-BCI Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C22H23NO |
| Molecular Weight | 317.424125909805 |
| Exact Mass | 317.177 |
| CAS # | 15982-84-0 |
| Related CAS # | BCI;1245792-51-1;BCI hydrochloride;95130-23-7 |
| PubChem CID | 5475586 |
| Appearance | Typically exists as solid at room temperature |
| LogP | 4.7 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 24 |
| Complexity | 470 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1CCC(CC1)NC\2C3=CC=CC=C3C(=O)/C2=C\C4=CC=CC=C4 |
| InChi Key | XJDKPLZUXCIMIS-HKWRFOASSA-N |
| InChi Code | InChI=1S/C22H23NO/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,2,5-6,11-12H2/b20-15- |
| Chemical Name | (2Z)-2-benzylidene-3-(cyclohexylamino)-3H-inden-1-one |
| Synonyms | (E/Z)BCI; (E/Z) BCI |
| 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 a time- and dose-dependent way, (E/Z)-BCI hydrochloride (2-10 μM; 72 hours) dramatically lowers the cell viability of gastric epithelial cells GES1, GC cell lines, and AGS cell lines [2]. In LPS-activated macrophages, (E/Z)-BCI hydrochloride (0.5–4 μM; 24 hours) dramatically reduces DUSP6 expression [1]. The expression of IL-1β, TNF-α, and IL-6 mRNA in LPS-activated macrophages was considerably reduced by (E/Z)-BCI hydrochloride (0.5-2 μM; 24 hours) treatment [1]. When LPS-activated macrophages are exposed to (E/Z)-BCI hydrochloride, they produce less ROS and activate the Nrf2 pathway [1]. The gastric cancer (GC) cells are more resistant to invasion, migration, and proliferation when exposed to (E/Z)-BCI hydrochloride, which also increases the cytotoxicity of CDDP (increased CDDP-induced cell death and apoptosis) [2]. |
| ln Vivo | Treatment with (E/Z)-BCI hydrochloride (35 mg/kg; intraperitoneal injection; every 7 days; for 4 weeks; female BALB/c nude mice) increased the effectiveness of cisplatin in the PDX model [2]. |
| Cell Assay |
Cell viability assay [2] Cell Types: gastric epithelial cells GES1, GC cell lines (HGC27, SGC7901, MKN45, BGC823, MGC803, SNU216, NUGC4), AGS cell lines. Tested Concentrations: 2 μM, 4 μM, 6 μM, 8 μM, 10 μM Incubation Duration: 72 hrs (hours) Experimental Results: Cell viability was Dramatically diminished in a time- and dose-dependent manner. Western Blot Analysis[1] Cell Types: RAW264.7 macrophages (LPS-activated macrophages) Tested Concentrations: 0.5 μM, 1 μM, 2 μM, 4 μM Incubation Duration: 24 hrs (hours) Experimental Results: DUSP6 protein activated by LPS Dramatically down-regulated macrophages. RT-PCR[1] Cell Types: RAW264.7 macrophages (LPS-activated macrophages) Tested Concentrations: 0.5 μM, 1 μM, 2 μM Incubation Duration: 24 hrs (hours) Experimental Results: IL-1β, TNF-α, and IL Expression of -6 mRNA was Dramatically inhibited in LPS-activated macrophages. |
| Animal Protocol |
Animal/Disease Models: Patient-derived xenograft (PDX) model (4-5 weeks old female BALB/c nude mice) [2] Doses: 35 mg/kg Route of Administration: intraperitoneal (ip) injection; once every 7 days; 4-week Experimental Results: Tumor weight in PDX models treated with CDDP was Dramatically suppressed compared to tumors in PDX model mice treated with either drug alone. |
| References |
[1]. 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. [2]. Pharmacological inhibition of DUSP6 suppresses gastric cancer growth and metastasis and overcomes cisplatin resistance. Cancer Lett. 2018 Jan 1;412:243-255. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1504 mL | 15.7520 mL | 31.5040 mL | |
| 5 mM | 0.6301 mL | 3.1504 mL | 6.3008 mL | |
| 10 mM | 0.3150 mL | 1.5752 mL | 3.1504 mL |