| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
| Targets |
NOS/nitric oxide synthase
nNOS (neuronal nitric oxide synthase). |
|---|---|
| ln Vitro |
The formation of nitric oxide (NO) from L-arginine by vascular endothelial cells and its relationship to endothelium-dependent relaxation of vascular rings was studied. The release of NO, measured by bioassay or chemiluminescence, from porcine aortic endothelial cells stimulated with bradykinin was enhanced by infusions of L-, but not D-arginine. The release of 15NO, determined by high resolution mass spectrometry, from L-guanidino 15N (99%) arginine was also observed, indicating that NO is formed from the terminal guanidino nitrogen atom(s) of L-arginine. L-NG-monomethyl arginine (L-NMMA), but not D-NMMA, inhibited both the generation of NO by endothelial cells in culture and the endothelium-dependent relaxation of rabbit aortic rings. Both these effects were reversed by L-arginine. These data indicate that L-arginine is the physiological precursor for the formation of NO which mediates endothelium-dependent relaxation[1].
Vinyl‑L‑NIO inhibits nNOS with Ki of approximately 100 nM, while Ki values for eNOS and iNOS are significantly higher, demonstrating its selectivity for the neuronal isoform. It inhibits nNOS activity and reduces NO production in a concentration‑dependent manner. |
| ln Vivo |
No direct in vivo data available. For selective nNOS inhibitors, typical in vivo models include rodent models of neuropathic pain (e.g., chronic constriction injury) or cerebral ischemia (middle cerebral artery occlusion). The test compound is administered (10‑30 mg/kg, i.p. or p.o.) and outcomes such as allodynia, infarct volume, or neuronal NO production are assessed.
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| Enzyme Assay |
Not explicitly reported. Generic nNOS inhibition assay: Purified recombinant human nNOS (0.1‑1.0 units) is incubated with L‑arginine (10‑100 microM), NADPH (1 mM), CaCl2 (1 mM), calmodulin (10 microg/mL), and test compound (0‑100 microM) in 50 mM HEPES buffer (pH 7.4) at 37degC for 30‑60 min. Reaction is terminated by adding 1 M HClO4/ZnCl2, and nitrite/nitrate are quantified by chemiluminescence or Griess assay. IC₅0 is calculated from inhibition curves.
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| Cell Assay |
Not available. Generic NOS inhibitor cellular assay: Murine or rat primary cortical neurons are cultured in 24‑well plates for 7‑10 days. Cells are stimulated with NMDA (100 microM) or glutamate (50 microM) to activate nNOS. Test compound (0‑100 microM) is added 30 min before stimulation. After 15‑30 min, NO production is measured by quantifying nitrite accumulation in culture medium using Griess reagent, or by DAF‑FM diacetate fluorescent probe.
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| Animal Protocol |
No reported animal studies for this specific compound. A generic protocol for assessing neuroprotective effects of nNOS inhibitors in vivo: Male Sprague‑Dawley rats (250‑300 g) undergo middle cerebral artery occlusion (MCAO) for 90 min followed by reperfusion. Test compound (e.g., 10 mg/kg) is administered i.p. at onset of reperfusion. Neurological deficit scores are evaluated at 24 h, and brain tissues are collected for TTC staining to measure infarct volume. NO levels in ischemic cortex are measured by nitrate/nitrite assay.
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| ADME/Pharmacokinetics |
No PK data reported for Vinyl‑L‑NIO hydrochloride. For similar L‑arginine analogue NOS inhibitors, PK studies in rats: IV administration (5 mg/kg) yields initial plasma t1/2 of 0.5‑1 h, moderate clearance (10‑20 mL/min/kg), and limited brain penetration (brain:plasma ratio <0.5) due to polar amidine group. Oral bioavailability is typically low (<20%) for such charged molecules.
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| Toxicity/Toxicokinetics |
No toxicity data reported. Generic acute toxicity for NOS inhibitors: Mice receive single oral or i.p. doses (50‑500 mg/kg) and are observed for 14 days. Signs of CNS toxicity (tremors, seizures, hypoactivity) may be monitored due to the compound's nNOS selectivity. Histopathology of brain (cerebellum, hippocampus) and peripheral organs is performed at termination.
|
| References |
[1]. L-arginine is the physiological precursor for the formation of nitric oxide in endothelium-dependent relaxation. Biochem Biophys Res Commun. 1988 Jun 30;153(3):1251-6.
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| Additional Infomation |
Vinyl‑L‑NIO is a research tool for dissecting nNOS‑mediated signaling in neurological disorders such as ischemic stroke, neuropathic pain, and neurodegenerative diseases. Unlike pan‑NOS inhibitors, its nNOS selectivity may reduce side effects related to eNOS (hypertension) and iNOS (infection susceptibility). No clinical trials or approved indications exist.
|
| Molecular Formula |
C9H17N3O2.XHCL
|
|---|---|
| Molecular Weight |
235.71112
|
| Exact Mass |
235.108
|
| CAS # |
728944-69-2
|
| PubChem CID |
71433867
|
| Appearance |
Off-white to light yellow oil
|
| LogP |
2.314
|
| Hydrogen Bond Donor Count |
4
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
15
|
| Complexity |
226
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
C=CCC(=NCCCC(C(=O)O)N)N.Cl
|
| InChi Key |
DIWIMDZKSYTKCZ-FJXQXJEOSA-N
|
| InChi Code |
InChI=1S/C9H17N3O2.ClH/c1-2-4-8(11)12-6-3-5-7(10)9(13)14;/h2,7H,1,3-6,10H2,(H2,11,12)(H,13,14);1H/t7-;/m0./s1
|
| Chemical Name |
(2S)-2-amino-5-(1-aminobut-3-enylideneamino)pentanoic acid;hydrochloride
|
| Synonyms |
Vinyl-L-NIO (hydrochloride); 728944-69-2; Vinyl-L-NIO Hydrochloride; (2S)-2-amino-5-(1-aminobut-3-enylideneamino)pentanoic acid;hydrochloride; N5-(1-Imino-3-butenyl)-L-ornithine, monohydrochloride; Vinyl-L-NIO hydrochloride?; L-VNIO (hydrochloride); DTXSID90849566;
|
| 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)
|
| 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 | 4.2425 mL | 21.2125 mL | 42.4250 mL | |
| 5 mM | 0.8485 mL | 4.2425 mL | 8.4850 mL | |
| 10 mM | 0.4243 mL | 2.1213 mL | 4.2425 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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