 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C4H8N4O2 |
| Molecular Weight | 144.13 |
| Exact Mass | 144.064 |
| CAS # | 140-79-4 |
| Related CAS # | N,N'-Dinitrosopiperazine-d8;69340-07-4 |
| PubChem CID | 8819 |
| Appearance | PALE YELLOW PLATES FROM WATER |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 406.1±38.0 °C at 760 mmHg |
| Melting Point | 158 °C |
| Flash Point | 199.4±26.8 °C |
| Vapour Pressure | 0.0±0.9 mmHg at 25°C |
| Index of Refraction | 1.648 |
| LogP | -0.88 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 0 |
| Heavy Atom Count | 10 |
| Complexity | 115 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1CN(CCN1N=O)N=O |
| InChi Key | WNSYEWGYAFFSSQ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C4H8N4O2/c9-5-7-1-2-8(6-10)4-3-7/h1-4H2 |
| Chemical Name | 1,4-dinitrosopiperazine |
| 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 |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | In the labeled 6-10B cells, N,N'-Dinitrosopiperazine (0.5-100 μM; 48 hours) does not exhibit any inhibitory effects, and DNP treatment in the 0.5-8 μM concentration range does not significantly change LDH activity. But starting at 10 μM, it becomes cytotoxic[1]. 6-10B cell invasion and motility are induced in a dose-dependent manner by N,N'-Dinitrosopiperazine (2-8 μM; 24 hours). At 6 μM, DNP increases cell motility by 328.2% and increases cell invasion by 421.7 percent compared to the control group[1]. In CNE1 cells, phospho-LYRIC s568 and LYRIC expression are upregulated by 6 μM of N,N'-Dinitrosopiperazine over a 24-hour period[1]. |
| ln Vivo | In vivo NPC metastasis is facilitated by N,N'-Dinitrosopiperazine (40 mg/kg; 30 days) injection into the tail veins, which decreases cell motility and invasion. Phospho-LYRIC expression is more prevalent in the metastatic tumors of DNP-treated mice compared to untreated control mice, according to an IHC result[1]. |
| Cell Assay |
Cell Viability Assay[1] Cell Types: The labeled 6-10B cells Tested Concentrations: 0.5, 1, 2, 4, 6, 8, 10, 20, 40, 80, or 100 μM Incubation Duration: 48 hrs (hours) Experimental Results: Had no inhibitory effects at the concentration 0-8 μM. Western Blot Analysis[1] Cell Types: The NPC cell line CNE1 Tested Concentrations: 6 μM Incubation Duration: 24 hrs (hours) Experimental Results: Increased phospho-LYRIC s568 and LYRIC expression. |
| Animal Protocol |
Animal/Disease Models: BABL/c nude mice injected with labeled 6-10B cell suspensions (1 × 104 cells) with or without DNP(40 mg/kg)[1] Doses: 40 mg/kg Route of Administration: Injected into the tail veins; 30 days Experimental Results: Induced LYRIC phosphorylation at serine 568 associated with NPC metastasis in vivo. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion AFTER IP ADMIN OF 10 MG/69.5 MUCI PER KG (2,5-(14)C)-N,N'-DINITROSOPIPERAZINE TO RATS 1% OF RADIOACTIVITY WAS EXHALED AS (14)CO2, 1% WAS EXCRETED VIA BILE & ABOUT 40% WAS EXCRETED IN URINE. Metabolism / Metabolites AFTER ADMIN OF (2,5-(14)C)-DINITROSOPIPERAZINE TO RATS TWO OF THE URINE METABOLITES WERE IDENTIFIED AS 3-HYDROXYNITROSOPYRROLIDINE & 1-NITROSOPIPERAZINONE-(3). |
| References |
[1]. Identification of Novel Signaling Components in N,N'-dinitrosopiperazine-mediated Metastasis of Nasopharyngeal Carcinoma by Quantitative Phosphoproteomics. BMC Cancer. 2014 Apr 5;14:243. |
| Additional Infomation | Carcinogen is any chemical, biological or physical agents that increase the risk of neoplasms in humans or animals. Carcinogens include natural or synthesized compounds, certain viruses, and various sources of radiation. A carcinogen may directly alter the genetic material of cells (genotoxic), thereby initiating or promoting the process of malignant transformation; it also may induce cancers by mechanisms that do not involve a direct alteration of cellular genetic material (non-genotoxic). (NCI04) |
Solubility Data
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.9382 mL | 34.6909 mL | 69.3818 mL | |
| 5 mM | 1.3876 mL | 6.9382 mL | 13.8764 mL | |
| 10 mM | 0.6938 mL | 3.4691 mL | 6.9382 mL |