Physicochemical Properties
| Molecular Formula | C12H9BRN2OS |
| Molecular Weight | 309.181 |
| Exact Mass | 307.961 |
| Elemental Analysis | C, 46.62; H, 2.93; Br, 25.84; N, 9.06; O, 5.17; S, 10.37 |
| CAS # | 304456-62-0 |
| Related CAS # | 304456-62-0 |
| PubChem CID | 721984 |
| Appearance | White to light yellow solid powder |
| Density | 1.6±0.1 g/cm3 |
| Boiling Point | 495.9±40.0 °C at 760 mmHg |
| Flash Point | 253.7±27.3 °C |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.685 |
| LogP | 2.88 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 17 |
| Complexity | 311 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1(/N=C/C2=CC=C(S2)Br)C=CC=CC=1C(=O)N |
| InChi Key | OZEADOPONHLEDS-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C12H9BrN2OS/c13-11-6-5-8(17-11)7-15-10-4-2-1-3-9(10)12(14)16/h1-7H,(H2,14,16) |
| Chemical Name | 2-[(5-bromothiophen-2-yl)methylideneamino]benzamide |
| Synonyms | BTYNB IMP1 Inhibitor |
| 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | IMP1; c-Myc; NF-κB |
| ln Vitro | Proteins encoded by target mRNAs are expressed more when the oncoembryonic mRNA binding protein IMP1 binds and stabilizes c-Myc, β-TrCP1, and other protein mRNAs [1]. In SK-MEL2 cells, BTYNB (10 μM; 0.5-1 hour) increases c-Myc mRNA and, in a dose-dependent manner, BTYNB (10-40 μM; 72 hours) lowers c-Myc expression [1]. 72-hour BTYNB (10–40 μM). In the presence of hormones, BTYNB (1-40 μM; 72 h) decreases CDC34, CALM1, β-TRCP1 and h) in T47D/(A1-2) cells and dose-dependently lowers IMP1 expression in SK-MEL2 cells [1]. The rapid proliferation of IMP1 cells is strongly inhibited by BTYNB, with IC50 values of 2.3 μM, 3.6 μM, and 4.5 μM in ES-2, IGROV-1, and SK-MEL2 cells, respectively. BTYNB did not suppress cell proliferation at any tested concentration, even 50 μM, and it had no effect on IMP1-negative cells [1]. |
| Cell Assay |
RT-PCR[1] Cell Types: T47D/(A1-2) Cell Tested Concentrations: 1μM; 10μM; 20μM; 30μM; 40 μM Incubation Duration: Experimental Results: diminished levels of multiple cancer-related IMP1 mRNA targets. |
| References |
[1]. A Novel IMP1 Inhibitor, BTYNB, Targets c-Myc and Inhibits Melanoma and Ovarian Cancer Cell Proliferation. Transl Oncol. |
Solubility Data
| Solubility (In Vitro) |
DMSO: ~62 mg/mL (~200.5 mM) Ethanol: ~4 mg/mL (~12.9 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.09 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), 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. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.09 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.09 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2344 mL | 16.1718 mL | 32.3436 mL | |
| 5 mM | 0.6469 mL | 3.2344 mL | 6.4687 mL | |
| 10 mM | 0.3234 mL | 1.6172 mL | 3.2344 mL |