| Size | Price | Stock | Qty |
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| 5mg |
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| Targets |
p38 MAPK
N-trans-feruloyloctopamine (FO) does not directly act on phosphorylated Akt or p38 MAPK based on molecular docking analysis. However, molecular docking revealed that FO binds to E‑cadherin via hydrogen bonds and hydrophobic interactions.[1] |
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| ln Vitro |
N-trans-feruloyloctopamine (FO) at 2 mM concentration significantly inhibited cell proliferation in Huh7 and HCCLM3 cell lines compared to DMSO control, as determined by Cell Counting Kit‑8 (CCK‑8) assay. [1]
FO treatment for 48 hours resulted in a significant reduction in invasive cell counts: Huh7 cells treated with FO showed 11.7 ± 3.1 invasive cells vs. 36.0 ± 6.0 for DMSO; HCCLM3 cells treated with FO showed 23.3 ± 2.5 invasive cells vs. 64.7 ± 9.3 for DMSO (P < 0.05), as measured by transwell Matrigel invasion assays. [1] In wound‑healing migration assays at 48 hours post‑wounding, FO treatment did not cause a significant delay in the relative cleared wound area compared to DMSO (P = 0.073 for Huh7; P = 0.1715 for HCCLM3). [1] Western blot analysis showed that FO (2 mM, 48 h) caused a significant decrease in the phosphorylation levels of Akt and p38 MAPK in Huh7 and HCCLM3 cells, while phosphorylation of p65 (NF‑κB pathway) and ERK1/2 was not affected. FO also resulted in a significant reduction of Slug expression and an increase in E‑cadherin expression compared to DMSO‑treated HCC cells (P < 0.05). [1] Molecular docking analysis indicated that FO does not directly bind to phosphorylated Akt or p38 MAPK, but hydrogen bonds and hydrophobic interactions are critical for FO binding to E‑cadherin. In the docked complex, the hydroxyl group of FO formed two hydrogen bonds with PRO5 (A) and PRO6 (A); one hydrogen bond between the phenolic hydroxyl group and SER8 (B); one hydrogen bond between the hydroxyl group of benzene and GLH13 (A); and the amino group of FO formed an H‑bond with PRO6 (B). Hydrophobic interactions involved residues LEU21 (B), ILE7 (B), VAL22 (B), PRO5 (B), ILE7 (A), PRO6 (A), PRO5 (A), and PRO6 (B). [1] |
| Cell Assay |
Cell viability and cytotoxicity were assessed using the Cell Counting Kit‑8 (CCK‑8) assay. HCC cell lines Huh7 and HCCLM3 were treated with various concentrations of N-trans-feruloyloctopamine (FO) or 5‑fluorouracil (5‑FU) for 48 hours. The concentration inhibiting cell growth by 50% (IC50) was determined. For Huh7 cells, IC50 values were 1.99 mM for FO and 2.98 mM for 5‑FU; for HCCLM3 cells, IC50 values were 2.27 mM for FO and 1.84 mM for 5‑FU. Following this, 2 mM FO was used for subsequent experiments. Cell viability percentage was presented as mean ± standard deviation from triplicate experiments. [1]
Cell proliferation was evaluated after treatment with 2 mM FO or 0.2% DMSO (vehicle control) for 48 hours in Huh7 and HCCLM3 cells. Significant inhibition of cell proliferation was observed in FO‑treated groups compared to DMSO. [1] Cell migration was assessed by wound‑healing assay. Cells were grown to confluence, a wound was created, and the relative cleared wound area was measured at 48 hours post‑wounding using Image J software. No significant difference in migration rate was found between FO‑treated and DMSO‑treated groups (P = 0.073 for Huh7; P = 0.1715 for HCCLM3). [1] Cell invasion was evaluated using transwell Matrigel invasion assays. Invasive cells were counted after 48 hours of treatment with 2 mM FO or DMSO. Counts of invasive Huh7 cells were 11.7 ± 3.1 (FO) vs. 36.0 ± 6.0 (DMSO); for HCCLM3 cells, 23.3 ± 2.5 (FO) vs. 64.7 ± 9.3 (DMSO) (P < 0.05). Data are mean ± standard deviation from three independent experiments. [1] Western blot analysis was performed to assess signaling pathway activation. Cells were treated with 2 mM FO or DMSO for 48 hours, then lysed, and protein expression was analyzed using antibodies against phosphorylated and total forms of AKT, p38 MAPK, ERK1/2, p65, as well as Slug, Snail, N‑cadherin, and E‑cadherin. FO significantly decreased phosphorylation of Akt and p38 MAPK, reduced Slug expression, and increased E‑cadherin expression, without affecting p65 or ERK1/2 phosphorylation. [1] |
| References | |
| Additional Infomation |
N-trans-feruloyl octylamine belongs to the methoxybenzene and phenolic compounds. It has been reported that N-trans-feruloyl octylamine exists in Capnoides sempervirens and Allium sativum, and relevant data are available for reference.
N-trans-feruloyloctopamine (FO) is a vanillin derivative (hydroxycinnamic acid amide) isolated from garlic skin. This study was the first to investigate its effect on HCC invasion. The mechanism of action involves direct binding to E‑cadherin protein (via hydrogen bonds and hydrophobic interactions) and indirect modulation of PI3K/Akt and p38 MAPK signaling pathways, leading to inhibition of Slug expression, restoration of E‑cadherin expression, and blockade of epithelial‑to‑mesenchymal transition (EMT). FO did not directly inhibit phosphorylated Akt or p38 MAPK. The compound shows promise as a potential therapeutic agent for HCC treatment and prognosis. [1] |
| Molecular Formula |
C18H19NO5
|
|---|---|
| Molecular Weight |
329.3472
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| Exact Mass |
329.126
|
| CAS # |
66648-44-0
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| PubChem CID |
24096391
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| Appearance |
White to light yellow solid
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
652.5±55.0 °C at 760 mmHg
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| Melting Point |
164 - 165 °C
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| Flash Point |
348.4±31.5 °C
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| Vapour Pressure |
0.0±2.1 mmHg at 25°C
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| Index of Refraction |
1.656
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| LogP |
1.03
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
|
| Heavy Atom Count |
24
|
| Complexity |
420
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O([H])C([H])(C1C([H])=C([H])C(=C([H])C=1[H])O[H])C([H])([H])N([H])C(/C(/[H])=C(\[H])/C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])O[H])=O
|
| InChi Key |
VJSCHQMOTSXAKB-YCRREMRBSA-N
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| InChi Code |
InChI=1S/C18H19NO5/c1-24-17-10-12(2-8-15(17)21)3-9-18(23)19-11-16(22)13-4-6-14(20)7-5-13/h2-10,16,20-22H,11H2,1H3,(H,19,23)/b9-3+
|
| Chemical Name |
(E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (~303.63 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.59 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 (7.59 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. 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 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: ≥ 2.5 mg/mL (7.59 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 | 3.0363 mL | 15.1814 mL | 30.3628 mL | |
| 5 mM | 0.6073 mL | 3.0363 mL | 6.0726 mL | |
| 10 mM | 0.3036 mL | 1.5181 mL | 3.0363 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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