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| 100mg |
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Purity: ≥98%
Isorhamnetin (also named as 3-Methylquercetin) is a flavonoid analog isolated from the Chinese herb Hippophae rhamnoides L. It demonstrates a variety of biological activities, such as reducing COX-2 expression and ROS production in edema, causing cell cycle arrest in colon cancer cells, and suppressing Src and β-catenin activity to halt DSS- and azoxymethane-induced carcinogenesis. Additionally, it has been claimed that isorhamnetin prevents skin cancer by directly inhibiting MEK1 and PI3K.
| Targets |
MEK1; PI3-K; Human Endogenous Metabolite
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|---|---|
| ln Vitro |
Isorhamnetin is a plant flavonoid found in fruits and therapeutic herbs. Isorhamnetin binds to PI3-K in an ATP-competitive manner and directly to MEK1 in an ATP-noncompetitive manner. The kinase activity of MAP/ERK kinase (MEK) 1 and PI3-K are both inhibited by isorhamnetin in vitro and ex vivo kinase assay data, and the inhibition is caused by direct binding with isorhamnetin[1]. The Akt/mTOR and MEK/ERK signaling pathways are inhibited by isorhamnetin, while the mitochondrial apoptosis signaling pathway is stimulated. The CCK-8 method is used to assess the inhibitory effects of isorhamnetin on breast cancer cells. Many breast cancer cell lines, such as MCF7, T47D, BT474, BT-549, MDA-MB-231, and MDA-MB-468, are inhibited from proliferating by isorhamnetin (IC50, ~10 µM), whereas the normal breast epithelial cell line MCF10A exhibits less inhibitory activity (IC50, 38 µM)[2].
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| ln Vivo |
Photographic evidence demonstrates that isorhamnetin treatment inhibits the growth of tumors in mice. At 4 weeks after inoculation, the average tumor volume in mice that have not been treated rises over time and reaches a volume of 623 mm3. In contrast, at this point in time, in mice treated with 1 or 5 mg/kg Isorhamnetin, the average tumor volume is only 280 or 198 mm3, respectively. When compared to the untreated control group, isorhamnetin treatment (1 or 5 mg/kg) at the end of the study reduces tumor weight[1].
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| Cell Assay |
The breast cancer cell lines MCF7, T47D, BT474, BT-549, MDA-MB-231, and MDA-MB-468 are seeded into 96-well plates at a density of 5×103 cells per well in 100 µL DMEM. A MCF10A normal breast epithelial cell line is used as a control. Isorhamnetin (100, 33.3, 11.1, 3.7, 1.2, 0.4, and 0 µM) is then applied to the cells for 48 hours, and the cell proliferation rates are assessed by adding 10 µL of CCK-8 solution before incubating the mixture at 37°C for two hours. SpectraMax 190 Microplate Reader used to measure absorbance at 450 nm wavelength. The half maximal inhibitory concentration (IC50) is calculated using the inhibition curve for each assay's four parallel wells and presented as the average of three separate experiments[2].
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| Animal Protocol |
Mice: A431 cells (1×106 cells in 50 μL of μL and 50 liters of Matrigel) are injected subcutaneously into the flanks of female athymic nude mice. Once the tumors have grown to a size of 40 mm3, the cells are allowed to form tumors. The mice are then divided into groups of six, and every other day for 28 days, they are given intraperitoneal injections of isorhamnetin (1 or 5 mg/kg body weight) or a placebo in 40% DMSO/PBS buffer. Weekly caliper measurements of the tumor size are used to determine the tumor volume. Whenever the control tumors grow to a size of roughly 600 mm3 after 28 days of treatment, mice are killed. The tumors are taken out, weighed, and photographed. For immunohistochemical analysis and western blot analysis, tumor tissues are used.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Isorhamnetin has known human metabolites that include (2S,3S,4S,5R)-6-[5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid. |
| References |
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| Additional Infomation |
Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of an isorhamnetin(1-).
Isorhamnetin has been reported in Caragana frutex, Camellia sinensis, and other organisms with data available. Isorhamnetin is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Peumus boldus leaf (part of). |
| Molecular Formula |
C16H12O7
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|---|---|
| Molecular Weight |
316.2623
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| Exact Mass |
316.058
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| Elemental Analysis |
C, 60.76; H, 3.82; O, 35.41
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| CAS # |
480-19-3
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| Related CAS # |
480-19-3
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| PubChem CID |
5281654
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
599.4±50.0 °C at 760 mmHg
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| Melting Point |
307°C
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| Flash Point |
227.8±23.6 °C
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| Vapour Pressure |
0.0±1.8 mmHg at 25°C
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| Index of Refraction |
1.741
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| LogP |
1.76
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
23
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| Complexity |
503
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1C2=C([H])C(=C([H])C(=C2C(C(=C1C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])O[H])O[H])=O)O[H])O[H]
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| InChi Key |
IZQSVPBOUDKVDZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
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| Chemical Name |
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
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| Synonyms |
3'-Methylquercetin; 4H-1-Benzopyran-4-one, 2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-; 3-Methylquercetin; Quercetin; Isorhamnetin; 3'-O-methyl Quercetin;
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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: ~100 mg/mL (~316.2 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.08 mg/mL (6.58 mM) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1620 mL | 15.8098 mL | 31.6196 mL | |
| 5 mM | 0.6324 mL | 3.1620 mL | 6.3239 mL | |
| 10 mM | 0.3162 mL | 1.5810 mL | 3.1620 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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