Physicochemical Properties
| Molecular Formula | C17H12BR2N2O3 |
| Molecular Weight | 452.1 |
| Exact Mass | 449.921 |
| CAS # | 382605-72-3 |
| Related CAS # | JUN-1111;874351-38-9 |
| PubChem CID | 381594 |
| Appearance | Orange to red solid powder |
| Density | 1.9±0.1 g/cm3 |
| Boiling Point | 575.1±50.0 °C at 760 mmHg |
| Flash Point | 301.6±30.1 °C |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
| Index of Refraction | 1.729 |
| LogP | 3.65 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 24 |
| Complexity | 528 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | OHPHDPYJEHZGDE-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H12Br2N2O3/c18-11-6-9(7-12(19)16(11)23)3-5-20-13-8-14(22)10-2-1-4-21-15(10)17(13)24/h1-2,4,6-8,20,23H,3,5H2 |
| Chemical Name | 7-[2-(3,5-dibromo-4-hydroxyphenyl)ethylamino]quinoline-5,8-dione |
| Synonyms | NSC668394; NSC 668394; NSC-668394 |
| 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 vitro, NSC668394 (10 μM; sham for 15 minutes) inhibits actin binding and ezrin T567 phosphorylation (IC50=8.1 μM) [1]. NSC668394 (1–10 μM; 2–6 h) prevents K7M2 skeletal growth mediated by ezrin. JM1 and JM2 dynasty cell line proliferation is severely inhibited by NSC668394 (20 μM) [2]. The horsefish (OS) cell motility phenotype on the thorax of HUVEC monolayers is diminished by NSC668394 (10 μM) [1]. |
| ln Vivo | In the lung, NSC668394 (0.226 mg/kg/day; intraperitoneally; 5 days a week) inhibits ezrin-coupled peripheral OS migratory growth [1]. |
| Cell Assay |
Western Blot analysis [1] Cell Types: K7M2 OS cells Tested Concentrations: 10 μM Incubation Duration: 6 hrs (hours) Experimental Results: Inhibits T567 phosphorylation and actin binding of endogenous ezrin without changing cellular ezrin levels. |
| Animal Protocol |
Animal/Disease Models: Female BALB/c and SCID/Beige mice were injected with K7M2 or MNNG-HOS tumor cells [1]. Doses: 0.226 mg/kg/day. Route of Administration: intraperitoneal (ip) injection, 5 days a week for 66 days. Experimental Results: Shows increased survival rates. Reduces the number of green fluorescent protein (GFP)-expressing metastases in lung tissue. |
| References |
[1]. Small molecule inhibitors of ezrin inhibit the invasive phenotype of osteosarcoma cells. Oncogene. 2012 Jan 19;31(3):269-81. [2]. Phosphorylated Ezrin (Thr567) Regulates Hippo Pathway and Yes-Associated Protein (Yap) in Liver. Am J Pathol. 2020 Jul;190(7):1427-1437. [3]. Ezrin Inhibition Up-regulates Stress Response Gene Expression. J Biol Chem. 2016 Jun 17;291(25):13257-70. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~110.60 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.53 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (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 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2119 mL | 11.0595 mL | 22.1190 mL | |
| 5 mM | 0.4424 mL | 2.2119 mL | 4.4238 mL | |
| 10 mM | 0.2212 mL | 1.1060 mL | 2.2119 mL |