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| 10mg |
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| Targets |
Erucin exerts its biological effects through multiple mechanisms. It induces apoptosis and inhibits cell proliferation in cancerous cells. Erucin releases H₂S and reduces ERK1/2 phosphorylation in AsPC-1 cells. It exerts anti-inflammatory properties in murine macrophages and mouse skin through the inhibition of NF-κB signaling. Erucin also acts as a non-competitive antagonist of the aryl hydrocarbon (Ah) receptor. It modulates detoxification enzymes, which may contribute to its protective effects against oxidative stress.
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| ln Vitro |
Erucic acid (ERU) (0-100 μM) decreases AsPC-1 cell viability in a concentration-dependent manner and produces H2S [1]. Erucic acid reduces the G0/G1 phase and increases the G2/M and S phases in the AsPC-1 cell cycle, inhibiting cell migration [1]. Erucin (30 μM, 72 h) slows cell migration and causes apoptosis in AsPC-1 cells [1]. In AsPC-1 cells, erucic acid lowers the amounts of phosphorylated ERK1/2 [1]. With an IC50 of 97.7 μM, erucin (0-200 μM, 24 hours) has anti-proliferative action in A549 cells [2]. In A549 cells, erucin (0-50 μM, 24 hours) enhances p53 and p21 protein expression and causes PARP-1 breakage at 50 μM [2]. Erucin decreases the amount of NO, prostaglandin E2 (PGE2), TNF-α, IL-6, and IL-1β that are produced in RAW 264.7 cells in response to LPS [3]. In RAW 264.7 cells, erucin decreases the production of cyclooxygenase (COX)-2 and inducible nitric oxide synthase (iNOS) caused by LPS [3]. Erucin prevents RAW 264.7 cells' NFκB signaling from being activated by LPS [3].
In vitro, erucin (30 µM, 72 h) inhibits proliferation and migration and induces apoptosis in AsPC-1 cells. At 2.5-5 µM, erucin induces significant neuroprotective and antioxidant effects. It exerts anti-inflammatory properties in murine macrophages through the inhibition of NF-κB signaling. Erucin induces apoptosis and cell cycle arrest through PARP-1 cleavage, p53 and p21 proteins, and modulation of cytochrome P450 and glutathione transferase pathways. |
| ln Vivo |
TPA-induced edema formation is markedly inhibited by erucin (ERU) (0-300 nM) [3]. Neuroprotective effects of erucic acid (30 μmol/kg; intraperitoneal injection; twice weekly for 4 weeks) have been reported [4].
In vivo, erucin has demonstrated anticancer and anti-inflammatory effects in animal models. It exerts anti-inflammatory properties in mouse skin through the inhibition of NF-κB signaling. Erucin's ability to modulate detoxification enzymes may contribute to its protective effects against oxidative stress and toxic compounds. The compound is being studied for its potential as a cancer-preventive agent. |
| Enzyme Assay |
Non-cellular enzyme assays for erucin involve assessing its antioxidant activity using cell-free systems. The compound's ability to scavenge free radicals can be evaluated using DPPH or ABTS assays. Its inhibition of NF-κB activity can be assessed using electrophoretic mobility shift assays (EMSA) with nuclear extracts. Its modulation of detoxification enzymes (e.g., quinone reductase, glutathione transferase) can be assessed using enzyme activity assays with purified enzymes.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: AsPC-1 Tested Concentrations: 10, 30 and 100 μM Incubation Duration: 72 hrs (hours) Experimental Results: demonstrated a significant and concentration-dependent decrease in cell viability. Cell cycle analysis [1] Cell Types: AsPC-1 Tested Concentrations: 30 μM Incubation Duration: 72 hrs (hours) Experimental Results: The number of cells in G2/M phase increased Dramatically (the number of cells in G2 phase was 36.6% ± 3.5 compared with vehicle-treated cells) / M phase: 24.0% ± 1.3) and S phase (18.1% ± 1.5 compared to vehicle-treated S phase cells: 11.0% ± 0.7), followed by a significant reduction in G0/G1 phase cells (35.1% ± 5.0 vs. vehicle Comparison of treated G0/G1 phase cells: 59.5% ± 1.8. Apoptosis analysis [1] Cell Types: AsPC-1 Tested Concentrations: 30 μM Incubation Duration: 72 hrs (hours) Experimental Results: The total cell number Dramatically increased apoptotic cells (apoptosis Dead and apoptotic live cells; Vehicle: 17.7% ± 2.5 vs. Erucin: 28.7% ± 4.2). Cell proliferation assay[2] Cell Types: A549 Tested Concentrations: 0-200 µM Incubation Duration: 72 h Experimental Results: demonstrated a significant and concentration‐dependent reduction of cell viability. In vitro cellular assays for erucin involve treating cancer cell lines (e.g., AsPC-1 pancreatic cancer cells) or immune cells with the compound and assessing cell viability, apoptosis, and signaling pathways. Cell viability is measured using MTT or CellTiter-Glo® assays. Apoptosis is assessed by flow cytometry using Annexin V/PI staining or by measuring caspase activity. ERK1/2 phosphorylation is assessed by Western blotting. NF-κB activation is assessed by measuring nuclear translocation of p65 or by reporter gene assays. |
