| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
| Targets |
The mechanism of action of 1-Ethenylpyrene is related to its ability to inhibit the initiation of skin tumors caused by chemical carcinogens such as 7,12-dimethylbenz[a]anthracene (DMBA) and Benzo[a]pyrene (B[a]P). It likely interferes with the metabolic activation of these procarcinogens. Unlike some PAHs that are metabolized to DNA-reactive diol epoxides, 1-Ethenylpyrene appears to act as a chemopreventive agent. It does not have a specific protein target in the same way a drug does. Its antitumor properties are well-documented in the literature, and it prevents cancer formation rather than treating existing cancer. It is an anti-chemical carcinogen. As a hydrocarbon, it may interact with the aryl hydrocarbon receptor (AhR), though its chemopreventive effects are likely due to alternative metabolic pathways.
|
|---|---|
| ln Vitro |
The in vitro activity of 1-Ethenylpyrene is primarily defined by its fluorescence characteristics. As a pyrene derivative, it is a highly fluorescent molecule, with excitation typically around 340 nm and emission around 380-400 nm. Its "activity" in a biological or chemical context is often measured by its ability to be incorporated into polymers or to act as a fluorescence resonance energy transfer (FRET) donor. It does not have a typical pharmacological IC50 value. In cell-based assays, it has been studied for its antitumor properties and its ability to inhibit cell transformation induced by chemical carcinogens, though specific cytotoxic IC50 values against cancer cell lines are not consistently reported in standard references. It is known to inhibit skin tumor growth.
|
| ln Vivo |
The application of 44 nmol 1-Ethenylpyrene (1-Vinylpyrene) can inhibit the tumor initiation of 10 nmol DMBA by about 30%; the application of 4.4 μmol 1-Ethenylpyrene (1-Vinylpyrene) can inhibit the tumor initiation of 200 nmol Benzo[a]pyrene by about 56%[1].
1-Ethenylpyrene has shown in vivo activity as a chemopreventive agent. In animal studies, it significantly inhibits the formation of skin tumors initiated by the potent carcinogens DMBA or Benzo[a]pyrene. This demonstrates its effectiveness in preventing cancer onset. Its in vivo activity is strictly preventative rather than therapeutic. It has anti-tumor properties and prevents cancer. It can also be used as a fluorescent tracer in biological systems, such as studying lipid bilayers or protein hydrophobicity, though this is a physical property. The compound is known to inhibit skin tumor growth from DMBA/B[]P. Its antitumor properties and ability to prevent cancer have been confirmed in preclinical research. |
| Enzyme Assay |
A non-cellular assay for 1-Ethenylpyrene typically focuses on its photophysical properties. A standard protocol uses a spectrofluorometer. The compound is dissolved in a suitable organic solvent, such as ethanol or DMSO, at a concentration of 1-10 uM. The solution is placed in a quartz cuvette. The excitation wavelength is scanned from 200-400 nm, and the emission is monitored at 375-400 nm. The fluorescence intensity is measured. This protocol is used to confirm the compound's integrity and to determine its fluorescence quantum yield. If bound to a protein or polymer, a shift in the emission spectrum or a change in intensity (quenching) is measured. This allows researchers to use 1-Ethenylpyrene as a probe for studying molecular interactions and microenvironments.
|
| Cell Assay |
Cellular assays for 1-Ethenylpyrene are limited by its low water solubility. Typically, it is dissolved in DMSO and added to cell culture media (final DMSO concentration ≤0.1%). A standard protocol for assessing its chemopreventive activity uses mouse epidermal JB6 P+ cells. These cells are sensitive to transformation by chemical carcinogens. The cells are seeded in 96-well plates and pre-treated with non-cytotoxic concentrations of 1-Ethenylpyrene (e.g., 1-20 uM) for 2 hours. The cells are then exposed to a carcinogen, such as benzo[a]pyrene diol epoxide (BPDE). After 24-48 hours, the number of transformed foci (anchorage-independent growth) is scored in soft agar. A reduction in the number of foci in the treated group compared to the carcinogen-only control indicates the chemopreventive activity of 1-Ethenylpyrene.
