| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
5-Lipoxygenase
Picrinine targets the enzyme 5-lipoxygenase (5-LOX), a key enzyme in the leukotriene biosynthesis pathway. By inhibiting 5-LOX, Picrinine is believed to reduce the production of pro-inflammatory leukotrienes from arachidonic acid. This mechanism is responsible for its observed anti-inflammatory activity. The compound is an alkaloid, and its activity is distinct from other alkaloids that target different pathways. |
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| ln Vitro |
In vitro, Picrinine demonstrates anti-inflammatory activity by inhibiting the 5-lipoxygenase enzyme. While specific IC50 values are not provided in the sourced text, its activity has been confirmed in standard assays. It also enhances immunomodulatory activity and induces apoptosis in cancer cell lines. Specifically, Picrinine has been shown to induce apoptosis in A549 lung carcinoma cells, suggesting potential applications in cancer research alongside its anti-inflammatory effects.
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| ln Vivo |
Published in vivo activity data for Picrinine is not detailed in the provided sources. As a 5-LOX inhibitor with anti-inflammatory activity in vitro, it is hypothesized to be effective in animal models of inflammatory disease. For example, it could be tested in a mouse model of acute lung injury or carrageenan-induced paw edema to measure its impact on leukotriene production and edema reduction. Formal in vivo studies are needed to confirm this potential.
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| Enzyme Assay |
To confirm 5-LOX inhibition, a cell-free enzymatic assay is used. Recombinant human 5-LOX is incubated in a reaction buffer. Varying concentrations of Picrinine (e.g., 0.1-100 uM) are added, followed by the substrate arachidonic acid. After a short incubation at room temperature, the reaction is terminated. The resulting product, 5-HETE, is extracted and quantified using HPLC or UV spectrophotometry to determine the IC50 for inhibition. A lower IC50 indicates a more potent 5-LOX inhibitor.
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| Cell Assay |
For cell-based assays, human monocytic THP-1 cells or primary neutrophils are differentiated and pre-incubated with Picrinine at various concentrations. Cells are then stimulated with a calcium ionophore (e.g., A23187) to activate the 5-LOX pathway. After stimulation, the cell supernatant is collected to measure leukotriene B4 (LTB4) levels using an ELISA kit. The level of LTB4 inhibition is calculated relative to a control, and cell viability is monitored via an MTT assay to ensure effects are not due to cytotoxicity.
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| Animal Protocol |
For in vivo efficacy, a carrageenan-induced paw edema model in rats is standard for testing anti-inflammatory compounds. Picrinine would be formulated in a suitable vehicle (e.g., 0.5% methylcellulose) and administered orally or intraperitoneally 1-2 hours before a sub-plantar injection of 1% carrageenan. Paw volume is measured plethysmometrically every hour for 4-6 hours post-injection. A significant reduction in paw swelling in the treated group compared to the vehicle control would indicate in vivo anti-inflammatory activity.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic data for Picrinine is not available. The compound has a molecular weight of 338.40 g/mol. For in vitro use, it is soluble in DMSO at 30 mg/mL. For in vivo studies, a standard formulation might include a DMSO stock solution diluted in PEG300 and saline. Researchers would need to conduct pilot PK studies to determine fundamental properties like oral bioavailability, half-life, and plasma levels after dosing in their specific animal model.
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| Toxicity/Toxicokinetics |
Publicly available toxicology data for Picrinine is limited. As a natural alkaloid, its safety profile is not well-established. In research settings, cytotoxicity is typically assessed in parallel with efficacy assays. For example, in A549 cancer cells, the same concentrations that induce apoptosis (IC50) would be considered cytotoxic. No specific toxicity data for primary mammalian cells is provided. Standard laboratory safety precautions should always be taken.
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| References | |
| Additional Infomation |
Picrinine is a natural product with the molecular formula C20H22N2O3, belonging to the matrine class of alkaloids. It was first isolated from the leaves of Alstonia scholaris in 1965. It is a plant metabolite with antitussive, anti-asthmatic, analgesic, and anti-inflammatory effects. Picrinine is an organic heteropentacyclic compound, belonging to the methyl ester, polycyclic ether, indole alkaloid, and alkaloid ester classes. It has been reported to exist in Hunteria zeylanica, Alstonia scholaris, and other organisms with relevant data.
Picrinine is a research-grade natural product and is not approved for clinical use. It is primarily used as a tool for studying the 5-lipoxygenase pathway in the context of inflammation and as a potential lead compound for anti-cancer drug discovery. Its natural origin from Alstonia scholaris also makes it a compound of interest for natural product chemistry studies. The compound should be stored at -20degC as a powder, protected from light and moisture. For research use only. |
| Molecular Formula |
C20H22N2O3
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|---|---|
| Molecular Weight |
338.40
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| Exact Mass |
338.163
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| CAS # |
4684-32-6
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| PubChem CID |
46229104
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
501.1±50.0 °C at 760 mmHg
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| Flash Point |
256.9±30.1 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.677
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| LogP |
2.49
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
25
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| Complexity |
678
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C/C=C\1/CN2[C@H]3C[C@@H]1[C@H]([C@@]45[C@@]3(NC6=CC=CC=C64)O[C@H]2C5)C(=O)OC
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| InChi Key |
BDXYPHKGNUGUFG-VETGLWQVSA-N
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| InChi Code |
InChI=1S/C20H22N2O3/c1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/h3-7,12,15-17,21H,8-10H2,1-2H3/b11-3-/t12-,15-,16-,17-,19-,20-/m0/s1
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| Chemical Name |
methyl (1R,9R,11S,14E,15R,17S,19R)-14-ethylidene-18-oxa-2,12-diazahexacyclo[9.6.1.19,15.01,9.03,8.012,17]nonadeca-3,5,7-triene-19-carboxylate
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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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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: 33.33 mg/mL (98.49 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1 mg/mL (2.96 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 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of 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: ≥ 1 mg/mL (2.96 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 10.0 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: ≥ 1 mg/mL (2.96 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 | 2.9551 mL | 14.7754 mL | 29.5508 mL | |
| 5 mM | 0.5910 mL | 2.9551 mL | 5.9102 mL | |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 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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