in fluorescence was monitored in a fluorescence plate reader at 485 nmexc/530 nmem. ROS production was calculated as changes in fluorescence/30 min/0.5 × 106 cells and expressed as the percentage of untreated values as described in our earlier studies. In vitro cell-based assays for 7-Hydroxyflavone use renal cell lines exposed to nicotine. Cells are treated with the compound, and cell viability is assessed using MTT or similar assays. The activation of the ERK/Nrf2/HO-1 pathway is confirmed by western blotting for phosphorylated ERK, Nrf2, and HO-1 protein levels. |
| Animal Protocol |
In vivo animal studies for 7-Hydroxyflavone are limited. Standard protocols for studying neuroprotective or anti-inflammatory effects would involve administering the compound to rodent models of cognitive impairment or inflammation, followed by behavioral tests and analysis of oxidative stress markers in tissues.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
The known metabolites of 7-hydroxyflavonoids include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-oxo-2-phenylchromene-7-yl)oxaoxane-2-carboxylic acid. 7-Hydroxyflavone has a molecular weight of 238.24 g/mol and a molecular formula of C₁₅H₁₀O₃. It is a flavonoid compound with a purity of ≥98%. It is soluble in organic solvents. Detailed pharmacokinetic parameters, such as oral bioavailability and half-life, have not been extensively characterized. |
| Toxicity/Toxicokinetics |
The toxicity profile of 7-Hydroxyflavone has not been fully characterized. As a natural flavonoid, it is generally considered to have low toxicity. However, its potent inhibition of CYP1A1 suggests potential for drug-drug interactions, and its safety profile should be carefully evaluated.
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| References |
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| Additional Infomation |
7-Hydroxyflavonoids are hydroxyflavonoid compounds in which the 7-position of the flavonoid nucleus is replaced by a hydroxyl group. They have been reported to be found in astragalus, alfalfa, and other organisms with relevant data.
7-Hydroxyflavone is a naturally occurring flavonoid with potent CYP1A1 inhibitory activity and anti-inflammatory properties. It protects renal cells from nicotine-induced cytotoxicity via the ERK/Nrf2/HO-1 pathway. It is used as a research tool in studies of drug metabolism, oxidative stress, and neuroprotection. It is also known as 7-Hydroxy-2-phenyl-4-benzopyrone. Not approved for clinical use. |
| Molecular Formula |
C15H10O3
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|---|---|
| Molecular Weight |
238.2381
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| Exact Mass |
238.062
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| CAS # |
6665-86-7
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| PubChem CID |
5281894
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
450.1±45.0 °C at 760 mmHg
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| Melting Point |
245-247 °C(lit.)
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| Flash Point |
176.3±22.2 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.666
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| LogP |
3.32
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
18
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| Complexity |
355
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
MQGPSCMMNJKMHQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H
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| Chemical Name |
7-hydroxy-2-phenylchromen-4-one
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| Synonyms |
7-Hydroxyflavone; 6665-86-7; 7-Hydroxy-2-phenyl-4H-chromen-4-one; 7-hydroxy-2-phenylchromen-4-one; 4H-1-Benzopyran-4-one, 7-hydroxy-2-phenyl-; Flavone, 7-hydroxy-; 7-Hydroxy-2-phenyl-4-benzopyrone; 7-Hydroxy-2-phenyl-chromen-4-one;
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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 : ~125 mg/mL (~524.68 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.73 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 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 (8.73 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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 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: ≥ 2.08 mg/mL (8.73 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 | 4.1974 mL | 20.9872 mL | 41.9745 mL | |
| 5 mM | 0.8395 mL | 4.1974 mL | 8.3949 mL | |
| 10 mM | 0.4197 mL | 2.0987 mL | 4.1974 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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