BCI hydrochloride [(E)-BCI] is a novel, potent and allosteric inhibitor of Dusp6 (dual specificity phosphatase), which acts within the phosphatase domain to prevent the catalytic stimulation of phosphatase activity induced by ERK2 substrate binding. It inhibits DUSP6 and DUSP1 with EC50s of 13.3 and 8.0 μM in cells, respectively.
Physicochemical Properties
| Exact Mass | 352.147 |
| CAS # | 95130-23-7 |
| Related CAS # | BCI;1245792-51-1;(E/Z)-BCI;15982-84-0 |
| PubChem CID | 20831631 |
| Appearance | Light yellow to yellow solid powder |
| Boiling Point | 484.6ºC at 760mmHg |
| Flash Point | 161.3ºC |
| LogP | 2.324 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 25 |
| Complexity | 470 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | Cl.O=C1C(=CC2C=CC=CC=2)C(NC2CCCCC2)C2C1=CC=CC=2 |
| InChi Key | JPATUDRDKCLPTI-CRDKNBMZSA-N |
| InChi Code | InChI=1S/C22H23NO.ClH/c24-22-19-14-8-7-13-18(19)21(23-17-11-5-2-6-12-17)20(22)15-16-9-3-1-4-10-16/h1,3-4,7-10,13-15,17,21,23H,2,5-6,11-12H21H/b20-15- |
| Chemical Name | 2-Benzylidene-3-(cyclohexylamino)-2,3-dihydro-1H-inden-1-one hydrochloride |
| Synonyms | BCI hydrochloride |
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 RAW264.7 macrophages, BCI hydrochloride (100 ng/mL; 24 h) suppresses DUSP6 expression [2]. Lipopolysaccharide (LPS)-activated macrophages are inhibited in their expression by BCI hydrochloride (0-1 nM; 24 h). On the other hand, BCI hydrochloride (0-4 nM; 24 h) decreases ROS production and stimulates Nrf2 staining, which activates phagocytosis in LPS-activated macrophages[2]. |
| Cell Assay |
Western Blot Analysis[2] Cell Types: RAW264.7 Macrophage Tested Concentrations: 100 ng/mL Incubation Duration: 24 hrs (hours) Experimental Results: demonstrated downregulation of DUSP6 protein. RT-PCR[2] Cell Types: RAW264.7 Macrophage Tested Concentrations: 0-1 nM Incubation Duration: 24 hrs (hours) Experimental Results: Inhibits the expression of IL-1β and IL-6 mRNA in LPS-activated macrophages. |
| References |
[1]. In vivo structure-activity relationship studies support allosteric targeting of a dual specificity phosphatase. Chembiochem. 2014 Jul 7;15(10):1436-45. [2]. DUSP6 Inhibitor (E/Z)-BCI Hydrochloride Attenuates Lipopolysaccharide-Induced Inflammatory Responses in Murine Macrophage Cells via Activating the Nrf2 Signaling Axis and Inhibiting the NF-κB Pathway. Inflammation. 2019 Apr;42(2):672-681. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~15.62 mg/mL (~44.14 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.56 mg/mL (4.41 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 15.6 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: ≥ 1.56 mg/mL (4.41 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 15.6 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: ≥ 1.56 mg/mL (4.41 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 15.6 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.) |