CCR6 antagonist 1 is a CCR6 antagonist with the potential to be used in autoimmune diseases, e.g. inflammatory bowel diseases (IBDs).
Physicochemical Properties
| Molecular Formula | C17H12F3NO2 |
| Molecular Weight | 319.277894973755 |
| Exact Mass | 319.082 |
| CAS # | 588674-64-0 |
| PubChem CID | 4504520 |
| Appearance | White to off-white solid powder |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 345.9±42.0 °C at 760 mmHg |
| Flash Point | 163.0±27.9 °C |
| Vapour Pressure | 0.0±0.8 mmHg at 25°C |
| Index of Refraction | 1.604 |
| LogP | 4.18 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 23 |
| Complexity | 432 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | VHAWUBMHTMNOJC-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H12F3NO2/c1-10-13-4-2-3-5-14(13)23-15(10)16(22)21-12-8-6-11(7-9-12)17(18,19)20/h2-9H,1H3,(H,21,22) |
| Chemical Name | 3-methyl-N-[4-(trifluoromethyl)phenyl]-1-benzofuran-2-carboxamide |
| 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 | The movement of CD4+ T cells generated by CCL20 is aggregated by CCR6 Antagonist 1 (Compound 1b, 50 μM, 3 hours) [1]. The CCR6 antagonist 1 (30 nM-300 μM, 20 min) inhibits the recruitment of miniGi to CCR6 induced by CCL20, as well as the recruitment of β-arrestin-1 to CCR6 and CCR5 (5 nM) induced by CCL20 and CCL5 [1]. |
| ln Vivo | CCR6 antagonist 1 (Compound 1b, 1 mg/kg, subcutaneous injection twice daily for 3 days) attenuates the trigger response of TNBS sensors [1]. CCR6 Antagonist 1 (1 mg/kg, sc, twice, |
| Cell Assay |
Cell migration assay [1] Cell Types: CCR6+CD4+ T cells induced by CCL20 (500 ng/mL) Tested Concentrations: 0.5, 5, 50 μM Incubation Duration: 3 hrs (hours) Experimental Results: Inhibition of CCL20-induced cell migration at 50 μM. |
| Animal Protocol |
Animal/Disease Models: Zymosan-induced peritonitis in mice[1] Doses: 1 mg/kg Route of Administration: subcutaneous injection, twice, before and after zymosan treatment Experimental Results: Dramatically diminished total protein content and myeloperoxidase activity in peritoneal lavage fluid. |
| References |
[1]. Discovery of small-molecules targeting the CCL20/CCR6 axis as first-in-class inhibitors for inflammatory bowel diseases. Eur J Med Chem. 2022 Aug 29;243:114703. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~313.20 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 | 3.1320 mL | 15.6602 mL | 31.3205 mL | |
| 5 mM | 0.6264 mL | 3.1320 mL | 6.2641 mL | |
| 10 mM | 0.3132 mL | 1.5660 mL | 3.1320 mL |