| Animal Protocol |
Animal/Disease Models: Female ICR mice (4 weeks old), TPA (12-O-tetradecanoylphorbol-13-acetate)-induced mouse ear edema model [3]
Doses: 0, 100 and 300 nM Route of Administration: Topically applied to mice 30 minutes before topical application of TPA, ear contact Experimental Results: Dramatically inhibited the formation of edema caused by TPA. Animal/Disease Models: Male C57Bl/6 mice (9 weeks old, body weight 25-30 g) [4] Doses: 30 μmol/kg Route of Administration: intraperitonealadministration, twice a week for 4 weeks (via striatum Injection 6-induced brain damage) OHDA) Experimental Results: Induced partial recovery in the rotational behavioral test. TH expression is upregulated. Counteracts neuronal death and DNA fragmentation in 6-OHDA-damaged mice. Increased total GSH and Nrf2 levels in 6-OHDA-lesioned mice. In vivo animal experiments with erucin are conducted in mouse models of inflammation and cancer. In inflammatory models, mice are treated with erucin via topical or oral administration, and skin inflammation is assessed by measuring edema, cytokine levels, and histology. In cancer models, the compound's effects on tumor growth and metastasis are evaluated. The compound's ability to modulate detoxification enzymes in the liver is assessed by measuring enzyme activities. |
| ADME/Pharmacokinetics |
Erucin has a molecular weight of 161.29 and a molecular formula of C₆H₁₁NS₂. It is a liquid or solid at room temperature with a purity of ≥98%. The compound is soluble in DMSO and other organic solvents. It is typically stored at -20°C, protected from light and moisture. The compound is stable under recommended storage conditions.
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| Toxicity/Toxicokinetics |
Erucin is a research compound for laboratory use only and is not approved for human therapeutic use. As a dietary isothiocyanate, it is generally considered to have low toxicity at the levels found in foods. Standard laboratory safety precautions should be followed when handling the compound. It may cause skin, eye, and respiratory irritation. Appropriate personal protective equipment should be used.
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| References |
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| Additional Infomation |
Glucosinolates are isothiocyanates. They have been reported to be found in golden-yellow turin, cabbage, and rapeseed, and relevant data are available for reference.
Erucin (ERU; CAS 4430-36-8) is an isothiocyanate abundant in arugula with anticancer, neuroprotective, and anti-inflammatory properties. It induces apoptosis, inhibits cell proliferation, and reduces ERK1/2 phosphorylation in cancer cells. Erucin exerts anti-inflammatory effects through inhibition of NF-κB signaling. The compound is used as a research tool for studying cancer prevention and inflammatory diseases. |
| Molecular Formula |
C6H11NS2
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|---|---|
| Molecular Weight |
161.28
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| Exact Mass |
161.033
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| CAS # |
4430-36-8
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| PubChem CID |
78160
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
250.6±23.0 °C at 760 mmHg
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| Melting Point |
52 °C
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| Flash Point |
105.4±22.6 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.531
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| LogP |
2.39
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
9
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| Complexity |
97.2
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CSCCCCN=C=S
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| InChi Key |
IHQDGXUYTSZGOG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H11NS2/c1-9-5-3-2-4-7-6-8/h2-5H2,1H3
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| Chemical Name |
1-isothiocyanato-4-methylsulfanylbutane
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| Synonyms |
CCRIS9056 CCRIS-9056 CCRIS 9056
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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 (~620.00 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.50 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 (15.50 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 (15.50 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 | 6.2004 mL | 31.0020 mL | 62.0040 mL | |
| 5 mM | 1.2401 mL | 6.2004 mL | 12.4008 mL | |
| 10 mM | 0.6200 mL | 3.1002 mL | 6.2004 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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