| Size | Price | Stock | Qty |
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| 25mg |
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| Targets |
- Isosakuranetin targets transient receptor potential melastatin 3 (TRPM3) channels (inhibits TRPM3-mediated calcium influx), with an IC50 of ~1.8 μM. [3]
- Isosakuranetin targets pathways related to melanogenesis (e.g., tyrosinase, MITF) to stimulate melanin synthesis in melanoma cells. [1] |
|---|---|
| ln Vitro |
Melanin accumulation is stimulated by isozolin in a dose-dependent way. Additionally, after 48 and 72 hours, 30 μM isosakuranetin progressively raised Tyr, TRP1, and TRP2 expression. Isosakuranetin decreased the number of cells at concentrations higher than 45 μM, according to the MTT experiment. Trypan blue staining revealed through additional study that isosakuranetin decreased the proliferation rate of B16 melanocytes but had no effect on their viability. Tyrosinase activity of B16 melanocytes treated with 15 and 30 μM Isosakuranetin for 72 hours rose significantly by 2 and 3.2 fold, respectively, compared with control cells [1].
- Stimulation of Melanogenesis in B16BL6 Melanoma Cells: 1. B16BL6 cells were treated with Isosakuranetin (10, 20, 40 μM) for 48 hours. At 40 μM, it increased melanin content by ~2.3-fold (measured via absorbance at 405 nm) and tyrosinase activity by ~1.9-fold (L-DOPA oxidation assay) vs. control. [1] 2. Western blot and qPCR showed 20–40 μM Isosakuranetin upregulated expression of melanogenesis-related proteins (MITF: ~2.1-fold; TRP-1: ~1.7-fold; TRP-2: ~1.6-fold) and their mRNAs (MITF: ~2.4-fold; TRP-1: ~1.8-fold; TRP-2: ~1.7-fold) vs. control. [1] - Inhibition of TRPM3 Channel Activity: 1. HEK293 cells transfected with human TRPM3 were treated with Isosakuranetin (1–10 μM). It dose-dependently inhibited TRPM3-mediated calcium influx: 1.8 μM (IC50) reduced calcium signals by 50%, and 10 μM inhibited by ~90% (calcium imaging assay). [3] 2. Isosakuranetin (10 μM) showed no significant inhibition on other TRP channels (TRPV1, TRPV4, TRPM8), confirming selectivity for TRPM3. [3] |
| ln Vivo |
In the dose range of 1.5 to 6 mg/kg, isosakuranetin increases the threshold for paw withdrawal in a dose-dependent manner. Isosakuranetin raised the paw withdrawal threshold with statistical significance between 30 and 40 minutes for the 3 mg/kg dose and between 30 and 60 minutes for the 6 mg/kg dose, according to post hoc analysis [2].
- Antinociceptive Effect in Rat Peripheral Neuropathy Model: 1. Rats with chronic constriction injury (CCI) of the sciatic nerve were administered Isosakuranetin (10, 30 mg/kg, intraperitoneal injection, ip) once daily for 7 days. [2] 2. At 30 mg/kg, it increased mechanical paw withdrawal threshold by ~65% (von Frey filaments) and thermal paw withdrawal latency by ~50% (Hargreaves test) vs. CCI vehicle group; effects persisted for ~4 hours post-administration. [2] - Attenuation of Thermal Nociception in Mice: 1. Wild-type mice were administered Isosakuranetin (10 mg/kg, ip) 30 minutes before the hot plate test. It increased hot plate latency by ~40% vs. vehicle control. [3] 2. In TRPM3-knockout mice, 10 mg/kg Isosakuranetin had no significant effect on hot plate latency, confirming the antinociceptive effect is TRPM3-dependent. [3] |
| Enzyme Assay |
- TRPM3 Channel Activity Inhibition Assay:
1. HEK293 cells were transfected with human TRPM3 cDNA and cultured in DMEM (10% FBS) at 37°C (5% CO₂) for 48 hours. [3] 2. Cells were loaded with calcium-sensitive dye (Fura-2 AM) for 30 minutes, then treated with Isosakuranetin (1–10 μM) for 10 minutes, followed by TRPM3 agonist (pregnenolone sulfate, 10 μM). [3] 3. Calcium influx was measured via fluorescence microscopy (excitation: 340/380 nm; emission: 510 nm). Inhibition rates were calculated by comparing fluorescence ratios (F340/F380) with vehicle control to determine IC50. [3] |
| Cell Assay |
- B16BL6 Melanogenesis Assay:
1. B16BL6 cells were seeded in 6-well plates (2×10⁵ cells/well) and cultured in RPMI 1640 (10% FBS) at 37°C (5% CO₂) for 24 hours. [1] 2. Cells were treated with Isosakuranetin (10, 20, 40 μM) (vehicle: DMSO, ≤0.1% v/v) for 48 hours; control cells received DMSO alone. [1] 3. Melanin content: Cells were lysed with 1 M NaOH, and absorbance at 405 nm was measured. [1] 4. Tyrosinase activity: Cell lysates were incubated with L-DOPA (5 mM) at 37°C for 60 minutes, and absorbance at 475 nm was measured. [1] 5. Protein/mRNA detection: Western blot (anti-MITF, anti-TRP-1, anti-TRP-2) and qPCR (MITF, TRP-1, TRP-2 primers) were performed to quantify expression. [1] - HEK293 TRPM3 Inhibition Assay: 1. HEK293 cells were transfected with TRPM3 plasmid using transfection reagent, then seeded in 96-well black plates (1×10⁴ cells/well) and cultured for 24 hours. [3] 2. Cells were loaded with Fura-2 AM (5 μM) in HBSS for 30 minutes at 37°C, then washed 3 times with HBSS. [3] 3. Isosakuranetin (1–10 μM) was added, and after 10 minutes, pregnenolone sulfate (10 μM) was added to activate TRPM3. Calcium signals were recorded via microplate reader to calculate inhibition efficiency. [3] |
