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| Targets |
Piperlonguminine targets multiple cellular pathways. It is an inhibitor of the Akt/mTOR signaling pathway, and modulates NF-κB and MAPK signaling. In melanogenesis, it acts by suppressing α-MSH-induced signaling through cyclic AMP (cAMP) to the cAMP response element-binding protein (CREB), thereby regulating the expression of microphthalmia-associated transcription factor (MITF), a key activator of the tyrosinase promoter. This leads to decreased tyrosinase expression without directly inhibiting tyrosinase catalytic activity.
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| ln Vitro |
Piperlonguminine demonstrates potent in vitro activity. It inhibits melanin production in melanoma B16 cells stimulated with α-MSH, 3-isobutyl-1-methylxanthine, or protoporphyrin IX, showing stronger depigmenting efficacy than kojic acid. It does not affect 1-oleoyl-2-acetyl-sn-glycerin-induced melanin production or protein kinase C-mediated melanogenesis. It shows anticancer, antihyperlipidemic, and anti-inflammatory activities. Additionally, it decreases levels of amyloid-β (Aβ) and amyloid precursor protein (APP) in vitro, suggesting potential benefit in Alzheimer's disease research.
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| ln Vivo |
Piperlonguminine exhibits significant in vivo neuroprotective effects. In rat models of cerebral ischemia, intraperitoneal injection at 2.4 mg/kg demonstrates obvious neuroprotective effects. It attenuates neurological deficit scores, reduces cerebral infarct volume, and decreases brain water content. These effects are mediated through inhibition of NF-κB and MAPK activation, protecting the brain from ischemic damage by reducing blood-brain barrier (BBB) impairment. It also shows antitumor and hypolipidemic effects in vivo.
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| Enzyme Assay |
The standard protocol for evaluating Piperlonguminine's mechanism involves cell-free tyrosinase activity assays. In these assays, the compound is incubated with cell-free tyrosinase from melanoma B16 cells to assess direct catalytic inhibition. Results indicate that Piperlonguminine does not inhibit the catalytic activity of cell-free tyrosinase. Its melanogenesis inhibition is instead attributed to the suppression of α-MSH-induced cAMP to CREB signaling, which downregulates tyrosinase mRNA expression. This demonstrates a transcriptional rather than direct enzymatic mechanism of action.
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| Cell Assay |
In vitro cellular activity is evaluated in melanoma B16 cells. Cells are cultured in appropriate media and treated with Piperlonguminine at concentrations ranging from 3 to 30 μM. Melanin production is measured after stimulation with α-MSH, 3-isobutyl-1-methylxanthine, or protoporphyrin IX. The compound's effect on tyrosinase expression is analyzed by Western immunoblotting to confirm downregulation of tyrosinase protein levels. Cell viability is concurrently assessed to ensure observed effects are not due to cytotoxicity. Each experiment includes appropriate positive controls (e.g., kojic acid) and vehicle controls.
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| Animal Protocol |
In vivo studies are conducted in cerebral ischemia rat models. Adult rats are subjected to middle cerebral artery occlusion to induce ischemic stroke. Piperlonguminine is administered via intraperitoneal injection at a dose of 2.4 mg/kg. Neurological deficit scores are assessed using standardized scales. Cerebral infarct volume is measured by TTC staining, and brain water content is determined by the wet/dry weight method. Blood-brain barrier integrity is evaluated, and NF-κB and MAPK activation in brain tissue is analyzed by Western blotting. Sample sizes typically range from 6-10 animals per group.
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| ADME/Pharmacokinetics |
Piperlonguminine has a molecular weight of 273.33 g/mol and a molecular formula of C16H19NO3. Solubility: DMSO 27.5 mg/mL (100.61 mM). Storage: powder at -20°C for up to 3 years; in solvent at -80°C for up to 1 year. It is a crystalline solid. Pharmacokinetic parameters such as bioavailability, half-life, and tissue distribution are not well-characterized in publicly available literature. Further studies are needed to establish its ADME profile for therapeutic development.
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| Toxicity/Toxicokinetics |
Comprehensive toxicology data for Piperlonguminine are limited. As a natural product-derived compound from Piper longum with a history of use in traditional medicine, it is generally considered to have low toxicity at moderate doses. In animal studies, no significant adverse effects have been reported at the tested doses (2.4 mg/kg, i.p.). Standard toxicology profiling would include acute, subchronic, and chronic toxicity assessments, genotoxicity screening, and reproductive toxicity evaluation. The compound is intended for research use only and has not undergone full preclinical safety evaluation for clinical development.
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| References |
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| Additional Infomation |
(E,E)-Piperlonguminine is a member of the benzodioxane class of compounds. Piperine has been reported to be found in peppermint, cassia pepper, and other organisms with relevant data.
Piperlonguminine is also known as N-Isobutylpiperamide and NSC 125178. Its chemical name is 5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)-2E,4E-pentadienamide. It is a bioactive isolate of Piper longum. Its mechanism involves inhibition of Akt/mTOR signaling, promoting autophagy and mediating cancer cell death. It is currently under preclinical investigation for cancer, neurological disorders, and inflammation. No clinical trials or regulatory approvals have been reported for this compound. It is strictly for laboratory research purposes only. |
| Molecular Formula |
C16H19NO3
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|---|---|
| Molecular Weight |
273.33
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| Exact Mass |
273.136
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| CAS # |
5950-12-9
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| PubChem CID |
5320621
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
476.9±45.0 °C at 760 mmHg
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| Melting Point |
167 - 169 °C
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| Flash Point |
242.2±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.577
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| LogP |
2.78
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
20
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| Complexity |
376
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)CNC(=O)/C=C/C=C/C1=CC2=C(C=C1)OCO2
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| InChi Key |
WHAAPCGHVWVUEX-GGWOSOGESA-N
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| InChi Code |
InChI=1S/C16H19NO3/c1-12(2)10-17-16(18)6-4-3-5-13-7-8-14-15(9-13)20-11-19-14/h3-9,12H,10-11H2,1-2H3,(H,17,18)/b5-3+,6-4+
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| Chemical Name |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide
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| Synonyms |
NSC 125178; NSC-125178
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6586 mL | 18.2929 mL | 36.5858 mL | |
| 5 mM | 0.7317 mL | 3.6586 mL | 7.3172 mL | |
| 10 mM | 0.3659 mL | 1.8293 mL | 3.6586 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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