(S)-N-trans-feruloyloctopamine
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine is a natural hydroxycinnamic acid amide compound derived from garlic husk, possessing tyrosinase inhibitory, FGF2 inhibitory, anti-melanogenic, and anti-tumor activities, and is used in research related to hepatocellular carcinoma, pigmentation disorders, and UVB-induced skin damage.
For research use only. We do not sell to patients.
- CAS No.: 640235-67-2
- Formula: C18H19NO5
- Molecular Weight:329.35
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Biological Activity
Description
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BRafV600E |
Ras |
MEK2 |
MEK1 |
p38 MAPK |
Akt |
Cellular Effect
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Cell Line
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Type | Value | Description | References |
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| Huh-7 | IC50 |
1.99 mM
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Cytotoxicity against human hepatocellular carcinoma Huh7 cells assessed as inhibition of cell proliferation incubated for 48 hrs by CCK-8 assay.
Cytotoxicity against human hepatocellular carcinoma Huh7 cells assessed as inhibition of cell proliferation incubated for 48 hrs by CCK-8 assay.
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28073674 |
| HCCLM3 | IC50 |
2.27 mM
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Cytotoxicity against human hepatocellular carcinoma HCCLM3 cells assessed as inhibition of cell proliferation incubated for 48 hrs by CCK-8 assay.
Cytotoxicity against human hepatocellular carcinoma HCCLM3 cells assessed as inhibition of cell proliferation incubated for 48 hrs by CCK-8 assay.
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28073674 |
| B16-F10 | IC50 |
>96 μM
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Cytotoxicity against murine B16F10 melanoma cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay.
Cytotoxicity against murine B16F10 melanoma cells assessed as reduction in cell viability incubated for 72 hrs by MTT assay.
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25726329 |
In Vitro
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (FO) (0.1-50 mM; 48 h) inhibits the proliferation of Huh7 and HCCLM3 cells with IC50 values of 1.99 mM and 2.27 mM, respectively[1].
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (NFO) binds to FGF2 with a KD of 8.507 × 10-6 M and disrupts the interaction between FGF2 and FGFR1-4 in HaCaT cells[4].
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (2 mM; 48 h) does not significantly inhibit the migration of Huh7 and HCCLM3 cells in the scratch wound healing assay[1].
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (2 mM; 48 h) potentially inhibits cell proliferation and invasion through the PI3K/Akt and p38 MAPK signaling pathways, and regulates EMT-related signaling in Huh7 and HCCLM3 cells by decreasing Slug and increasing E-cadherin; it directly binds to E-cadherin to inhibit EMT-related cell invasion[1].
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (1.5-96.0 μM; 72 h) shows little or no cytotoxicity against B16F10 cells, with an IC50 of >96 μM[3].
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (1.5-96.0 μM) inhibits α-MSH-induced melanogenesis in B16F10 cells in a dose-dependent manner without cytotoxicity[3].
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (48.0-96.0 μM; 1 h pre-treatment, followed by 24 h incubation with α-MSH) downregulates tyrosinase mRNA and protein expression in α-MSH-stimulated B16F10 cells[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Huh7 and HCCLM3
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Concentration:0.1, 0.5, 5, 2, 4, 10, 20, 50 mM
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Incubation Time:48 h
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Result:Reached an IC50 of 1.99 mM in Huh7 cells.
Reached an IC50 of 2.27 mM in HCCLM3 cells.
Significantly inhibited cell proliferation compared to DMSO-treated controls.
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Cell Line:Huh7 and HCCLM3
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Concentration:2 mM
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Incubation Time:48 h
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Result:Revealed no significant delay in the relative cleared area between target reagent-treated groups and DMSO-treated groups in Huh7 cells and HCCLM3 cells.
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Cell Line:Huh7 and HCCLM3
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Concentration:2 mM
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Incubation Time:48 h
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Result:Did not affect the phosphorylation of p65 and ERK1/2.
Caused a significant decrease in the phosphorylation levels of Akt and p38 MAPK.
Resulted in a significant reduction of Slug and an upsurge of E-cadherin compared to DMSO-treated cells.
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Cell Line:B16F10 melanoma cells
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Concentration:1.5, 3.0, 6.0, 12.0, 24.0, 48.0, 96.0 μM
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Incubation Time:72 h
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Result:Displayed little or no cytotoxicity at all concentrations examined.
Exhibited an IC50 value of >96 μM.
Showed cytotoxicity values of 102.2% at 1.5 μM, 104.8% at 3.0 μM, 97.8% at 6.0 μM, 99.4% at 12.0 μM, 98.3% at 24.0 μM, 97.2% at 48.0 μM, and 96.0% at 96.0 μM.
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Cell Line:B16F10 melanoma cells
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Concentration:48.0, 96.0 μM
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Incubation Time:1 h pre-treatment, followed by 24 h incubation with α-MSH
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Result:Dose-dependently decreased tyrosinase mRNA expression levels in α-MSH-stimulated cells.
Significantly inhibited α-MSH-induced tyrosinase mRNA expression.
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Cell Line:B16F10 melanoma cells
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Concentration:48.0, 96.0 μM
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Incubation Time:1 h pre-treatment, followed by 24 h incubation with α-MSH
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Result:Dose-dependently decreased tyrosinase protein expression levels in α-MSH-stimulated cells.
Significantly inhibited α-MSH-induced tyrosinase protein expression.
In Vivo
(S)-N-trans-feruloyloctopamine is an isomer of N-trans-feruloyloctopamine (HY-N2232). N-trans-feruloyloctopamine (10% NFO-TSG; topical administration) acts primarily locally and rarely enters the systemic circulation, thereby reducing the potential risk of systemic toxicity[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6J mice (6-8 weeks old, 18-20 g, male)[4]
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Dosage:10% (w/v) NFO gel, 500 µL per mouse
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Administration:topical; twice daily; 14 days
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Result:Ameliorated UVB-induced skin damage and hyperpigmentation.
Inhibited pathological collagen fiber hyperplasia.
Significantly reduced pigmentation.
Inhibited functional activity of FGF2, blocking activation of the Ras/Raf/MEK/ERK signaling pathway.
Prevented UVB-induced inflammatory responses and cell proliferation.
Significantly reduced neutrophil (MPO and Ly6G) and macrophage (F4/80) recruitment to the skin.
Downregulated protein and mRNA expression of chemokines CXCL3, CCL4, and CCL5.
Alleviated UVB-induced pigmentation by inhibiting protein and mRNA expression of Mc1r, Dct, Tyr, and Tyrp1.
Chemical Information
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CAS No. 640235-67-2
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Molecular Weight 329.35
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Formula C18H19NO5
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SMILES
C(=C/C(NC[C@@H](O)C1=CC=C(O)C=C1)=O)\C2=CC(OC)=C(O)C=C2
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Structure Classification
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Bai ZT, et al. Inhibition of invasion by N-trans-feruloyloctopamine via AKT, p38MAPK and EMT related signals in hepatocellular carcinoma cells. Bioorganic & medicinal chemistry letters. 2017 Feb 15;27(4):989-993. [Content Brief]
[2]. Ma B, et al. N--Feruloyloctopamine Wakes Up BBC3, DDIT3, CDKN1A, and NOXA Signals to Accelerate HCC Cell Apoptosis. Analytical cellular pathology (Amsterdam). 2021;2021:1560307. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
(S)-N-trans-feruloyloctopamine Related Classifications
HY-N11517 Related Classifications
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