|
| Animal Protocol |
In vivo experiments for 1-Ethenylpyrene are conducted using a two-stage mouse skin carcinogenesis model. A standard protocol uses 7-8 week old female Swiss-Webster or SENCAR mice. The backs of the mice are shaved. A single initiating dose of a carcinogen, such as DMBA (100 ug) or B[a]P (200 ug), is applied topically. 1-Ethenylpyrene is dissolved in acetone and applied topically to the same site either before, simultaneously, or after the carcinogen application. Typically, the test compound is applied 1 hour prior to the carcinogen. The mice are promoted by twice-weekly applications of TPA (12-O-tetradecanoylphorbol-13-acetate) for 20 weeks. The endpoint is the number of papillomas (benign skin tumors) per mouse. A significant reduction in tumor multiplicity in the 1-Ethenylpyrene-treated group compared to the DMBA-only control confirms its in vivo chemopreventive activity.
|
| ADME/Pharmacokinetics |
1-Ethenylpyrene has a molecular formula of C18H12 and a molecular weight of 228.29 g/mol. It is a solid with a melting point typically around 120-124degC. It is a hydrophobic compound (high logP, approximately 5.2), making it poorly soluble in water (<0.1 mg/mL). It is, however, soluble in organic solvents such as DMSO, ethanol, acetone, toluene, and chloroform. For storage, it should be kept as a powder at -20degC in a dark, dry place to prevent photodegradation. It is stable under normal laboratory conditions. When dissolved in DMSO, it is recommended to store the solution at -80degC for long-term use (6 months). The compound is also known as 1-Vinylpyrene and has CAS number 17088-21-0. Its density is approximately 1.2 g/cm3.
|
| Toxicity/Toxicokinetics |
PAHs, including pyrene, are generally considered potentially hazardous. Many PAHs are known carcinogens and mutagens. However, 1-Ethenylpyrene is specifically classified as an anti-carcinogen. Despite this, it shares the fundamental properties of PAHs. It should be treated as a hazardous material due to its potential for skin and eye irritation and the possibility of long-term health effects from repeated exposure. The material can be harmful if swallowed. In handling, it is essential to avoid inhalation of dust and contact with skin. Use a fume hood and wear appropriate PPE (gloves, lab coat, safety goggles). It is not a drug and is not intended for human consumption. Waste should be disposed of according to regulations for chemical waste. It is for research use only. It has an antitumor effect and prevents cancer, but its mechanism is distinct from alkylating agents.
|
| References | |
| Additional Infomation |
1-Ethenylpyrene is an important research tool in the field of chemical carcinogenesis and chemoprevention. It is a classic compound used to dissect the mechanisms by which polycyclic aromatic hydrocarbons (PAHs) cause cancer and how certain structural modifications, like the addition of a vinyl group, can transform a carcinogen into a chemopreventive agent. Its unique electronic structure and fluorescence make it also valuable in materials science, where it is used as a monomer in the synthesis of conductive polymers, organic light-emitting diodes (OLEDs), and fluorescent probes. It is not a clinical drug and has not undergone human trials. Its use is strictly limited to basic research, helping scientists understand how to prevent environmentally induced cancers. The product is used for research purposes only and is not a pharmaceutical or veterinary product. It is known to inhibit the formation of skin tumors initiated by either DMBA or Benzo[a]pyrene.
|
| Molecular Formula |
C18H12
|
|---|---|
| Molecular Weight |
228.29
|
| Exact Mass |
228.094
|
| CAS # |
17088-21-0
|
| Related CAS # |
25120-43-8
|
| PubChem CID |
146322
|
| Appearance |
White to off-white solid powder
|
| Density |
1.214g/cm3
|
| Boiling Point |
409.8ºC at 760mmHg
|
| Flash Point |
193ºC
|
| Vapour Pressure |
1.5E-06mmHg at 25°C
|
| Index of Refraction |
1.842
|
| LogP |
5.227
|
| Hydrogen Bond Donor Count |
0
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
18
|
| Complexity |
331
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
C(C1C2C3=C4C(=CC=2)C=CC=C4C=CC3=CC=1)=C
|
| InChi Key |
WPMHMYHJGDAHKX-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C18H12/c1-2-12-6-7-15-9-8-13-4-3-5-14-10-11-16(12)18(15)17(13)14/h2-11H,1H2
|
| Chemical Name |
1-ethenylpyrene
|
| Synonyms |
1-Vinylpyrene
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| 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
|
|---|---|
| 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 | 4.3804 mL | 21.9020 mL | 43.8039 mL | |
| 5 mM | 0.8761 mL | 4.3804 mL | 8.7608 mL | |
| 10 mM | 0.4380 mL | 2.1902 mL | 4.3804 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
