Physicochemical Properties
| Molecular Formula | C17H13F2NO |
| Molecular Weight | 285.288031339645 |
| Exact Mass | 285.096 |
| CAS # | 2757804-89-8 |
| PubChem CID | 163322396 |
| Appearance | White to off-white solid powder |
| LogP | 3.7 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 21 |
| Complexity | 370 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | N1C2=C(C=CC=C2)C2CCOC(C3=CC(F)=CC(F)=C3)C1=2 |
| InChi Key | XBYJYKHTEFYLFX-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H13F2NO/c18-11-7-10(8-12(19)9-11)17-16-14(5-6-21-17)13-3-1-2-4-15(13)20-16/h1-4,7-9,17,20H,5-6H2 |
| Chemical Name | 1-(3,5-difluorophenyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole |
| 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 | PI3K/Akt/mTOR-IN-2 (Compound 23) shown strong anticancer effects with an IC50 ranging from 2.29 to 24.63 μM during a 72-hour period. This included MDA-MB-231, which had an IC50 of 2.29 μM [1]. Through cell cycle arrest in G0/G1, PI3K/Akt/mTOR-IN-2 (1 μM, 2 μM, and 4 μM; 24 hours) causes growth suppression of MDA-MB-231 cells. [1]. In MDA-MB-231 cells, PI3K/Akt/mTOR-IN-2 (1 μM, 2 μM, and 4 μM; 24, 48, and 72 hours) causes apoptosis in a way that is dependent on both time and dose [1]. Bax expression is upregulated and Bcl-2 expression is downregulated in MDA-MB-231 cells when exposed to PI3K/Akt/mTOR-IN-2 (1 μM, 2 μM, and 4 μM; 48 hours) [1]. By interfering with MMPs, building up ROS, decreasing GSH, and increasing intracellular toxins, PI3K/Akt/mTOR-IN-2 (1 μM, 2 μM, and 4 μM; 24 hours) causes mitochondrial dependency in MDA-MB-231 cells. Calcium-mediated apoptosis[1]. |
| Cell Assay |
Cell Proliferation Assay Cell Types: PC3, BGC-823, A549, MCF-7, MDA-MB-231 cells and MCF-10A cells [1] Tested Concentrations: 0.5 - 100 μM Incubation Duration: 72 hrs (hours) Experimental Results: Demonstrated effective anti- The IC50 of cancer activity is 2.29 - 24.63 μM, among which the IC50 of MDA-MB-231 is 2.29 μM. Cell cycle analysis Cell Types: MDA-MB-231[1] Tested Concentrations: 1 μM, 2 μM and 4 μM Incubation Duration: 24 hrs (hours) Experimental Results: Induced growth inhibition of MDA-MB-231 cells via cell cycle arrest at G0/G1 . Apoptosis analysis Cell Types: MDA-MB-231[1] Tested Concentrations: 1 μM, 2 μM and 4 μM Incubation Duration: 24, 48 and 72 hrs (hours) Experimental Results: Both dose and time induced apoptosis in MDA-MB-231 cells The way. Western Blot Analysis Cell Types: MDA-MB-231[1] Tested Concentrations: 1 μM, 2 μM and 4 μM Incubation Duration: 48 hrs (hours) Experimental Results: Increased expression of Bax and diminished expression of Bcl-2 |
| References |
[1]. Design, synthesis and biological evaluation of novel 1,3,4,9-tetrahydropyrano[3,4-b]indoles as potential treatment of triple negative breast cancer by suppressing PI3K/AKT/mTOR pathway [published online ahead of print, 2021 Dec. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~350.52 mM) |
| 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 | 3.5052 mL | 17.5260 mL | 35.0521 mL | |
| 5 mM | 0.7010 mL | 3.5052 mL | 7.0104 mL | |
| 10 mM | 0.3505 mL | 1.7526 mL | 3.5052 mL |