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MNS (NSC170724; NSC-170724; NSC 170724; 5-(2-Nitrovinyl)benzodioxole)) is a novel, potent and selective TKI-tyrosine kinase inhibitor with anti-platelet activity. It has an IC50 of 2.5 μM, 29.3 μM, and 1.7 μM for several kinases, including Syk, Src, and p97, respectively, and inhibits them all.
Physicochemical Properties
| Molecular Formula | C9H7NO4 | |
| Molecular Weight | 193.16 | |
| Exact Mass | 193.037 | |
| Elemental Analysis | C, 55.96; H, 3.65; N, 7.25; O, 33.13 | |
| CAS # | 1485-00-3 | |
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| PubChem CID | 672296 | |
| Appearance | Light yellow to green yellow solid powder | |
| Density | 1.4±0.1 g/cm3 | |
| Boiling Point | 334.9±11.0 °C at 760 mmHg | |
| Melting Point | 159-163 °C | |
| Flash Point | 168.8±21.3 °C | |
| Vapour Pressure | 0.0±0.7 mmHg at 25°C | |
| Index of Refraction | 1.640 | |
| LogP | 2.27 | |
| Hydrogen Bond Donor Count | 0 | |
| Hydrogen Bond Acceptor Count | 4 | |
| Rotatable Bond Count | 1 | |
| Heavy Atom Count | 14 | |
| Complexity | 248 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | O=[N+]([O-])/C=C/C1=CC(OCO2)=C2C=C1 |
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| InChi Key | KFLWBZPSJQPRDD-ONEGZZNKSA-N | |
| InChi Code | InChI=1S/C9H7NO4/c11-10(12)4-3-7-1-2-8-9(5-7)14-6-13-8/h1-5H,6H2/b4-3+ | |
| Chemical Name | 5-[(E)-2-nitroethenyl]-1,3-benzodioxole | |
| Synonyms | SYK Inhibitor III; MNS | |
| HS Tariff Code | 2934.99.03.00 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| 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
| Targets | p97 ( IC50 = 1.7 μM ); Syk ( IC50 = 2.5 μM ); HDAC4 ( IC50 = 510 nM ); Src ( IC50 = 29.3 μM ) | ||
| ln Vitro |
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| ln Vivo | MNS (3,4-methyl-enedioxy-β-nitrostyrene) completely inhibits 2 μM U46619-(a thromboxane A2 mimic), 5 μM ADP-, 100 μM arachidonic acid-(AA), 10 μg/ml collagen-, and 0.1 U/ml thrombin-induced platelet aggregation in a concentration-dependent manner with IC50 of 2.1 μM, 4.1 μM, 5.8 μM, 7.0 μM, and 12.7 μM, respectively. MNS inhibits platelet aggregation caused by either the calcium ionophore A23187 (1 μM) or the protein kinase C (PKC) activator PDBu (200 nM) with IC50 of 25.9 μM and 4.8 μM, respectively. MNS (20 μM) decreases dthrombin-induced P-selectin expression on platelets to levels comparable to those observed in PGE1-treated platelets. MNS (20 μM) markedly inhibits thrombin-but not PDBu-induced MARCKS phosphorylation in platelets. MNS (20 μM) markedly inhibits protein tyrosine phosphorylation at either 0.5 min or 3 min after thrombin or collagen stimulation in platelets. MNS stimulates UbG76V-GFP and ODD-Luc degradation with IC50 of 1.6 μM and 5.9 μM, respectively. MNS inhibits MG132-induced accumulation of the reporter with IC50 of 2.1 μM. MNS inhibits Gram-positive (Staphylococcus aureus and Enterococcus faecalis) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria with minimum inhibitory concentrations (MICs) of 128 mg/L. MNS is much more potent than genistein in inhibiting platelet aggregation and protein tyrosine phosphorylation. MNS (3,4-Methylenedioxy-β-nitrostyrene) is equally potent as inhibitors of platelet aggregation as 3,4-dimethoxy-β-nitrostyrene. MNS (20 μM) concentration-dependently prevents ATP release from platelets stimulated by thrombin or collagen. MNS (20 μM) inhibits thrombin-induced PAC-1 binding to human platelets. | ||
| Animal Protocol |
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| References |
[1]. Mol Pharmacol . 2006 Oct;70(4):1380-9. [2]. J Biol Chem . 2011 May 13;286(19):16546-54. [3]. Bioorg Med Chem . 2006 Jun 15;14(12):4078-88. [4]. Biochem Pharmacol . 2007 Aug 15;74(4):601-11. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 39~50 mg/mL ( 201.9~258.9 mM ) H2O : ~0.7 mg/mL (~3.5 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (12.94 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), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (12.94 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 3: 2% DMSO + corn oil: 5mg/ml (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.1771 mL | 25.8853 mL | 51.7706 mL | |
| 5 mM | 1.0354 mL | 5.1771 mL | 10.3541 mL | |
| 10 mM | 0.5177 mL | 2.5885 mL | 5.1771 mL |