Physicochemical Properties
| Molecular Formula | C28H28N2O2 |
| Molecular Weight | 424.53 |
| Exact Mass | 424.21507 |
| CAS # | 2418579-17-4 |
| PubChem CID | 156021169 |
| Appearance | White to off-white solid powder |
| LogP | 5.5 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 32 |
| Complexity | 496 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1=CC=C(C=C1)C2=CC=C(C=C2)CNCC(COC3=CC=CC(=C3)NC4=CC=CC=C4)O |
| InChi Key | OOXIDWAKDUZBSL-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C28H28N2O2/c31-27(20-29-19-22-14-16-24(17-15-22)23-8-3-1-4-9-23)21-32-28-13-7-12-26(18-28)30-25-10-5-2-6-11-25/h1-18,27,29-31H,19-21H2 |
| Chemical Name | 1-(3-anilinophenoxy)-3-[(4-phenylphenyl)methylamino]propan-2-ol |
| Synonyms | Anti-melanoma agent 1; 2418579-17-4; CHEMBL4647987; |
| 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
| Targets | Apoptosis |
| ln Vitro | Against melanoma cells, antimelanoma agent 1 (compound 5m) (0-100 μM, 48 hours) demonstrated antiproliferative action [1]. In SK-MEL-28, colony development is inhibited by anti-melanoma agent 1 (0-10 μM) [1]. Anti-melanoma agent 1 (1 and 2 μM) slows cell migration (48 hours), promotes apoptosis (24 hours), stops the cell cycle in the G2/M phase (12 hours), and damages the microtubule network within the cell [1]. |
| Cell Assay |
Cell proliferation assay[1] Cell Types: SK-MEL-5, SK-MEL-28 and A375 Tested Concentrations: 0-100 μM Incubation Duration: 48 hrs (hours) Experimental Results: Displayed anti-proliferative activity with IC50 values of 3.70 ± 0.17, 3.30 ± 0.06 and 1.98 ± 0.10 μM for SK-MEL-5, SK-MEL-28 and A375 cells respectively. Apoptosis analysis [1] Cell Types: SK-MEL-28 Tested Concentrations: 1 μM and 2 μM Incubation Duration: 24 h Experimental Results: Induction of apoptosis. Cell cycle analysis[1] Cell Types: SK-MEL-28 Tested Concentrations: 1 μM and 2 μM Incubation Duration: 12 hrs (hours) Experimental Results: Cell cycle arrested in G2/M phase. Cell migration assay[1] Cell Types: SK-MEL-28 Tested Concentrations: 1 μM and 2 μM Incubation Duration: 48 hrs (hours) Experimental Results: Cell migration was inhibited. |
| References |
[1]. Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents. Bioorg Med Chem. 2020 May 1;28(9):115404. |
| Additional Infomation | Malignant melanoma (MM) presents as the highest morbidity and mortality type in skin cancer. Herein, inspired by the previously reported anti-melanoma effect of propranolol, a widely applied β adrenergic receptor antagonist as cardiovascular drug, we set out to exploit its potential as anti-melanoma therapy based on the drug repurposing strategy. Structural optimization of propranolol yielded 5m, which exhibits dramatically improved potency on human melanoma cell growth (1.98-3.70 μM), compared to propranolol (59.5-75.8 μM). Further investigation demonstrated that 5m could inhibit colony formation of melanoma cell line (completely abolished at 2 μM for 5m, partially inhibited at 50 μM for propranolol), induce cell apoptosis and cell cycle arrest in the G2/M phase (both observed at 1 μM). Preliminary mechanism study indicated that 5m could disrupt the cellular microtubule network, which suggested tubulin as a potential target. Docking study provided a structural insight into the interaction between 5m and tubulin. In summary, our study presents a drug repurposing case that redirects a cardiovascular agent to an anti-melanoma agent.[1] |
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 | 2.3555 mL | 11.7777 mL | 23.5555 mL | |
| 5 mM | 0.4711 mL | 2.3555 mL | 4.7111 mL | |
| 10 mM | 0.2356 mL | 1.1778 mL | 2.3555 mL |