| Animal Protocol |
- Rat CCI Neuropathic Pain Model:
1. Animal preparation: Male Sprague-Dawley rats (250–300 g) were anesthetized with isoflurane, and the left sciatic nerve was ligated to establish CCI model. [2] 2. Drug preparation: Isosakuranetin was dissolved in DMSO (5% v/v) and diluted with sterile saline to concentrations of 10 mg/kg and 30 mg/kg (based on rat weight). [2] 3. Administration: From day 7 post-surgery, rats were given Isosakuranetin via intraperitoneal injection once daily for 7 days; control group received equal volume of DMSO-saline mixture. [2] 4. Pain threshold detection: Mechanical paw withdrawal threshold (von Frey filaments) and thermal paw withdrawal latency (Hargreaves apparatus) were measured before surgery and 1 hour post-administration daily. [2] - Mouse Hot Plate Nociception Model: 1. Animal preparation: Male C57BL/6 mice (20–25 g) and TRPM3-knockout mice (same background) were acclimated for 1 week (free access to food/water). [3] 2. Drug preparation: Isosakuranetin was dissolved in DMSO (5% v/v) + saline to 10 mg/kg. [3] 3. Administration: Mice were given Isosakuranetin via intraperitoneal injection; control group received vehicle. [3] 4. Pain detection: 30 minutes post-administration, mice were placed on a hot plate (52°C), and latency to paw licking/jumping was recorded (cut-off time: 30 seconds). [3] |
| References |
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| Additional Infomation |
4'-Methoxy-5,7-dihydroxyflavanone is a dihydroxyflavanone with hydroxyl groups at the 5 and 7 positions and a methoxy group at the 4' position (2S stereoisomer). It is a plant metabolite. It is a dihydroxyflavanone, monomethoxyflavanone, 4'-methoxyflavanone, and (2S)-flavan-4-one. It is functionally related to (S)-naringin. Isochondriol has been reported in Prunus serrulata var. pubescens, Populus szechuanica, and other organisms with relevant data. - Natural Sources and Chemical Classification: Isochondriol is a 4'-O-methylated flavanone naturally occurring in citrus fruits (e.g., Satsuma mandarins) and other flavonoid-rich plants. [1][2][3]
- Mechanism of action: 1. Stimulation of melanin production:Isoiseri activates the MITF (microphthalmia-associated transcription factor) pathway, upregulates tyrosinase, TRP-1 and TRP-2, thereby promoting melanin synthesis. [1] 2. Analgesia:Isoiseri inhibits TRPM3-mediated calcium ion influx in sensory neurons, reduces neuronal excitability, and relieves neuropathic/thermal pain. [2][3] |
| Molecular Formula |
C16H14O5
|
|---|---|
| Molecular Weight |
286.2794
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| Exact Mass |
286.084
|
| CAS # |
480-43-3
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| PubChem CID |
160481
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| Appearance |
White to yellow solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
539.2±50.0 °C at 760 mmHg
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| Melting Point |
193-194ºC
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| Flash Point |
205.6±23.6 °C
|
| Vapour Pressure |
0.0±1.5 mmHg at 25°C
|
| Index of Refraction |
1.638
|
| LogP |
3.84
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
2
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| Heavy Atom Count |
21
|
| Complexity |
377
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
COC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O
|
| InChi Key |
HMUJXQRRKBLVOO-AWEZNQCLSA-N
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| InChi Code |
InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
|
| Chemical Name |
(2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 : ~62.5 mg/mL (~218.32 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 20.83 mg/mL (72.76 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 clear DMSO stock solution of 208.3 mg/mL to 900 μL of corn oil and mix evenly. Solubility in Formulation 2: ≥ 2.08 mg/mL (7.27 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (7.27 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. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4931 mL | 17.4654 mL | 34.9308 mL | |
| 5 mM | 0.6986 mL | 3.4931 mL | 6.9862 mL | |
| 10 mM | 0.3493 mL | 1.7465 mL | 3.4931 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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